From d3c0a7cda56ab5beacf52d50256f529918ad5791 Mon Sep 17 00:00:00 2001
From: Clay Tercek <30105080+claytercek@users.noreply.github.com>
Date: Thu, 31 Oct 2024 15:05:42 -0400
Subject: [PATCH 1/4] use error classes for all throws in content

---
 .../__tests__/content-plugin-driver.test.js   | 22 ++---
 .../lib/__tests__/launchpad-content.test.js   | 38 +++++----
 packages/content/lib/content-plugin-driver.js |  7 +-
 packages/content/lib/launchpad-content.js     | 20 ++---
 .../lib/plugins/__tests__/md-to-html.test.js  |  2 +-
 .../plugins/__tests__/sanity-to-html.test.js  |  2 +-
 .../__tests__/sanity-to-markdown.test.js      |  2 +-
 .../plugins/__tests__/sanity-to-plain.test.js |  6 +-
 .../sources/__tests__/airtable-source.test.js | 11 ++-
 .../__tests__/contentful-source.test.js       |  9 ++-
 .../lib/sources/__tests__/json-source.test.js | 13 ++-
 .../sources/__tests__/sanity-source.test.js   |  5 +-
 .../sources/__tests__/strapi-source.test.js   |  9 ++-
 .../content/lib/sources/airtable-source.js    | 27 +++----
 .../content/lib/sources/contentful-source.js  | 13 ++-
 packages/content/lib/sources/json-source.js   | 11 ++-
 packages/content/lib/sources/sanity-source.js | 13 ++-
 packages/content/lib/sources/source-errors.js | 27 -------
 packages/content/lib/sources/source.js        | 54 ++++++++++++-
 packages/content/lib/sources/strapi-source.js | 11 ++-
 .../__tests__/content-transform-utils.test.js |  2 +-
 .../lib/utils/__tests__/data-store.test.js    | 17 ++--
 .../utils/__tests__/fetch-paginated.test.js   | 12 +--
 .../lib/utils/__tests__/file-utils.test.js    |  4 +-
 .../__tests__/markdown-it-italic-bold.test.js | 80 +++++++++----------
 .../lib/utils/__tests__/safe-ky.test.js       |  6 +-
 .../lib/utils/content-transform-utils.js      |  6 +-
 packages/content/lib/utils/data-store.js      | 54 +++++++------
 packages/content/lib/utils/fetch-paginated.js | 10 +--
 packages/content/lib/utils/file-utils.js      | 60 +++++++-------
 packages/content/lib/utils/safe-ky.js         | 53 ++++++------
 31 files changed, 321 insertions(+), 285 deletions(-)
 delete mode 100644 packages/content/lib/sources/source-errors.js

diff --git a/packages/content/lib/__tests__/content-plugin-driver.test.js b/packages/content/lib/__tests__/content-plugin-driver.test.js
index 647432c5..f6ff5073 100644
--- a/packages/content/lib/__tests__/content-plugin-driver.test.js
+++ b/packages/content/lib/__tests__/content-plugin-driver.test.js
@@ -113,16 +113,13 @@ describe('ContentPluginDriver', () => {
 				})
 			});
 
+			const contentErr = new ContentError('Plugin setup failed', error);
 			contentDriver.add(plugin);
-			await contentDriver.runHookSequential('onSetupError', new ContentError('Plugin setup failed', error));
+			await contentDriver.runHookSequential('onSetupError', contentErr);
 
 			expect(onSetupError).toHaveBeenCalledWith(
-				expect.any(Object),
-				expect.objectContaining({
-					name: 'ContentError',
-					message: 'Plugin setup failed',
-					cause: error
-				})
+				expect.anything(),
+				contentErr
 			);
 		});
 
@@ -146,16 +143,13 @@ describe('ContentPluginDriver', () => {
 				})
 			});
 
+			const contentErr = new ContentError('Content fetch failed', error);
 			contentDriver.add(plugin);
-			await contentDriver.runHookSequential('onContentFetchError', new ContentError('Content fetch failed', error));
+			await contentDriver.runHookSequential('onContentFetchError', contentErr);
 
 			expect(onContentFetchError).toHaveBeenCalledWith(
-				expect.any(Object),
-				expect.objectContaining({
-					name: 'ContentError',
-					message: 'Content fetch failed',
-					cause: error
-				})
+				expect.anything(),
+				expect.any(ContentError)
 			);
 		});
 	});
diff --git a/packages/content/lib/__tests__/launchpad-content.test.js b/packages/content/lib/__tests__/launchpad-content.test.js
index 77c04129..cfa9189c 100644
--- a/packages/content/lib/__tests__/launchpad-content.test.js
+++ b/packages/content/lib/__tests__/launchpad-content.test.js
@@ -22,25 +22,23 @@ describe('LaunchpadContent', () => {
 	 */
 	const createBasicConfig = (plugins = []) => {
 		return {
-			content: {
-				downloadPath: '/downloads',
-				tempPath: '/temp',
-				backupPath: '/backups',
-				sources: [
-					defineSource({
-						id: 'test',
-						fetch: () => {
-							return ok([{
+			downloadPath: '/downloads',
+			tempPath: '/temp',
+			backupPath: '/backups',
+			sources: [
+				defineSource({
+					id: 'test',
+					fetch: () => {
+						return ok([{
+							id: 'doc1',
+							dataPromise: okAsync([{
 								id: 'doc1',
-								dataPromise: okAsync([{
-									id: 'doc1',
-									data: 'doc1'
-								}])
-							}]);
-						}
-					})
-				]
-			},
+								data: 'doc1'
+							}])
+						}]);
+					}
+				})
+			],
 			plugins
 		};
 	};
@@ -56,7 +54,7 @@ describe('LaunchpadContent', () => {
 			const config = createBasicConfig();
 			const content = new LaunchpadContent(config, createMockLogger());
 			expect(content).toBeInstanceOf(LaunchpadContent);
-			expect(content._config).toEqual(resolveContentOptions(config.content));
+			expect(content._config).toEqual(resolveContentOptions(config));
 		});
 	});
 
@@ -79,7 +77,7 @@ describe('LaunchpadContent', () => {
 			vol.writeFileSync('/downloads/test/old.json', '{}');
 
 			const config = {
-				...createBasicConfig().content,
+				...createBasicConfig(),
 				keep: ['.keep']
 			};
 
diff --git a/packages/content/lib/content-plugin-driver.js b/packages/content/lib/content-plugin-driver.js
index 5dcaca11..b216ee5d 100644
--- a/packages/content/lib/content-plugin-driver.js
+++ b/packages/content/lib/content-plugin-driver.js
@@ -2,11 +2,10 @@ import { HookContextProvider } from '@bluecadet/launchpad-utils/lib/plugin-drive
 
 export class ContentError extends Error {
 	/**
-	 * @param {string} [message]
-	 * @param {Error} [cause]
+	 * @param {ConstructorParameters<typeof Error>} args
 	 */
-	constructor(message, cause) {
-		super(message, { cause });
+	constructor(...args) {
+		super(...args);
 		this.name = 'ContentError';
 	}
 }
diff --git a/packages/content/lib/launchpad-content.js b/packages/content/lib/launchpad-content.js
index ff4040ed..19b38656 100644
--- a/packages/content/lib/launchpad-content.js
+++ b/packages/content/lib/launchpad-content.js
@@ -93,7 +93,7 @@ export class LaunchpadContent {
 						this._logger.error('Error in content fetch process:', e);
 						this._logger.info('Restoring from backup...');
 						return this.restore(sources).andThen(() => {
-							return err(new ContentError('Failed to download content. Restored from backup.'));
+							return err(new ContentError('Failed to download content. Restored from backup.', { cause: e }));
 						});
 					})
 					.andThen(() => this.clear(sources, {
@@ -143,7 +143,7 @@ export class LaunchpadContent {
 			}
 			return ResultAsync.combine(tasks);
 		})).andThen(() => {
-			/** @type {ResultAsync<void, string>[]} */
+			/** @type {ResultAsync<void, FileUtils.FileUtilsError>[]} */
 			const tasks = [];
 			if (removeIfEmpty) {
 				if (temp) tasks.push(FileUtils.removeDirIfEmpty(this.getTempPath()));
@@ -153,7 +153,7 @@ export class LaunchpadContent {
 			return ResultAsync.combine(tasks);
 		})
 			.map(() => undefined) // return void instead of void[]
-			.mapErr(error => new ContentError(`Failed to clear directories: ${error instanceof Error ? error.message : String(error)}`));
+			.mapErr(error => new ContentError('Failed to clear directories', { cause: error }));
 	}
 
 	/**
@@ -176,7 +176,7 @@ export class LaunchpadContent {
 					return FileUtils.copy(downloadPath, backupPath);
 				});
 		}))
-			.mapErr(e => new ContentError(`Failed to backup sources: ${e}`))
+			.mapErr(e => new ContentError('Failed to backup sources', { cause: e }))
 			.map(() => undefined); // return void instead of void[]
 	}
 
@@ -267,10 +267,10 @@ export class LaunchpadContent {
 			ResultAsync.fromPromise(
 				// wrap source in promise to ensure it's awaited
 				Promise.resolve(source),
-				error => new ContentError(error instanceof Error ? error.message : String(error))
+				error => new ContentError('Failed to build source', { cause: error })
 			).andThen(awaited => {
 				if ('value' in awaited || 'error' in awaited) {
-					return awaited.mapErr(e => new ContentError(e instanceof Error ? e.message : String(e)));
+					return awaited.mapErr(e => new ContentError('Failed to build source', { cause: e }));
 				}
 				return ok(awaited);
 			})
@@ -296,7 +296,7 @@ export class LaunchpadContent {
 					.asyncAndThen(calls => {
 						return ResultAsync.combine(calls.map(call => call.dataPromise));
 					})
-					.mapErr(e => new ContentError(`Failed to fetch source ${source.id}: ${e instanceof Error ? e.message : String(e)}`))
+					.mapErr(e => new ContentError(`Failed to fetch source ${source.id}`, { cause: e }))
 					.andThrough(fetchResults => {
 						/** @type {Map<string, unknown>} */
 						const map = new Map();
@@ -305,7 +305,7 @@ export class LaunchpadContent {
 							map.set(result.id, result.data);
 						}
 
-						return this._dataStore.createNamespaceFromMap(source.id, map).mapErr(e => new ContentError(`Unable to create namespace for source ${source.id}: ${e}`));
+						return this._dataStore.createNamespaceFromMap(source.id, map).mapErr(e => new ContentError(`Unable to create namespace for source ${source.id}`, { cause: e }));
 					});
 			}))
 			.map(() => undefined); // return void instead of void[]
@@ -328,7 +328,7 @@ export class LaunchpadContent {
 					return FileUtils.saveJson(document.data, filePath);
 				})
 			))
-			.mapErr(e => new ContentError(`Failed to write data store to disk: ${e}`))
+			.mapErr(e => new ContentError('Failed to write data store to disk', { cause: e }))
 			.map(() => undefined); // return void instead of void[]
 	}
 
@@ -351,7 +351,7 @@ export class LaunchpadContent {
 	
 						return okAsync(undefined);
 					});
-			}).mapErr(e => new ContentError(e));
+			}).mapErr(e => new ContentError(`Failed to clear directory: ${dirPath}`, { cause: e }));
 	}
 
 	/**
diff --git a/packages/content/lib/plugins/__tests__/md-to-html.test.js b/packages/content/lib/plugins/__tests__/md-to-html.test.js
index b7bb2746..2666a381 100644
--- a/packages/content/lib/plugins/__tests__/md-to-html.test.js
+++ b/packages/content/lib/plugins/__tests__/md-to-html.test.js
@@ -57,6 +57,6 @@ describe('mdToHtml plugin', () => {
 		ctx.data.insert('test', 'doc1', { content: { foo: 'bar' } });
 
 		const plugin = mdToHtml({ path: '$.content' });
-		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Can\'t convert non-string content to html.');
+		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Error applying content transform');
 	});
 });
diff --git a/packages/content/lib/plugins/__tests__/sanity-to-html.test.js b/packages/content/lib/plugins/__tests__/sanity-to-html.test.js
index e3b4177e..4bb845ec 100644
--- a/packages/content/lib/plugins/__tests__/sanity-to-html.test.js
+++ b/packages/content/lib/plugins/__tests__/sanity-to-html.test.js
@@ -45,6 +45,6 @@ describe('sanityToHtml plugin', () => {
 		ctx.data.insert('test', 'doc1', { content: 'not a block' });
 
 		const plugin = sanityToHtml({ path: '$.content' });
-		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Content is not a valid Sanity text block');
+		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Error applying content transform');
 	});
 });
diff --git a/packages/content/lib/plugins/__tests__/sanity-to-markdown.test.js b/packages/content/lib/plugins/__tests__/sanity-to-markdown.test.js
index 068e0d9b..de7c11d6 100644
--- a/packages/content/lib/plugins/__tests__/sanity-to-markdown.test.js
+++ b/packages/content/lib/plugins/__tests__/sanity-to-markdown.test.js
@@ -45,6 +45,6 @@ describe('sanityToMd plugin', () => {
 		ctx.data.insert('test', 'doc1', { content: 'not a block' });
 
 		const plugin = sanityToMd({ path: '$.content' });
-		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Content is not a valid Sanity text block');
+		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Error applying content transform');
 	});
 });
diff --git a/packages/content/lib/plugins/__tests__/sanity-to-plain.test.js b/packages/content/lib/plugins/__tests__/sanity-to-plain.test.js
index f33a6c99..d70d77c3 100644
--- a/packages/content/lib/plugins/__tests__/sanity-to-plain.test.js
+++ b/packages/content/lib/plugins/__tests__/sanity-to-plain.test.js
@@ -49,7 +49,7 @@ describe('sanityToPlain plugin', () => {
 		ctx.data.insert('test', 'doc1', { content: 'not a block' });
 
 		const plugin = sanityToPlain({ path: '$.content' });
-		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Content is not a valid Sanity text block');
+		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Error applying content transform');
 	});
 
 	it('should throw error for block without children', () => {
@@ -60,7 +60,7 @@ describe('sanityToPlain plugin', () => {
 		ctx.data.insert('test', 'doc1', { content: invalidBlock });
 
 		const plugin = sanityToPlain({ path: '$.content' });
-		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Content is not a valid Sanity text block');
+		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Error applying content transform');
 	});
 
 	it('should throw error for block with invalid children', () => {
@@ -77,7 +77,7 @@ describe('sanityToPlain plugin', () => {
 		ctx.data.insert('test', 'doc1', { content: invalidBlock });
 
 		const plugin = sanityToPlain({ path: '$.content' });
-		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Content is not a valid Sanity text block');
+		expect(() => plugin.hooks.onContentFetchDone(ctx)).toThrow('Error applying content transform');
 	});
 
 	it('should concatenate multiple text spans', () => {
diff --git a/packages/content/lib/sources/__tests__/airtable-source.test.js b/packages/content/lib/sources/__tests__/airtable-source.test.js
index bcca8ebe..fc1648c6 100644
--- a/packages/content/lib/sources/__tests__/airtable-source.test.js
+++ b/packages/content/lib/sources/__tests__/airtable-source.test.js
@@ -4,6 +4,7 @@ import { http, HttpResponse } from 'msw';
 import airtableSource from '../airtable-source.js';
 import { createMockLogger } from '@bluecadet/launchpad-testing/test-utils.js';
 import { DataStore } from '../../utils/data-store.js';
+import { SourceFetchError, SourceParseError } from '../source.js';
 
 const server = setupServer();
 
@@ -206,7 +207,7 @@ describe('airtableSource', () => {
 		const fetchPromises = result._unsafeUnwrap();
 		const data = await fetchPromises[0].dataPromise;
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toBe('fetch');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceFetchError);
 		expect(data._unsafeUnwrapErr().message).toContain('Failed to fetch data from Airtable');
 	});
 
@@ -242,8 +243,10 @@ describe('airtableSource', () => {
 		const data = await fetchPromises[0].dataPromise;
 
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toBe('parse');
-		expect(data._unsafeUnwrapErr().message).toContain('At least 2 columns required');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceParseError);
+		expect(data._unsafeUnwrapErr().message).toContain('Error processing table invalid-table from Airtable');
+		// @ts-expect-error cause is unknown
+		expect(data._unsafeUnwrapErr().cause.message).toContain('At least 2 columns required');
 	});
 
 	it('should handle unauthorized access', async () => {
@@ -269,7 +272,7 @@ describe('airtableSource', () => {
 		const fetchPromises = result._unsafeUnwrap();
 		const data = await fetchPromises[0].dataPromise;
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toBe('fetch');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceFetchError);
 		expect(data._unsafeUnwrapErr().message).toContain('Failed to fetch data from Airtable');
 	});
 });
diff --git a/packages/content/lib/sources/__tests__/contentful-source.test.js b/packages/content/lib/sources/__tests__/contentful-source.test.js
index 09efbf42..d3834a75 100644
--- a/packages/content/lib/sources/__tests__/contentful-source.test.js
+++ b/packages/content/lib/sources/__tests__/contentful-source.test.js
@@ -4,6 +4,7 @@ import { http, HttpResponse } from 'msw';
 import contentfulSource from '../contentful-source.js';
 import { createMockLogger } from '@bluecadet/launchpad-testing/test-utils.js';
 import { DataStore } from '../../utils/data-store.js';
+import { SourceConfigError, SourceFetchError } from '../source.js';
 
 const server = setupServer();
 
