Email troubleshooting

[thunderlizard]

Some of my emails to and from Company X are failing to arrive. My emails to and from everybody else seem OK, but a little slow. Company X claims that it's just me they're having the problem with. (of course, there could be other emails going astray here and there that I just don't know about.)

what could possibly be going wrong, anybody-more-skilled-then-I?

[robnjc]

Can only offer pretty obvious suggestions:

I assume you have asked your and their email admin to check gateways and filters for the lost emails?

Are you sending attachments? Some gateways are configured to block emails above a certain size, or with certain attachment file types.

Is there any way your email could be deemed to spam by a spam filter?

I often have problems sending email to a friend whose employer filters often seemingly inocuous words as "inappropriate in a business communication".

[thunderlizard]

Cheers robnjc,
I'll look into those. It could well be the attachments thing. They may be obvious to you, but my specialisms lie elsewhere!

[kirk]

do you know how to SMTP manually?

from a DOS prompt, telnet their mail server on port 25 (see if you can communicate with their server) as you \ your ISP may be blocked.

If you need any more info let me know and I can detail the whole procedure.