diff --git a/packages/amplify-cli/src/__tests__/context-manager.test.ts b/packages/amplify-cli/src/__tests__/context-manager.test.ts
index 82785cd268d..c0f19504c88 100644
--- a/packages/amplify-cli/src/__tests__/context-manager.test.ts
+++ b/packages/amplify-cli/src/__tests__/context-manager.test.ts
@@ -55,6 +55,7 @@ describe('test attachUsageData', () => {
     assignProjectIdentifier: jest.fn(),
     getUsageDataPayload: jest.fn(),
     calculatePushNormalizationFactor: jest.fn(),
+    getSessionUuid: jest.fn(),
   };
 
   const stateManagerMocked = stateManager as jest.Mocked<typeof stateManager>;
diff --git a/packages/amplify-cli/src/__tests__/execution-manager.test.ts b/packages/amplify-cli/src/__tests__/execution-manager.test.ts
index d5f1beb70b6..6842b10a29c 100644
--- a/packages/amplify-cli/src/__tests__/execution-manager.test.ts
+++ b/packages/amplify-cli/src/__tests__/execution-manager.test.ts
@@ -77,6 +77,7 @@ describe('execution manager', () => {
     assignProjectIdentifier: jest.fn(),
     getUsageDataPayload: jest.fn(),
     calculatePushNormalizationFactor: jest.fn(),
+    getSessionUuid: jest.fn(),
   };
 
   beforeEach(() => {
diff --git a/packages/amplify-cli/src/__tests__/test-aborting.test.ts b/packages/amplify-cli/src/__tests__/test-aborting.test.ts
index 9ecb7712de8..843da006551 100644
--- a/packages/amplify-cli/src/__tests__/test-aborting.test.ts
+++ b/packages/amplify-cli/src/__tests__/test-aborting.test.ts
@@ -88,6 +88,7 @@ describe('test SIGINT with execute', () => {
       assignProjectIdentifier: jest.fn(),
       getUsageDataPayload: jest.fn(),
       calculatePushNormalizationFactor: jest.fn(),
+      getSessionUuid: jest.fn(),
     };
     mockContext.projectHasMobileHubResources = false;
 
diff --git a/packages/amplify-cli/src/amplify-exception-handler.ts b/packages/amplify-cli/src/amplify-exception-handler.ts
index 4be1d157865..f1d5484abd5 100644
--- a/packages/amplify-cli/src/amplify-exception-handler.ts
+++ b/packages/amplify-cli/src/amplify-exception-handler.ts
@@ -7,7 +7,7 @@ import {
   HooksMeta,
 } from 'amplify-cli-core';
 import { logger } from 'amplify-cli-logger';
-import { AmplifyPrinter, printer, isDebug } from 'amplify-prompts';
+import { AmplifyPrinter, printer } from 'amplify-prompts';
 import { reportError } from './commands/diagnose';
 import { isHeadlessCommand } from './context-manager';
 import { Context } from './domain/context';
@@ -37,48 +37,40 @@ export const handleException = async (exception: unknown): Promise<void> => {
     amplifyException = genericErrorToAmplifyException(exception);
   }
 
+  const deepestException = getDeepestAmplifyException(amplifyException);
+  if (context && isHeadlessCommand(context)) {
+    printHeadlessAmplifyException(deepestException);
+  } else {
+    printAmplifyException(deepestException);
+  }
+
   if (context?.usageData) {
     await executeSafely(
-      () => context?.usageData.emitError(amplifyException), 'Failed to emit error to usage data',
+      () => {
+        context?.usageData.emitError(deepestException);
+        printer.blankLine();
+        printer.info(`Session Identifier: ${context?.usageData.getSessionUuid()}`);
+      }, 'Failed to emit error to usage data',
     );
   }
 
