Sending, receiving, and organizing email in Outlook on the web for business
Dear S Richards,
Thanks for choosing Microsoft Community.
Based on your question title and your question category, it seems that you are using Outlook on the web, but through your description(I closed the app and reopened it and tried again), it seems that you are using Outlook client. So to better help you, could you please be kindly to check whether you are using Outlook on the web or outlook client?
And since you said there is a window pop up, so to narrow down whether it is a Windows setting issue, please be kindly to try to paste in any other product and check if this can work. If this can work in other product, it means there is something wrong with your outlook.
Then if you use Outlook on the web, please be kindly to log in your account in outlook on the web under InPrivate Mode and then check the result. InPrivate mode: Right click the browser>click InPrivate window>Copy https://outlook.office.com/ to the browser and then log in your account. If nothing works in private mode, please be kindly to user different browser and check the result.
If you are using Outlook client, please be kindly to try to Create an Outlook profile (microsoft.com) and then check the result. Noted: please do not delete the old profile to protect your date.
If there is any update, please feel free to let me know. I will continue to help you based on the information you provide. Your understanding and co-operation are highly appreciated.
Thanks for your precious time. Have a nice day.
Sincerely,
Katherine