@@ -37,7 +38,7 @@ describe('contentfulSource', () => {
 		});
 
 		expect(result).toBeErr();
-		expect(result._unsafeUnwrapErr().type).toBe('config');
+		expect(result._unsafeUnwrapErr()).toBeInstanceOf(SourceConfigError);
 		expect(result._unsafeUnwrapErr().message).toContain('no deliveryToken is provided');
 	});
 
@@ -51,7 +52,7 @@ describe('contentfulSource', () => {
 		});
 
 		expect(result).toBeErr();
-		expect(result._unsafeUnwrapErr().type).toBe('config');
+		expect(result._unsafeUnwrapErr()).toBeInstanceOf(SourceConfigError);
 		expect(result._unsafeUnwrapErr().message).toContain('no previewToken is provided');
 	});
 
@@ -251,7 +252,7 @@ describe('contentfulSource', () => {
 		const fetchPromises = result._unsafeUnwrap();
 		const data = await fetchPromises[0].dataPromise;
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toBe('fetch');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceFetchError);
 		expect(data._unsafeUnwrapErr().message).toContain('Error fetching page');
 	});
 
@@ -280,7 +281,7 @@ describe('contentfulSource', () => {
 		const fetchPromises = result._unsafeUnwrap();
 		const data = await fetchPromises[0].dataPromise;
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toBe('fetch');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceFetchError);
 		expect(data._unsafeUnwrapErr().message).toContain('Invalid content type');
 	});
 
diff --git a/packages/content/lib/sources/__tests__/json-source.test.js b/packages/content/lib/sources/__tests__/json-source.test.js
index 74a20c09..09437430 100644
--- a/packages/content/lib/sources/__tests__/json-source.test.js
+++ b/packages/content/lib/sources/__tests__/json-source.test.js
@@ -4,6 +4,7 @@ import { http, HttpResponse } from 'msw';
 import jsonSource from '../json-source.js';
 import { createMockLogger } from '@bluecadet/launchpad-testing/test-utils.js';
 import { DataStore } from '../../utils/data-store.js';
+import { SourceFetchError, SourceParseError } from '../source.js';
 
 const server = setupServer();
 
@@ -89,7 +90,7 @@ describe('jsonSource', () => {
 
 		const data = await fetchPromises[0].dataPromise;
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toMatch('fetch');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceFetchError);
 	});
 
 	it('should handle parse errors', async () => {
@@ -119,7 +120,7 @@ describe('jsonSource', () => {
 
 		const data = await fetchPromises[0].dataPromise;
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toMatch('parse');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceParseError);
 	});
 
 	it('should respect the maxTimeout option', async () => {
@@ -151,7 +152,11 @@ describe('jsonSource', () => {
     
 		const data = await fetchPromises[0].dataPromise;
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toMatch('fetch');
-		expect(data._unsafeUnwrapErr().message).toContain('Request timed out');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceFetchError);
+		expect(data._unsafeUnwrapErr().message).toContain('Could not fetch json from https://api.example.com/slow');
+		// @ts-expect-error cause is unknown
+		expect(data._unsafeUnwrapErr().cause.message).toContain('Error during request');
+		// @ts-expect-error cause is unknown
+		expect(data._unsafeUnwrapErr().cause.cause.message).toContain('Request timed out');
 	});
 });
diff --git a/packages/content/lib/sources/__tests__/sanity-source.test.js b/packages/content/lib/sources/__tests__/sanity-source.test.js
index f6bbf0c6..964f3ece 100644
--- a/packages/content/lib/sources/__tests__/sanity-source.test.js
+++ b/packages/content/lib/sources/__tests__/sanity-source.test.js
@@ -4,6 +4,7 @@ import { http, HttpResponse } from 'msw';
 import sanitySource from '../sanity-source.js';
 import { createMockLogger } from '@bluecadet/launchpad-testing/test-utils.js';
 import { DataStore } from '../../utils/data-store.js';
+import { SourceConfigError, SourceFetchError } from '../source.js';
 
 const server = setupServer();
 
@@ -35,7 +36,7 @@ describe('sanitySource', () => {
 		});
 
 		expect(result).toBeErr();
-		expect(result._unsafeUnwrapErr().type).toBe('config');
+		expect(result._unsafeUnwrapErr()).toBeInstanceOf(SourceConfigError);
 		expect(result._unsafeUnwrapErr().message).toContain('Missing projectId and/or apiToken');
 	});
 
@@ -203,7 +204,7 @@ describe('sanitySource', () => {
 		const fetchPromises = result._unsafeUnwrap();
 		const data = await fetchPromises[0].dataPromise;
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toBe('fetch');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceFetchError);
 		expect(data._unsafeUnwrapErr().message).toContain('Could not fetch page');
 	});
 
diff --git a/packages/content/lib/sources/__tests__/strapi-source.test.js b/packages/content/lib/sources/__tests__/strapi-source.test.js
index 98df91b4..cab20e59 100644
--- a/packages/content/lib/sources/__tests__/strapi-source.test.js
+++ b/packages/content/lib/sources/__tests__/strapi-source.test.js
@@ -4,6 +4,7 @@ import { http, HttpResponse } from 'msw';
 import strapiSource from '../strapi-source.js';
 import { createMockLogger } from '@bluecadet/launchpad-testing/test-utils.js';
 import { DataStore } from '../../utils/data-store.js';
+import { SourceConfigError, SourceFetchError } from '../source.js';
 
 const server = setupServer();
 
@@ -39,7 +40,7 @@ describe('strapiSource', () => {
 		});
 
 		expect(result).toBeErr();
-		expect(result._unsafeUnwrapErr().type).toBe('config');
+		expect(result._unsafeUnwrapErr()).toBeInstanceOf(SourceConfigError);
 		expect(result._unsafeUnwrapErr().message).toContain('Unsupported strapi version');
 	});
 
@@ -314,8 +315,8 @@ describe('strapiSource', () => {
 
 		expect(source).toBeErr();
 		const sourceValue = source._unsafeUnwrapErr();
-		expect(sourceValue.type).toBe('fetch');
-		expect(sourceValue.message).toContain('401');
+		expect(sourceValue).toBeInstanceOf(SourceFetchError);
+		expect(sourceValue.message).toContain('Could not complete request to get JWT for test@example.com');
 	});
 
 	it('should handle API errors', async () => {
@@ -347,7 +348,7 @@ describe('strapiSource', () => {
 		const data = await fetchPromises[0].dataPromise;
 
 		expect(data).toBeErr();
-		expect(data._unsafeUnwrapErr().type).toBe('fetch');
+		expect(data._unsafeUnwrapErr()).toBeInstanceOf(SourceFetchError);
 		expect(data._unsafeUnwrapErr().message).toContain('Could not fetch page');
 	});
 });
diff --git a/packages/content/lib/sources/airtable-source.js b/packages/content/lib/sources/airtable-source.js
index 26bfff6e..99b71592 100644
--- a/packages/content/lib/sources/airtable-source.js
+++ b/packages/content/lib/sources/airtable-source.js
@@ -1,6 +1,5 @@
 import { err, errAsync, ok, okAsync, Result, ResultAsync } from 'neverthrow';
-import { defineSource } from './source.js';
-import { configError, fetchError, parseError } from './source-errors.js';
+import { defineSource, SourceConfigError, SourceFetchError, SourceMissingDependencyError, SourceParseError } from './source.js';
 
 /**
  * @typedef AirtableOptions
@@ -34,7 +33,7 @@ const AIRTABLE_OPTION_DEFAULTS = {
  * @param {import("airtable").Base} base 
  * @param {string} tableId 
  * @param {string} [defaultView]
- * @returns {ResultAsync<import("airtable").Record<import("airtable").FieldSet>[], import('./source-errors.js').SourceError>}
+ * @returns {ResultAsync<import("airtable").Record<import("airtable").FieldSet>[], SourceFetchError>}
  */
 function fetchData(base, tableId, defaultView) {
 	return ResultAsync.fromPromise(
@@ -70,7 +69,7 @@ function fetchData(base, tableId, defaultView) {
 					}
 				);
 		}),
-		(error) => fetchError(`Failed to fetch data from Airtable: ${error instanceof Error ? error.message : error}`)
+		(error) => new SourceFetchError('Failed to fetch data from Airtable', { cause: error })
 	);
 }
 
@@ -91,7 +90,7 @@ function isBoolStr(value) {
 /**
  * @param {import("airtable").Record<import("airtable").FieldSet>[]} tableData 
  * @param {boolean} isKeyValueTable
- * @returns {Result<unknown, import('./source-errors.js').SourceError>}
+ * @returns {Result<unknown, SourceParseError>}
  */
 function processTableToSimplified(tableData, isKeyValueTable) {
 	if (isKeyValueTable) {
@@ -104,7 +103,7 @@ function processTableToSimplified(tableData, isKeyValueTable) {
 			const fields = row._rawJson.fields;
 
 			if (Object.keys(fields).length < 2) {
-				return err(parseError('At least 2 columns required to map table to a key-value pair'));
+				return err(new SourceParseError('At least 2 columns required to map table to a key-value pair'));
 			}
 
 			const regex = /(.*)\[([0-9]*)\]$/g;
@@ -148,14 +147,14 @@ export default function airtableSource(options) {
 	};
 
 	if (!assembledOptions.apiKey) {
-		return errAsync(configError('apiKey is required'));
+		return errAsync(new SourceConfigError('apiKey is required'));
 	}
 
 	if (!assembledOptions.baseId) {
-		return errAsync(configError('baseId is required'));
+		return errAsync(new SourceConfigError('baseId is required'));
 	}
 
-	return ResultAsync.fromPromise(import('airtable'), () => configError('Could not find module "airtable". Make sure you have installed it.'))
+	return ResultAsync.fromPromise(import('airtable'), () => new SourceMissingDependencyError('Could not find module "airtable". Make sure you have installed it.'))
 		.map(({ default: Airtable }) => {
 			Airtable.configure({
 				endpointUrl: assembledOptions.endpointUrl,
@@ -173,7 +172,7 @@ export default function airtableSource(options) {
 			 * @param {string} tableId 
 			 * @param {boolean} force
 			 * @param {import("@bluecadet/launchpad-utils").Logger} logger
-			 * @returns {ResultAsync<import("airtable").Record<import("airtable").FieldSet>[], import('./source-errors.js').SourceError>}
+			 * @returns {ResultAsync<import("airtable").Record<import("airtable").FieldSet>[], SourceFetchError>}
 			 */
 			function getDataCached(tableId, force = false, logger) {
 				logger.debug(`Fetching ${tableId} from Airtable`);
@@ -208,8 +207,8 @@ export default function airtableSource(options) {
 								const simplifiedTable = processTableToSimplified(data, false);
 
 								if (simplifiedTable.isErr()) {
-									ctx.logger.error(`Error processing ${tableId} from Airtable: ${simplifiedTable.error}`);
-									return err(simplifiedTable.error);
+									ctx.logger.error(`Error processing ${tableId} from Airtable`);
+									return err(new SourceParseError(`Error processing table ${tableId} from Airtable`, { cause: simplifiedTable.error }));
 								}
 
 								return ok([{
@@ -230,8 +229,8 @@ export default function airtableSource(options) {
 								const simplifiedTable = processTableToSimplified(data, true);
 
 								if (simplifiedTable.isErr()) {
-									ctx.logger.error(`Error processing ${tableId} from Airtable: ${simplifiedTable.error}`);
-									return err(simplifiedTable.error);
+									ctx.logger.error(`Error processing ${tableId} from Airtable`);
+									return err(new SourceParseError(`Error processing table ${tableId} from Airtable`, { cause: simplifiedTable.error }));
 								}
 
 								return ok([{
diff --git a/packages/content/lib/sources/contentful-source.js b/packages/content/lib/sources/contentful-source.js
index b97268fc..401a2e62 100644
--- a/packages/content/lib/sources/contentful-source.js
+++ b/packages/content/lib/sources/contentful-source.js
@@ -1,6 +1,5 @@
 import { err, errAsync, ok, ResultAsync } from 'neverthrow';
-import { defineSource } from './source.js';
-import { configError, fetchError } from './source-errors.js';
+import { defineSource, SourceConfigError, SourceFetchError, SourceMissingDependencyError } from './source.js';
 import { fetchPaginated } from '../utils/fetch-paginated.js';
 
 /**
@@ -75,13 +74,13 @@ export default function contentfulSource(options) {
 
 	if (assembled.usePreviewApi) {
 		if (!assembled.previewToken) {
-			return errAsync(configError('usePreviewApi is set to true, but no previewToken is provided'));
+			return errAsync(new SourceConfigError('usePreviewApi is set to true, but no previewToken is provided'));
 		}
 		assembled.host = 'preview.contentful.com';
 		assembled.accessToken = assembled.previewToken;
 	} else {
 		if (!('deliveryToken' in assembled) || !assembled.deliveryToken) {
-			return errAsync(configError('usePreviewApi is set to false, but no deliveryToken is provided'));
+			return errAsync(new SourceConfigError('usePreviewApi is set to false, but no deliveryToken is provided'));
 		}
 
 		assembled.accessToken = assembled.deliveryToken;
@@ -92,7 +91,7 @@ export default function contentfulSource(options) {
 	}
 
 	return ResultAsync
-		.fromPromise(import('contentful'), () => configError('Could not find module "contentful". Make sure you have installed it.'))
+		.fromPromise(import('contentful'), () => new SourceMissingDependencyError('Could not find module "contentful". Make sure you have installed it.'))
 		.map(({ createClient }) => {
 			const client = createClient(assembled);
 
@@ -104,10 +103,10 @@ export default function contentfulSource(options) {
 					/** @type {ReturnType<typeof fetchPaginated<{entries: import('contentful').Entry<unknown>[], assets: import('contentful').Asset[]}>>} */
 					const fetchResult = fetchPaginated({
 						fetchPageFn: (params) => {
-							return ResultAsync.fromPromise(client.getEntries({ ...assembled.searchParams, skip: params.offset, limit: params.limit }), (error) => fetchError(`Error fetching page: ${error instanceof Error ? error.message : error}`))
+							return ResultAsync.fromPromise(client.getEntries({ ...assembled.searchParams, skip: params.offset, limit: params.limit }), (error) => new SourceFetchError(`Error fetching page: ${error instanceof Error ? error.message : error}`))
 								.andThen((rawPage) => {
 									if (rawPage.errors) {
-										return err(fetchError(`Error fetching page: ${rawPage.errors.map(e => e.message).join(', ')}`));
+										return err(new SourceFetchError(`Error fetching page: ${rawPage.errors.map(e => e.message).join(', ')}`));
 									}
 
 									const page = rawPage.toPlainObject();
diff --git a/packages/content/lib/sources/json-source.js b/packages/content/lib/sources/json-source.js
index ba58cdb4..67e2fafd 100644
--- a/packages/content/lib/sources/json-source.js
+++ b/packages/content/lib/sources/json-source.js
@@ -1,8 +1,7 @@
 import chalk from 'chalk';
 import { ok, okAsync } from 'neverthrow';
-import { defineSource } from './source.js';
-import { fetchError, parseError } from './source-errors.js';
-import { safeKy, SafeKyError } from '../utils/safe-ky.js';
+import { defineSource, SourceFetchError, SourceParseError } from './source.js';
+import { safeKy, SafeKyParseError } from '../utils/safe-ky.js';
 
 /**
  * @typedef {object} JsonSourceOptions
@@ -25,10 +24,10 @@ export default function jsonSource({ id, files, maxTimeout = 30_000 }) {
 						id: key,
 						dataPromise: safeKy(url, { timeout: maxTimeout }).json()
 							.mapErr((e) => {
-								if (e instanceof SafeKyError.ParseError) {
-									return parseError(e.message);
+								if (e instanceof SafeKyParseError) {
+									return new SourceParseError(`Could not parse json from ${url}`, { cause: e });
 								}
-								return fetchError(e.message);
+								return new SourceFetchError(`Could not fetch json from ${url}`, { cause: e });
 							})
 							.map(data => {
 								return [{
diff --git a/packages/content/lib/sources/sanity-source.js b/packages/content/lib/sources/sanity-source.js
index 368b7b60..c4f78855 100644
--- a/packages/content/lib/sources/sanity-source.js
+++ b/packages/content/lib/sources/sanity-source.js
@@ -1,7 +1,6 @@
 import { err, errAsync, ok, okAsync, Result, ResultAsync } from 'neverthrow';
-import { defineSource } from './source.js';
+import { defineSource, SourceConfigError, SourceFetchError, SourceMissingDependencyError } from './source.js';
 import { fetchPaginated } from '../utils/fetch-paginated.js';
-import { configError, fetchError } from './source-errors.js';
 
