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This is my first question, so please be gentle... :-) I'm a department of one for a small engineering company. My primary job is to develop software, but my CS degree clearly makes me an expert on all things IT, right? We use a 2003 Small Business Server with as many default-settings as I can muster, but one of our remote users recently complained that she was expecting a couple emails with some large attachments (...some time in the last 10 days). She says she's getting other emails, and as usual, the SBS "Failed Mail" folder only contains emails from wealthy, deposed African princes (not Qaddafi...yet).

She's not even sure about one of these messages' sender address... Just that it should 'look like an architect/contractor address'... I know how to use "Message Tracking" but it doesn't let me look at message content--just when it was delivered. I've always avoided learning how to get into the mailboxes of other people, but after 5 years of annoying problems like this one, I'm starting to care less about the privacy of the sheep.

I realize that--at some point--she's just screwed, but what do you think? Should I open Pandora's box? If so, how can I do it without letting her know I've done it? I don't want to turn into anybody's email gopher.

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And your question is ... ? You want to help her without letting her know that you are trying to help her? –  rems Feb 23 '11 at 16:22
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If she doesn't know the address to tell you what to look for, tell her to go screw. IMO. –  mfinni Feb 23 '11 at 16:27
    
Tell sender to send using something that looks like a USB thumb drive. –  Bart Silverstrim Feb 23 '11 at 16:49
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3 Answers

up vote 3 down vote accepted

OK, I'm being gentle - I promise!

one of our remote users recently complained that she was
expecting a couple emails with some large attachments

Electronic Mail is NOT a file distribution system. Sending "large" files via email is like trying to send your car via the US Postal Service: There is a weight (file size) limit, and you may be exceeding it.


(...some time in the last 10 days).

If that's the best time frame she can produce it's not even worth looking in the logs. If you want to try to help her have the messages re-sent at a known time, watch your server's logs for a window before/after that time (say an hour or 2 on each side), and see if anything turns up.
You will need to know the sender's address unless you enjoy long painful walks through mail server logs looking for the proverbial needle in the equally proverbial haystack :-)


Should I open Pandora's box?

If at all possible avoid getting involved with email. It is a bottomless pit of trouble and heartache and naught but insanity awaits those who meddle in it.


If so, how can I do it without letting her know I've done it?

You can't: You need the cooperation of both the sender and the recipient (and often the IT team on the sender's side) in order to really troubleshoot email.

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You need the cooperation of both the sender and the recipient (and often the IT team on the sender's side) in order to really troubleshoot email. True, but it takes so much longer and in the meantime they think you're an a##hole while you try to get something else done. –  phillihp Feb 23 '11 at 17:09
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If you're a sysadmin and you aren't used to users thinking you're an @#$%...you're probably new. –  Bart Silverstrim Feb 23 '11 at 17:30
    
@phillihp I've found if you can get all of those parties together at the same time you can typically solve the problem in 15 minutes. They fight getting together like harpooned whales like you mentioned, but at least it gets fixed, and then the IT guys are the heros who made it work, rather than the a##holes who got in the way :) –  voretaq7 Feb 23 '11 at 18:27
    
all that said -- if you can run away, RUN. :-) –  voretaq7 Feb 23 '11 at 18:31
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as @voretaq7 said email is not a file distribution mechanism; anything large is best sent via another mechanism.

She's screwed. Explain nicely and suggest alternative methods of sending large files privately and securely.

Don't open pandora's box, at all, as you will find that all the evils of the world are as nothing compared to email problems....

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thanks. consider it unopened. ;-) –  phillihp Feb 23 '11 at 17:11
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As others have said, finding out what happened is difficult and annoying at best, assuming you've done it before :)

Point her to yousendit.com for a free file distribution service.

If she complains, tell whoever is above you that many times even seasoned sysadmins have trouble figuring out what happened, and honestly, the answer is going to be "your email got lost because it had a big attachment".

Good luck :)

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