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Email – Taming the Beast

Don’t you just love email? When it works smoothly, that is. And when you’re not being spammed. But unfortunately, it never seems to be that constant. Just when you think it’s under control, suddenly out of the blue something changes and life is never the same again. The annoying thing is that very often there is no clue as to what has brought about the change in the first place.

The majority of us lay people don’t seem to know much about how email works – it’s a bit like electricity really. Flick the switch on and the room lights up – do we need to know how the power is generated? As long as it works and doesn’t cause us any grief (apart from the ridiculous cost of course), we tend to take it for granted.


How email works

There are two servers directly involved in the delivery of email. The sending server and the receiving server; each runs mail software that is responsible for various services that allow for the transfer of mail as well as delivery into the recipient’s email client. An email client is the software used, for example Outlook.

The sending server receives the email that is sent from the email client (Outlook, Thunderbird, etc) via SMTP (Simple Mail Transport Protocol). From the email client point of view, the email has been sent, but in reality, it has only been sent to the sender’s SMTP service. The SMTP Service then drops the email into a queue which is then processed when the SMTP service is ready to do so. The SMTP service extracts the domain name from the recipient’s email address and using DNS (Domain Name Service) looks up the MX (Mail Exchanger) records to determine what the SMTP service location is for the recipient.

The sending server then looks up the IP address for the domain name for the recipient’s SMTP service from the MX records. It then connects to the recipient’s SMTP service and tells the recipient’s SMTP service that it has an email for it. The recipient’s SMTP service then performs some anti-spam / virus checking on the email and if it’s all good, drops the email into a queue for further processing when it’s ready.

If the recipient’s SMTP service is busy dealing with a backlog of email, it may tell the sender’s SMTP service that it’s too busy and to try again in a defined period of time. This is also used as an anti-spam technique referred to as grey-listing. The recipient’s SMTP service then delivers the email into the recipient’s inbox in the server. Note: if the recipient’s email account doesn’t exist, then the recipient’s SMTP service sends an email to the sender telling them that the email can’t be delivered and the reason why. This is referred to as the bounce email. 

Finally, the recipient’s email client connects to the POP3 service (Post Office Protocol), IMAP4 Service (Internet Message Access Protocol), or similar, to check if there are any new emails waiting and if there are, they are sent to the email client which saves the email in the recipient’s local inbox ready for the user to read.

A compromised email account can cause your email to be black-listed, even if it isn’t your account that has been compromised. That’s why it’s equally important that everyone works as a team, by using secure passwords for their email accounts. One weak password can cause a world or grief for everyone.


Reporting the problem

When providing us with details on email issues, we need a copy of the original email (that has the issue) as an attachment. Hidden in the email content is what is called the message headers which contain all the details of how the email ended up in the recipient’s inbox. When the email is forwarded, these headers are replaced with new message headers for the delivery of the forwarded message, so it is of no value in diagnosing issues. An example of what a header looks like follows:

Received: from mail.expert.services ( by

WIN-A8C7GLTAD6J.business.local ( with Microsoft SMTP Server (TLS) id

14.3.319.2; Thu, 8 Oct 2020 13:27:02 +1300

Received-SPF: pass (expert.services: domain of mail.paypal.com designates as permitted sender)


Received: from mta105bb.pmx1.epsl1.com ([]) by expert.services

with MailEnable ESMTPS (version=TLS1_2

cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384); Thu, 8 Oct 2020 13:26:52 +1300

Return-Path: <bounce@mail.paypal.com>

DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=mail.paypal.com;

                s=pp-epsilon1; t=1602116796;









Received: from [] ([])                 by pc1udsmtn2n14

(envelope-from <bounce@mail.paypal.com>)   (ecelerity

r(Core: with ECSTREAM               id C9/D9-37774-CBC5E7F5; Thu, 08 Oct 2020

00:26:36 +0000

List-Unsubscribe: <mailto:bounce-HP2v600000175059a3d0bb76d0d6e965fd798000@mail.paypal.com?subject=list-unsubscribe>

Message-ID: <HP2v600000175059a3d0bb76d0d6e965fd798000@mail.paypal.com>

MIME-Version: 1.0

Feedback-ID: edcce047-ccac-4df1-b828-81ec074a7b42:c295c937-7bdd-428c-a295-c246cb792b58:email:epslh1

X-NSS: edcce047-ccac-4df1-b828-81ec074a7b42

Reply-To: "noreply@mail.paypal.com"


