So I see you found this here:
https://support.google.com/accounts/answer/185833?hl=en
Well it certainly sounded good, but it didnt work for me and I did everything right, I enabled the 2 factor authentication. I tried adding the account from scratch from Outlook File ... Info ... + Add Account. At the Outlook dialog box, entered my email address and Advanced Options "Let me setup my account manually". Click Connect, choose POP option from the list of choices, the "POP Account Settings" dialog then asks for the password, fill it in and click "Connect". Immediately the small "Internet Email - <my email address>" dialog box popped up asking me for my Password (which it had already pre-entered for me since I entered it just a second ago, and I just click OK (or also try pasting it in just to be sure). Then the Outlook dialog "Something went wrong" "We couldnt connect to the incoming (POP) server. The connection timed out." is displayed and it allows me to change any of the settings via "Change Account Settings" to display "POP Account Settings" dialog but its the same old **** I have dealt with for a whole day now. pop.gmail.com / 995, smtp.gmail.com / 465, "This server requires an encrypted connection (SSL/TLS)", bla bla bla. I have it all right and it just wont work.
I generated a second 16-digit app password and continued to get the same problem with that. I even tried a third time thinking maybe I needed to log out of my google account first and log back and and then generate the password and that didnt work, you get the idea, I am grasping at straws, something is fundamentally flawed here as to why this is not working for me, and I cannot figure for the life of me what that is.
While I feel like I have learned something new "in theory" which I never knew about, I cannot seem to apply it and I have no idea why not, well at least partially .... Now just to at least test this App pw feature, I generated a pw for my iphone and added the account successfully with that password (there is a feature it appears on iphone that allows adding the account to the phone without entering ANY pw, not sure how that works, but if you specify Google from the list of the 6 major providers then it works that way, so anyway in order to test this app pw feature, I chose "Other" email account type, and was forced to enter the server URLs and pw and it worked (if I modified the pw it didnt work, so I know for sure that this app pw feature CAN work and that the actual pw is critical).
So something is broke for my "Outlook Office Professional Plus 2016" and I have no idea what it is.
thanks
dd