diff --git a/src/commands/project/retrieve/start.ts b/src/commands/project/retrieve/start.ts
index fef75887..e40d8041 100644
--- a/src/commands/project/retrieve/start.ts
+++ b/src/commands/project/retrieve/start.ts
@@ -373,6 +373,19 @@ const buildRetrieveAndDeleteTargets = async (
     }
     return result;
   } else {
+    // check if we're retrieving metadata based on a pattern ...
+    let retrieveFromOrg: string | undefined;
+    if (flags.metadata) {
+      flags.metadata.some((mdEntry) => {
+        const mdName = mdEntry.split(':')[1];
+        if (mdName?.includes('*') && mdName?.length > 1 && !mdName?.includes('.*')) {
+          retrieveFromOrg = flags['target-org'].getUsername();
+          return true;
+        }
+        return false;
+      });
+    }
+
     return {
       componentSetFromNonDeletes: await ComponentSetBuilder.build({
         sourceapiversion: (
@@ -399,6 +412,7 @@ const buildRetrieveAndDeleteTargets = async (
               },
             }
           : {}),
+        org: retrieveFromOrg ? { username: retrieveFromOrg, exclude: [] } : undefined,
       }),
     };
   }
diff --git a/test/commands/retrieve/start.test.ts b/test/commands/retrieve/start.test.ts
index f71211bf..dbfdfceb 100644
--- a/test/commands/retrieve/start.test.ts
+++ b/test/commands/retrieve/start.test.ts
@@ -169,6 +169,23 @@ describe('project retrieve start', () => {
     ensureRetrieveArgs({ format: 'source' });
   });
 
+  it('should pass along metadata and org for wildcard matching', async () => {
+    const metadata = ['ApexClass:MyC*'];
+    const result = await RetrieveMetadata.run(['--metadata', metadata[0], '--json']);
+    expect(result).to.deep.equal(expectedResults);
+    ensureCreateComponentSetArgs({
+      metadata: {
+        metadataEntries: metadata,
+        directoryPaths: [expectedDirectoryPath],
+      },
+      org: {
+        username: testOrg.username,
+        exclude: [],
+      },
+    });
+    ensureRetrieveArgs({ format: 'source' });
+  });
+
   it('should pass along manifest', async () => {
     const manifest = 'package.xml';
     const result = await RetrieveMetadata.run(['--manifest', manifest, '--json']);
diff --git a/test/nuts/deploy/metadata.nut.ts b/test/nuts/deploy/metadata.nut.ts
new file mode 100644
index 00000000..dfa818f8
--- /dev/null
+++ b/test/nuts/deploy/metadata.nut.ts
@@ -0,0 +1,51 @@
+/*
+ * Copyright (c) 2023, salesforce.com, inc.
+ * All rights reserved.
+ * Licensed under the BSD 3-Clause license.
+ * For full license text, see LICENSE.txt file in the repo root or https://opensource.org/licenses/BSD-3-Clause
+ */
+
+import { fileURLToPath } from 'node:url';
+import { expect } from 'chai';
+import { SourceTestkit } from '@salesforce/source-testkit';
+import { DeployResultJson } from '../../../src/utils/types.js';
+
+describe('deploy metadata NUTs', () => {
+  let testkit: SourceTestkit;
+
+  before(async () => {
+    testkit = await SourceTestkit.create({
+      repository: 'https://github.com/trailheadapps/dreamhouse-lwc.git',
+      nut: fileURLToPath(import.meta.url),
+    });
+    await testkit.deploy({ args: '--source-dir force-app', exitCode: 0 });
+  });
+
+  after(async () => {
+    await testkit?.clean();
+  });
+
+  it('should deploy ApexClasses from wildcard match (single character)', async () => {
+    const response = await testkit.deploy({ args: '--metadata "ApexClass:P*"' });
+    expect(response?.status).to.equal(0);
+    const result = response?.result as unknown as DeployResultJson;
+    expect(result.success).to.be.true;
+    expect(result.files.length).to.equal(4);
+    result.files.forEach((f) => {
+      expect(f.type).to.equal('ApexClass');
+      expect(['PagedResult', 'PropertyController']).to.include(f.fullName);
+    });
+  });
+
+  it('should deploy ApexClasses from wildcard match (2 characters)', async () => {
+    const response = await testkit.deploy({ args: '--metadata "ApexClass:Pa*"' });
+    expect(response?.status).to.equal(0);
+    const result = response?.result as unknown as DeployResultJson;
+    expect(result.success).to.be.true;
+    expect(result.files.length).to.equal(2);
+    result.files.forEach((f) => {
+      expect(f.type).to.equal('ApexClass');
+      expect(f.fullName).to.equal('PagedResult');
+    });
+  });
+});
diff --git a/test/nuts/retrieve/metadata.nut.ts b/test/nuts/retrieve/metadata.nut.ts
index 8b2bad21..bad269f7 100644
--- a/test/nuts/retrieve/metadata.nut.ts
+++ b/test/nuts/retrieve/metadata.nut.ts
@@ -11,6 +11,7 @@ import { fileURLToPath } from 'node:url';
 import { execCmd } from '@salesforce/cli-plugins-testkit';
 import { SourceTestkit } from '@salesforce/source-testkit';
 import { expect } from 'chai';
+import { RetrieveResultJson } from '../../../src/utils/types.js';
 
