You have a gmail.com address, you want to use it in Outlook instead of using webmail.
You went to gmail.com, settings, and enabled POP3 & IMAP, when you went to add gmail to your Outlook, it fails asking you for the password over and over again.
Here's why.
You did nothing wrong, you missed one step on the gmail.com web site, not only must you enable POP/IMAP, you must UNBLOCK less secure client software connection ( Outlook is not secure ?? Correct, according to Google ). Here's what to do.
Go to Gmail.com, Settings, Accounts and Imports ( top blue row ), Other Google Account settings ( third line from top ), go to the Signing in section ( 2nd or third group from top ), change "Access for less secure apps" from blocked to allowed.
From here you can safely and freely add your gmail.com address to Outlook, use auto setup to save you the hassle of manually adding SSL, TLS, port number etc...
Answered provided by Sak Chen 03/11/2015