 /**
  * @typedef BaseSanityOptions
@@ -34,7 +33,7 @@ const SANITY_OPTION_DEFAULTS = {
  */
 export default function sanitySource(options) {
 	if (!options.projectId || !options.apiToken) {
-		return errAsync(configError('Missing projectId and/or apiToken'));
+		return errAsync(new SourceConfigError('Missing projectId and/or apiToken'));
 	}
 
 	const assembledOptions = {
@@ -42,7 +41,7 @@ export default function sanitySource(options) {
 		...options
 	};
 
-	return ResultAsync.fromPromise(import('@sanity/client'), () => configError('Could not find "@sanity/client". Make sure you have installed it.'))
+	return ResultAsync.fromPromise(import('@sanity/client'), () => new SourceMissingDependencyError('Could not find "@sanity/client". Make sure you have installed it.'))
 		.map(({ createClient }) => {
 			const sanityClient = createClient({
 				projectId: assembledOptions.projectId,
@@ -96,7 +95,7 @@ export default function sanitySource(options) {
 								dataPromise: fetchPaginated({
 									fetchPageFn: (params) => {
 										const q = `${queryFull}[${params.offset}..${params.offset + params.limit - 1}]`;
-										return ResultAsync.fromPromise(sanityClient.fetch(q), (e) => fetchError(`Could not fetch page with query: '${q}'`));
+										return ResultAsync.fromPromise(sanityClient.fetch(q), (e) => new SourceFetchError(`Could not fetch page with query: '${q}'`, { cause: e }));
 									},
 									limit: assembledOptions.limit,
 									logger: ctx.logger
@@ -108,7 +107,7 @@ export default function sanitySource(options) {
 								dataPromise: fetchPaginated({
 									fetchPageFn: (params) => {
 										const q = `${query.query}[${params.offset}..${params.offset + params.limit - 1}]`;
-										return ResultAsync.fromPromise(sanityClient.fetch(q), (e) => fetchError(`Could not fetch page with query: '${q}'`));
+										return ResultAsync.fromPromise(sanityClient.fetch(q), (e) => new SourceFetchError(`Could not fetch page with query: '${q}'`, { cause: e }));
 									},
 									limit: assembledOptions.limit,
 									logger: ctx.logger
@@ -116,7 +115,7 @@ export default function sanitySource(options) {
 							});
 						} else {
 							ctx.logger.error(`Invalid query: ${query}`);
-							return err(configError(`Invalid query: ${query}`));
+							return err(new SourceFetchError(`Invalid query: ${query}`));
 						}
 					}
 
diff --git a/packages/content/lib/sources/source-errors.js b/packages/content/lib/sources/source-errors.js
deleted file mode 100644
index 02366276..00000000
--- a/packages/content/lib/sources/source-errors.js
+++ /dev/null
@@ -1,27 +0,0 @@
-/**
- * @param {string} [message]
- */
-export const fetchError = (message) => ({
-	type: /** @type {const} */ ('fetch'),
-	message
-});
-
-/**
- * @param {string} [message]
- */
-export const parseError = (message) => ({
-	type: /** @type {const} */ ('parse'),
-	message
-});
-
-/**
- * @param {string} [message]
- */
-export const configError = (message) => ({
-	type: /** @type {const} */ ('config'),
-	message
-});
-
-/**
- * @typedef {ReturnType<typeof fetchError> | ReturnType<typeof parseError> | ReturnType<typeof configError>} SourceError
- */
diff --git a/packages/content/lib/sources/source.js b/packages/content/lib/sources/source.js
index 7b21621c..6d111d88 100644
--- a/packages/content/lib/sources/source.js
+++ b/packages/content/lib/sources/source.js
@@ -11,7 +11,7 @@
  * @template [T=unknown]
  * @typedef {object} SourceFetchPromise
  * @prop {string} id Id of the fetch request, used for logging and debugging
- * @prop {import('neverthrow').ResultAsync<Array<SourceFetchResultDocument<T>>, import('./source-errors.js').SourceError>} dataPromise Promise that resolves to an array of documents
+ * @prop {import('neverthrow').ResultAsync<Array<SourceFetchResultDocument<T>>, SourceFetchError | SourceParseError>} dataPromise Promise that resolves to an array of documents
  */
 
 /**
@@ -24,13 +24,13 @@
  * @template [T=unknown]
  * @typedef {object} ContentSource
  * @prop {string} id Id of the source. This will be the 'namespace' for the documents fetched from this source.
- * @prop {(ctx: FetchContext) => import('neverthrow').Result<Array<SourceFetchPromise<T>>, import('./source-errors.js').SourceError>} fetch
+ * @prop {(ctx: FetchContext) => import('neverthrow').Result<Array<SourceFetchPromise<T>>, SourceFetchError | SourceParseError>} fetch
  */
 
 /**
  * @template O
  * @template [T=unknown]
- * @typedef {(options: O) => import('neverthrow').ResultAsync<ContentSource<T>, import('./source-errors.js').SourceError>} ContentSourceBuilder
+ * @typedef {(options: O) => import('neverthrow').ResultAsync<ContentSource<T>, SourceConfigError | SourceMissingDependencyError>} ContentSourceBuilder
  */
 
 /**
@@ -42,3 +42,51 @@
 export function defineSource(src) {
 	return src;
 }
+
+export class SourceFetchError extends Error {
+	/**
+	 * @param {string} message
+	 * @param {object} [options]
+	 * @param {unknown} [options.cause]
+	 */
+	constructor(message, { cause } = {}) {
+		super(message, { cause });
+		this.name = 'SourceFetchError';
+	}
+}
+
+export class SourceConfigError extends Error {
+	/**
+	 * @param {string} message
+	 * @param {object} [options]
+	 * @param {unknown} [options.cause]
+	 */
+	constructor(message, { cause } = {}) {
+		super(message, { cause });
+		this.name = 'SourceConfigError';
+	}
+}
+
+export class SourceParseError extends Error {
+	/**
+	 * @param {string} message
+	 * @param {object} [options]
+	 * @param {unknown} [options.cause]
+	 */
+	constructor(message, { cause } = {}) {
+		super(message, { cause });
+		this.name = 'SourceParseError';
+	}
+}
+
+export class SourceMissingDependencyError extends Error {
+	/**
+	 * @param {string} message
+	 * @param {object} [options]
+	 * @param {unknown} [options.cause]
+	 */
+	constructor(message, { cause } = {}) {
+		super(message, { cause });
+		this.name = 'SourceMissingDependencyError';
+	}
+}
diff --git a/packages/content/lib/sources/strapi-source.js b/packages/content/lib/sources/strapi-source.js
index 91668d99..7703356c 100644
--- a/packages/content/lib/sources/strapi-source.js
+++ b/packages/content/lib/sources/strapi-source.js
@@ -1,7 +1,6 @@
 import qs from 'qs';
-import { defineSource } from './source.js';
+import { defineSource, SourceConfigError, SourceFetchError } from './source.js';
 import { errAsync, ok, okAsync } from 'neverthrow';
-import { configError, fetchError } from './source-errors.js';
 import { fetchPaginated } from '../utils/fetch-paginated.js';
 import { safeKy } from '../utils/safe-ky.js';
 
@@ -252,7 +251,7 @@ class StrapiV3 extends StrapiVersionUtils {
  * @param {string} baseUrl
  * @param {string} identifier
  * @param {string} password
- * @returns {import('neverthrow').ResultAsync<string, import('./source-errors.js').SourceError>} The JSON web token generated by Strapi
+ * @returns {import('neverthrow').ResultAsync<string, SourceFetchError>} The JSON web token generated by Strapi
  */
 function getJwt(baseUrl, identifier, password) {
 	const url = new URL('/auth/local', baseUrl);
@@ -262,7 +261,7 @@ function getJwt(baseUrl, identifier, password) {
 		json: { identifier, password }
 	}).json()
 		.map(response => response.jwt)
-		.mapErr(e => fetchError(`Could not complete request to get JWT for ${identifier}: ${e.message}`));
+		.mapErr(e => new SourceFetchError(`Could not complete request to get JWT for ${identifier}`, { cause: e }));
 }
 
 /**
@@ -286,7 +285,7 @@ export default function strapiSource(options) {
 	};
 
 	if (assembledOptions.version !== '4' && assembledOptions.version !== '3') {
-		return errAsync(configError(`Unsupported strapi version '${assembledOptions.version}'`));
+		return errAsync(new SourceConfigError(`Unsupported strapi version '${assembledOptions.version}'`));
 	}
 
 	return getToken(assembledOptions).map(token =>
@@ -339,7 +338,7 @@ export default function strapiSource(options) {
 
 										return transformedContent;
 									})
-									.mapErr(e => fetchError(`Could not fetch page ${pageNum} of ${parsedQuery.contentType}: ${e.message}`));
+									.mapErr(e => new SourceFetchError(`Could not fetch page ${pageNum} of ${parsedQuery.contentType}`, { cause: e }));
 							},
 							limit: assembledOptions.limit,
 							logger: ctx.logger
diff --git a/packages/content/lib/utils/__tests__/content-transform-utils.test.js b/packages/content/lib/utils/__tests__/content-transform-utils.test.js
index f1f2887f..a8e6053f 100644
--- a/packages/content/lib/utils/__tests__/content-transform-utils.test.js
+++ b/packages/content/lib/utils/__tests__/content-transform-utils.test.js
@@ -65,7 +65,7 @@ describe('content-transform-utils', () => {
 				transformFn,
 				logger,
 				keys: ['test']
-			})).toThrow(/Transform error/);
+			})).toThrow(/Error applying content transform/);
 		});
 	});
 
diff --git a/packages/content/lib/utils/__tests__/data-store.test.js b/packages/content/lib/utils/__tests__/data-store.test.js
index 54efec09..c5a08321 100644
--- a/packages/content/lib/utils/__tests__/data-store.test.js
+++ b/packages/content/lib/utils/__tests__/data-store.test.js
@@ -1,5 +1,5 @@
 import { describe, it, expect } from 'vitest';
-import { DataStore, Document } from '../data-store.js';
+import { DataStore, DataStoreError, Document } from '../data-store.js';
 
 describe('Document', () => {
 	it('should create a document with id and data', () => {
@@ -27,7 +27,11 @@ describe('Document', () => {
 			throw new Error('Test error');
 		});
 		expect(result).toBeErr();
-		expect(result._unsafeUnwrapErr().message).toBe('Test error');
+		expect(result._unsafeUnwrapErr()).toBeInstanceOf(DataStoreError);
+		expect(result._unsafeUnwrapErr().message).toBe('Error applying content transform');
+		expect(result._unsafeUnwrapErr().cause).toBeInstanceOf(Error);
+		// @ts-expect-error cause is unknown
+		expect(result._unsafeUnwrapErr().cause.message).toBe('Test error');
 	});
 });
 
@@ -43,7 +47,8 @@ describe('DataStore', () => {
 		store.createNamespace('test-namespace');
 		const result = store.createNamespace('test-namespace');
 		expect(result).toBeErr();
-		expect(result._unsafeUnwrapErr()).toBe('Namespace test-namespace already exists in data store');
+		expect(result._unsafeUnwrapErr()).toBeInstanceOf(DataStoreError);
+		expect(result._unsafeUnwrapErr().message).toBe('Namespace test-namespace already exists in data store');
 	});
 
 	it('should insert a document into a namespace', () => {
@@ -59,7 +64,8 @@ describe('DataStore', () => {
 		store.insert('test-namespace', 'test-doc', { content: 'test content' });
 		const result = store.insert('test-namespace', 'test-doc', { content: 'duplicate content' });
 		expect(result).toBeErr();
-		expect(result._unsafeUnwrapErr()).toBe('Document test-doc already exists in namespace test-namespace');
+		expect(result._unsafeUnwrapErr()).toBeInstanceOf(DataStoreError);
+		expect(result._unsafeUnwrapErr().message).toBe('Document test-doc already exists in namespace test-namespace');
 	});
 
 	it('should get a document from a namespace', () => {
@@ -76,7 +82,8 @@ describe('DataStore', () => {
 		store.createNamespace('test-namespace');
 		const result = store.get('test-namespace', 'non-existent-doc');
 		expect(result).toBeErr();
-		expect(result._unsafeUnwrapErr()).toBe('Document non-existent-doc not found in namespace test-namespace');
+		expect(result._unsafeUnwrapErr()).toBeInstanceOf(DataStoreError);
+		expect(result._unsafeUnwrapErr().message).toBe('Document non-existent-doc not found in namespace test-namespace');
 	});
 
 	it('should delete a document from a namespace', () => {
diff --git a/packages/content/lib/utils/__tests__/fetch-paginated.test.js b/packages/content/lib/utils/__tests__/fetch-paginated.test.js
index 6eb6c27a..92b02793 100644
--- a/packages/content/lib/utils/__tests__/fetch-paginated.test.js
+++ b/packages/content/lib/utils/__tests__/fetch-paginated.test.js
@@ -4,7 +4,7 @@ import { http, HttpResponse } from 'msw';
 import { fetchPaginated } from '../fetch-paginated.js';
 import { ResultAsync } from 'neverthrow';
 import { createMockLogger } from '@bluecadet/launchpad-testing/test-utils.js';
-import { fetchError } from '../../sources/source-errors.js';
+import { SourceFetchError } from '../../sources/source.js';
 
 const server = setupServer();
 
@@ -45,7 +45,7 @@ describe('fetchPaginated', () => {
 			fetchPageFn: ({ limit, offset }) =>
 				ResultAsync.fromPromise(
 					fetch(`http://example.com/api?limit=${limit}&offset=${offset}`).then(res => res.json()),
-					() => fetchError('Failed to fetch')
+					(e) => new SourceFetchError('Failed to fetch', { cause: e })
 				)
 		});
 
@@ -74,7 +74,7 @@ describe('fetchPaginated', () => {
 			fetchPageFn: ({ limit, offset }) =>
 				ResultAsync.fromPromise(
 					fetch(`http://example.com/api?limit=${limit}&offset=${offset}`).then(res => res.json()),
-					() => fetchError('Failed to fetch')
+					(e) => new SourceFetchError('Failed to fetch', { cause: e })
 				)
 		});
 
@@ -100,13 +100,13 @@ describe('fetchPaginated', () => {
 						if (!res.ok) throw new Error('API error');
 						return res.json();
 					}),
-					() => fetchError('Failed to fetch')
+					(e) => new SourceFetchError('Failed to fetch', { cause: e })
 				)
 		});
 
 		expect(result).toBeErr();
 		const error = result._unsafeUnwrapErr();
-		expect(error.type).toBe('fetch');
+		expect(error).toBeInstanceOf(SourceFetchError);
 		expect(error.message).toBe('Failed to fetch');
 	});
 
@@ -129,7 +129,7 @@ describe('fetchPaginated', () => {
 			fetchPageFn: ({ limit, offset }) =>
 				ResultAsync.fromPromise(
 					fetch(`http://example.com/api?limit=${limit}&offset=${offset}`).then(res => res.json()),
-					() => fetchError('Failed to fetch')
+					(e) => new SourceFetchError('Failed to fetch', { cause: e })
 				)
 		});
 
diff --git a/packages/content/lib/utils/__tests__/file-utils.test.js b/packages/content/lib/utils/__tests__/file-utils.test.js
index 92ce7f82..ef19314b 100644
--- a/packages/content/lib/utils/__tests__/file-utils.test.js
+++ b/packages/content/lib/utils/__tests__/file-utils.test.js
@@ -55,7 +55,7 @@ describe('FileUtils', () => {
 				'/test-dir': {
 					'file1.txt': 'content',
 					'file2.json': '{}',
-					'subdir': {
+					subdir: {
 						'file3.csv': 'data'
 					}
 				}
@@ -71,7 +71,7 @@ describe('FileUtils', () => {
 		it('should exclude specified files', async () => {
 			const result = await FileUtils.removeFilesFromDir('/test-dir', ['*.json', '**/*.csv']);
 			expect(result).toBeOk();
-      expect(vol.readdirSync('/test-dir', {recursive: true})).toEqual(expect.arrayContaining(['file2.json', 'subdir/file3.csv', 'subdir']));
+			expect(vol.readdirSync('/test-dir', { recursive: true })).toEqual(expect.arrayContaining(['file2.json', 'subdir/file3.csv', 'subdir']));
 		});
 	});
 
diff --git a/packages/content/lib/utils/__tests__/markdown-it-italic-bold.test.js b/packages/content/lib/utils/__tests__/markdown-it-italic-bold.test.js
index 43e9df11..9be85869 100644
--- a/packages/content/lib/utils/__tests__/markdown-it-italic-bold.test.js
+++ b/packages/content/lib/utils/__tests__/markdown-it-italic-bold.test.js
@@ -1,47 +1,47 @@
-import { describe, it, expect } from 'vitest'
-import MarkdownIt from 'markdown-it'
-import italicBoldPlugin from '../markdown-it-italic-bold.js'
+import { describe, it, expect } from 'vitest';
+import MarkdownIt from 'markdown-it';
+import italicBoldPlugin from '../markdown-it-italic-bold.js';
 
 describe('markdown-it-italic-bold plugin', () => {
-  it('should convert * to <i> for italics', () => {
-    const md = new MarkdownIt()
-    md.use(italicBoldPlugin)
-    const result = md.render('*italic*')
-    expect(result.trim()).toBe('<p><i>italic</i></p>')
-  })
+	it('should convert * to <i> for italics', () => {
+		const md = new MarkdownIt();
+		md.use(italicBoldPlugin);
+		const result = md.render('*italic*');
+		expect(result.trim()).toBe('<p><i>italic</i></p>');
+	});
 
