Outlook keeps asking me to sign in.

Hi Jackson,

Welcome to post your concern in community.

Regarding your situation, may I first know whether your given work exchange account is an Office 365 Business account or not? Since this symptom may be more likely related to your account.

And you can first try these suggestions to see if they can help:

1) Uncheck "Always prompt for logon credential". In Outlook, go to File > Account Settings > Account Settings, select the Exchange account and click "Change" button. Click "More Settings", in "Security tab", uncheck "Always prompt for logon credentials".

2) Remove stored credentials in Credential Manager. Open the Control Panel, click Credential Manager, find the credential sets that Outlook in the name, expand the set and click on "Remove from Vault".

3) Set up 2-stps verification for Office 365. If your admin has enabled multi-factor authentication for your account, we recommend to use it. Or use the app password in Outlook. For details, please refer to this article: https://support.office.com/en-us/article/set-up-2-step-verification-for-office-365-ace1d096-61e5-449b-a875-58eb3d74de14

Best,

Shawn

I do not believe it is an Office 365 Business account. As far as working on the steps you mentioned:

1) "Always prompt for logon credentials" was grayed out and already unchecked

2) Removing the stored credentials from the vault did not resolve the issue.

Hi Jackson,

Since this issue is related to non Office 365 business account, things will be different, we moved your thread into Outlook / Windows 10 / Office 2019 for better help.

Regards,

Shawn

Hi Jackson,

Since this issue is related to non Office 365 business account, things will be different, we moved your thread into Outlook / Windows 10 / Office 2019 for better help.

Regards,

Shawn

Is there anyway I could receive further guidance on this from Microsoft now that my question has been moved to a new thread? This issue is ongoing. Thank you!