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Didn't want to hijack Charles' thread on Office 365 so I'm posting a new one.

The other day my Outlook 365 decided it wont send any emails. I can receive, but when I hit send, it goes to my outbox and then a popup asks for my password. I put it in, but it just keeps popping up again. I confirmed my password was correct with my on line email access (Roadrunner) and it is correct. I can also send and receive no problem with the built in mail program in Windows 10.

I downloaded the Office 365 repair program, but it didn't fix the problem. What's up with this (asking the experts)? Any help will be appreciated.

It sounds like roadrunner may have changed their policy on the way mail gets sent. I know they tend to be annoying when it comes to IMAP/SMTP settings. My guess is that your account settings in outlook are set as send-after-receive, which is a way you can send email without passing login credentials by using them on the receive portion first. My best guess is that roadrunner disabled that, causing outlook to ask you for your password now that it gets asked. I'd go into the account settings and check your send mail settings. You may also want to contact roadrunner directly, as much of the documentation floating around online may be outdated.