New
#1
Sorry its - Secure Password Authentication, was thinking of someting else for a second!
What client are you configuring?
I used "Log on using clear text authentication."
The 2nd option is for active directory login which is domain client setup.
The 3rd option is for encryption. Not sure of it's implementation.
Been a while since I configured Gmail in a client but they do have a configuration page for certain clients here > Supported POP Client List
I use Windows Live Mail with Gmail and have it set to clear text.
Pop and SMTP server ports are non standard, they're 995 and 465 respectively. Both require SSL enabled :)
As I use Avast Mail Shield, to scan my mail, SSL must be turned OFF for it to work.
As I also use Outpost FW Pro, I don't get a connection unless I shut it down and turn ON Windows FW.
I tried the other items in my red box. 2 & 3 failed.