diff --git a/packages/amazonq/.changes/next-release/Bug Fix-6b8cf110-2050-4ac1-8a3b-637ed54980cf.json b/packages/amazonq/.changes/next-release/Bug Fix-6b8cf110-2050-4ac1-8a3b-637ed54980cf.json
new file mode 100644
index 00000000000..011b5eb6c62
--- /dev/null
+++ b/packages/amazonq/.changes/next-release/Bug Fix-6b8cf110-2050-4ac1-8a3b-637ed54980cf.json	
@@ -0,0 +1,4 @@
+{
+	"type": "Bug Fix",
+	"description": "Amazon Q /doc: Fix uploading file method throwing incorrect workspace too large error message"
+}
diff --git a/packages/core/src/amazonq/errors.ts b/packages/core/src/amazonq/errors.ts
new file mode 100644
index 00000000000..cf45cb61265
--- /dev/null
+++ b/packages/core/src/amazonq/errors.ts
@@ -0,0 +1,13 @@
+/*!
+ * Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ * SPDX-License-Identifier: Apache-2.0
+ *
+ */
+
+import { ToolkitError } from '../shared/errors'
+
+export class CommonAmazonQContentLengthError extends ToolkitError {
+    constructor(message: string) {
+        super(message, { code: 'CommonAmazonQContentLengthError' })
+    }
+}
diff --git a/packages/core/src/amazonq/util/files.ts b/packages/core/src/amazonq/util/files.ts
index 848e6c5d807..eef133c514f 100644
--- a/packages/core/src/amazonq/util/files.ts
+++ b/packages/core/src/amazonq/util/files.ts
@@ -12,7 +12,7 @@ import {
     getWorkspaceFoldersByPrefixes,
 } from '../../shared/utilities/workspaceUtils'
 
-import { ContentLengthError, PrepareRepoFailedError } from '../../amazonqFeatureDev/errors'
+import { PrepareRepoFailedError } from '../../amazonqFeatureDev/errors'
 import { getLogger } from '../../shared/logger/logger'
 import { maxFileSizeBytes } from '../../amazonqFeatureDev/limits'
 import { CurrentWsFolders, DeletedFileInfo, NewFileInfo, NewFileZipContents } from '../../amazonqDoc/types'
@@ -28,6 +28,7 @@ import { ZipStream } from '../../shared/utilities/zipStream'
 import { isPresent } from '../../shared/utilities/collectionUtils'
 import { AuthUtil } from '../../codewhisperer/util/authUtil'
 import { TelemetryHelper } from '../util/telemetryHelper'
+import { CommonAmazonQContentLengthError } from '../errors'
 
 export const SvgFileExtension = '.svg'
 
@@ -186,7 +187,7 @@ export async function prepareRepoData(
     } catch (error) {
         getLogger().debug(`featureDev: Failed to prepare repo: ${error}`)
         if (error instanceof ToolkitError && error.code === 'ContentLengthError') {
-            throw new ContentLengthError()
+            throw new CommonAmazonQContentLengthError(error.message)
         }
         throw new PrepareRepoFailedError()
     }
diff --git a/packages/core/src/amazonqDoc/session/session.ts b/packages/core/src/amazonqDoc/session/session.ts
index f132799d8ae..73f725118ea 100644
--- a/packages/core/src/amazonqDoc/session/session.ts
+++ b/packages/core/src/amazonqDoc/session/session.ts
@@ -30,6 +30,8 @@ import fs from '../../shared/fs/fs'
 import globals from '../../shared/extensionGlobals'
 import { extensionVersion } from '../../shared/vscode/env'
 import { getLogger } from '../../shared/logger/logger'
+import { ContentLengthError } from '../errors'
+import { CommonAmazonQContentLengthError } from '../../amazonq/errors'
 
