I can no longer connect to outlook.com (formerly hotmail.com) via IMAP and sync emails to Outlook 2007. I unfortunately haven't figure out a solution -- if there is one. I am noting the error here to help others confirm that yes, there's at least one other person in the world having this problem. As of now, I haven't find much mentioning of the issue online. The issue started a few weeks ago, so around mid November of 2019. When I try to get new emails, I get the following error:
Task 'XXX@hotmail.com: Folder:Inbox Check for new mail.' reported error (0x800CCC0E) : 'Outlook cannot download folder Inbox from the IMAP e-mail server for account XXX@hotmail.com. Error: Cannot connect to the server. If you continue to receive this message, contact your server administrator or Internet service provide (ISP).'I rechecked the server and ports from the outlook.com help pages. I had used the IMAP server imap-mail.outlook.com before the connection problem, but changing it to outlook.office365.com doesn't help. SMTP doesn't work either.
My outlook android app works fine, so I suspect the IMAP-connection-related encryption got changed on the server side and so Outlook 2007 no longer works with outlook.com. I tried all the possible encryption options with port 993 -- auto, ssl, tls, none; all failed. I don't have newer desktop versions of Outlook, and from looking online the newer versions has something called STARTTLS as an encryption option. So newer versions of Outlook might continue to work just fine.