Outlook cannot connect to GMail server does not support the connection encryption type

Is there a reason you are using POP3 rather than IMAP?

I know Google were upping the security on mail apps that can connect to it's servers, you may need to allow less secure apps - Sign in - Google Accounts


edit

See here for fix - Outlook cannot connect to GMail server does not support the connection encryption type

I'd start by switching to IMAP which is the standard these days and see how it goes from there.

Edit - try Denis's settings below first to save messing.

I also use
Outlook 2007
pop
gmail

Mine continues to work.

My Advanced settings smtp & encyrption type are different.



Actually, mine appear to be an old set but they are definitely working.
Read Gmail messages on other email clients using POP - Gmail Help

Perhaps GMail happens to have a fault that is blocking those who use the correct settings.

[equivalent IMAP page Check Gmail through other email platforms - Gmail Help]

Denis

What settings did you use for imap?

do you have 2 step verification enabled? Then have a look at the "Generate App Password". I had the same problem with my Outlook 2016 and had to use the App Password from my Gmail account settings.

Sign in using App Passwords - Google Account Help

I think you should revert to the settings Google suggest and then contact them for assistance.
1 Use the search box on the page I linked to
2 Use the Community tab on the page I linked to

Denis