GNOME Bugzilla – Bug 726289
sending via a fresh outlook.com account fails, then succeeds
Last modified: 2019-01-15 03:29:15 UTC
I just tried to send a message from a relatively unused outlook.com account. Geary prompted me for my password because it wasn't remembered for that account, then I got a notice saying the message couldn't be sent. Immediately, a new message came into my inbox from outlook saying: To continue sending messages, please sign in and validate your Outlook.com account. This helps us stop automated programs from sending junk email. Then Geary tried sending the message again automatically and it succeeded. When I tried to reproduce the problem, it sent as expected the first time after prompting for my password. We should figure out what, if anything, Geary is doing wrong, and make sure it doesn't happen. It sounds like we may be trying to send without authenticating first, to avoid prompting in the case when the account doesn't use SMTP auth. Maybe outlook doesn't like that.
It looks like this isn't a rare occurrence and rather annoying for some of Microsoft's customers: http://answers.microsoft.com/en-us/outlook_com/forum/oemail-osend/please-sign-in-to-your-outlookcom-account-over-and/8c846f62-98aa-46ca-94da-63e3aa8c1160 One clue from the Microsoft representative: "I checked your account and found out that it was recently created. Please be informed that new Outlook.com users are limited to a lower limit compared to an older account which is a temporary restriction and is upgraded to the maximum recipients limit as soon as the user establishes credibility in the system. It frequently depends on the reputation of the account within Outlook.com. Once a good reputation is established, this process will then be lifted. To build a good reputation, I suggest you to use Outlook.com regularly and send email that do not contain suspicious contents that might trigger our spam filter." Charles, correct me if I'm wrong, but I suspect you don't use your account that often. I should say that I don't use mine often either and haven't seen this. Later another Microserf suggested verifying the account, although I don't recall doing this step either: http://windows.microsoft.com/en-us/windows/outlook/errors-sending-mail Whatever the issue, I'm less and less inclined to suspect the problem is Geary's. We'll leave this open for now until more information is obtained.
*** This bug has been marked as a duplicate of bug 714053 ***