Hi @Marc Zekofsky
Thank you for posting your question in the Q&A Forum.
Since your email works fine on your iPhone, which shows your account and password are correct. The repeated password prompts on your desktop are usually caused by old or corrupted login information stored on your computer, preventing Outlook from connecting properly.
Please try these steps to resolve this sign-in issue:
1. Clear Cached Credentials
- Close Outlook and all other Office apps.
- Open Control Panel > Credential Manager > Windows Credentials.
- Under Generic Credentials, delete any entries related to MicrosoftOffice, your email address, or Outlook.
Note: You may need to sign back into Word or Excel once after this.
2. Reconnect your Account to Windows
- Go to Windows Settings > Accounts > Access work or school.
- Select your email address and click Disconnect (this won't delete your emails).
- Click Connect and sign in again with your current password to refresh the link.
3. Create a New, Clean Outlook Profile
- Open Control Panel and search for Mail (Microsoft Outlook).
- Click Show Profiles... and then click Add to create a new profile.
- Name it (e.g., "NewProfile") and follow the setup wizard to add your account.
- In the Mail window, ensure "Always use this profile" is set to your new profile.
- Open Outlook. It will re-sync your mailbox from the server and should stop asking for the password.
Please attempt these three steps first and let us know the outcome. If the sign-in prompts persist, reply here and we can guide you through additional troubleshooting.
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