Hi Geoff,
At Microsoft, we are committed to continuous improvement. Thanks for taking the time to share your experience so we can take steps to improve.
We totally understand the inconvenience caused by keep popping out the error message to let you re-enter your password for your account. Based on your description, the issue you have encountered is that Outlook continually prompt for your password when you
try to connect to Office 365. If my understanding is correct, I would like to confirm if you've already referred to this article: https://support.microsoft.com/en-sg/kb/2984912
Actually, Outlook keeps prompting for password could be caused by several reasons:
- Outlook is configured to prompt you for credentials
- Incorrect password cached in credential storage
- Required Authentication Settings for outgoing server and incoming server
- Outlook Anywhere is not configured to use NTLM Authentication
- Corrupt Outlook profile
- Slow or unstable network connection
So please see what we can try as below:
- Delete the old credentials - Open Control Panel>User Account (View by: Category)>Choose “Manage Windows Credentials” (under Credential Manager)>find your Outlook account and remove. Then, creating
a new Outlook profile to see if there is any improvement.
2. Checked the setting “Encrypt data between Microsoft Outlook and Microsoft Exchange” by clicking File > Account settings > Account settings
> more settings > security tab > "Encrypt data between Microsoft Outlook and Microsoft Exchange"
If all above with no luck, we may need the following information for next troubleshooting:
- The tenant information, also known as the email address you are using to log in. I have sent you a private message to get that and you can click the link below to access the pm:
https://answers.microsoft.com/en-us/privatemessages/list
- Some screenshots about the error you meet.
- The detailed version of Outlook on your PC and phone.
- How many users encounter the same issue in your organization?
- Have your organization deployed an on-premises Exchange server or under a hybrid environment?
About the help section and the admin section of office 365, we really appreciate if if you can submit your feedback via https://office365.uservoice.com/forums/273493-office-365-admin.
Understanding your experience helps us to make our product and service better for you and others.
Thanks,
Lance