 const ELECTRON = { id: '04t6A000002zgKSQAY', name: 'ElectronBranding' };
 
@@ -57,6 +58,48 @@ describe('retrieve metadata NUTs', () => {
       await testkit.retrieve({ args: '--metadata ApexClass AuraDefinitionBundle --output-dir myOutput' });
       await testkit.expect.filesToBeRetrieved(['myOutput/classes/*', 'myOutput/aura/**/*']);
     });
+
+    it('should retrieve ApexClasses from wildcard match', async () => {
+      const response = await testkit.retrieve({ args: '--metadata "ApexClass:Test*"' });
+      expect(response?.status).to.equal(0);
+      const result = response?.result as unknown as RetrieveResultJson;
+      expect(result.success).to.be.true;
+      expect(result.files.length).to.equal(4);
+      result.files.forEach((f) => {
+        expect(f.type).to.equal('ApexClass');
+        expect(['TestSampleDataController', 'TestPropertyController']).to.include(f.fullName);
+      });
+      await testkit.expect.filesToBeRetrieved(['force-app/main/default/classes/Test*']);
+    });
+
+    it('should retrieve ApexClasses from wildcard match without already existing in the project', async () => {
+      const forceAppDir = path.join(testkit.projectDir, 'force-app');
+      const forceAppDirTmp = path.join(testkit.projectDir, 'force-app-tmp');
+
+      try {
+        fs.cpSync(forceAppDir, forceAppDirTmp, { recursive: true });
+        fs.rmSync(forceAppDir, { recursive: true, force: true });
+        expect(fs.existsSync(forceAppDir)).to.be.false;
+        const defaultDir = path.join(forceAppDir, 'main', 'default');
+        fs.mkdirSync(defaultDir, { recursive: true });
+
+        const response = await testkit.retrieve({ args: '--metadata "ApexClass:Test*"' });
+        expect(response?.status).to.equal(0);
+        const result = response?.result as unknown as RetrieveResultJson;
+        expect(result.success).to.be.true;
+        expect(result.files.length).to.equal(4);
+        result.files.forEach((f) => {
+          expect(f.type).to.equal('ApexClass');
+          expect(['TestSampleDataController', 'TestPropertyController']).to.include(f.fullName);
+        });
+        await testkit.expect.filesToBeRetrieved(['force-app/main/default/classes/Test*']);
+      } finally {
+        if (fs.existsSync(forceAppDirTmp)) {
+          fs.cpSync(forceAppDirTmp, forceAppDir, { recursive: true });
+          fs.rmSync(forceAppDirTmp, { recursive: true, force: true });
+        }
+      }
+    });
   });
 
   describe('--manifest flag', () => {