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Where, Oh, Where Has My Email Gone?

By Vivian Manning

We are so used to instant gratification when it comes to communication — instant messaging, texting, all-access all-the-time smartphones. We can’t even get away from it when we travel, especially now that more and more flights are Internet connected. For goodness sakes, Parks Canada is even talking about making Wi-Fi available at national parks!

Since we are so accustomed to our always-on connections, we notice more when they aren’t “on” — especially when that email that we sent, or expect, doesn’t arrive at its destination immediately. Email today is nearly flawless in its ubiquity, speed and accuracy in finding you, wherever you may be. Except when it doesn’t.

It Doesn’t Always Take a Specialist

Some years ago, spam email about certain male enhancement products was arriving in certain email inboxes by the bucketful. We tried blocking the senders, but the senders kept changing and the unwanted emails kept coming. (Spam filtering tools were not nearly as good then as they are now.) In desperation, I set up an email rule that targeted a certain word and its variations, to ensure that any email containing that word was automatically “poofed” — bypassing even the user’s deleted items folder, disappearing before it was seen. The firm’s users were happy, I was happy, and we promptly forgot the rule was even in place.

Years later, a particular lawyer was having trouble getting email from a certain sender to land in his inbox. I stepped through the usual troubleshooting and, while everything else was okay, this recipient definitely could not receive this sender’s email messages. Suddenly it dawned on me (never the sharpest tool in the shed) to check the recipient’s email rules. I went poking around for one that could affect this sender’s emails, and I found it: The sender’s signature line contained the word “specialist.”

I’ll let you figure out from there what the rule was.

When the Email Doesn’t Get There

Here’s a hint before I go on. When an email fails to arrive, it’s never a good idea to call tech support and announce, “Something’s wrong with our email!” Chances are, your email is not the problem. Chances are also quite good that you’ll end up with a ticked-off techie.

With that in mind, here is a list of “what might have gone wrong” when that sent email doesn’t immediately land where you expected it to land.

  1. The sender hasn’t noticed that the email hasn’t actually left his or her Outbox and is instead stuck in “Drafts” in the Outbox.
  2. The sender misaddressed the email.
  3. The sender included an attachment that was too large for the sender’s outgoing email server to handle, or for the incoming email server to accept.
  4. The sender’s email attachment contains a .zip, .exe, .scr or other unacceptable file attachment blocked by many mail servers for security reasons. (This does not always trigger a non-delivery report.)
  5. The sender’s email is caught in an external spam filter (and does not trigger a non-delivery report).
  6. The sender’s email was directed to the addressee’s email junk folder.
  7. The sender is somehow blacklisted (so the blacklisting service have trapped all sends).
  8. The sender’s email is infected, or incorrectly flagged as infected, and rejected by the incoming email server (which does not always trigger a non-delivery report).
  9. The sender’s email address isn’t resolving correctly. (This problem could be at either end, or along the way somewhere.)
  10. The sender’s email has been redirected to an unexpected folder or deleted based on the recipient’s mailbox rules (see above).
  11. The sender’s email is delayed somewhere along the way. (Email can pass through many servers on its way from the sender to the recipient.)
  12. The sender’s email server is down.
  13. The recipient’s inbox is closed down for receipt because the mailbox has exceeded size limits.
  14. The recipient’s email server is down.
  15. The recipient’s email client is offline. (The person wouldn’t be receiving any emails at all if this were the case.)
  16. The recipient inadvertently and unknowingly moved or deleted the email — don’t laugh, it happens.

As you can see, there are a ton of reasons that emails fail to arrive (I haven’t identified them all), some of which are not within the recipient’s or sender’s control, some of which are temporary (causing delay rather than non-delivery), and some of which are email item-specific. To diagnose an email issue, your techie needs to identify and troubleshoot all the steps taken and repeat them until the issue is identified. This can take some time, and even then, the honest answer may be “it’s out of our control,” and there is nothing wrong with the mail server either.

So maybe don’t throw out those old fax machines. Or just pick up that desk handset and call the sender. Sometimes low-tech works best.

Vivian Manning is the IT Manager at Burgar Rowe PC in Barrie, Bracebridge and Cookstown, Ontario. Prior to moving into IT, Vivian practiced law at Burgar Rowe, primarily in the area of municipal land development, with a total of 17 years in private practice before switching to the IT end of the law office. She currently indulges her love of teaching tech through her blog Small City Law Firm Tech, where she provides “tips of the day.” Read more of her Power User columns by clicking here.

Categories: Communications Skills, Daily Dispatch, Legal Technology, Power User
Originally published May 19, 2014
Last updated May 7, 2018
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Vivian Manning

Vivian Manning retired from Barriston Law LLP in Barrie, Bracebridge and Cookstown, Ontario in 2019. For more than 16 years she served as the firm’s IT manager, office manager and technology trainer. Prior to moving into IT, Vivian practiced law at Barriston LLP (formerly Burgar Rowe PC) primarily in the area of Municipal Land Development, with a total of 17 years in private practice before switching to the IT side of the law office.


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