-  if (context && isHeadlessCommand(context)) {
-    printHeadlessAmplifyException(amplifyException);
-  } else {
-    printAmplifyException(amplifyException);
-
-    let { downstreamException } = amplifyException;
-    while (isDebug && downstreamException) {
-      printer.blankLine();
-
-      if (downstreamException instanceof AmplifyException) {
-        printAmplifyException(downstreamException);
-        downstreamException = downstreamException.downstreamException;
-      } else {
-        printError(downstreamException);
-        downstreamException = undefined;
-      }
-    }
-  }
-
   // Swallow and continue if any operations fail
   if (context) {
-    await executeSafely(() => reportError(context, amplifyException), 'Failed to report error');
+    await executeSafely(() => reportError(context, deepestException), 'Failed to report error');
   }
 
   await executeSafely(
     () => executeHooks(HooksMeta.getInstance(undefined, 'post', {
-      message: amplifyException.message ?? 'undefined error in Amplify process',
-      stack: amplifyException.stack ?? 'undefined error stack',
+      message: deepestException.message ?? 'undefined error in Amplify process',
+      stack: deepestException.stack ?? 'undefined error stack',
     })),
     'Failed to execute hooks',
   );
 
   await executeSafely(
     () => logger.logError({
-      message: amplifyException.message,
-      error: amplifyException,
+      message: deepestException.message,
+      error: deepestException,
     }),
     'Failed to log error',
   );
@@ -86,6 +78,14 @@ export const handleException = async (exception: unknown): Promise<void> => {
   process.exitCode = 1;
 };
 
+const getDeepestAmplifyException = (amplifyException: AmplifyException): AmplifyException => {
+  let deepestAmplifyException = amplifyException;
+  while (deepestAmplifyException.downstreamException && deepestAmplifyException.downstreamException instanceof AmplifyException) {
+    deepestAmplifyException = deepestAmplifyException.downstreamException;
+  }
+  return deepestAmplifyException;
+};
+
 /**
  * Utility function to ensure a passed in function does not invoke the exception handler to avoid an infinite loop
  *
@@ -117,15 +117,20 @@ const printAmplifyException = (amplifyException: AmplifyException): void => {
   if (link) {
     printer.info(`Learn more at: ${link}`);
   }
-  printer.blankLine();
+
   if (stack) {
+    printer.debug('');
     printer.debug(stack);
   }
+
+  if (amplifyException.downstreamException) {
+    printError(amplifyException.downstreamException);
+  }
 };
 
 const printError = (err: Error): void => {
-  printer.error(err.message);
-  printer.blankLine();
+  printer.debug('');
+  printer.debug(err.message);
   if (err.stack) {
     printer.debug(err.stack);
   }
diff --git a/packages/amplify-cli/src/domain/amplify-usageData/NoUsageData.ts b/packages/amplify-cli/src/domain/amplify-usageData/NoUsageData.ts
index 5df1b1f01a7..d0f00e4a928 100644
--- a/packages/amplify-cli/src/domain/amplify-usageData/NoUsageData.ts
+++ b/packages/amplify-cli/src/domain/amplify-usageData/NoUsageData.ts
@@ -53,6 +53,13 @@ export class NoUsageData implements IUsageData, IFlowData {
     /* noop */
   }
 
+  /**
+   * Noop implementation of getSessionUuid
+   */
+  getSessionUuid(): string {
+    return '';
+  }
+
   /**
    * Noop implementation of emitError
    */
diff --git a/packages/amplify-cli/src/domain/amplify-usageData/UsageData.ts b/packages/amplify-cli/src/domain/amplify-usageData/UsageData.ts
index 8c68992a147..a689fb53ec2 100644
--- a/packages/amplify-cli/src/domain/amplify-usageData/UsageData.ts
+++ b/packages/amplify-cli/src/domain/amplify-usageData/UsageData.ts
@@ -83,6 +83,13 @@ export class UsageData implements IUsageData {
     return UsageData.instance;
   }
 
+  /**
+   * returns current sessionUuid
+   */
+  getSessionUuid(): string {
+    return this.sessionUuid;
+  }
+
   /**
    * Emit usage data on error
    */
diff --git a/packages/amplify-cli/src/domain/amplify-usageData/UsageDataTypes.ts b/packages/amplify-cli/src/domain/amplify-usageData/UsageDataTypes.ts
index 1f5af4ffed0..d1f0abd3c1b 100644
--- a/packages/amplify-cli/src/domain/amplify-usageData/UsageDataTypes.ts
+++ b/packages/amplify-cli/src/domain/amplify-usageData/UsageDataTypes.ts
@@ -21,6 +21,7 @@ interface IUsageMetricsData {
   startCodePathTimer: (codePath: StartableTimedCodePath) => void;
   stopCodePathTimer: (codePath: StoppableTimedCodePath) => void;
   calculatePushNormalizationFactor: (events: { StackId: string, PhysicalResourceId: string } [], StackId: string) => void;
+  getSessionUuid: () => string;
 }
 
 /**