-  it('should convert _ to <i> for italics', () => {
-    const md = new MarkdownIt()
-    md.use(italicBoldPlugin)
-    const result = md.render('_italic_')
-    expect(result.trim()).toBe('<p><i>italic</i></p>')
-  })
+	it('should convert _ to <i> for italics', () => {
+		const md = new MarkdownIt();
+		md.use(italicBoldPlugin);
+		const result = md.render('_italic_');
+		expect(result.trim()).toBe('<p><i>italic</i></p>');
+	});
 
-  it('should convert ** to <b> for bold', () => {
-    const md = new MarkdownIt()
-    md.use(italicBoldPlugin)
-    const result = md.render('**bold**')
-    expect(result.trim()).toBe('<p><b>bold</b></p>')
-  })
+	it('should convert ** to <b> for bold', () => {
+		const md = new MarkdownIt();
+		md.use(italicBoldPlugin);
+		const result = md.render('**bold**');
+		expect(result.trim()).toBe('<p><b>bold</b></p>');
+	});
 
-  it('should convert __ to <b> for bold', () => {
-    const md = new MarkdownIt()
-    md.use(italicBoldPlugin)
-    const result = md.render('__bold__')
-    expect(result.trim()).toBe('<p><b>bold</b></p>')
-  })
+	it('should convert __ to <b> for bold', () => {
+		const md = new MarkdownIt();
+		md.use(italicBoldPlugin);
+		const result = md.render('__bold__');
+		expect(result.trim()).toBe('<p><b>bold</b></p>');
+	});
 
-  it('should handle mixed italic and bold', () => {
-    const md = new MarkdownIt()
-    md.use(italicBoldPlugin)
-    const result = md.render('*italic* and **bold**')
-    expect(result.trim()).toBe('<p><i>italic</i> and <b>bold</b></p>')
-  })
+	it('should handle mixed italic and bold', () => {
+		const md = new MarkdownIt();
+		md.use(italicBoldPlugin);
+		const result = md.render('*italic* and **bold**');
+		expect(result.trim()).toBe('<p><i>italic</i> and <b>bold</b></p>');
+	});
 
-  it('should handle nested italic and bold', () => {
-    const md = new MarkdownIt()
-    md.use(italicBoldPlugin)
-    const result = md.render('**bold *italic* text**')
-    expect(result.trim()).toBe('<p><b>bold <i>italic</i> text</b></p>')
-  })
-})
+	it('should handle nested italic and bold', () => {
+		const md = new MarkdownIt();
+		md.use(italicBoldPlugin);
+		const result = md.render('**bold *italic* text**');
+		expect(result.trim()).toBe('<p><b>bold <i>italic</i> text</b></p>');
+	});
+});
diff --git a/packages/content/lib/utils/__tests__/safe-ky.test.js b/packages/content/lib/utils/__tests__/safe-ky.test.js
index 2d16b0a6..d65d027f 100644
--- a/packages/content/lib/utils/__tests__/safe-ky.test.js
+++ b/packages/content/lib/utils/__tests__/safe-ky.test.js
@@ -1,7 +1,7 @@
 import { describe, it, expect, beforeAll, afterAll, afterEach, vi } from 'vitest';
 import { setupServer } from 'msw/node';
 import { http, HttpResponse } from 'msw';
-import { safeKy, SafeKyError } from '../safe-ky.js';
+import { safeKy, SafeKyFetchError, SafeKyParseError } from '../safe-ky.js';
 import { ok } from 'neverthrow';
 
 const server = setupServer();
@@ -53,7 +53,7 @@ describe('safeKy', () => {
 
 		const jsonResult = await result.json();
 		expect(jsonResult).toBeErr();
-		expect(jsonResult._unsafeUnwrapErr()).toBeInstanceOf(SafeKyError.FetchError);
+		expect(jsonResult._unsafeUnwrapErr()).toBeInstanceOf(SafeKyFetchError);
 		expect(jsonResult._unsafeUnwrapErr().message).toContain('Error during request');
 	});
 
@@ -70,7 +70,7 @@ describe('safeKy', () => {
 
 		const jsonResult = await result.json();
 		expect(jsonResult).toBeErr();
-		expect(jsonResult._unsafeUnwrapErr()).toBeInstanceOf(SafeKyError.ParseError);
+		expect(jsonResult._unsafeUnwrapErr()).toBeInstanceOf(SafeKyParseError);
 		expect(jsonResult._unsafeUnwrapErr().message).toContain('Error parsing JSON');
 	});
 });
diff --git a/packages/content/lib/utils/content-transform-utils.js b/packages/content/lib/utils/content-transform-utils.js
index dbc822dd..be59e6f4 100644
--- a/packages/content/lib/utils/content-transform-utils.js
+++ b/packages/content/lib/utils/content-transform-utils.js
@@ -1,10 +1,10 @@
 import chalk from 'chalk';
-import { err, ok, Result } from 'neverthrow';
+import { ok } from 'neverthrow';
 
 /**
  * @param {import('./data-store.js').DataStore} dataStore
  * @param {import('./data-store.js').DataKeys } [ids] A list containing a combination of namespace ids, and namespace/document id tuples. If not provided, all documents will be matched.
- * @returns {import('neverthrow').Result<Iterable<import('./data-store.js').Document>, string>}
+ * @returns {import('neverthrow').Result<Iterable<import('./data-store.js').Document>, Error>}
  */
 export function getMatchingDocuments(dataStore, ids) {
 	if (!ids) {
@@ -29,7 +29,7 @@ export function applyTransformToFiles({ dataStore, path, transformFn, logger, ke
 	const matchingDocuments = getMatchingDocuments(dataStore, keys);
 
 	if (matchingDocuments.isErr()) {
-		throw new Error(matchingDocuments.error);
+		throw matchingDocuments.error;
 	}
 
 	for (const document of matchingDocuments.value) {
diff --git a/packages/content/lib/utils/data-store.js b/packages/content/lib/utils/data-store.js
index a75b9124..6e22a830 100644
--- a/packages/content/lib/utils/data-store.js
+++ b/packages/content/lib/utils/data-store.js
@@ -1,6 +1,16 @@
 import { JSONPath } from 'jsonpath-plus';
 import { ok, err, Result } from 'neverthrow';
 
+export class DataStoreError extends Error {
+	/**
+	 * @param {ConstructorParameters<typeof Error>} args
+	 */
+	constructor(...args) {
+		super(...args);
+		this.name = 'DataStoreError';
+	}
+}
+
 /**
  * @typedef {Array<string | [string] | [string, string]>} DataKeys A list containing a combination of namespace ids, and namespace/document id tuples.
  */
@@ -54,7 +64,7 @@ export class Document {
    * Apply a function to each element matching the given jsonpath.
    * @param {string} pathExpression
    * @param {(x: unknown) => unknown} fn
-   * @returns {Result<void, Error>}
+   * @returns {Result<void, DataStoreError>}
    */
 	apply(pathExpression, fn) {
 		// catch errrors thrown from JSONPath OR the fn callback
@@ -70,11 +80,7 @@ export class Document {
 
 			return ok(undefined);
 		} catch (e) {
-			if (e instanceof Error) {
-				return err(e);
-			}
-
-			return err(new Error(String(e)));
+			return err(new DataStoreError('Error applying content transform', { cause: e }));
 		}
 	}
 }
@@ -107,11 +113,11 @@ class Namespace {
 	/**
    * @param {string} id
    * @param {unknown} data
-   * @returns {Result<void, string>}
+   * @returns {Result<void, DataStoreError>}
    */
 	insert(id, data) {
 		if (this.#documents.has(id)) {
-			return err(`Document ${id} already exists in namespace ${this.#id}`);
+			return err(new DataStoreError(`Document ${id} already exists in namespace ${this.#id}`));
 		}
 
 		this.#documents.set(id, new Document(id, data));
@@ -120,12 +126,12 @@ class Namespace {
 
 	/**
    * @param {string} id
-   * @returns {Result<Document, string>}
+   * @returns {Result<Document, DataStoreError>}
    */
 	get(id) {
 		const document = this.#documents.get(id);
 		if (!document) {
-			return err(`Document ${id} not found in namespace ${this.#id}`);
+			return err(new DataStoreError(`Document ${id} not found in namespace ${this.#id}`));
 		}
 
 		return ok(document);
@@ -137,7 +143,7 @@ class Namespace {
 
 	/**
    * @param {string} id
-   * @returns {Result<void, string>}
+   * @returns {Result<void, DataStoreError>}
    */
 	delete(id) {
 		this.#documents.delete(id);
@@ -147,7 +153,7 @@ class Namespace {
 	/**
    * @param {string} id
    * @param {unknown} data
-   * @returns {Result<void, string>}
+   * @returns {Result<void, DataStoreError>}
    */
 	update(id, data) {
 		this.#documents.set(id, new Document(id, data));
@@ -168,12 +174,12 @@ export class DataStore {
 	/**
    * @param {string} namespaceId
    * @param {string} documentId
-   * @returns {Result<Document, string>}
+   * @returns {Result<Document, DataStoreError>}
    */
 	get(namespaceId, documentId) {
 		const namespace = this.#namespaces.get(namespaceId);
 		if (!namespace) {
-			return err(`Namespace ${namespaceId} not found in data store`);
+			return err(new DataStoreError(`Namespace ${namespaceId} not found in data store`));
 		}
 
 		return namespace.get(documentId);
@@ -181,12 +187,12 @@ export class DataStore {
 
 	/**
    * @param {string} namespaceId
-   * @returns {Result<Iterable<Document>, string>}
+   * @returns {Result<Iterable<Document>, DataStoreError>}
    */
 	namespace(namespaceId) {
 		const namespace = this.#namespaces.get(namespaceId);
 		if (!namespace) {
-			return err(`Namespace ${namespaceId} not found in data store`);
+			return err(new DataStoreError(`Namespace ${namespaceId} not found in data store`));
 		}
 
 		return ok(namespace.documents());
@@ -207,11 +213,11 @@ export class DataStore {
 
 	/**
    * @param {string} namespaceId
-   * @returns {Result<void, string>}
+   * @returns {Result<void, DataStoreError>}
    */
 	createNamespace(namespaceId) {
 		if (this.#namespaces.has(namespaceId)) {
-			return err(`Namespace ${namespaceId} already exists in data store`);
+			return err(new DataStoreError(`Namespace ${namespaceId} already exists in data store`));
 		}
 
 		this.#namespaces.set(namespaceId, new Namespace(namespaceId));
@@ -221,7 +227,7 @@ export class DataStore {
 	/**
    * @param {string} namespaceId
    * @param {Map<string, unknown>} map
-   * @returns {Result<void, string>}
+   * @returns {Result<void, DataStoreError>}
    */
 	createNamespaceFromMap(namespaceId, map) {
 		const namespaceResult = this.createNamespace(namespaceId);
@@ -244,12 +250,12 @@ export class DataStore {
    * @param {string} namespaceId
    * @param {string} documentId
    * @param {unknown} data
-   * @returns {Result<void, string>}
+   * @returns {Result<void, DataStoreError>}
    */
 	insert(namespaceId, documentId, data) {
 		const namespace = this.#namespaces.get(namespaceId);
 		if (!namespace) {
-			return err(`Namespace ${namespaceId} not found in data store`);
+			return err(new DataStoreError(`Namespace ${namespaceId} not found in data store`));
 		}
 
 		return namespace.insert(documentId, data);
@@ -258,12 +264,12 @@ export class DataStore {
 	/**
    * @param {string} namespaceId
    * @param {string} documentId
-   * @returns {Result<void, string>}
+   * @returns {Result<void, DataStoreError>}
    */
 	delete(namespaceId, documentId) {
 		const namespace = this.#namespaces.get(namespaceId);
 		if (!namespace) {
-			return err(`Namespace ${namespaceId} not found in data store`);
+			return err(new DataStoreError(`Namespace ${namespaceId} not found in data store`));
 		}
 
 		return namespace.delete(documentId);
@@ -272,7 +278,7 @@ export class DataStore {
 	/**
 	 * Get lists of documents matching the passed DataKeys grouped by namespace.
 	 * @param {DataKeys} [ids] A list containing a combination of namespace ids, and namespace/document id tuples. If not provided, all documents will be matched.
-	 * @returns {Result<Array<{namespaceId: string; documents: Array<Document> }>, string>}
+	 * @returns {Result<Array<{namespaceId: string; documents: Array<Document> }>, DataStoreError>}
 	 */
 	filter(ids) {
 		if (!ids) {
diff --git a/packages/content/lib/utils/fetch-paginated.js b/packages/content/lib/utils/fetch-paginated.js
index 9baf6b87..4fe140e3 100644
--- a/packages/content/lib/utils/fetch-paginated.js
+++ b/packages/content/lib/utils/fetch-paginated.js
@@ -1,19 +1,19 @@
 import { ResultAsync, err, errAsync, ok, okAsync } from 'neverthrow';
-import { fetchError } from '../sources/source-errors.js';
+import { SourceFetchError } from '../sources/source.js';
 
 /**
  * @template {unknown} T
  * @typedef FetchPaginatedOptions
  * @property {number} limit The number of items to fetch per page
  * @property {number} [maxFetchCount] The maximum number of pages to fetch. If this is reached, the fetch will be terminated early.
- * @property {(params: {limit: number, offset: number}) => ResultAsync<T | null, import('../sources/source-errors.js').SourceError>} fetchPageFn A function that takes a params object and returns a ResultAsync of an array of T. To indicate the end of pagination, return an empty array, or null.
+ * @property {(params: {limit: number, offset: number}) => ResultAsync<T | null, SourceFetchError>} fetchPageFn A function that takes a params object and returns a ResultAsync of an array of T. To indicate the end of pagination, return an empty array, or null.
  * @property {import('@bluecadet/launchpad-utils').Logger} logger A logger instance
  */
 
 /**
  * @template {unknown} T
  * @template {unknown} M
- * @typedef {ResultAsync<M extends undefined ? {pages: Array<T>} : {pages: Array<T>, meta: M}, import('../sources/source-errors.js').SourceError>} FetchPaginatedResult
+ * @typedef {ResultAsync<M extends undefined ? {pages: Array<T>} : {pages: Array<T>, meta: M}, SourceFetchError>} FetchPaginatedResult
  */
 
 /**
@@ -29,7 +29,7 @@ export function fetchPaginated({ fetchPageFn, limit, logger, maxFetchCount = 100
 	let page = 0;
 
 	/**
-	 * @returns {ResultAsync<T | null, import('../sources/source-errors.js').SourceError>}
+	 * @returns {ResultAsync<T | null, SourceFetchError>}
 	 */
 	const fetchNextPage = () => {
 		logger.debug(`Fetching page ${page}`);
@@ -42,7 +42,7 @@ export function fetchPaginated({ fetchPageFn, limit, logger, maxFetchCount = 100
 					page++;
 
 					if (page >= maxFetchCount) {
-						return errAsync(fetchError('Maximum fetch count reached. This is likely a bug.'));
+						return errAsync(new SourceFetchError('Maximum fetch count reached. This is likely a bug. Make sure your fetchPageFn ret'));
 					}
 
 					return fetchNextPage();
diff --git a/packages/content/lib/utils/file-utils.js b/packages/content/lib/utils/file-utils.js
index 629381c2..be281345 100644
--- a/packages/content/lib/utils/file-utils.js
+++ b/packages/content/lib/utils/file-utils.js
@@ -3,6 +3,16 @@ import fs from 'fs';
 import { glob } from 'glob';
 import { okAsync, ResultAsync } from 'neverthrow';
 
+export class FileUtilsError extends Error {
+	/**
+	 * @param {ConstructorParameters<typeof Error>} args
+	 */
+	constructor(...args) {
+		super(...args);
+		this.name = 'FileUtilsError';
+	}
+}
+
 /**
  * @param {string} dirPath
  */
@@ -15,7 +25,7 @@ export function isDir(dirPath) {
  * @param {unknown} json 
  * @param {string} filePath 
  * @param {boolean} appendJsonExtension
- * @returns {ResultAsync<void, string>}
+ * @returns {ResultAsync<void, FileUtilsError>}
  */
 export function saveJson(json, filePath, appendJsonExtension = true) {
 	if (appendJsonExtension && !(filePath + '').endsWith('.json')) {
@@ -24,14 +34,14 @@ export function saveJson(json, filePath, appendJsonExtension = true) {
 	const jsonStr = (typeof json === 'string') ? json : JSON.stringify(json, null, 0);
 
 	return ensureDir(path.dirname(filePath))
-		.andThen(() => ResultAsync.fromPromise(fs.promises.writeFile(filePath, jsonStr), (_) => `Could not write file ${filePath}`));
+		.andThen(() => ResultAsync.fromPromise(fs.promises.writeFile(filePath, jsonStr), (e) => new FileUtilsError(`Could not write file ${filePath}`, { cause: e })));
 }
     
