I can't change my password in outlook classic and I absolutely HATE HATE HATE the new version!!!

Hello Dawn,

Thank you for posting to the Microsoft Q&A forum. I understand how frustrating this must be, especially after having to change your password following a security issue. 

To answer your question about why it used to be simpler: Classic Outlook previously used a method called Basic Authentication, which allowed you to update your password directly in the app. However, Google has since disabled this method as part of their security improvements. 
Because of this change, Gmail accounts now need to connect through Google’s secure sign-in process. If the password is changed on the Google side, the previous connection in Classic Outlook becomes invalid, which is why the old “change password” method no longer works. 

The most reliable way to fix this is to remove the broken connection and re-add it: 

Step 1: Remove the Gmail Account from Classic Outlook 

1. Open Classic Outlook. 
2. Click File in the top left corner. 
3. Click Account Settings, and then click Account Settings again from the drop-down. 
4. Under the Email tab, select your Gmail account and click Remove. (Don't worry, this does not delete your emails, as they are safely stored on Google's servers). 
5. Close Outlook completely, then open it again. 

Step 2: Re-add to Trigger the Secure Prompt 

1. Go back to File > Add Account. 
2. Type in your Gmail address and click Connect. 
3. Classic Outlook will now launch a secure Google sign-in window. Enter your new Gmail password here. 
4. Crucial Step: When it asks for permissions, make absolutely sure to check the box that says "Read, compose, send, and permanently delete all your email from Gmail", then click Allow. 

I hope my explanation of why the password process has changed and the recommendations work for you to get everything running smoothly in Classic Outlook again. Please don't hesitate to reach out if you run into any trouble with these steps. 

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

In classic Outlook, the Gmail password cannot be changed directly inside Outlook until it has first been changed with Google, and for many Gmail accounts an app password (not the normal Gmail password) is required.

Use these steps in order:

1. Confirm the Gmail password and app password
   • Make sure the Gmail account password was successfully changed on Google’s website and that sign-in to Gmail via a browser works.
   • If the Gmail account has 2-step verification enabled, Outlook classic usually needs a Google app password, not the regular Gmail password. If Outlook is using a Microsoft app password by mistake, it will fail; this was the root cause in a similar case where the user discovered they were using a Microsoft App Password instead of a Google App Password and the problem was fixed.
2. Update the password stored in classic Outlook
   • After the password is changed with Google, classic Outlook will prompt for the updated password when sending/receiving. Enter the correct Google app password (or the new Gmail password if app passwords are not required).
   • If Outlook keeps asking for the password:
     • Verify Caps Lock is off.
     • Confirm the username is the full Gmail address (for example, ******@contoso.com).
     • This repeated prompt usually means either the password in Outlook does not match the one set with Google, or the wrong type of password (e.g., Microsoft app password instead of Google app password) is being used.
3. Check account type and IMAP/POP settings
   • Ensure the Gmail account in classic Outlook is configured with the correct account type and server settings (IMAP or POP) that match Google’s requirements. If the account type or server settings are wrong, Outlook may not accept the password even if it’s correct.
   • If classic Outlook is not syncing messages and folders as expected, verify that the account type matches the provider (for Gmail, use the proper Gmail/IMAP configuration rather than an incorrect type like Exchange or Microsoft 365).
4. If Outlook never prompts for a password
   • For IMAP accounts like Gmail, if Outlook classic never asks for a password:
     • Edit the account settings and make sure Require logon using Secure Password Authentication (SPA) is unchecked on the IMAP details page.
     • If that does not work, use Control Panel → Mail → Email Accounts → New, and re-add the Gmail account, entering the correct Gmail address and the correct Google app password when prompted.
5. Why it feels harder than before
   • Classic Outlook used to feel simpler because many accounts did not use modern security like 2-factor authentication and app passwords. Now, with providers like Google enforcing stronger security, Outlook must use the correct app password and server settings, which adds steps compared to older setups.
6. Talking to a real person
   • For direct help with sign-in, password, or suspected hacking issues on the Microsoft side, support agents can be contacted via Microsoft Support. In similar cases, users were advised to sign in with any Microsoft account (or create a new one) and then use the “Contact Support” flow under Products and Services → Microsoft 365 and Office → Manage Account Security → Chat with a support agent in your web browser to speak with a real person.
   • For Gmail-specific password or app-password issues, Google’s own support and help pages for changing or resetting passwords should be used.

References:

• I can't send or receive messages in Outlook
• Troubleshoot Outlook email setup
• Change or update your email password in Outlook for Windows
• Change or update email password on Outlook for Mac
• Set up email in the Outlook for Android app
• Unable to change password in my Outlook - Microsoft Q&A
• I need to speak with a real person and it seems impossible. - Microsoft Q&A
• search for solutions another user has found - Microsoft Q&A