diff --git a/packages/core/src/amazonq/errors.ts b/packages/core/src/amazonq/errors.ts
index cf45cb61265..799206d7ab9 100644
--- a/packages/core/src/amazonq/errors.ts
+++ b/packages/core/src/amazonq/errors.ts
@@ -4,10 +4,15 @@
  *
  */
 
+/**
+ * Shared error type for content length validation.
+ * When thrown from common components, individual agents can catch and transform this error
+ * to provide their own customized error messages.
+ */
 import { ToolkitError } from '../shared/errors'
 
-export class CommonAmazonQContentLengthError extends ToolkitError {
+export class ContentLengthError extends ToolkitError {
     constructor(message: string) {
-        super(message, { code: 'CommonAmazonQContentLengthError' })
+        super(message, { code: 'ContentLengthError' })
     }
 }
diff --git a/packages/core/src/amazonq/util/files.ts b/packages/core/src/amazonq/util/files.ts
index eef133c514f..b7c25c7f887 100644
--- a/packages/core/src/amazonq/util/files.ts
+++ b/packages/core/src/amazonq/util/files.ts
@@ -28,7 +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'
+import { ContentLengthError } from '../errors'
 
 export const SvgFileExtension = '.svg'
 
@@ -185,9 +185,9 @@ export async function prepareRepoData(
             zipFileChecksum: zipResult.hash,
         }
     } catch (error) {
-        getLogger().debug(`featureDev: Failed to prepare repo: ${error}`)
+        getLogger().debug(`Failed to prepare repo: ${error}`)
         if (error instanceof ToolkitError && error.code === 'ContentLengthError') {
-            throw new CommonAmazonQContentLengthError(error.message)
+            throw new ContentLengthError(error.message)
         }
         throw new PrepareRepoFailedError()
     }
diff --git a/packages/core/src/amazonqDoc/session/session.ts b/packages/core/src/amazonqDoc/session/session.ts
index 73f725118ea..301a9d0e0fa 100644
--- a/packages/core/src/amazonqDoc/session/session.ts
+++ b/packages/core/src/amazonqDoc/session/session.ts
@@ -31,7 +31,7 @@ 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'
+import { ContentLengthError as CommonAmazonQContentLengthError } from '../../amazonq/errors'
 
 export class Session {
     private _state?: SessionState | Omit<SessionState, 'uploadId'>
@@ -153,6 +153,7 @@ export class Session {
             return resp.interaction
         } catch (e) {
             if (e instanceof CommonAmazonQContentLengthError) {
+                getLogger().debug(`Content length validation failed: ${e.message}`)
                 throw new ContentLengthError()
             }
             throw e
diff --git a/packages/core/src/amazonqFeatureDev/session/session.ts b/packages/core/src/amazonqFeatureDev/session/session.ts
index 447d078d3cb..6d692c297a4 100644
--- a/packages/core/src/amazonqFeatureDev/session/session.ts
+++ b/packages/core/src/amazonqFeatureDev/session/session.ts
@@ -33,7 +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'
+import { ContentLengthError as CommonAmazonQContentLengthError } from '../../amazonq/errors'
 export class Session {
     private _state?: SessionState | Omit<SessionState, 'uploadId'>
     private task: string = ''
@@ -160,6 +160,7 @@ export class Session {
             return resp.interaction
         } catch (e) {
             if (e instanceof CommonAmazonQContentLengthError) {
+                getLogger().debug(`Content length validation failed: ${e.message}`)
                 throw new ContentLengthError()
             }
             throw e