have your email call my email

July 29, 2009 12:57 PM

How can you mitigate the disaster of an email message that disappears en route?

I work for a small nonprofit. We have a pretty reliable mail server. It's older technology (SIMS on OS 9 for geekoids) but is fantastic for the price, meaning it's free.

One of our worker bees has had a few message disappear into the ether over a few months time. As far as we know, they were handed off to a remote mail server then got munged, filtered, or otherwise shunted into the fifth dimension.

The missing messages cause consternation because they mean missed appointments and a general concern that messages are disappearing.

Since email is not a 'guaranteed' service, what do people do to mitigate the possibility of disaster caused by an email that goes awry? Technically we can't change anything at the moment and think our mail server is working correctly.

It's the overall big picture of crucial emails and an imperfect world that is the crux. Perhaps there is some technical service that could help (hopefully free or cheap). I'm basically wondering what people do to make sure they don't get boned by a missing email, to put it in a rather ludicrous context.

posted by diode to computers & internet (16 comments total)

If this is happening to just one person out of many people, I would doublecheck that person's story, not necessarily because they're lying (but they might be) but because they might not understand the program or shortcut keys or something else and they're saving all their messages to a drafts folder or something...servers generally don't target a particular person, over and over.
posted by A Terrible Llama at 12:59 PM on July 29 [1 favorite]

E-mails do simply vanish sometimes, though it's very rare. I have had maybe one in five thousand go unaccountably absent. There are so many places along the way it could go wrong that it is very hard to know why.

But as ATL says, if it's just one user out of many on the same network, then something seems odd. In addition to the ideas he mentions (maybe they're not being sent at all), it's possible they are one of those people who forgets to put a Subject in the message or does some other odd thing that is getting it rejected as spam somewhere down the line.

I don't know SIMS (wow, old), but since it's a mail server you should be able to confirm that the message in question left your network, at least, and see where it was next handed off (with a timestamp). That will narrow down the options somewhat, and you may be able to coordinate with a system admin at that next network to see what happened after that.

Do you use a particularly small or known-flaky ISP as your next 'hop' to the Internet?

E-mail is not guaranteed, no, but it's pretty easy to trace if you have access to the right logs.
posted by rokusan at 1:05 PM on July 29

How do you know these messages didn't get caught in some organization or ISP's spam filter or blacklist?
posted by alms at 1:07 PM on July 29

By the way, integrating Gmail or moving to Gmail might be an option for you, I'm pretty sure you can use your existing organizational email addresses -- there's supposedly some way to do this, though I haven't.

They're delightfully free as well.
posted by A Terrible Llama at 1:12 PM on July 29

an imperfect world that is the crux

Also, as Rokusan said, I too have maybe lost one in five thousand emails. It's an imperfect world, and email is not guaranteed, but it's really generally pretty damn good--so good that this is generally not a problem for people any more. I kind of remember missing emails being a problem in the mid-nineties, and my mother, for whom settling in front of a keyboard is like getting into a raft to float down the Amazon, will occasionally lose one, but we can safely assume this is because she never actually hit the Send button.

Other than that, it's been a long time since I've heard of this being a problem.
posted by A Terrible Llama at 1:16 PM on July 29

Have you considered non-technical approaches, like confirming receipt of important emails (either through an annoying "read receipt" or just by saying hey, did you get my email?) or appointments? I realize that getting all the "worker bees" to pursue the same best practice is a challenge, but the beauty of this approach is that it really doesn't matter whether it's user error, a leak in one of the Internet tubes, or any other problem.
posted by chesty_a_arthur at 1:29 PM on July 29 [1 favorite]

The missing messages cause consternation because they mean missed appointments...

Yes, chesty has a couple of points here too. Ahem.

Appointments in particular should be confirmed. You can't make an appointment without a confirmation, after all. Seinfeldian scholars might argue it's not even an appointment until it's confrimed.

For example, I wouldn't expect my airplane tickets to be waiting for me if I didn't get a confirmation number back, or expect a date to show up if I'd never received a response to that drunken text.
posted by rokusan at 1:34 PM on July 29 [1 favorite]

I have received e-mails months after they were originally sent, so I agree it is possible for Weird Stuff to happen out in the ether. I also agree that transitioning to, say, Google Apps for Your Domain might be a good idea. But most problems like this are PEBCAK (problem exists between chair and keyboard) or caused by false-positives in spam filtering.

The low-tech solution is to simply get in the habit of requesting/sending confirmation by reply. My clients always acknowledge receipt of files that I send them, and if I don't get a reply pretty quickly, I call.
posted by adamrice at 1:50 PM on July 29

As far as we know, they were handed off to a remote mail server

You should know for certain. Your email server will have SMTP logs that state the email was delivered to *somewhere*. This is the electronic equivalent to having a picture of someone putting a letter in a mailbox. Once it's handed off top the world, it's out of your control and there are tons of things that can go wrong; Aggressive spam/content filtering, non-standard SMTP implementations, unplanned downtime, DNS issues, people not checking their junk mail folder, etc etc etc.

