Email - Under the Covers

Portland Group IT Recommendations

As part of my day to day work, I regularly come across customers who are frustrated with their email experience. “How could my client who I send emails to every day suddenly not receive my email”.

Well, the truth is there are many reasons why this may be the case, in this blog I explain the most common email delivery problems I come across.

Each day on the way to work I stop by my post office box to pick up the daily mail. At least a dozen times a year, the postman has put someone else’s mail in my box, an innocent and understandable mistake, after all, when you are dealing with hundreds of envelopes a day, a 6 and an 8 can look very similar. I bring this scenario up because I think there is a general acceptance in the community that snail mail can get lost, yet when it comes to mail of the electronic form, we don’t tolerate non delivery.

I believe this is because email to most people is a black box.

I recently had a client call me to say there is something wrong with their email. I was told that an important client of theirs had sent an email but it didn’t arrive. How did they know this? Well unfortunately for the staff member, the sender CC’d the boss, who did get the email. The boss was following up with their staff member as to why he hadn’t responded to the client, who of course claimed innocence because he hadn’t received the email.

Thus this series of events became my problem. I received a call and was subsequently asked to fix their mail server. In events like this, the standard practice is to acquire some basic information.

1.       Who sent the email?

2.       What was the approximate date of the email?

3.       Did the sender receive a bounced message? In this situation the answer was no.

So armed with this information I subsequently went through the logs. The mail server showed a history of the email, but only arriving to the boss, not the employee. This customer also had a cloud based spam filter, which enabled me to check email flow before hitting the server, but once again I found the same results.

It was clear to me that the sender did not send to my clients work email. After discussing this with my client I was quickly sent a screen shot showing the email that the boss received that clearly showed my contacts name in the To: field.

There was no disputing this, but my challenge then became trying to explain that just because your name appears in the To: field, doesn’t mean that address book entry corresponds to the expected email address. The slightly aggressive response I received was, “But this person sends email to me every week and I have never had a problem”. With a calm head, I asked him to speak to the sender to check that the email address that was used was the correct one.

After half a day, the sender responded with an apology that the email address on file was a Gmail address, my client doesn’t check that account.

As you can imagine, it was a very satisfying note for me to receive, I had no doubt that the email was never sent to my client’s mail server. The problem I faced was proving this to my client, while I know logs never lie; it is not so easy to explain this to someone for which email is just a black box.

I come back to the example of old fashioned mail, when you put a letter in a post box, you have no idea how many bags and trucks and miles that letter has passed through before reaching the destination, the same applies to email.

Common reasons for email not arriving

1         Incorrectly addressed

a.       Non-existent email – this generally results in a bounced back message, which if reviewed will clearly show this problem

b.      Correct email but sent to the wrong address – as in the example above, you won’t get a bounce back message and heavily relies on the sender reviewing who they sent it to.

2         Blocked by spam filter – this is a complete discussion on its own and one I will detail in the next blog.

3         Domain has expired – the silent assassin of email problems. If the email address on record for your domain is no longer current, you won’t receive alerts that your domain is due to expire. Once this happens, email, website and any other services associated with that domain, will no longer work.

4         It did arrive, however email rules setup previously automatically moved it to a subfolder. This is surprisingly common and one which I must admit has caught me out before.

So after reading this, I hope I have cleared up some of the mysteries behind why an email sent from Point A didn’t arrive at Point B.

For an obligation free assessment and discussion about your current IT infrastructure, I warmly welcome hearing from you.


Daniel Butt


Tel: +61 2 9369 1566












Email - Under the Covers

  • We have a maintenance plan with them that is both inexpensive and we have someone check everything once a month even if the system is working smoothly.
    Can highly recommend to anyone.
    Elijah Udovitch, Spectacular Specs
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