diff --git a/src/cli/cli.ts b/src/cli/cli.ts
index efd4ea60932..da2fea836b6 100644
--- a/src/cli/cli.ts
+++ b/src/cli/cli.ts
@@ -5,7 +5,7 @@ import os from 'os';
 import path from 'path';
 import { fileURLToPath, pathToFileURL } from 'url';
 import yargs from 'yargs-parser';
-import { ZodError } from 'zod';
+import { ZodCustomIssue, ZodError, ZodIssue } from 'zod';
 import Command, { CommandArgs, CommandError } from '../Command.js';
 import GlobalOptions from '../GlobalOptions.js';
 import config from '../config.js';
@@ -186,14 +186,34 @@ async function execute(rawArgs: string[]): Promise<void> {
         break;
       }
       else {
-        const hasNonRequiredErrors = result.error.errors.some(e => e.code !== 'invalid_type' || e.received !== 'undefined');
         const shouldPrompt = cli.getSettingWithDefaultValue<boolean>(settingsNames.prompt, true);
 
-        if (hasNonRequiredErrors === false &&
-          shouldPrompt) {
+        if (!shouldPrompt) {
+          result.error.errors.forEach(e => {
+            if (e.code === 'invalid_type' &&
+              e.received === 'undefined') {
+              e.message = `Required option not specified`;
+            }
+          });
+          return cli.closeWithError(result.error, cli.optionsFromArgs, true);
+        }
+
+        const missingRequiredValuesErrors: ZodIssue[] = result.error.errors
+          .filter(e => (e.code === 'invalid_type' && e.received === 'undefined') ||
+            (e.code === 'custom' && e.params?.customCode === 'required'));
+        const optionSetErrors: ZodCustomIssue[] = result.error.errors
+          .filter(e => e.code === 'custom' && e.params?.customCode === 'optionSet') as ZodCustomIssue[];
+        const otherErrors: ZodIssue[] = result.error.errors
+          .filter(e => !missingRequiredValuesErrors.includes(e) && !optionSetErrors.includes(e as ZodCustomIssue));
+
+        if (otherErrors.some(e => e)) {
+          return cli.closeWithError(result.error, cli.optionsFromArgs, true);
+        }
+
+        if (missingRequiredValuesErrors.some(e => e)) {
           await cli.error('🌶️  Provide values for the following parameters:');
 
-          for (const error of result.error.errors) {
+          for (const error of missingRequiredValuesErrors) {
             const optionName = error.path.join('.');
             const optionInfo = cli.commandToExecute.options.find(o => o.name === optionName);
             const answer = await cli.promptForValue(optionInfo!);
@@ -206,15 +226,14 @@ async function execute(rawArgs: string[]): Promise<void> {
               return cli.closeWithError(e.message, cli.optionsFromArgs, true);
             }
           }
+
+          continue;
         }
-        else {
-          result.error.errors.forEach(e => {
-            if (e.code === 'invalid_type' &&
-              e.received === 'undefined') {
-              e.message = `Required option not specified`;
-            }
-          });
-          return cli.closeWithError(result.error, cli.optionsFromArgs, true);
+
+        if (optionSetErrors.some(e => e)) {
+          for (const error of optionSetErrors) {
+            await promptForOptionSetNameAndValue(cli.optionsFromArgs, error.params?.options);
+          }
         }
       }
     }
@@ -1057,6 +1076,16 @@ function shouldTrimOutput(output: string | undefined): boolean {
   return output === 'text';
 }
 
+async function promptForOptionSetNameAndValue(args: CommandArgs, options: string[]): Promise<void> {
+  await cli.error(`🌶️  Please specify one of the following options:`);
+
+  const selectedOptionName = await prompt.forSelection<string>({ message: `Option to use:`, choices: options.map((choice: any) => { return { name: choice, value: choice }; }) });
+  const optionValue = await prompt.forInput({ message: `${selectedOptionName}:` });
+
+  args.options[selectedOptionName] = optionValue;
+  await cli.error('');
+}
+
 export const cli = {
   closeWithError,
   commands,
diff --git a/src/index.ts b/src/index.ts
index c1af5314a04..179a7403d4a 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -17,5 +17,14 @@ await (async () => {
     updateNotifier.default({ pkg: app.packageJson() as any }).notify({ defer: false });
   }
 