 export class Session {
     private _state?: SessionState | Omit<SessionState, 'uploadId'>
@@ -126,28 +128,35 @@ export class Session {
         return this.nextInteraction(msg, mode, folderPath)
     }
     private async nextInteraction(msg: string, mode: Mode, folderPath?: string) {
-        const resp = await this.state.interact({
-            task: this.task,
-            msg,
-            fs: this.config.fs,
-            mode: mode,
-            folderPath: folderPath,
-            messenger: this.messenger,
-            telemetry: this.telemetry,
-            tokenSource: this.state.tokenSource,
-            uploadHistory: this.state.uploadHistory,
-        })
+        try {
+            const resp = await this.state.interact({
+                task: this.task,
+                msg,
+                fs: this.config.fs,
+                mode: mode,
+                folderPath: folderPath,
+                messenger: this.messenger,
+                telemetry: this.telemetry,
+                tokenSource: this.state.tokenSource,
+                uploadHistory: this.state.uploadHistory,
+            })
+
+            if (resp.nextState) {
+                if (!this.state?.tokenSource?.token.isCancellationRequested) {
+                    this.state?.tokenSource?.cancel()
+                }
 
-        if (resp.nextState) {
-            if (!this.state?.tokenSource?.token.isCancellationRequested) {
-                this.state?.tokenSource?.cancel()
+                // Move to the next state
+                this._state = resp.nextState
             }
 
-            // Move to the next state
-            this._state = resp.nextState
+            return resp.interaction
+        } catch (e) {
+            if (e instanceof CommonAmazonQContentLengthError) {
+                throw new ContentLengthError()
+            }
+            throw e
         }
-
-        return resp.interaction
     }
 
     public async updateFilesPaths(
diff --git a/packages/core/src/amazonqFeatureDev/session/session.ts b/packages/core/src/amazonqFeatureDev/session/session.ts
index 3ce3000757e..447d078d3cb 100644
--- a/packages/core/src/amazonqFeatureDev/session/session.ts
+++ b/packages/core/src/amazonqFeatureDev/session/session.ts
@@ -14,7 +14,7 @@ import {
     type SessionStateConfig,
     UpdateFilesPathsParams,
 } from '../../amazonq/commons/types'
-import { ConversationIdNotFoundError } from '../errors'
+import { ContentLengthError, ConversationIdNotFoundError } from '../errors'
 import { featureDevChat, referenceLogText, featureDevScheme } from '../constants'
 import fs from '../../shared/fs/fs'
 import { FeatureDevClient } from '../client/featureDev'
@@ -33,6 +33,7 @@ import { UpdateAnswerMessage } from '../../amazonq/commons/connector/connectorMe
 import { FollowUpTypes } from '../../amazonq/commons/types'
 import { SessionConfig } from '../../amazonq/commons/session/sessionConfigFactory'
 import { Messenger } from '../../amazonq/commons/connector/baseMessenger'
+import { CommonAmazonQContentLengthError } from '../../amazonq/errors'
 export class Session {
     private _state?: SessionState | Omit<SessionState, 'uploadId'>
     private task: string = ''
@@ -137,25 +138,32 @@ export class Session {
     }
 
     private async nextInteraction(msg: string) {
-        const resp = await this.state.interact({
-            task: this.task,
-            msg,
-            fs: this.config.fs,
-            messenger: this.messenger,
-            telemetry: this.telemetry,
-            tokenSource: this.state.tokenSource,
-            uploadHistory: this.state.uploadHistory,
-        })
+        try {
+            const resp = await this.state.interact({
+                task: this.task,
+                msg,
+                fs: this.config.fs,
+                messenger: this.messenger,
+                telemetry: this.telemetry,
+                tokenSource: this.state.tokenSource,
+                uploadHistory: this.state.uploadHistory,
+            })
 
-        if (resp.nextState) {
-            if (!this.state?.tokenSource?.token.isCancellationRequested) {
-                this.state?.tokenSource?.cancel()
+            if (resp.nextState) {
+                if (!this.state?.tokenSource?.token.isCancellationRequested) {
+                    this.state?.tokenSource?.cancel()
+                }
+                // Move to the next state
+                this._state = resp.nextState
             }
-            // Move to the next state
-            this._state = resp.nextState
-        }
 
-        return resp.interaction
+            return resp.interaction
+        } catch (e) {
+            if (e instanceof CommonAmazonQContentLengthError) {
+                throw new ContentLengthError()
+            }
+            throw e
+        }
     }
 
     public async updateFilesPaths(params: UpdateFilesPathsParams) {