 /**
  * Removes all files and subdirectories of `dirPath`, except for `exclude`.
  * @param {string} dirPath Any absolute directory path
  * @param {string[]} [exclude] Array of glob patterns to exclude (e.g. ['*.json', '** /*.csv', 'my-important-folder/**']). Glob patterns are relative to `dirPath`.
- * @returns {ResultAsync<void, string>}
+ * @returns {ResultAsync<void, FileUtilsError>}
  */
 export function removeFilesFromDir(dirPath, exclude = []) {
 	return ResultAsync.fromPromise(
@@ -40,13 +50,13 @@ export function removeFilesFromDir(dirPath, exclude = []) {
 			dot: true,
 			nodir: true // Only match files, not directories
 		}),
-		(error) => `Failed to glob directory ${dirPath}: ${error}`
+		(error) => new FileUtilsError(`Failed to glob directory ${dirPath}`, { cause: error })
 	)
 		.andThen((files) => {
 			const deletePromises = files.map((file) =>
 				ResultAsync.fromPromise(
 					fs.promises.unlink(file), // Use unlink instead of rm to only remove files
-					(error) => `Failed to remove ${file}: ${error}`
+					(error) => new FileUtilsError(`Failed to remove ${file}`, { cause: error })
 				)
 			);
 			return ResultAsync.combine(deletePromises);
@@ -59,7 +69,7 @@ export function removeFilesFromDir(dirPath, exclude = []) {
 					dot: true,
 					nodir: false // Match directories this time
 				}),
-				(error) => `Failed to glob directories in ${dirPath}: ${error}`
+				(error) => new FileUtilsError(`Failed to glob directories in ${dirPath}`, { cause: error })
 			)
 				.andThen((dirs) => {
 					// Sort directories by depth (deepest first)
@@ -68,7 +78,7 @@ export function removeFilesFromDir(dirPath, exclude = []) {
 					const removeDirPromises = dirs.map((dir) =>
 						ResultAsync.fromPromise(
 							fs.promises.rmdir(dir),
-							(error) => `Failed to remove directory ${dir}: ${error}`
+							(error) => new FileUtilsError(`Failed to remove directory ${dir}`, { cause: error })
 						).orElse(() => okAsync(undefined)) // Ignore errors if directory is not empty
 					);
 					return ResultAsync.combine(removeDirPromises);
@@ -95,7 +105,7 @@ export function pad(num, size) {
     
 /**
  * @param {string} dirPath
- * @returns {ResultAsync<void, string>}
+ * @returns {ResultAsync<void, FileUtilsError>}
  */
 export function removeDirIfEmpty(dirPath) {
 	if (!isDir(dirPath)) {
@@ -111,47 +121,47 @@ export function removeDirIfEmpty(dirPath) {
 	
 /**
  * @param {string} dirPath
- * @returns {ResultAsync<boolean, string>}
+ * @returns {ResultAsync<boolean, FileUtilsError>}
  */
 export function isDirEmpty(dirPath) {
 	// @see https://stackoverflow.com/a/39218759/782899
-	return ResultAsync.fromPromise(fs.promises.readdir(dirPath), (_) => `Could not read dir ${dirPath}`)
+	return ResultAsync.fromPromise(fs.promises.readdir(dirPath), (e) => new FileUtilsError(`Could not read dir ${dirPath}`, { cause: e }))
 		.andThen(files => okAsync(files.length === 0));
 }
 
 /**
  * Ensures that the directory exists. If the directory structure does not exist, it is created.
  * @param {string} dirPath 
- * @returns {ResultAsync<void, string>}
+ * @returns {ResultAsync<void, FileUtilsError>}
  */
 export function ensureDir(dirPath) {
 	return ResultAsync.fromPromise(
 		fs.promises.mkdir(dirPath, { recursive: true }),
-		wrapError(`Failed to create directory ${dirPath}`)
+		(e) => new FileUtilsError(`Failed to create directory ${dirPath}`, { cause: e })
 	).map(() => undefined); // return void on success
 }
 
 /**
  * Removes a file or directory. The directory can have contents. If the path does not exist, silently does nothing.
  * @param {string} dir 
- * @returns {ResultAsync<void, string>}
+ * @returns {ResultAsync<void, FileUtilsError>}
  */
 export function remove(dir) {
 	return ResultAsync.fromPromise(
 		fs.promises.rm(dir, { recursive: true, force: true }),
-		wrapError(`Failed to remove ${dir}`)
+		(e) => new FileUtilsError(`Failed to remove ${dir}`, { cause: e })
 	);
 }
 
 /**
  * returns true if the path exists, false otherwise
  * @param {string} dir 
- * @returns {ResultAsync<boolean, string>}
+ * @returns {ResultAsync<boolean, FileUtilsError>}
  */
 export function pathExists(dir) {
 	return ResultAsync.fromPromise(
 		fs.promises.access(dir).then(() => true).catch(() => false),
-		wrapError(`Failed to check if path exists ${dir}`)
+		(e) => new FileUtilsError(`Failed to check if path exists ${dir}`, { cause: e })
 	);
 }
 
@@ -161,12 +171,12 @@ export function pathExists(dir) {
  * @param {string} dest
  * @param {object} [options]
  * @param {boolean} [options.preserveTimestamps]
- * @returns {ResultAsync<void, string>}
+ * @returns {ResultAsync<void, FileUtilsError>}
  */
 export function copy(src, dest, options = { preserveTimestamps: true }) {
 	return ResultAsync.fromPromise(
 		fs.promises.stat(src),
-		wrapError(`Failed to get file stats for ${src}`)
+		(e) => new FileUtilsError(`Failed to get file stats for ${src}`, { cause: e })
 	).andThrough((stats) => {
 		if (stats.isDirectory()) {
 			return copyDir(src, dest, options);
@@ -175,7 +185,7 @@ export function copy(src, dest, options = { preserveTimestamps: true }) {
 		}
 	}).andThen((stats) => {
 		if (options.preserveTimestamps) {
-			return ResultAsync.fromPromise(fs.promises.utimes(dest, stats.atime, stats.mtime), wrapError(`Failed to set file timestamps for ${dest}`));
+			return ResultAsync.fromPromise(fs.promises.utimes(dest, stats.atime, stats.mtime), (e) => new FileUtilsError(`Failed to set file timestamps for ${dest}`, { cause: e }));
 		}
 		return okAsync(undefined);
 	});
@@ -187,11 +197,11 @@ export function copy(src, dest, options = { preserveTimestamps: true }) {
  * @param {string} dest
  * @param {object} [options]
  * @param {boolean} [options.preserveTimestamps]
- * @returns {ResultAsync<void, string>}
+ * @returns {ResultAsync<void, FileUtilsError>}
  */
 function copyDir(src, dest, options = { preserveTimestamps: true }) {
 	return ensureDir(dest)
-		.andThen(() => ResultAsync.fromPromise(fs.promises.readdir(src), wrapError(`Failed to read dir ${src}`)))
+		.andThen(() => ResultAsync.fromPromise(fs.promises.readdir(src), (e) => new FileUtilsError(`Failed to read dir ${src}`, { cause: e })))
 		.andThen((entries) =>
 			ResultAsync.combine(entries.map((entry) =>
 				copy(path.join(src, entry), path.join(dest, entry), options)
@@ -203,15 +213,11 @@ function copyDir(src, dest, options = { preserveTimestamps: true }) {
  * Copies a file from `src` to `dest`.
  * @param {string} src
  * @param {string} dest
- * @returns {ResultAsync<void, string>}
+ * @returns {ResultAsync<void, FileUtilsError>}
  */
 function copyFile(src, dest) {
 	return ResultAsync.fromPromise(
 		fs.promises.copyFile(src, dest),
-		wrapError(`Failed to copy file ${src} to ${dest}`)
+		(e) => new FileUtilsError(`Failed to copy file ${src} to ${dest}`, { cause: e })
 	);
 }
-
-const wrapError = (/** @type string */ message) => (/** @type unknown */ error) => {
-	return (error instanceof Error) ? `${message}: ${error.message}` : `${message}: ${error}`;
-};
diff --git a/packages/content/lib/utils/safe-ky.js b/packages/content/lib/utils/safe-ky.js
index fd503902..5771dfa4 100644
--- a/packages/content/lib/utils/safe-ky.js
+++ b/packages/content/lib/utils/safe-ky.js
@@ -1,26 +1,25 @@
 import ky from 'ky';
 import { Err, err, Ok, ok, ResultAsync } from 'neverthrow';
 
-class BaseSafeKyError extends Error {
+export class SafeKyFetchError extends Error {
 	/**
-   * @param {string} message 
-   * @param {unknown} [cause]  
-   */
-	constructor(message, cause) {
-		if (cause === undefined) {
-			super(message);
-		} else if (cause instanceof Error) {
-			super(`${message}: ${cause.message}`, { cause });
-		} else {
-			super(`${message}: ${cause}`);
-		}
+	 * @param {ConstructorParameters<typeof Error>} args
+	 */
+	constructor(...args) {
+		super(...args);
+		this.name = 'SafeKyFetchError';
 	}
 }
 
-export const SafeKyError = {
-	FetchError: class extends BaseSafeKyError { },
-	ParseError: class extends BaseSafeKyError { }
-};
+export class SafeKyParseError extends Error {
+	/**
+	 * @param {ConstructorParameters<typeof Error>} args
+	 */
+	constructor(...args) {
+		super(...args);
+		this.name = 'SafeKyParseError';
+	}
+}
 
 /**
  * Wraps a ky request in a ResultAsync
@@ -36,17 +35,17 @@ export function safeKy(input, options) {
  * @template [T=unknown]
  * @typedef { Omit<import('ky').KyResponse<T>, 'json' | 'text' | 'arrayBuffer' | 'blob'>
  *  & {
- *    json: () => import('neverthrow').ResultAsync<any, BaseSafeKyError>,
- *    text: () => import('neverthrow').ResultAsync<string, BaseSafeKyError>,
- *    arrayBuffer: () => import('neverthrow').ResultAsync<ArrayBuffer, BaseSafeKyError>,
- *    blob: () => import('neverthrow').ResultAsync<Blob, BaseSafeKyError>
+ *    json: () => import('neverthrow').ResultAsync<any, SafeKyParseError>,
+ *    text: () => import('neverthrow').ResultAsync<string, SafeKyParseError>,
+ *    arrayBuffer: () => import('neverthrow').ResultAsync<ArrayBuffer, SafeKyParseError>,
+ *    blob: () => import('neverthrow').ResultAsync<Blob, SafeKyParseError>
  *  }
  * } SafeKyResponseResult
  */
 
 /**
  * @template T
- * @extends {ResultAsync<SafeKyResponseResult<T>, BaseSafeKyError>}
+ * @extends {ResultAsync<SafeKyResponseResult<T>, SafeKyFetchError | SafeKyParseError>}
  */
 class SafeKyResultAsync extends ResultAsync {
 	/**
@@ -66,16 +65,16 @@ class SafeKyResultAsync extends ResultAsync {
 					url: res.url,
 					redirected: res.redirected,
 					body: res.body,
-					json: () => ResultAsync.fromPromise(res.json(), (error) => new SafeKyError.ParseError('Error parsing JSON', error)),
-					text: () => ResultAsync.fromPromise(res.text(), (error) => new SafeKyError.ParseError('Error parsing text', error)),
-					arrayBuffer: () => ResultAsync.fromPromise(res.arrayBuffer(), (error) => new SafeKyError.ParseError('Error parsing array buffer', error)),
-					blob: () => ResultAsync.fromPromise(res.blob(), (error) => new SafeKyError.ParseError('Error parsing blob', error))
+					json: () => ResultAsync.fromPromise(res.json(), (error) => new SafeKyParseError('Error parsing JSON', { cause: error })),
+					text: () => ResultAsync.fromPromise(res.text(), (error) => new SafeKyParseError('Error parsing text', { cause: error })),
+					arrayBuffer: () => ResultAsync.fromPromise(res.arrayBuffer(), (error) => new SafeKyParseError('Error parsing array buffer', { cause: error })),
+					blob: () => ResultAsync.fromPromise(res.blob(), (error) => new SafeKyParseError('Error parsing blob', { cause: error }))
 				};
 				
-				return /** @type {Ok<SafeKyResponseResult, BaseSafeKyError>} */ (new Ok(remapped));
+				return /** @type {Ok<SafeKyResponseResult, SafeKyFetchError | SafeKyParseError>} */ (new Ok(remapped));
 			})
 			.catch((error) => {
-				return /** @type {Err<SafeKyResponseResult, BaseSafeKyError>} */(new Err(new SafeKyError.FetchError('Error during request', error)));
+				return /** @type {Err<SafeKyResponseResult, SafeKyFetchError | SafeKyParseError>} */(new Err(new SafeKyFetchError('Error during request', { cause: error })));
 			});
 
 		return new SafeKyResultAsync(newPromise);

From 07b76968bee15111d1232379246a6e0b9b82570f Mon Sep 17 00:00:00 2001
From: Clay Tercek <30105080+claytercek@users.noreply.github.com>
Date: Thu, 31 Oct 2024 18:23:44 -0400
Subject: [PATCH 2/4] fix some tests and types

---
 .../__tests__/content-plugin-driver.test.js    | 18 ++++++++++--------
 packages/content/lib/content-options.js        |  4 +++-
 packages/utils/lib/plugin-driver.js            |  1 +
 3 files changed, 14 insertions(+), 9 deletions(-)

diff --git a/packages/content/lib/__tests__/content-plugin-driver.test.js b/packages/content/lib/__tests__/content-plugin-driver.test.js
index f6ff5073..ddc4eac0 100644
--- a/packages/content/lib/__tests__/content-plugin-driver.test.js
+++ b/packages/content/lib/__tests__/content-plugin-driver.test.js
@@ -15,14 +15,14 @@ describe('ContentPluginDriver', () => {
 		});
 
 		const paths = {
-			/** @param {string | undefined} source */
+			/** @param {string} [source] */
 			getDownloadPath: (source) => source ? `/downloads/${source}` : '/downloads',
 			/**
-			 * @param {string | undefined} source
-			 * @param {string | undefined} plugin
+			 * @param {string} [source]
+			 * @param {string} [plugin]
 			 */
 			getTempPath: (source, plugin) => source ? `/temp/${plugin}/${source}` : `/temp/${plugin}`,
-			/** @param {string | undefined} source */
+			/** @param {string} [source] */
 			getBackupPath: (source) => source ? `/backups/${source}` : '/backups'
 		};
 
@@ -46,8 +46,8 @@ describe('ContentPluginDriver', () => {
 					onContentFetchDone(ctx) {
 						expect(ctx.data).toBe(dataStore);
 						expect(ctx.contentOptions).toBe(options);
-						expect(ctx.paths.getDownloadPath).toBe(paths.getDownloadPath);
-						expect(ctx.paths.getBackupPath).toBe(paths.getBackupPath);
+						expect(ctx.paths.getDownloadPath()).toBe(paths.getDownloadPath());
+						expect(ctx.paths.getBackupPath()).toBe(paths.getBackupPath());
 						// Test plugin-specific temp path
 						expect(ctx.paths.getTempPath('source')).toBe('/temp/test-plugin/source');
 					}
@@ -55,7 +55,8 @@ describe('ContentPluginDriver', () => {
 			});
 
 			contentDriver.add(plugin);
-			await contentDriver.runHookSequential('onContentFetchDone');
+			const result = await contentDriver.runHookSequential('onContentFetchDone');
+			expect(result).toBeOk();
 		});
 
 		it('should handle plugin-specific temp paths correctly', async () => {
@@ -88,7 +89,8 @@ describe('ContentPluginDriver', () => {
 
 			contentDriver.add(plugin1);
 			contentDriver.add(plugin2);
-			await contentDriver.runHookSequential('onContentFetchDone');
+			const result = await contentDriver.runHookSequential('onContentFetchDone');
+			expect(result).toBeOk();
 		});
 	});
 
diff --git a/packages/content/lib/content-options.js b/packages/content/lib/content-options.js
index aa36ad01..c0232362 100644
--- a/packages/content/lib/content-options.js
+++ b/packages/content/lib/content-options.js
@@ -1,10 +1,12 @@
+import { SourceConfigError } from './sources/source.js';
+
 export const DOWNLOAD_PATH_TOKEN = '%DOWNLOAD_PATH%';
 export const TIMESTAMP_TOKEN = '%TIMESTAMP%';
 
