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An email client, email reader or more formally mail user agent (MUA) is a computer program in the category of groupware environments used to access and manage a user's email. A web application that provides message management, composition, and reception functions may internally act as an email client; as a whole, it is commonly referred to as webmail. Likewise, email client may be referred to a piece of computer hardware or software whose primary or most visible role is to work as an email client. Email clients can also have other systems, like calendars, notes and contact managers.
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But first, since he is at home on his home network, make sure his router and any firewall software/hardware has opened ports 25, 465, and 587 for outbound smtp. In my case, I had to have the ISP open SMTP on their end, then I had to open ports specifically for OUTBOUND connections on my router, then I had to do the same for the ports in my software firewall.
Re the telnet test, here is an exhaustive article, of which the last bullet in the intro is of the most interest:
http://technet.microsoft.com/en-us/library/aa995718(EXCHG.65).aspx
Here is a more succinct article:
http://support.microsoft.com/kb/153119
Lastly, If the mail server is under your control, I would also look at relay permissions and relay rules.
Also, do you know anyone else who has an account on this mail server? If it is possible, test whether anyone else is having the same problem. It is possible that inbound (pop) is working fine but smtp is broken for everyone.