Problems with SSL/TLS email configuration

Good morning, I have problems using emails with Outlook, they work perfectly with a non-SSL connection, but I can't get them to work with an SSL connection.

Show us your main.cf and master.cf file content. Hide the IP.
And tell us which ports are you using for SSL in outlook. And also tell us if this is Android Outlook or PC Outlook?
If PC, tell us which "Add email account" dialog did you use, the one inside Outlook or the one through Windows Control panel?

I know a great deal about how painful it is to setup a IMAP/SMTP account on Outlook. It's just that Microsoft is using outdated connection standards for IMAP/SMTP but isn't telling us about it in any documentation.

Thank you very much for answering the problem was solved with the following configuration

POP3 Port: 995
SMTP: 465
with SSL

Nice to see you find your way to the answer. I exactly had the same problem.
Port 995 and 465 is an old standard (SSL) and Outlook is still forcing it. The new standard (TLS) where every other clients works with is port 587 and 143.

I had 995 and 465 disabled on my server for months without problems using Outlook, but at some point, Outlook decided that it would only work with those SSL ports instead of TLS ports.

But this problem is only there with Android Outlook.
PC outlook should work with 587 and 143, but there is a bug with the new internal "add email account" dialog (probably the same as the Android Outlook problem). So, using the "Mail (Microsoft Outlook)" dialog which is available through Windows Control panel will bring out the old/classic version "add email account" dialog.

By the way. It is NOT recommended to use POP3, because when an email message is downloaded to your Outlook, it will delete the copy that's available on your email server, leaving your mail there with no backup available in case your Outlook client corrupts your mail database on your pc/phone (which happens more than you think on PC Outlook)