 /**
  * @typedef {import('./sources/source.js').ContentSource
  * | Promise<import('./sources/source.js').ContentSource>
- * | import('neverthrow').ResultAsync<import('./sources/source.js').ContentSource, import('./sources/source-errors.js').SourceError>
+ * | ReturnType<import('./sources/source.js').ContentSourceBuilder<unknown>>
  * } ConfigContentSource
  */
 
diff --git a/packages/utils/lib/plugin-driver.js b/packages/utils/lib/plugin-driver.js
index 6c981e09..94c3b677 100644
--- a/packages/utils/lib/plugin-driver.js
+++ b/packages/utils/lib/plugin-driver.js
@@ -1,6 +1,7 @@
 import chalk from 'chalk';
 import onExit from './on-exit.js';
 import { err, ok, okAsync, ResultAsync } from 'neverthrow';
+import { AssertionError } from 'assert';
 
 class PluginError extends Error {
 	/**

From 704b36a587636881d47ddd388756c3f6df65d34b Mon Sep 17 00:00:00 2001
From: Clay Tercek <30105080+claytercek@users.noreply.github.com>
Date: Thu, 31 Oct 2024 13:03:57 -0400
Subject: [PATCH 3/4] fix exports

---
 package-lock.json                     | 228 ++++++++++++++------------
 packages/cli/package.json             |   3 +-
 packages/content/lib/plugins/index.js |   1 +
 packages/content/package.json         |   6 +-
 4 files changed, 132 insertions(+), 106 deletions(-)

diff --git a/package-lock.json b/package-lock.json
index cfb896ec..52c71e26 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -394,9 +394,9 @@
       }
     },
     "node_modules/@babel/parser": {
-      "version": "7.26.1",
-      "resolved": "https://registry.npmjs.org/@babel/parser/-/parser-7.26.1.tgz",
-      "integrity": "sha512-reoQYNiAJreZNsJzyrDNzFQ+IQ5JFiIzAHJg9bn94S3l+4++J7RsIhNMoB+lgP/9tpmiAQqspv+xfdxTSzREOw==",
+      "version": "7.26.2",
+      "resolved": "https://registry.npmjs.org/@babel/parser/-/parser-7.26.2.tgz",
+      "integrity": "sha512-DWMCZH9WA4Maitz2q21SRKHo9QXZxkDsbNZoVD62gusNtNBBqDg9i7uOhASfTfIGNzW+O+r7+jAlM8dwphcJKQ==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
@@ -1682,9 +1682,9 @@
       }
     },
     "node_modules/@mswjs/interceptors": {
-      "version": "0.36.6",
-      "resolved": "https://registry.npmjs.org/@mswjs/interceptors/-/interceptors-0.36.6.tgz",
-      "integrity": "sha512-issnYydStyH0wPEeU7CMwfO7kI668ffVtzKRMRS7H7BliOYuPuwEZxh9dwiXV+oeHBxT5SXT0wPwV8T7V2PJUA==",
+      "version": "0.36.7",
+      "resolved": "https://registry.npmjs.org/@mswjs/interceptors/-/interceptors-0.36.7.tgz",
+      "integrity": "sha512-sdx02Wlus5hv6Bx7uUDb25gb0WGjCuSgnJB2LVERemoSGuqkZMe3QI6nEXhieFGtYwPrZbYrT2vPbsFN2XfbUw==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
@@ -2578,9 +2578,9 @@
       "license": "MIT"
     },
     "node_modules/@types/node": {
-      "version": "20.17.3",
-      "resolved": "https://registry.npmjs.org/@types/node/-/node-20.17.3.tgz",
-      "integrity": "sha512-tSQrmKKatLDGnG92h40GD7FzUt0MjahaHwOME4VAFeeA/Xopayq5qLyQRy7Jg/pjgKIFBXuKcGhJo+UdYG55jQ==",
+      "version": "20.17.4",
+      "resolved": "https://registry.npmjs.org/@types/node/-/node-20.17.4.tgz",
+      "integrity": "sha512-Fi1Bj8qTJr4f1FDdHFR7oMlOawEYSzkHNdBJK+aRjcDDNHwEV3jPPjuZP2Lh2QNgXeqzM8Y+U6b6urKAog2rZw==",
       "devOptional": true,
       "license": "MIT",
       "dependencies": {
@@ -2892,23 +2892,23 @@
       }
     },
     "node_modules/@vue/devtools-api": {
-      "version": "7.6.0",
-      "resolved": "https://registry.npmjs.org/@vue/devtools-api/-/devtools-api-7.6.0.tgz",
-      "integrity": "sha512-FGxX7jatS0ZcsglIBcdxAQciYSUpb/eXt610x0YDVBdIJaH0x6iDg0vs4MhbzSIrRCywjFmW+ZwpYus/eFIS8Q==",
+      "version": "7.6.1",
+      "resolved": "https://registry.npmjs.org/@vue/devtools-api/-/devtools-api-7.6.1.tgz",
+      "integrity": "sha512-W99uw1nJKWeG4V2Bgp/pR1vnIREfixmnYW71wjtID7Gn/XnHH+nhfJmNy/0DjxcXOM14POVBDkl9JGlsOx1UjQ==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
-        "@vue/devtools-kit": "^7.6.0"
+        "@vue/devtools-kit": "^7.6.1"
       }
     },
     "node_modules/@vue/devtools-kit": {
-      "version": "7.6.0",
-      "resolved": "https://registry.npmjs.org/@vue/devtools-kit/-/devtools-kit-7.6.0.tgz",
-      "integrity": "sha512-82Mhrk/PRiTGfLwj73mXfrrocnCbWEPLLk3r4HhIkcieTa610Snlqc0a9OBiSsldX98YI6rOcL04+Dud1tLIKg==",
+      "version": "7.6.1",
+      "resolved": "https://registry.npmjs.org/@vue/devtools-kit/-/devtools-kit-7.6.1.tgz",
+      "integrity": "sha512-cCcdskZDLqKwJUHq1+kH9zAfYM+y9OFq8J2NT0xcAUYpu8K5IJd03ydZkvr7ydOd9UKBxrGyZpYe9PpJ0ChrVw==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
-        "@vue/devtools-shared": "^7.6.0",
+        "@vue/devtools-shared": "^7.6.1",
         "birpc": "^0.2.19",
         "hookable": "^5.5.3",
         "mitt": "^3.0.1",
@@ -2918,9 +2918,9 @@
       }
     },
     "node_modules/@vue/devtools-shared": {
-      "version": "7.6.0",
-      "resolved": "https://registry.npmjs.org/@vue/devtools-shared/-/devtools-shared-7.6.0.tgz",
-      "integrity": "sha512-ANh0nvp/oQXaz5PaSXL78I9X3v767kD0Cbit8u6mOd1oZmC+sj115/1CBH8BBBdRuLg8HCjpE2444a6cbXjKTA==",
+      "version": "7.6.1",
+      "resolved": "https://registry.npmjs.org/@vue/devtools-shared/-/devtools-shared-7.6.1.tgz",
+      "integrity": "sha512-SdIif2YoOWo8/s8c1+NU67jcx8qoSjM9caetQnjl3++Kufo0qa5JRZe95iV6vvupQzVGGo3ACY0LTyAsMfGeCg==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
@@ -2983,15 +2983,15 @@
       "license": "MIT"
     },
     "node_modules/@vueuse/core": {
-      "version": "11.1.0",
-      "resolved": "https://registry.npmjs.org/@vueuse/core/-/core-11.1.0.tgz",
-      "integrity": "sha512-P6dk79QYA6sKQnghrUz/1tHi0n9mrb/iO1WTMk/ElLmTyNqgDeSZ3wcDf6fRBGzRJbeG1dxzEOvLENMjr+E3fg==",
+      "version": "11.2.0",
+      "resolved": "https://registry.npmjs.org/@vueuse/core/-/core-11.2.0.tgz",
+      "integrity": "sha512-JIUwRcOqOWzcdu1dGlfW04kaJhW3EXnnjJJfLTtddJanymTL7lF1C0+dVVZ/siLfc73mWn+cGP1PE1PKPruRSA==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
         "@types/web-bluetooth": "^0.0.20",
-        "@vueuse/metadata": "11.1.0",
-        "@vueuse/shared": "11.1.0",
+        "@vueuse/metadata": "11.2.0",
+        "@vueuse/shared": "11.2.0",
         "vue-demi": ">=0.14.10"
       },
       "funding": {
@@ -3026,14 +3026,14 @@
       }
     },
     "node_modules/@vueuse/integrations": {
-      "version": "11.1.0",
-      "resolved": "https://registry.npmjs.org/@vueuse/integrations/-/integrations-11.1.0.tgz",
-      "integrity": "sha512-O2ZgrAGPy0qAjpoI2YR3egNgyEqwG85fxfwmA9BshRIGjV4G6yu6CfOPpMHAOoCD+UfsIl7Vb1bXJ6ifrHYDDA==",
+      "version": "11.2.0",
+      "resolved": "https://registry.npmjs.org/@vueuse/integrations/-/integrations-11.2.0.tgz",
+      "integrity": "sha512-zGXz3dsxNHKwiD9jPMvR3DAxQEOV6VWIEYTGVSB9PNpk4pTWR+pXrHz9gvXWcP2sTk3W2oqqS6KwWDdntUvNVA==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
-        "@vueuse/core": "11.1.0",
-        "@vueuse/shared": "11.1.0",
+        "@vueuse/core": "11.2.0",
+        "@vueuse/shared": "11.2.0",
         "vue-demi": ">=0.14.10"
       },
       "funding": {
@@ -3120,9 +3120,9 @@
       }
     },
     "node_modules/@vueuse/metadata": {
-      "version": "11.1.0",
-      "resolved": "https://registry.npmjs.org/@vueuse/metadata/-/metadata-11.1.0.tgz",
-      "integrity": "sha512-l9Q502TBTaPYGanl1G+hPgd3QX5s4CGnpXriVBR5fEZ/goI6fvDaVmIl3Td8oKFurOxTmbXvBPSsgrd6eu6HYg==",
+      "version": "11.2.0",
+      "resolved": "https://registry.npmjs.org/@vueuse/metadata/-/metadata-11.2.0.tgz",
+      "integrity": "sha512-L0ZmtRmNx+ZW95DmrgD6vn484gSpVeRbgpWevFKXwqqQxW9hnSi2Ppuh2BzMjnbv4aJRiIw8tQatXT9uOB23dQ==",
       "dev": true,
       "license": "MIT",
       "funding": {
@@ -3130,9 +3130,9 @@
       }
     },
     "node_modules/@vueuse/shared": {
-      "version": "11.1.0",
-      "resolved": "https://registry.npmjs.org/@vueuse/shared/-/shared-11.1.0.tgz",
-      "integrity": "sha512-YUtIpY122q7osj+zsNMFAfMTubGz0sn5QzE5gPzAIiCmtt2ha3uQUY1+JPyL4gRCTsLPX82Y9brNbo/aqlA91w==",
+      "version": "11.2.0",
+      "resolved": "https://registry.npmjs.org/@vueuse/shared/-/shared-11.2.0.tgz",
+      "integrity": "sha512-VxFjie0EanOudYSgMErxXfq6fo8vhr5ICI+BuE3I9FnX7ePllEsVrRQ7O6Q1TLgApeLuPKcHQxAXpP+KnlrJsg==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
@@ -3431,24 +3431,6 @@
         "url": "https://github.com/chalk/ansi-styles?sponsor=1"
       }
     },
-    "node_modules/ansi-styles/node_modules/color-convert": {
-      "version": "2.0.1",
-      "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-2.0.1.tgz",
-      "integrity": "sha512-RRECPsj7iu/xb5oKYcsFHSppFNnsj/52OVTRKb4zP5onXwVF3zVmmToNcOfGC+CRDpfK/U584fMg38ZHCaElKQ==",
-      "license": "MIT",
-      "dependencies": {
-        "color-name": "~1.1.4"
-      },
-      "engines": {
-        "node": ">=7.0.0"
-      }
-    },
-    "node_modules/ansi-styles/node_modules/color-name": {
-      "version": "1.1.4",
-      "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.4.tgz",
-      "integrity": "sha512-dOy+3AuW3a2wNbZHIuMZpTcgjGuLU/uBL/ubcZF9OXbDo8ff4O8yVp5Bf0efS8uEoYo5q4Fx7dY9OgQGXgAsQA==",
-      "license": "MIT"
-    },
     "node_modules/anymatch": {
       "version": "3.1.3",
       "resolved": "https://registry.npmjs.org/anymatch/-/anymatch-3.1.3.tgz",
@@ -4222,18 +4204,21 @@
       }
     },
     "node_modules/color-convert": {
-      "version": "1.9.3",
-      "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-1.9.3.tgz",
-      "integrity": "sha512-QfAUtd+vFdAtFQcC8CCyYt1fYWxSqAiK2cSD6zDB8N3cpsEBAvRxp9zOGg6G/SHHJYAT88/az/IuDGALsNVbGg==",
+      "version": "2.0.1",
+      "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-2.0.1.tgz",
+      "integrity": "sha512-RRECPsj7iu/xb5oKYcsFHSppFNnsj/52OVTRKb4zP5onXwVF3zVmmToNcOfGC+CRDpfK/U584fMg38ZHCaElKQ==",
       "license": "MIT",
       "dependencies": {
-        "color-name": "1.1.3"
+        "color-name": "~1.1.4"
+      },
+      "engines": {
+        "node": ">=7.0.0"
       }
     },
     "node_modules/color-name": {
-      "version": "1.1.3",
-      "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.3.tgz",
-      "integrity": "sha512-72fSenhMw2HZMTVHeCA9KCmpEIbzWiQsjN+BHcBbS9vr1mtt+vJjPdksIBNUmKAW8TFUDPJK5SUU3QhE9NEXDw==",
+      "version": "1.1.4",
+      "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.4.tgz",
+      "integrity": "sha512-dOy+3AuW3a2wNbZHIuMZpTcgjGuLU/uBL/ubcZF9OXbDo8ff4O8yVp5Bf0efS8uEoYo5q4Fx7dY9OgQGXgAsQA==",
       "license": "MIT"
     },
     "node_modules/color-string": {
@@ -4246,6 +4231,21 @@
         "simple-swizzle": "^0.2.2"
       }
     },
+    "node_modules/color/node_modules/color-convert": {
+      "version": "1.9.3",
+      "resolved": "https://registry.npmjs.org/color-convert/-/color-convert-1.9.3.tgz",
+      "integrity": "sha512-QfAUtd+vFdAtFQcC8CCyYt1fYWxSqAiK2cSD6zDB8N3cpsEBAvRxp9zOGg6G/SHHJYAT88/az/IuDGALsNVbGg==",
+      "license": "MIT",
+      "dependencies": {
+        "color-name": "1.1.3"
+      }
+    },
+    "node_modules/color/node_modules/color-name": {
+      "version": "1.1.3",
+      "resolved": "https://registry.npmjs.org/color-name/-/color-name-1.1.3.tgz",
+      "integrity": "sha512-72fSenhMw2HZMTVHeCA9KCmpEIbzWiQsjN+BHcBbS9vr1mtt+vJjPdksIBNUmKAW8TFUDPJK5SUU3QhE9NEXDw==",
+      "license": "MIT"
+    },
     "node_modules/colorspace": {
       "version": "1.1.4",
       "resolved": "https://registry.npmjs.org/colorspace/-/colorspace-1.1.4.tgz",
@@ -7950,6 +7950,15 @@
         "url": "https://github.com/sponsors/ljharb"
       }
     },
+    "node_modules/minipass": {
+      "version": "7.1.2",
+      "resolved": "https://registry.npmjs.org/minipass/-/minipass-7.1.2.tgz",
+      "integrity": "sha512-qOOzS1cBTWYF4BH8fVePDBOO9iptMnGUEZwNc/cMWnTV2nVLZ7VoNWEPHkYczZA0pdoA7dl6e7FL659nX9S2aw==",
+      "license": "ISC",
+      "engines": {
+        "node": ">=16 || 14 >=14.17"
+      }
+    },
     "node_modules/minisearch": {
       "version": "7.1.0",
       "resolved": "https://registry.npmjs.org/minisearch/-/minisearch-7.1.0.tgz",
@@ -8746,6 +8755,31 @@
       "integrity": "sha512-LDJzPVEEEPR+y48z93A0Ed0yXb8pAByGWo/k5YYdYgpY2/2EsOsksJrq7lOHxryrVOn1ejG6oAp8ahvOIQD8sw==",
       "license": "MIT"
     },
+    "node_modules/path-scurry": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/path-scurry/-/path-scurry-2.0.0.tgz",
+      "integrity": "sha512-ypGJsmGtdXUOeM5u93TyeIEfEhM6s+ljAhrk5vAvSx8uyY/02OvrZnA0YNGUrPXfpJMgI1ODd3nwz8Npx4O4cg==",
+      "license": "BlueOak-1.0.0",
+      "dependencies": {
+        "lru-cache": "^11.0.0",
+        "minipass": "^7.1.2"
+      },
+      "engines": {
+        "node": "20 || >=22"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/isaacs"
+      }
+    },
+    "node_modules/path-scurry/node_modules/lru-cache": {
+      "version": "11.0.1",
+      "resolved": "https://registry.npmjs.org/lru-cache/-/lru-cache-11.0.1.tgz",
+      "integrity": "sha512-CgeuL5uom6j/ZVrg7G/+1IXqRY8JXX4Hghfy5YE0EhoYQWvndP1kufu58cmZLNIDKnRhZrXfdS9urVWx98AipQ==",
+      "license": "ISC",
+      "engines": {
+        "node": "20 || >=22"
+      }
+    },
     "node_modules/path-to-regexp": {
       "version": "6.3.0",
       "resolved": "https://registry.npmjs.org/path-to-regexp/-/path-to-regexp-6.3.0.tgz",
@@ -11151,9 +11185,9 @@
       }
     },
     "node_modules/vitepress": {
-      "version": "1.4.2",
-      "resolved": "https://registry.npmjs.org/vitepress/-/vitepress-1.4.2.tgz",
-      "integrity": "sha512-10v92Lqx0N4r7YC3cQLBvu+gRS2rHviE7vgdKiwlupUGfSWkyiQDqYccxM5iPStDGSi1Brnec1lf+lmhaQcZXw==",
+      "version": "1.4.3",
+      "resolved": "https://registry.npmjs.org/vitepress/-/vitepress-1.4.3.tgz",
+      "integrity": "sha512-956c2K2Mr0ubY9bTc2lCJD3g0mgo0mARB1iJC/BqUt4s0AM8Wl60wSU4zbFnzV7X2miFK1XJDKzGZnuEN90umw==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
@@ -11698,10 +11732,10 @@
     },
     "packages/cli": {
       "name": "@bluecadet/launchpad-cli",
-      "version": "1.0.0",
+      "version": "2.0.0-next.0",
       "license": "ISC",
       "dependencies": {
-        "@bluecadet/launchpad-utils": "~1.5.0",
+        "@bluecadet/launchpad-utils": "~2.0.0-next.0",
         "auto-bind": "^5.0.1",
         "chalk": "^5.0.0",
         "dotenv": "^16.4.5",
@@ -11719,15 +11753,13 @@
         "npm": ">=8.5.1"
       },
       "optionalDependencies": {
-        "@bluecadet/launchpad-content": "~1.14.0",
-        "@bluecadet/launchpad-monitor": "~1.8.0",
-        "@bluecadet/launchpad-scaffold": "~1.8.0"
+        "@bluecadet/launchpad-content": "~2.0.0-next.0",
+        "@bluecadet/launchpad-monitor": "~2.0.0-next.0",
+        "@bluecadet/launchpad-scaffold": "~2.0.0-next.0"
       }
     },
     "packages/cli/node_modules/dotenv": {
       "version": "16.4.5",
-      "resolved": "https://registry.npmjs.org/dotenv/-/dotenv-16.4.5.tgz",
-      "integrity": "sha512-ZmdL2rui+eB2YwhsWzjInR8LldtZHGDoQ1ugH85ppHKwpUHL7j7rN0Ti9NCnGiQbhaZ11FpR+7ao1dNsmduNUg==",
       "license": "BSD-2-Clause",
       "engines": {
         "node": ">=12"
@@ -11738,10 +11770,10 @@
     },
     "packages/content": {
       "name": "@bluecadet/launchpad-content",
-      "version": "1.14.1",
+      "version": "2.0.0-next.0",
       "license": "ISC",
       "dependencies": {
-        "@bluecadet/launchpad-utils": "~1.5.0",
+        "@bluecadet/launchpad-utils": "~2.0.0-next.0",
         "@portabletext/to-html": "2.0.0",
         "@sanity/block-content-to-markdown": "^0.0.5",
         "chalk": "^5.0.0",
@@ -11751,6 +11783,7 @@
         "markdown-it": "^12.2.0",
         "neverthrow": "^8.0.0",
         "p-queue": "^7.1.0",
+        "path-scurry": "^2.0.0",
         "qs": "^6.11.1",
         "sanitize-html": "^2.5.1"
       },
@@ -11767,6 +11800,9 @@
         "vitest": "^2.1.3"
       },
       "optionalDependencies": {
+        "@bluecadet/launchpad-content": "~2.0.0-next.0",
+        "@bluecadet/launchpad-monitor": "~2.0.0-next.0",
+        "@bluecadet/launchpad-scaffold": "~2.0.0-next.0",
         "@sanity/client": "^6.4.9",
         "airtable": "^0.11.1",
         "contentful": "^9.0.0"
@@ -11774,8 +11810,6 @@
     },
     "packages/content/node_modules/@types/markdown-it": {
       "version": "12.2.3",
-      "resolved": "https://registry.npmjs.org/@types/markdown-it/-/markdown-it-12.2.3.tgz",
-      "integrity": "sha512-GKMHFfv3458yYy+v/N8gjufHO6MSZKCOXpZc5GXIWWy8uldwfmPn98vp81gZ5f9SVw8YYBctgfJ22a2d7AOMeQ==",
       "dev": true,
       "license": "MIT",
       "dependencies": {
@@ -11785,8 +11819,6 @@
     },
     "packages/content/node_modules/argparse": {
       "version": "2.0.1",
-      "resolved": "https://registry.npmjs.org/argparse/-/argparse-2.0.1.tgz",
-      "integrity": "sha512-8+9WqebbFzpX9OR+Wa6O29asIogeRMzcGtAINdpMHHyAg10f05aSFVBbcEqGf/PXw1EjAZ+q2/bEBg3DvurK3Q==",
       "license": "Python-2.0"
     },
     "packages/content/node_modules/brace-expansion": {
@@ -11798,8 +11830,6 @@
     },
     "packages/content/node_modules/entities": {
       "version": "2.1.0",
-      "resolved": "https://registry.npmjs.org/entities/-/entities-2.1.0.tgz",
-      "integrity": "sha512-hCx1oky9PFrJ611mf0ifBLBRW8lUUVRlFolb5gWRfIELabBlbp9xZvrqZLZAs+NxFnbfQoeGd8wDkygjg7U85w==",
       "license": "BSD-2-Clause",
       "funding": {
         "url": "https://github.com/fb55/entities?sponsor=1"
@@ -11828,8 +11858,6 @@
     },
     "packages/content/node_modules/linkify-it": {
       "version": "3.0.3",
-      "resolved": "https://registry.npmjs.org/linkify-it/-/linkify-it-3.0.3.tgz",
-      "integrity": "sha512-ynTsyrFSdE5oZ/O9GEf00kPngmOfVwazR5GKDq6EYfhlpFug3J2zybX56a2PRRpc9P+FuSoGNAwjlbDs9jJBPQ==",
       "license": "MIT",
       "dependencies": {
         "uc.micro": "^1.0.1"
@@ -11837,8 +11865,6 @@
     },
     "packages/content/node_modules/markdown-it": {
       "version": "12.3.2",
-      "resolved": "https://registry.npmjs.org/markdown-it/-/markdown-it-12.3.2.tgz",
-      "integrity": "sha512-TchMembfxfNVpHkbtriWltGWc+m3xszaRD0CZup7GFFhzIgQqxIfn3eGj1yZpfuflzPvfkt611B2Q/Bsk1YnGg==",
       "license": "MIT",
       "dependencies": {
         "argparse": "^2.0.1",
@@ -11853,8 +11879,6 @@
     },
     "packages/content/node_modules/mdurl": {
       "version": "1.0.1",
-      "resolved": "https://registry.npmjs.org/mdurl/-/mdurl-1.0.1.tgz",
-      "integrity": "sha512-/sKlQJCBYVY9Ers9hqzKou4H6V5UWc/M59TH2dvkt+84itfnq7uFOMLpOiOS4ujvHP4etln18fmIxA5R5fll0g==",
       "license": "MIT"
     },
     "packages/content/node_modules/minimatch": {
@@ -11872,16 +11896,14 @@
     },
     "packages/content/node_modules/uc.micro": {
       "version": "1.0.6",
-      "resolved": "https://registry.npmjs.org/uc.micro/-/uc.micro-1.0.6.tgz",
-      "integrity": "sha512-8Y75pvTYkLJW2hWQHXxoqRgV7qb9B+9vFEtidML+7koHUFapnVJAZ6cKs+Qjz5Aw3aZWHMC6u0wJE3At+nSGwA==",
       "license": "MIT"
     },
     "packages/dashboard": {
       "name": "@bluecadet/launchpad-dashboard",
-      "version": "1.5.0",
+      "version": "2.0.0-next.0",
       "license": "ISC",
       "dependencies": {
-        "@bluecadet/launchpad-utils": "~1.5.0"
+        "@bluecadet/launchpad-utils": "~2.0.0-next.0"
       },
       "bin": {
         "launchpad-dashboard": "index.js"
@@ -11892,15 +11914,15 @@
     },
     "packages/launchpad": {
       "name": "@bluecadet/launchpad",
-      "version": "1.5.2",
+      "version": "2.0.0-next.0",
       "license": "ISC",
       "dependencies": {
-        "@bluecadet/launchpad-cli": "~1.0.0",
-        "@bluecadet/launchpad-content": "~1.14.0",
-        "@bluecadet/launchpad-dashboard": "~1.5.0",
-        "@bluecadet/launchpad-monitor": "~1.8.0",
-        "@bluecadet/launchpad-scaffold": "~1.8.0",
-        "@bluecadet/launchpad-utils": "~1.5.0",
+        "@bluecadet/launchpad-cli": "~2.0.0-next.0",
+        "@bluecadet/launchpad-content": "~2.0.0-next.0",
+        "@bluecadet/launchpad-dashboard": "~2.0.0-next.0",
+        "@bluecadet/launchpad-monitor": "~2.0.0-next.0",
+        "@bluecadet/launchpad-scaffold": "~2.0.0-next.0",
+        "@bluecadet/launchpad-utils": "~2.0.0-next.0",
         "auto-bind": "^5.0.1",
         "chalk": "^5.0.0"
       },
@@ -11914,10 +11936,10 @@
     },
     "packages/monitor": {
       "name": "@bluecadet/launchpad-monitor",
-      "version": "1.8.0",
+      "version": "2.0.0-next.0",
       "license": "ISC",
       "dependencies": {
-        "@bluecadet/launchpad-utils": "~1.5.0",
+        "@bluecadet/launchpad-utils": "~2.0.0-next.0",
         "auto-bind": "^5.0.1",
         "axon": "^2.0.3",
         "chalk": "^5.0.0",
@@ -11938,10 +11960,10 @@
     },
     "packages/scaffold": {
       "name": "@bluecadet/launchpad-scaffold",
-      "version": "1.8.1",
+      "version": "2.0.0-next.0",
       "license": "ISC",
       "dependencies": {
-        "@bluecadet/launchpad-utils": "~1.5.0",
+        "@bluecadet/launchpad-utils": "~2.0.0-next.0",
         "sudo-prompt": "^9.2.1"
       },
       "bin": {
@@ -11960,7 +11982,7 @@
       },
       "devDependencies": {
         "@bluecadet/launchpad-tsconfig": "0.1.0",
-        "@bluecadet/launchpad-utils": "*"
+        "@bluecadet/launchpad-utils": "2.0.0-next.0"
       }
     },
     "packages/tsconfig": {
@@ -11969,7 +11991,7 @@
     },
     "packages/utils": {
       "name": "@bluecadet/launchpad-utils",
-      "version": "1.5.2",
+      "version": "2.0.0-next.0",
       "license": "ISC",
       "dependencies": {
         "@sindresorhus/slugify": "^2.1.0",
@@ -11991,8 +12013,6 @@
     },
     "packages/utils/node_modules/strip-json-comments": {
       "version": "4.0.0",
-      "resolved": "https://registry.npmjs.org/strip-json-comments/-/strip-json-comments-4.0.0.tgz",
-      "integrity": "sha512-LzWcbfMbAsEDTRmhjWIioe8GcDRl0fa35YMXFoJKDdiD/quGFmjJjdgPjFJJNwCMaLyQqFIDqCdHD2V4HfLgYA==",
       "license": "MIT",
       "engines": {
         "node": "^12.20.0 || ^14.13.1 || >=16.0.0"
diff --git a/packages/cli/package.json b/packages/cli/package.json
index 52420ecc..6793700b 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -17,6 +17,7 @@
   "bin": {
     "launchpad": "./lib/cli.js"
   },
+  "main": "./lib/index.js",
   "files": [
     "types",
     "index.js",
@@ -101,4 +102,4 @@
     "tools",
     "windows-desktop"
   ]
-}
+}
\ No newline at end of file
diff --git a/packages/content/lib/plugins/index.js b/packages/content/lib/plugins/index.js
index 36bf041d..b5d314d6 100644
--- a/packages/content/lib/plugins/index.js
+++ b/packages/content/lib/plugins/index.js
@@ -2,3 +2,4 @@ export { default as mdToHtml } from './md-to-html.js';
 export { default as sanityToHtml } from './sanity-to-html.js';
 export { default as sanityToPlain } from './sanity-to-plain.js';
 export { default as sanityToMd } from './sanity-to-markdown.js';
+export { default as mediaDownloader } from './media-downloader.js';
diff --git a/packages/content/package.json b/packages/content/package.json
index 78cb5dfc..d5472ff4 100644
--- a/packages/content/package.json
+++ b/packages/content/package.json
@@ -41,10 +41,14 @@
     "markdown-it": "^12.2.0",
     "neverthrow": "^8.0.0",
     "p-queue": "^7.1.0",
+    "path-scurry": "^2.0.0",
     "qs": "^6.11.1",
     "sanitize-html": "^2.5.1"
   },
   "optionalDependencies": {
+    "@bluecadet/launchpad-content": "~2.0.0-next.0",
+    "@bluecadet/launchpad-monitor": "~2.0.0-next.0",
+    "@bluecadet/launchpad-scaffold": "~2.0.0-next.0",
     "@sanity/client": "^6.4.9",
     "airtable": "^0.11.1",
     "contentful": "^9.0.0"
@@ -61,4 +65,4 @@
     "msw": "^2.5.1",
     "vitest": "^2.1.3"
   }
-}
\ No newline at end of file
+}

