Users Don't Get Attachments, In More Ways Than One

"Can you please train the lawyers and legal assistants that you work for to actually attach a document when they're sending it to an outside entity, like the one I work for? I'm really tired of getting yelled at by my users because they can't open the attachments when all that really got sent to them was a link to the document as it exists in your document management system. Obviously, from here, that link is useless."
— "Life of a one-man IT department"

Amen to that. Some e-mail attachment horror stories I've dealt with first-hand:

1. A woman sends a link to our website to a potential client. Rather than just say "feel free to browse our site, www.website.com", she decides that she wants to attach a Windows URL shortcut from her Desktop to the message, which is of course converted into MIME to create a file called "Link to www.website.com". The potential client's antivirus spots the ".com" MIME attachment and does what any normal AV software would do: flag it as an MS executable file and consider it dangerous. Who gets the phone call to sort this out? I do.
2. This is the same woman who often sends out revised calendars to various people throughout the building with messages like "Updated changes to the event on 11/20. Very important. See attached." Do I even need to tell you that she regularly forgets to attach the very calendars she's distributing? I didn't think so.
3. One time, I got an urgent e-mail from my boss telling me that someone had received a message from a potential big-money grant-issuing body, but the attachment was stripped by our firewalled SMTP proxy and I needed to update it to never, ever do that to that address again. I took one look at the message and concluded it was a virus and that the proxy did exactly what it was supposed to do. "It's a virus," I reply. The user who received the message swears up and down that it was not, in fact, a virus. "Yes it is," I tell him. I'm not just guessing that it might be a virus: I have content-type information to support my diagnosis. The user argues that he's expecting to receive mail from them, so naturally anything from them must be completely 100% legitimate. Finally, my boss calls me to see why I haven't worked a miracle yet. "It's still a virus and it's always been a virus," I complain. Nonetheless, my boss insists I check again. "Explain this to me," I ask my boss, "why would the National Science Foundation bury this user's grant decision in a WAV sound file with the .SCR screensaver extension?" My boss thanked me, hung up, and I never heard another word about it.
4. One day, a user came up to me and asked me what the size limit on e-mail messages was. This is never good. "Sixteen megabytes," I tell them. "Why? How big is the file you're trying to send?" I ask. "Oh, about eighty megabytes. Is there anything you can do about that?"

Not an attachment horror story, but certainly in the same vein:

Before I finally convinced my boss to buy a new mail server, a woman called me to complain that I'd singled her out for having a huge quantity of e-mail sitting on our old mail server. Lots of mail meant slow response times and big inboxes would sometimes crash the system, which was already critically low on disk space, bringing all mail service down for the entire building. "How dare you tell me that I've got too much e-mail!" she yells.

"I just went through the server and picked the users with the ten largest mailboxes and asked them if they could delete unnecessary mail to help the system and benefit for everyone," I say. She won't have any of it. "I only keep important messages and I can't delete any of them! This is my job, and my mail is work-related and I cannot believe you're asking me to erase some of it because of some limit you're imposing!" "Look," I say, starting to get pissed. "You've got four hundred megs of mail stored on the company mail server. That's more than anybody else in the building has, and you're telling me you need every last message? All I'm asking you to do is go through your mail and delete any old mail you might not need anymore. It's up to you." She hangs up, furious.

Later that day she calls back, her voice dripping with an unspoken "Gotcha!". She says "I just called a friend of mine, (pause for effect), who works at (some place I don't remember), and he says that every user there gets one hundred megabytes of mail storage." I can hear the "Take that!" she tacks onto it in her mind. "So?" I ask. I got "A's" in math class. She clearly didn't. "How much space am I using, then, huh?" she asks. "Four hundred megabytes," I remind her. I drive the last nail in: "That means you're already using four times the maximum limit that your friend has total." Check and mate, bitch.

Epilogue: a few months later the user quit, and I confided in her replacement, who also got responsibility for handling the e-mail account, that it was the largest in the building's history and that I'd greatly appreciate it if she could whittle it down over the next few months. A few days later, it was down from 400MB to 40MB. I even got a call from the replacement. "Yeah, a lot of it was old junk from years ago. Like two-line replies from people saying 'Thanks' and stuff like that." I shudder to think what 400MB of thank-you mail looks like.