Hunting down missing email

While most parts of the internet have become more reliable over the years - email would appear to have actually become less reliable.

All too often, I come into contact with someone who is positive they sent something to me, or someone else, but yet it never made it to the intended recipient.

Sometimes the email in question wasn't that important. The concern is that if one email message got lost, presumably others could for the same reason. Hence, figuring out what happened to any missing message is important for someone in control of an email server.

Here's a list of things to check when trying to hunt down a missing message.

Did the person really send it?
Verify the supposed sender actually did send the message by having them check their "Sent Items" folder.

In today's world people often work on a half-dozen tasks at once. It's easy to compose a new message, but then minimize the window and forget to actually send it. Sometimes a composed but unsent message will end-up in the "Drafts" folder.

Annoyingly, sometimes messages get stuck in Outlook's "outbox" due to server problems (this may also be caused by a bug in Outlook).

Did the sender get a "bounce" message?
Any SMTP server between the sender and the recipient can decide to "bounce" a message back to the sender. Sometimes even Outlook itself will generate such a message.

These messages can sometimes be ambiguous, but often specifically describe why the message was not delivered.

Common reasons for being "bounced" include:

Did they get the email address right? Usually sending a message to a non-existent address will generate a bounce message, but not always. Examining the original message in the "sent items" folder can help confirm it was correctly addressed.

Corrupted address book entries in Outlook can often cause a message to be incorrectly addressed. Determining for sure if this is the underlying problem can be difficult. When in doubt, locate the problematic address book entry and delete it; it's easy enough to recreate later.

Did Outlook (or Thunderbird) move it to the Junk Mail folder or delete it?
Outlook has its own junk email filtering as do other email clients. These filters aren't perfect - and sometimes are downright arbitrary when processing email. Have the recipient check their "Junk Mail" folder to verify it didn't land there.

Also, make sure Outlook's spam blocker isn't configured to just delete messages it thinks are spam. If it is, you'll never know what could be getting lost.

Users will sometimes create custom rules for dealing with email. They will frequently come up with rules that they think would provide a good way to eliminate spam, but are actually quite bad ideas.

For example, I had a user who had decided that filtering any message that contained the word "spam" in it was a good idea. This resulted in them getting none of my email. After a while they became perturbed that I was apparently not answering any of their support requests.

Did your ISP's filter eat it?
Almost all ISP's at least offer some degree of spam filtering. Many deploy it for all their users with or without customer consent.

Some server-side filter systems will result in bounce messages being sent back to the attempted message sender. Some do not send bounce messages, or send them only in certain circumstances.

From my experience, most ISP-run spam blocker sofware does not let users readily review messages that were blocked. This is a major weakness in this approach to minimizing junk mail.

One way or the other, you may want to look into what your ISP is doing server-side when trying to hunt down a missing email message.

Did your anti-spam or anti-virus program eat it?
Client-based email filtering packages usually let users readily review email messages that were blocked. Some (like SpamButcher) actually let users search intercepted email for a given sender or message content.

Users often forget that their anti-virus package might also be analyzing and intercepting their email messages. With some packages the only messages blocked are ones that contain actual viruses. However, some programs may stop any message containing certain kinds of attachments.

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