Outlook work account keeps prompting for password or fails to connect

Hi @Lakin Marquieta

Thank you for posting your question in Microsoft Q&A. 

As your description, your account seem works fine in Outlook on the web, this confirms it's likely a client-side authentication or profile issue on the desktop app, common with cached credentials, outdated settings, or profile corruption. 

You could try to follow these steps to troubleshoot it: 

1.Clear Cached Credentials

Outdated or corrupted stored passwords often trigger repeated login prompts. 

Open Credential Manager: Search for it in the Windows Start menu. 

Go to the Windows Credentials tab. 

Look for entries related to your email (for example your domain, Outlook, MicrosoftAccount, or Exchange). 

Expand each relevant entry and click Remove. 

Close Credential Manager. 

Reopen Outlook and sign in when prompted. 

2. Disable "Always Prompt for Logon" in Account Settings 

This setting can force authentication even when credentials are valid. 

In Outlook, go to File -> Account Settings -> Account Settings. 

Select your work account and click Change. 

Click More Settings -> Security tab. 

Uncheck "Always prompt for logon credentials". 

Click OK -> Next -> Finish, then restart Outlook. 

3.Create a New Outlook Profile 

Corrupted profiles could cause persistent issues. A new profile helps isolate the problem. 

Close Outlook. 

Open Control Panel -> Mail (Microsoft Outlook). 

Click Show Profiles -> Add, name it and set it up with your email. 

Back in the Profiles window, choose either:  

Prompt for a profile to be used, or Always use this profile (select the new one). 

Open Outlook, select the new profile, and sign in again. 

4.Update your Outlook application: 

Outdated versions might cause compatibility issues in your app. 

In Outlook, go to File -> Office Account -> Update Options -> Update Now. 

Then, you could restart and check if the issue still persists.

Please understand that our initial reply may not always immediately resolve the issue. However, with your help and more detailed information, we can work together to find a solution. 

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.