diff --git a/packages/core/src/amazonqGumby/chat/controller/controller.ts b/packages/core/src/amazonqGumby/chat/controller/controller.ts
index ae277ca24f9..90706cbf731 100644
--- a/packages/core/src/amazonqGumby/chat/controller/controller.ts
+++ b/packages/core/src/amazonqGumby/chat/controller/controller.ts
@@ -580,10 +580,14 @@ export class GumbyController {
             return
         }
         const fileContents = await fs.readFileText(fileUri[0].fsPath)
-        const isValidFile = await validateCustomVersionsFile(fileContents)
+        const missingKey = await validateCustomVersionsFile(fileContents)
 
-        if (!isValidFile) {
-            this.messenger.sendUnrecoverableErrorResponse('invalid-custom-versions-file', message.tabID)
+        if (missingKey) {
+            this.messenger.sendMessage(
+                CodeWhispererConstants.invalidCustomVersionsFileMessage(missingKey),
+                message.tabID,
+                'ai-prompt'
+            )
             return
         }
         this.messenger.sendMessage(CodeWhispererConstants.receivedValidConfigFileMessage, message.tabID, 'ai-prompt')
diff --git a/packages/core/src/amazonqGumby/chat/controller/messenger/messenger.ts b/packages/core/src/amazonqGumby/chat/controller/messenger/messenger.ts
index 59c144a8605..409ee89ab04 100644
--- a/packages/core/src/amazonqGumby/chat/controller/messenger/messenger.ts
+++ b/packages/core/src/amazonqGumby/chat/controller/messenger/messenger.ts
@@ -50,7 +50,6 @@ export type UnrecoverableErrorType =
     | 'job-start-failed'
     | 'unsupported-source-db'
     | 'unsupported-target-db'
-    | 'invalid-custom-versions-file'
     | 'error-parsing-sct-file'
     | 'invalid-zip-no-sct-file'
     | 'invalid-from-to-jdk'
@@ -453,9 +452,6 @@ export class Messenger {
             case 'unsupported-target-db':
                 message = CodeWhispererConstants.invalidMetadataFileUnsupportedTargetDB
                 break
-            case 'invalid-custom-versions-file':
-                message = CodeWhispererConstants.invalidCustomVersionsFileMessage
-                break
             case 'error-parsing-sct-file':
                 message = CodeWhispererConstants.invalidMetadataFileErrorParsing
                 break
diff --git a/packages/core/src/codewhisperer/models/constants.ts b/packages/core/src/codewhisperer/models/constants.ts
index 4db98727765..3e72ca1de19 100644
--- a/packages/core/src/codewhisperer/models/constants.ts
+++ b/packages/core/src/codewhisperer/models/constants.ts
@@ -582,8 +582,8 @@ export const invalidMetadataFileUnsupportedSourceDB =
 export const invalidMetadataFileUnsupportedTargetDB =
     'I can only convert SQL for migrations to Aurora PostgreSQL or Amazon RDS for PostgreSQL target databases. The provided .sct file indicates another target database for this migration.'
 
-export const invalidCustomVersionsFileMessage =
-    "I wasn't able to parse the dependency upgrade file. Check that it's configured properly and try again. For an example of the required dependency upgrade file format, see the [documentation](https://docs.aws.amazon.com/amazonq/latest/qdeveloper-ug/code-transformation.html#dependency-upgrade-file)."
+export const invalidCustomVersionsFileMessage = (missingKey: string) =>
+    `The dependency upgrade file provided is missing required field \`${missingKey}\`. Check that it is configured properly and try again. For an example of the required dependency upgrade file format, see the [documentation](https://docs.aws.amazon.com/amazonq/latest/qdeveloper-ug/code-transformation.html#dependency-upgrade-file).`
 
 export const invalidMetadataFileErrorParsing =
     "It looks like the .sct file you provided isn't valid. Make sure that you've uploaded the .zip file you retrieved from your schema conversion in AWS DMS."
diff --git a/packages/core/src/codewhisperer/service/transformByQ/transformFileHandler.ts b/packages/core/src/codewhisperer/service/transformByQ/transformFileHandler.ts
index 2ec6fdb7c37..6aad4fd15f6 100644
--- a/packages/core/src/codewhisperer/service/transformByQ/transformFileHandler.ts
+++ b/packages/core/src/codewhisperer/service/transformByQ/transformFileHandler.ts
@@ -117,15 +117,16 @@ export async function parseBuildFile() {
     return undefined
 }
 
+// return the first missing key in the custom versions file, or undefined if all required keys are present
 export async function validateCustomVersionsFile(fileContents: string) {
-    const requiredKeys = ['dependencyManagement:', 'identifier:', 'targetVersion:']
+    const requiredKeys = ['dependencyManagement', 'identifier', 'targetVersion', 'originType']
     for (const key of requiredKeys) {
         if (!fileContents.includes(key)) {
             getLogger().info(`CodeTransformation: .YAML file is missing required key: ${key}`)
-            return false
+            return key
         }
     }
-    return true
+    return undefined
 }
 
 export async function validateSQLMetadataFile(fileContents: string, message: any) {
diff --git a/packages/core/src/test/codewhisperer/commands/transformByQ.test.ts b/packages/core/src/test/codewhisperer/commands/transformByQ.test.ts
index 554d24c855a..8d2017100b9 100644
--- a/packages/core/src/test/codewhisperer/commands/transformByQ.test.ts
+++ b/packages/core/src/test/codewhisperer/commands/transformByQ.test.ts
@@ -571,14 +571,14 @@ dependencyManagement:
     })
 
     it(`WHEN validateCustomVersionsFile on fully valid .yaml file THEN passes validation`, async function () {
-        const isValidFile = await validateCustomVersionsFile(validCustomVersionsFile)
-        assert.strictEqual(isValidFile, true)
+        const missingKey = await validateCustomVersionsFile(validCustomVersionsFile)
+        assert.strictEqual(missingKey, undefined)
     })
 
     it(`WHEN validateCustomVersionsFile on invalid .yaml file THEN fails validation`, async function () {
         const invalidFile = validCustomVersionsFile.replace('dependencyManagement', 'invalidKey')
-        const isValidFile = await validateCustomVersionsFile(invalidFile)
-        assert.strictEqual(isValidFile, false)
+        const missingKey = await validateCustomVersionsFile(invalidFile)
+        assert.strictEqual(missingKey, 'dependencyManagement')
     })
 
     it(`WHEN validateMetadataFile on fully valid .sct file THEN passes validation`, async function () {