I am preparing the first beta release of a new application that is used for diagnosing problems with SMTP. The program allows the user to test account settings against an SMTP server by sending a test message.

I have been testing the program from various locations including the hotel here in Atlanta. I was surprised to see that the network here redirects SMTP requests to its own SMTP server which relays the message to the appropriate destination. No wonder laptop users have problems with email. The experience behind the scenes can be different based on the network and the user may never know.


Click image to enlarge.

posted by Kirby | 09-Jun-2005 10:19 PM | comments (5)


The relaying to another SMTP server is usually for virus scan purposes. If you run something like Norton Internet Security and integrate it with outlook, it really sets up its on little smtp server. outlook sends it to that, which norton then scans and sends it out. I ran into this yesterday setting up some computers for a client - outlook sent the mail (gone from outbox, no errors), then I get norton popups that the mail couldn't be delivered.. unfortunatly now the mail is lost.. gotta go to "sent items" and resend. Kinda annoying.

posted by Frank | June 10 07:59 AM


I agree it is annoying. Recently I had a client who was trying to send me a .zip file. The email was sent through a virus scanner but the virus scanner was unable to read the .zip file. Instead of notifying the sender the recipient which in this cause was me was notified that the attachment could not be read.

It was a really annoying problem because the client was unaware of a virus scanner on his server. And as I mentioned in last night's posting the email may have never passed through the client's SMTP server. Example, emails sent from the hotel I'm at will pass through an SMTP server on the hotel's network which performs a virus scan on the outgoing email.

Troubleshooting these types of problems can be a pain when IP traffic is re-routed through other servers. But I will be prepared next time with my SMTP Diagnostic program. [Shameless plug I know.]

posted by Kirby Turner | June 10 03:09 PM


Another concern I have after reading this is that for each SMTP server a message passes through, there is potentially another COPY of your email sitting on someone's server, right? Couldn't someone at the hotel access the mail you send, especially if not encrypted?

posted by Mike | June 12 08:13 AM


Sure, it is possible for the server software to do whatever it wants with the information it receives such as store a copy of every e-mail sent through the server. You definitely want to encrypt information that you do not want others to see.

posted by Kirby Turner | June 12 10:03 AM


I wonder if we are at a point in time where Email should be "direct" or "point-to-point" (sorta peer-to-peer - and ZERO mail-servers) or what have you? I think the Email infrastructure as it exists now is outdated and poorly designed (just think of all the SPAM and server-hacks/hijacks/impersonations/exploits).

What I see as the "future" is something where we each have a "direct inbox" (at an IP address) that ONLY accepts email from those persons that pass an AUTH-KEY (GUID or even more restrictive impossible-to-guess number/value or such) that we issue. In addition, the inbox should not allow ANY attachments - just a "link" to the sender's attachements (with a proper RSA checksum or what have you), that is "retrieved" only when you tell them to be retrieved (and then, you too pass a "KEY" value to access them; checksums are compared; and THEN you get them). And of course, everything should be PGP encypted or such. Ideally the "IP-Address" I mention is an end-user-machine so there is no intermediate storage, but if all the other steps (encryption, keys, etc) were taken, we could still have mail-servers around if needed -- just need them to fundamentally change how they work.

Bye bye SPAM, bye bye prying eyes. Yes, some serious "paradigm shift" for how we think of Email and all, but se la vi.

posted by Mike | June 13 10:46 AM

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