diff --git a/client/src/components/ContentNavigator/ContentModel.ts b/client/src/components/ContentNavigator/ContentModel.ts
index 8a939cac6..288d05c58 100644
--- a/client/src/components/ContentNavigator/ContentModel.ts
+++ b/client/src/components/ContentNavigator/ContentModel.ts
@@ -1,6 +1,8 @@
 // Copyright © 2023, SAS Institute Inc., Cary, NC, USA.  All Rights Reserved.
 // SPDX-License-Identifier: Apache-2.0
-import { Uri } from "vscode";
+import { Uri, l10n } from "vscode";
+
+import { extname } from "path";
 
 import { ALL_ROOT_FOLDERS, Messages } from "./const";
 import { ContentAdapter, ContentItem } from "./types";
@@ -92,6 +94,43 @@ export class ContentModel {
     );
   }
 
+  public async createUniqueFileOfPrefix(
+    parentItem: ContentItem,
+    fileName: string,
+    buffer?: ArrayBufferLike,
+  ) {
+    const itemsInFolder = await this.getChildren(parentItem);
+    const uniqueFileName = getUniqueFileName();
+
+    return await this.createFile(parentItem, uniqueFileName, buffer);
+
+    function getUniqueFileName(): string {
+      const ext = extname(fileName);
+      const basename = fileName.replace(ext, "");
+      const usedFlowNames = itemsInFolder.reduce((carry, item) => {
+        if (item.name.endsWith(ext)) {
+          return { ...carry, [item.name]: true };
+        }
+        return carry;
+      }, {});
+
+      if (!usedFlowNames[fileName]) {
+        return fileName;
+      }
+
+      let number = 1;
+      let newFileName;
+      do {
+        newFileName = l10n.t("{basename}_Copy{number}.flw", {
+          basename,
+          number: number++,
+        });
+      } while (usedFlowNames[newFileName]);
+
+      return newFileName || fileName;
+    }
+  }
+
   public async createFolder(
     item: ContentItem,
     name: string,
diff --git a/client/src/components/ContentNavigator/convert.ts b/client/src/components/ContentNavigator/convert.ts
index be54ca318..4a8783e2a 100644
--- a/client/src/components/ContentNavigator/convert.ts
+++ b/client/src/components/ContentNavigator/convert.ts
@@ -411,7 +411,7 @@ export class NotebookToFlowConverter {
     }
 
     const parentItem = await this.parent();
-    const newItem = await this.contentModel.createFile(
+    const newItem = await this.contentModel.createUniqueFileOfPrefix(
       parentItem,
       outputName,
       flowDataUint8Array,
diff --git a/client/src/connection/rest/RestSASServerAdapter.ts b/client/src/connection/rest/RestSASServerAdapter.ts
index 0466e8a0a..b5e6e31c0 100644
--- a/client/src/connection/rest/RestSASServerAdapter.ts
+++ b/client/src/connection/rest/RestSASServerAdapter.ts
@@ -146,22 +146,26 @@ class RestSASServerAdapter implements ContentAdapter {
     fileName: string,
     buffer?: ArrayBufferLike,
   ): Promise<ContentItem | undefined> {
-    const response = await this.fileSystemApi.createFileOrDirectory({
-      sessionId: this.sessionId,
-      fileOrDirectoryPath: this.trimComputePrefix(parentItem.uri),
-      fileProperties: { name: fileName, isDirectory: false },
-    });
+    try {
+      const response = await this.fileSystemApi.createFileOrDirectory({
+        sessionId: this.sessionId,
+        fileOrDirectoryPath: this.trimComputePrefix(parentItem.uri),
+        fileProperties: { name: fileName, isDirectory: false },
+      });
 
-    const contentItem = this.filePropertiesToContentItem(response.data);
+      const contentItem = this.filePropertiesToContentItem(response.data);
 
-    if (buffer) {
-      await this.updateContentOfItemAtPath(
-        this.trimComputePrefix(contentItem.uri),
-        new TextDecoder().decode(buffer),
-      );
-    }
+      if (buffer) {
+        await this.updateContentOfItemAtPath(
+          this.trimComputePrefix(contentItem.uri),
+          new TextDecoder().decode(buffer),
+        );
+      }
 
-    return contentItem;
+      return contentItem;
+    } catch (error) {
+      return;
+    }
   }
 
   public async deleteItem(item: ContentItem): Promise<boolean> {