-  await cli.execute(process.argv.slice(2));
+  try {
+    await cli.execute(process.argv.slice(2));
+  }
+  catch (err) {
+    if (err instanceof Error && err.name === 'ExitPromptError') {
+      process.exit(1);
+    }
+
+    cli.closeWithError(err, cli.optionsFromArgs || { options: {} });
+  }
 })();
diff --git a/src/m365/commands/login.ts b/src/m365/commands/login.ts
index 60649cce0dc..6d7bb827b4f 100644
--- a/src/m365/commands/login.ts
+++ b/src/m365/commands/login.ts
@@ -52,19 +52,32 @@ class LoginCommand extends Command {
     return schema
       .refine(options => typeof options.appId !== 'undefined' || cli.getClientId() || options.authType === 'identity' || options.authType === 'federatedIdentity', {
         message: `appId is required. TIP: use the "m365 setup" command to configure the default appId.`,
-        path: ['appId']
+        path: ['appId'],
+        params: {
+          customCode: 'required'
+        }
       })
       .refine(options => options.authType !== 'password' || options.userName, {
         message: 'Username is required when using password authentication.',
-        path: ['userName']
+        path: ['userName'],
+        params: {
+          customCode: 'required'
+        }
       })
       .refine(options => options.authType !== 'password' || options.password, {
         message: 'Password is required when using password authentication.',
-        path: ['password']
+        path: ['password'],
+        params: {
+          customCode: 'required'
+        }
       })
       .refine(options => options.authType !== 'certificate' || !(options.certificateFile && options.certificateBase64Encoded), {
         message: 'Specify either certificateFile or certificateBase64Encoded, but not both.',
-        path: ['certificateBase64Encoded']
+        path: ['certificateBase64Encoded'],
+        params: {
+          customCode: 'optionSet',
+          options: ['certificateFile', 'certificateBase64Encoded']
+        }
       })
       .refine(options => options.authType !== 'certificate' ||
         options.certificateFile ||
@@ -72,13 +85,20 @@ class LoginCommand extends Command {
         cli.getConfig().get(settingsNames.clientCertificateFile) ||
         cli.getConfig().get(settingsNames.clientCertificateBase64Encoded), {
         message: 'Specify either certificateFile or certificateBase64Encoded.',
-        path: ['certificateFile']
+        path: ['certificateFile'],
+        params: {
+          customCode: 'optionSet',
+          options: ['certificateFile', 'certificateBase64Encoded']
+        }
       })
       .refine(options => options.authType !== 'secret' ||
         options.secret ||
         cli.getConfig().get(settingsNames.clientSecret), {
         message: 'Secret is required when using secret authentication.',
-        path: ['secret']
+        path: ['secret'],
+        params: {
+          customCode: 'required'
+        }
       });
   }
 
diff --git a/src/utils/prompt.ts b/src/utils/prompt.ts
index 56bc9d4e9a7..70177d86397 100644
--- a/src/utils/prompt.ts
+++ b/src/utils/prompt.ts
@@ -83,14 +83,7 @@ export const prompt = {
     const errorOutput: string = cli.getSettingWithDefaultValue(settingsNames.errorOutput, 'stderr');
 
     return inquirerInput
-      .default(config, { output: errorOutput === 'stderr' ? process.stderr : process.stdout })
-      .catch(error => {
-        if (error instanceof Error && error.name === 'ExitPromptError') {
-          return ''; // noop; handle Ctrl + C
-        }
-
-        throw error;
-      });
+      .default(config, { output: errorOutput === 'stderr' ? process.stderr : process.stdout });
   },
 
   /* c8 ignore next 9 */