From 166ce90fbe30908ae1c832e0ddb6d3993e9aa7e3 Mon Sep 17 00:00:00 2001
From: Clay Tercek <30105080+claytercek@users.noreply.github.com>
Date: Fri, 1 Nov 2024 09:02:52 -0400
Subject: [PATCH 4/4] super verbose logging

---
 packages/cli/lib/commands/content.js          |  24 ++--
 packages/cli/lib/commands/monitor.js          |  39 ++++---
 packages/cli/lib/commands/scaffold.js         |   4 +-
 packages/cli/lib/commands/start.js            |  51 ++++----
 packages/cli/lib/utils/command-utils.js       | 109 ++++++++++++++++++
 packages/cli/lib/utils/load-config-and-env.js |  48 --------
 packages/content/lib/launchpad-content.js     |  17 ++-
 packages/monitor/lib/launchpad-monitor.js     |   8 +-
 packages/scaffold/index.js                    |   4 -
 packages/utils/lib/log-manager.js             |   3 +-
 10 files changed, 186 insertions(+), 121 deletions(-)
 create mode 100644 packages/cli/lib/utils/command-utils.js
 delete mode 100644 packages/cli/lib/utils/load-config-and-env.js

diff --git a/packages/cli/lib/commands/content.js b/packages/cli/lib/commands/content.js
index 2660882c..24f5a9f4 100644
--- a/packages/cli/lib/commands/content.js
+++ b/packages/cli/lib/commands/content.js
@@ -1,21 +1,23 @@
-import { ResultAsync } from 'neverthrow';
+import { err, ok, ResultAsync } from 'neverthrow';
 import { ImportError } from '../errors.js';
-import { loadConfigAndEnv } from '../utils/load-config-and-env.js';
+import { handleFatalError, initializeLogger, loadConfigAndEnv } from '../utils/command-utils.js';
 
 /**
  * @param {import("../cli.js").LaunchpadArgv} argv
  */
 export function content(argv) {
-	return loadConfigAndEnv(argv).andThen(config => {
-		return importLaunchpadContent().map(({ LaunchpadContent }) => {
-			const contentInstance = new LaunchpadContent(config.content);
-			return contentInstance.download();
+	return loadConfigAndEnv(argv)
+		.andThen(initializeLogger)
+		.andThen(({ config, rootLogger }) => {
+			return importLaunchpadContent().andThen(({ LaunchpadContent }) => {
+				if (!config.content) {
+					return err(new Error('No content config found in your config file.'));
+				}
+
+				const contentInstance = new LaunchpadContent(config.content, rootLogger);
+				return contentInstance.download();
+			}).orElse(error => handleFatalError(error, rootLogger));
 		});
-	}).mapErr(error => {
-		console.error('Content failed to download.');
-		console.error(error.message);
-		process.exit(1);
-	});
 }
 
 export function importLaunchpadContent() {
diff --git a/packages/cli/lib/commands/monitor.js b/packages/cli/lib/commands/monitor.js
index e3188c88..34e93008 100644
--- a/packages/cli/lib/commands/monitor.js
+++ b/packages/cli/lib/commands/monitor.js
@@ -1,27 +1,30 @@
-import { ResultAsync } from 'neverthrow';
+import { err, ok, ResultAsync } from 'neverthrow';
 import { ImportError, MonitorError } from '../errors.js';
-import { loadConfigAndEnv } from '../utils/load-config-and-env.js';
+import { handleFatalError, initializeLogger, loadConfigAndEnv } from '../utils/command-utils.js';
 
