@Vivaldi I don't currently have 2FA setup. When I try logging in with OAuth, it sits for several minutes, trying to connect and I finally get a message that says "Login for smtp-mail.outlook.com failed. [object Object]" When I use the password option, it sits for several minutes, trying to connect and I finally get the message that says "Login for outlook.office365.com failed. LOGIN failed." So I setup 2FA, used the app specific password that Outlook.com gave me, and... same error message.