Zach, yes, this user was complaining and sent me the email settings that is using. That is how I found out. And now I can explain all the fails in the gmail reports.
Heimir, I did have comcast few years ago and had a similar (most likely the same) problem, all standard ports blocked. Every time I was going from the office to the house I had to change my outgoing mail settings or nothing was going out. So I assume she is bound to do the same. From the screenshot I received I could not see the the advanced connection settings details like port.
I could only see user/ password/host for POP (to connect to our server) and user/ password/host for SMTP (comcast).
In any case including the comcast server should solve both our issues for the moment. If I have another younger user with a similar problem, will ask to play with connection ports.