Subject: Upcoming changes to our PayPal legal agreements

From: PayPal <paypal@mail.paypal.com>

To: <aaron.main@expert.services>

Date: Thu, 8 Oct 2020 00:26:36 +0000

Content-Type: multipart/alternative;


X-ME-CountryOrigin: US

X-Envelope-Sender: bounce@mail.paypal.com

X-ME-Bayesian: 0.000000

X-MS-Exchange-Organization-AuthSource: WIN-A8C7GLTAD6J.business.local

X-MS-Exchange-Organization-AuthAs: Anonymous


There is obviously a huge science (and machine) behind all of this and it goes back for decades. If you’d like to know more about the history of email check this out for some really riveting reading.


So, what happens to make it all go so wrong?

With all great inventions, there will always be some killjoy who just wants to mess things up and ruin our enjoyment. In the case of emails, there are a range of hot spots that attract the wrong sort of attention. There are copious quantities of spam – junk mail that just never stops, despite the anti-spamming legislation, and unsubscribing to them only seems to encourage them. On-selling lists of email addresses is really big business for unscrupulous operators and it’s like constantly fighting an uphill battle trying to keep your inbox free of this rubbish.

A more insidious threat are the scam emails from the world’s largest and most populated continents – Northern Europe, North America, Asia and Africa – usually asking you to click on a dodgy link or open an attachment that is bound to be riddled with viruses, malware or trojans. The main purpose of these scams is to separate you from your money, one way or another.

Over the years the scammers have got better at creating emails that look authentic and recipients from all walks of life get caught up in these extortion attempts.



To offer some protection from these unscrupulous thieves, email service providers create rules of their own, and this in itself can be problematic. A common response is for the email service provider to blacklist emails sent from URLs that have misbehaved, and of course these emails never get delivered. The biggest problem with this is if a sender has been put on a black list by accident and their email is genuine. 

We get calls from our clients saying that there’s a problem with their emails getting delivered and they often seem to think this is of Expert’s making, which, in most cases, it isn’t. But we still investigate and provide advice on how they can clear the blockage. Expert provides an email service to clients as a value-add, rather than as our core business, and we can spend a disproportionate amount of time trying to help our clients with their email problems, so we’re always looking at ways we might be able to streamline such issues, or even prevent them from occurring.

Some email service providers, such as Outlook, have grey lists, where they hold on to emails they think might be a bit dodgy to see if any effort goes into trying to get them sent once they’ve been corralled into a holding pen. If the sending server keeps trying to send it, it might get through. If not, it ends up being dumped.

There are also spam filters built into Outlook. Obviously, we have no control over how Outlook manages its spam filters, as it’s not our product.

Ultimately though, if email is being flagged as spam at the recipient’s end, then it’s something that needs to be addressed by the sender rather than the recipient. We suggest that it is raised with the sender and they should make changes to prevent their emails from being flagged as spam if they want them to get through.


Updates and Junk Folders

Updates are frequently applied to mail servers and this might cause settings to change, resulting in some emails being considered as junk and forwarded to junk folders. It’s an automated process, so the best way to manage it is to check your junk and spam folders on a regular basis, at least daily, and transfer any emails you want to keep to your inbox. To prevent emails going into your junk folder from people you want to hear from, you can add them to your Safe Senders list.

In case you aren’t familiar with doing this, the following might help if you use Outlook


  1. Select Actions from the toolbar at the top of the screen.
  2. Select Junk E-mail.
  3. Select Junk E-mail Options...
  4. Click the Safe Sender tab.
  5. Click Add.
  6. Type in the email address you wish to add to your safe sender list.
  7. Click OK


Well, as much as we wish we could wave the proverbial magic wand and all your email hassles would disappear, unfortunately life is never that simple. The best we can do is help you to understand why these things happen, so that you can do some preliminary checking. If Expert is your email host and you are experiencing problems with your email, please provide us with as much background information as possible when you contact us to sort it for you, as mentioned earlier. Refer to ‘Reporting the Problem’ above. It really helps us to know what’s been going on and will save everyone time in the long run. 

And if you find checking your junk and spam folders a chore, and you think you shouldn’t have to do it; I’m sorry, but you do. That’s life. If you’re happy to miss an authentic message, that’s really your decision.

The next blog in the ‘Email’ series will be about email storage management – looking at the difference between storage and e-hoarding.

Contact us@expert.services for more information.


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