I'm basically wondering what people do to make sure they don't get boned by a missing email, to put it in a rather ludicrous context.

Don't hit send and assume they got it, ask for follow up verification. If you don't get a reply, follow up with a phone call. If it's critical, it shouldn't be (only) in email.
posted by anti social order at 1:57 PM on July 29

I do a number of things that are pretty email intensive and I had, at one point, a boss who I seemed to have an email problem with. I use gmail and he was at a school server and he would send me "this is the schedule" emails and I wouldn't even know they had been sent because gmail somehow blackholed the email before it even arrived in my inbox. For my part, I didn't know there was a schedule sent.

Fortunately, I knew the guy and I saw him odften enough that we figurd out that there was a problem and as soon as we figured this out, we troubleshot the hell out of it. I had him send multiple emails, from multiple computers (same address) to me different times and also to multiple email addresses. Each email would say something like "This is email one of three I am sending it from my work computer to your gmail account" "This is email two of three I am sending it from my home computer to your gmail account" etc. I never did figure out what the problem was, but I was able to isolate

- it seemed to be his address at the school specifically. I could send and receive email to/from other people at the school
- it was school + gmail specifically. when I bounced the email from him that came to another account to gmail it would similarly disappear

"Solving the problem" meant that he had to email me at a different address and if I wanted to work for him I had to check that address. My point, in a roundabout way, is that most email doesn't "just disappear" Many people who don't understand technology like to think that it does because it absolves them of both learning the technology, learning to troubleshoot it, and being culpable if things go wonrg.

So I'd be doing three things

- having the worker bee cc you on these emails [or someone else] to see if you can get an idea of what might be going wrong, as someone sid before, lack of subject or something
- try to troubleshoot the problem with teh person who missed the meeting. Even if you can't figure it out, this shows willingness to own the problem which is part of the consternation factor.
- find a redundant way to confirm meetings or even something simple like "please RSVP, we're troubleshooting some stuff with our email" and then call people who don't RSVP to confirm.

I know it's a headache, but I'd much rather see this in a big SOLVED file, than put into the "sometimes you just don't know why technology does what it does *waves hands*" bin.
posted by jessamyn at 1:58 PM on July 29

Check your SMTP logs, you'll be able to tell if the problem is on your end or on their end.
posted by Brian Puccio at 2:22 PM on July 29

Ask for the person to reply to yours to let you know they got it, send reminder emails, call them, etc. Those are all the things we do at my work to make sure the scheduling goes as planned.
posted by losvedir at 2:22 PM on July 29

Can you check their "sent" messages folder and see if there's anything that stands out? (or if they even exist?) I have to say that it's pretty unlikely that only one person is being hit with this problem - especially if you all use the same email program/server/service.
posted by The Light Fantastic at 2:23 PM on July 29

There are technical things you can do to possibly make your mailserver more reliable, but I think from the way you put your question you're looking for something on the user end — how do you deal with the fact that email isn't always 100% reliable?

My answer is the same way you deal with the fact that postal mail isn't 100% reliable, either: you ask for a response on anything that's important. If you don't get a response back, you assume the person didn't get the message and politely ask them to respond again. If they don't respond the second time, you either assume they're not interested / not coming / on vacation / are blowing you off, and you follow up with a phone call if it's really that important.

The etiquette is the same as with traditional letters; just tell people to "please respond if you plan on attending." Since email is so trivial to send, I wouldn't think twice about asking people for this, particularly if I'm not working on a system (like Outlook/Exchange, Notes) that does automatic scheduling and responses to meeting requests.
posted by Kadin2048 at 2:50 PM on July 29

Definitely get confirmation of appointments and the like, and double-check the worker bee who has "had a few message disappear into the ether over a few months time"—frankly, that's very suspicious. People keep saying e-mail isn't guaranteed, and I'm sure that's true, but I personally can't remember having a message vanish and I would probably not believe someone who claimed they'd sent me something that I didn't get.
posted by languagehat at 3:09 PM on July 29

Just a data-point to throw into the mix: Emails disappear on a fairly regular basis around my workplace. I sent out a series of emails to nominees for a contest recently, for instance, and many of them were either shunted straight into those individuals' spam folders or (apparently) never arrived in the first place. On a fairly consistent basis many of us in the office tend to receive initial emails in employee-only threads well after subsequent emails have arrived. Every so often, our email server discharges a burst of "stuck" emails from months before. Even after several years' worth of periodic troubleshooting and upgrades to our email server, these problems persist.

So it's quite possible that there really is some sort of sticky problem with your email server or end-users' email clients or the network itself—definitely don't rule out your office's network connection or router—that could lead to something like this occurring.

What do we do? If it's an important or time-sensitive email and we haven't heard back about it, we drop the recipient a polite quick email or phone call to double-check. That's just standard practice regardless of how reliable your email is, I'd say—if it's important, double-check. Don't assume an employee is being dodgy; they may simply never have received your message.
posted by limeonaire at 5:58 PM on July 29