 /**
  * @param {import("../cli.js").LaunchpadArgv} argv
  */
 export function monitor(argv) {
-	return loadConfigAndEnv(argv).andThen(config => {
-		return importLaunchpadMonitor()
-			.map(({ LaunchpadMonitor }) => {
-				return new LaunchpadMonitor(config.monitor);
-			})
-			.andThrough((monitorInstance) => {
-				return ResultAsync.fromPromise(monitorInstance.connect(), () => new MonitorError('Failed to connect to monitor'));
-			})
-			.andThrough((monitorInstance) => {
-				return ResultAsync.fromPromise(monitorInstance.start(), () => new MonitorError('Failed to start monitor'));
-			});
-	}).mapErr(error => {
-		console.error('Monitor failed to start.');
-		console.error(error.message);
-		process.exit(1);
-	});
+	return loadConfigAndEnv(argv)
+		.andThen(initializeLogger)
+		.andThen(({ config, rootLogger }) => {
+			return importLaunchpadMonitor()
+				.andThen(({ LaunchpadMonitor }) => {
+					if (!config.monitor) {
+						return err(new Error('No monitor config found in your config file.'));
+					}
+
+					const monitorInstance = new LaunchpadMonitor(config.monitor, rootLogger);
+					return ok(monitorInstance);
+				})
+				.andThrough((monitorInstance) => {
+					return ResultAsync.fromPromise(monitorInstance.connect(), () => new MonitorError('Failed to connect to monitor'));
+				})
+				.andThrough((monitorInstance) => {
+					return ResultAsync.fromPromise(monitorInstance.start(), () => new MonitorError('Failed to start monitor'));
+				}).orElse(error => handleFatalError(error, rootLogger));
+		});
 }
 
 export function importLaunchpadMonitor() {
diff --git a/packages/cli/lib/commands/scaffold.js b/packages/cli/lib/commands/scaffold.js
index f9a3eb37..998a19d3 100644
--- a/packages/cli/lib/commands/scaffold.js
+++ b/packages/cli/lib/commands/scaffold.js
@@ -1,8 +1,10 @@
 import { launchScaffold } from '@bluecadet/launchpad-scaffold';
+import { LogManager } from '@bluecadet/launchpad-utils';
 
 /**
  * @param {import("../cli.js").LaunchpadArgv} argv
  */
 export async function scaffold(argv) {
-	await launchScaffold();
+	const rootLogger = LogManager.configureRootLogger();
+	await launchScaffold(rootLogger);
 }
diff --git a/packages/cli/lib/commands/start.js b/packages/cli/lib/commands/start.js
index eceb08e8..906fac61 100644
--- a/packages/cli/lib/commands/start.js
+++ b/packages/cli/lib/commands/start.js
@@ -1,30 +1,39 @@
-import { loadConfigAndEnv } from '../utils/load-config-and-env.js';
+import { handleFatalError, initializeLogger, loadConfigAndEnv } from '../utils/command-utils.js';
 import { importLaunchpadMonitor } from './monitor.js';
 import { importLaunchpadContent } from './content.js';
-import { ResultAsync } from 'neverthrow';
+import { err, ok, ResultAsync } from 'neverthrow';
 import { MonitorError } from '../errors.js';
 
 /**
  * @param {import("../cli.js").LaunchpadArgv} argv
  */
 export async function start(argv) {
-	return loadConfigAndEnv(argv).andThen(config => {
-		return importLaunchpadContent().map(({ LaunchpadContent }) => {
-			const contentInstance = new LaunchpadContent(config.content);
-			return contentInstance.start();
-		}).andThen(() => importLaunchpadMonitor())
-			.map(({ LaunchpadMonitor }) => {
-				return new LaunchpadMonitor(config.monitor);
-			})
-			.andThrough((monitorInstance) => {
-				return ResultAsync.fromPromise(monitorInstance.connect(), () => new MonitorError('Failed to connect to monitor'));
-			})
-			.andThrough((monitorInstance) => {
-				return ResultAsync.fromPromise(monitorInstance.start(), () => new MonitorError('Failed to start monitor'));
-			});
-	}).mapErr(error => {
-		console.error('Launchpad failed to start.');
-		console.error(error.message);
-		process.exit(1);
-	});
+	return loadConfigAndEnv(argv)
+		.andThen(initializeLogger)
+		.andThen(({ config, rootLogger }) => {
+			return importLaunchpadContent()
+				.andThen(({ LaunchpadContent }) => {
+					if (!config.content) {
+						return err(new Error('No content config found in your config file.'));
+					}
+
+					const contentInstance = new LaunchpadContent(config.content, rootLogger);
+					return contentInstance.start();
+				})
+				.andThen(() => importLaunchpadMonitor())
+				.andThen(({ LaunchpadMonitor }) => {
+					if (!config.monitor) {
+						return err(new Error('No monitor config found in your config file.'));
+					}
+
+					const monitorInstance = new LaunchpadMonitor(config.monitor, rootLogger);
+					return ok(monitorInstance);
+				})
+				.andThrough((monitorInstance) => {
+					return ResultAsync.fromPromise(monitorInstance.connect(), () => new MonitorError('Failed to connect to monitor'));
+				})
+				.andThrough((monitorInstance) => {
+					return ResultAsync.fromPromise(monitorInstance.start(), () => new MonitorError('Failed to start monitor'));
+				}).orElse(error => handleFatalError(error, rootLogger));
+		});
 }
diff --git a/packages/cli/lib/utils/command-utils.js b/packages/cli/lib/utils/command-utils.js
new file mode 100644
index 00000000..6b2fbedb
--- /dev/null
+++ b/packages/cli/lib/utils/command-utils.js
@@ -0,0 +1,109 @@
+import { err, errAsync, ok, ResultAsync } from 'neverthrow';
+import { findConfig, loadConfigFromFile } from './config.js';
+import { ConfigError } from '../errors.js';
+import path from 'path';
+import { resolveEnv } from './env.js';
+import { resolveLaunchpadOptions } from '../launchpad-options.js';
+import chalk from 'chalk';
+import { LogManager } from '@bluecadet/launchpad-utils';
+
+/**
+ * @param {import("../cli.js").LaunchpadArgv} argv
+ * @returns {import('neverthrow').ResultAsync<import('../launchpad-options.js').ResolvedLaunchpadOptions, ConfigError>}
+ */
+export function loadConfigAndEnv(argv) {
+	const configPath = argv.config ?? findConfig();
+
+	if (!configPath) {
+		return errAsync(new ConfigError('No config file found.'));
+	}
+
+	const configDir = path.dirname(configPath);
+
+	if (argv.env) {
+		// if env arg is passed, resolve paths relative to the CWD
+		const rootDir = process.env.INIT_CWD ?? '';
+		resolveEnv(
+			argv.env.map(p => path.resolve(rootDir, p.toString()))
+		);
+	} else if (argv.envCascade) {
+		// if env-cascade arg is passed, resolve paths relative to the config file
+
+		// Load order: .env < .env.local < .env.[override] < .env.[override].local
+		resolveEnv([
+			path.resolve(configDir, '.env'),
+			path.resolve(configDir, '.env.local'),
+			path.resolve(configDir, `.env.${argv.envCascade}`),
+			path.resolve(configDir, `.env.${argv.envCascade}.local`)
+		]);
+	} else {
+		// default to loading .env and .env.local in the config dir
+		resolveEnv([
+			path.resolve(configDir, '.env'),
+			path.resolve(configDir, '.env.local')
+		]);
+	}
+
+	return ResultAsync.fromPromise(loadConfigFromFile(configPath), (e) => new ConfigError(`Failed to load config file at path: ${chalk.white(configPath)}`))
+		.map(config => resolveLaunchpadOptions(config));
+}
+
+/**
+ * 
+ * @param {import('../launchpad-options.js').LaunchpadOptions} config 
+ */
+export function initializeLogger(config) {
+	const rootLogger = LogManager.configureRootLogger(config.logging);
+
+	return ok({ config, rootLogger });
+}
+
+/**
+ * 
+ * @param {Error} error 
+ * @param {import('@bluecadet/launchpad-utils').Logger} rootLogger
+ * @returns {never}
+ */
+export function handleFatalError(error, rootLogger) {
+	rootLogger.error('Content failed to download.');
+	logFullErrorChain(rootLogger, error);
+	process.exit(1);
+}
+
+/**
+ * @param {import('@bluecadet/launchpad-utils').Logger} logger
+ * @param {Error} error
+ */
+export function logFullErrorChain(logger, error) {
+	/** @type {Error | undefined} */
+	let currentError = error;
+	while (currentError) {
+		logger.error(`${chalk.red('┌─')} ${chalk.red.bold(currentError.name)}: ${chalk.red(currentError.message)}`);
+		const callstack = currentError.stack;
+		// logger.error(`${chalk.red(callstack ? '│' : '└')} `);
+		if (callstack) {
+			const lines = callstack.split('\n').slice(1);
+			// log up to 3 lines of the callstack
+			let loggedLines = 0;
+			for (const line of lines) {
+				const isLastLine = loggedLines === lines.length - 1 || loggedLines > 2;
+				logger.error(`${chalk.red('│')} ${chalk.red.dim((isLastLine && lines.length > 3) ? '...' : line.trim())}`);
+				if (isLastLine) {
+					logger.error(`${chalk.red('└──────────────────')}`);
+				}
+				loggedLines++;
+
+				if (loggedLines > 3) {
+					break;
+				}
+			}
+		}
+		if (currentError.cause && currentError.cause instanceof Error) {
+			currentError = currentError.cause;
+			logger.error(`    ${chalk.red.dim('│')} ${chalk.red.dim('Caused by:')}`);
+			logger.error(`    ${chalk.red.dim('│')}`);
+		} else {
+			currentError = undefined;
+		}
+	}
+}
diff --git a/packages/cli/lib/utils/load-config-and-env.js b/packages/cli/lib/utils/load-config-and-env.js
deleted file mode 100644
index 87f2a472..00000000
--- a/packages/cli/lib/utils/load-config-and-env.js
+++ /dev/null
@@ -1,48 +0,0 @@
-import { err, errAsync, ok, ResultAsync } from 'neverthrow';
-import { findConfig, loadConfigFromFile } from './config.js';
-import { ConfigError } from '../errors.js';
-import path from 'path';
-import { resolveEnv } from './env.js';
-import { resolveLaunchpadOptions } from '../launchpad-options.js';
-import chalk from 'chalk';
-
-/**
- * @param {import("../cli.js").LaunchpadArgv} argv
- * @returns {import('neverthrow').ResultAsync<import('../launchpad-options.js').ResolvedLaunchpadOptions, ConfigError>}
- */
-export function loadConfigAndEnv(argv) {
-	const configPath = argv.config ?? findConfig();
-
-	if (!configPath) {
-		return errAsync(new ConfigError('No config file found.'));
-	}
-
-	const configDir = path.dirname(configPath);
-
-	if (argv.env) {
-		// if env arg is passed, resolve paths relative to the CWD
-		const rootDir = process.env.INIT_CWD ?? '';
-		resolveEnv(
-			argv.env.map(p => path.resolve(rootDir, p.toString()))
-		);
-	} else if (argv.envCascade) {
-		// if env-cascade arg is passed, resolve paths relative to the config file
-
-		// Load order: .env < .env.local < .env.[override] < .env.[override].local
-		resolveEnv([
-			path.resolve(configDir, '.env'),
-			path.resolve(configDir, '.env.local'),
-			path.resolve(configDir, `.env.${argv.envCascade}`),
-			path.resolve(configDir, `.env.${argv.envCascade}.local`)
-		]);
-	} else {
-		// default to loading .env and .env.local in the config dir
-		resolveEnv([
-			path.resolve(configDir, '.env'),
-			path.resolve(configDir, '.env.local')
-		]);
-	}
-
-	return ResultAsync.fromPromise(loadConfigFromFile(configPath), (e) => new ConfigError(`Failed to load config file at path: ${chalk.white(configPath)}`))
-		.map(config => resolveLaunchpadOptions(config));
-}
diff --git a/packages/content/lib/launchpad-content.js b/packages/content/lib/launchpad-content.js
index 19b38656..4ba9a3eb 100644
--- a/packages/content/lib/launchpad-content.js
+++ b/packages/content/lib/launchpad-content.js
@@ -30,16 +30,12 @@ export class LaunchpadContent {
 	_dataStore;
 
 	/**
-	 * @param {import('./content-options.js').ContentOptions} [config]
-	 * @param {import('@bluecadet/launchpad-utils').Logger} [parentLogger]
+	 * @param {import('./content-options.js').ContentOptions} config
+	 * @param {import('@bluecadet/launchpad-utils').Logger} parentLogger
 	 */
 	constructor(config, parentLogger) {
 		this._config = resolveContentOptions(config);
 
-		if (!parentLogger) {
-			LogManager.configureRootLogger();
-		}
-
 		this._logger = LogManager.getLogger('content', parentLogger);
 
 		this._dataStore = new DataStore();
@@ -93,6 +89,7 @@ export class LaunchpadContent {
 						this._logger.error('Error in content fetch process:', e);
 						this._logger.info('Restoring from backup...');
 						return this.restore(sources).andThen(() => {
+							console.log('HERE');
 							return err(new ContentError('Failed to download content. Restored from backup.', { cause: e }));
 						});
 					})
@@ -108,7 +105,7 @@ export class LaunchpadContent {
 	 * Alias for start(source)
 	 * @param {import('./content-options.js').ConfigContentSource[]?} rawSources
 	 */
-	async download(rawSources = null) {
+	download(rawSources = null) {
 		return this.start(rawSources);
 	}
 
@@ -197,17 +194,17 @@ export class LaunchpadContent {
 				}
 				return ok(undefined);
 			}).andTee(() => {
-				this._logger.info(`Restoring ${source} from backup`);
+				this._logger.info(`Restoring ${chalk.white(source.id)} from backup`);
 			}).andThen(() => {
 				return FileUtils.copy(backupPath, downloadPath, { preserveTimestamps: true });
 			}).andThen(() => {
 				if (removeBackups) {
-					this._logger.debug(`Removing backup for ${source}`);
+					this._logger.debug(`Removing backup for ${chalk.white(source.id)}`);
 					return FileUtils.remove(backupPath);
 				}
 
 				return okAsync(undefined);
-			}).mapErr(e => new ContentError(`Failed to restore source ${source.id}: ${e}`));
+			}).mapErr(e => new ContentError(`Failed to restore source ${chalk.white(source.id)}: ${e}`));
 		})).map(() => undefined); // return void instead of void[]
 	}
 
diff --git a/packages/monitor/lib/launchpad-monitor.js b/packages/monitor/lib/launchpad-monitor.js
index 2972c618..c70b36a2 100644
--- a/packages/monitor/lib/launchpad-monitor.js
+++ b/packages/monitor/lib/launchpad-monitor.js
@@ -72,16 +72,12 @@ export class LaunchpadMonitor {
 	
 	/**
 	 * 
-	 * @param {import('./monitor-options.js').MonitorOptions} [config] 
-   * @param {import('@bluecadet/launchpad-utils').Logger} [parentLogger]
+	 * @param {import('./monitor-options.js').MonitorOptions} config
+   * @param {import('@bluecadet/launchpad-utils').Logger} parentLogger
 	 */
 	constructor(config, parentLogger) {
 		autoBind(this);
 
-		if (!parentLogger) {
-			LogManager.configureRootLogger();
-		}
-
 		this._logger = LogManager.getLogger('monitor', parentLogger);
 		
 		this._config = resolveMonitorConfig(config);
diff --git a/packages/scaffold/index.js b/packages/scaffold/index.js
index a07cb423..7ef23cdb 100755
--- a/packages/scaffold/index.js
+++ b/packages/scaffold/index.js
@@ -8,10 +8,6 @@ import * as path from 'path';
  * @param {import('@bluecadet/launchpad-utils').Logger} [parentLogger]
  */
 export function launchScaffold(parentLogger) {
-	if (!parentLogger) {
-		LogManager.configureRootLogger();
-	}
-
 	const logger = LogManager.getLogger('scaffold', parentLogger);
 
 	if (process.platform !== 'win32') {
diff --git a/packages/utils/lib/log-manager.js b/packages/utils/lib/log-manager.js
index d2b79601..306ad446 100644
--- a/packages/utils/lib/log-manager.js
+++ b/packages/utils/lib/log-manager.js
@@ -8,7 +8,6 @@ import 'winston-daily-rotate-file';
 import slugify from '@sindresorhus/slugify';
 import moment from 'moment';
 import chalk from 'chalk';
-import { text } from 'stream/consumers';
 
 /**
  * @callback createChildLogger
@@ -160,7 +159,7 @@ export class LogManager {
 			this._instance._rootLogger.warn('Root logger already configured. Ignoring.');
 		}
 
-		return this._instance;
+		return this._instance._rootLogger;
 	}
 
 	/**