Periodically, when I send an email using Outlook 365 on my PC, the message will not be sent and I'll be prompted for my email address and password repeatedly. Typically speaking if I exit Outlook 365 and return later on the message will go through. I put a post out on Microsoft's Community Forum and someone sent me a link to an article entitled "Modern Authentication Methods Now Needed To Continue Syncing Outlook Email from Non-Microsoft Email Apps"



In this article it stated that if I was using an email client like Thunderbird I would soon need to change it to use Oauth2 instead of a password and that right now there would be intermittent failures to send messages that would result in repeated password prompts.

Well, I'm confused as the article was in reference to non-Microsoft Email Apps but it also appears to reference older versions of Outlook. But at the same time, I'm seeing the repeated intermittent failures to send in my copy of Outlook 365 that's part of my current subscription to Microsoft 365.

I tried to create a new account for my outlook.com email address and when I did, the only option I had was to provide my password with no option to setup OAuth2 within Outlook 365. So, has anyone else been seeing intermittent email send issue from Outlook 365 and know what the problem is assuming that it's unrelated to the requirement for other email clients to use OAuth2 instead of a password?