Seems that attachments generated on his computer simply do not attach in outgoing mail. Outlook shows that the document is sent but alas, the receipent does not receive the attachment. He can receive attachments and forward them without problem.
Anti-virus has been disabled, firewall disabled and I know for a fact he is "logged on." Connection via DSL.
Would appreciate any applicable pearls of wisdom in this matter.
Is he over a proxy server? If so, check all proxy connections/ addresses.
Outlook will NOT allow you to send attachements with a few suffix's. Such suffices are .exe (executable), bat (Batch file), vbs (visual basic) and a few others.
This is intentional, because a fool could then open 'Virus.exe' and infect his network; then this same fool would then blame Microsoft for allowing the virus to be installed.
The way around this, is to append another file type to the file name. So, a file named 'Application.exe' would be renamed 'Application.exe.jpg'. Now Outlook thinks the file is a picture.
The recipient simply removes the .jpg suffix; and off you go. And, never, ever, ever run an attached executable file from someone you do not know. If you have received an executable file from someone you do know, make sure that your friend REALLY did send it, and that it's not from a virus on your friend's machine. If it's not expected, chances are it's not good news.
If some fool (and I use the word 'fool' in the kindest way possible) sends you an email and asks you to forward it to your friend 'x' times so you can see a cartoon .... ask them this:
"You have intentionally given me some application written by someone you do not know, from a company or entity you have never heard of, with the message originating from someone you do not know; which will 'alledgedly' run some program you can not vouch for, on my machine (full of my personal information - tax, credit card accounts, address books) and you have freely given this program to all of your friends. Do you think this is a smart thing to do?"
Outlook ->Tools ->Options
If I'm not mistaken, there is a setting that will enable and disable the ability to enclose files and pictures.