• April 26, 2023

Did you get my email? – The pitfalls of email delivery

This is something that anyone with an email address these days can hear or say quite often. Because? Well, due to the relatively unreliable nature of email delivery systems.

Here is a complete list of what happens in your email to be delivered:

* Virus checks: Most viruses (and worms) these days travel the Internet via email messages. To protect valuable network systems from virus attacks, most corporate networks and Internet service providers employ virus scanners that scan for viruses and worms in the same way as the virus scanners on your desktop computer. Most email servers are set up to delete or quarantine any message that tests positive for a virus.

* SPAM filters and the huge growth of SPAM – Everybody hates SPAM! So much so, that people will change their ISP providers or email host for better SPAM protection. As a result, companies like AOL and MSN spend tons of money finding new ways to provide “better” spam protection to their subscribers to reduce their churn rates.

* SPAM filtering methods:

  • Phrase filters: watch what you say! Many email servers use a list of unacceptable or offensive words and phrases and will reject or place the message in a spam folder if it matches, so be careful what you say, or your message could be rejected.
  • Connection checks: Misconfigured email servers can cause lost messages. This is most likely out of your control (unless you’re a server administrator), but be aware that when email servers talk to each other, some are very picky about allowing a connection and can reject it if the origin server does not “check out” correctly.
  • Statistical analysis: Used to detect some of the techniques used by spammers, such as many repeated words or a lot of unrelated words in the message (usually to try to remove spam filters). Your message can become a victim of this if you do something like copy and paste a data file into the body of your message or if you were to insert a data file (such as a mailing list or spreadsheet) into your message, instead of attaching the file.
  • Domain Blacklists – Your ISP doesn’t like your friend’s ISP! – server administrators will use a list of lists of trusted (and sometimes not-so-trusted) domains and/or IP addresses to filter incoming messages. If you are using one of the “bad” service providers, your messages could be lost. Be careful with the company you keep!
  • HTML Checking and Filtering – Don’t go too far with your HTML emails. Many servers are configured to reject messages that contain certain html code. Especially scripts, deceptive URLs or scrambled text.
  • Discretionary blocking by email address, domain or IP blocking. – Most email servers give the administrator the power to place a lock on their server to deny access to any server or domain of their choosing.
  • Server Rule Sets – In addition to all of the above hurdles, most email servers can be custom configured with rules that will redirect or delete messages on just about any content you can think of. An incorrectly coded rule could create a virtual sink for messages.

Now, assuming your message passes all of the above checks, the next stumbling block is your email client program, such as Outlook.

* Email Client Rules and Filters – Just as servers can have rule sets that redirect or delete messages, most email client software also has the ability to create custom rules to delete or move messages to a file. Again, a poorly coded rule could create a black hole for your message.

* Spam Filters or Junk Filters: Most email client software also provides some sort of spam filter, such as the Outlook Spam Filter and plug-in filters such as SpamAssassin. These filters have become quite reliable, but a small percentage of false positives will still occur. Your message could be the victim of one of those false positives.

Other traps:

* Non-enforced standards: Although there are sets of standards (RFCs) that software vendors and server administrators are supposed to adhere to, many times the standards are laxly enforced. In fact, most email server software gives the administrator the option to enable or disable specific RFC features at will or desire.

* False Positives – virus and spam filters. – Each content filtering technology has a certain percentage of false positives that are considered acceptable.

* Proprietary systems: There are many internally developed systems that are simply poorly written and not up to standards.

* The Wild Wild West… each one configures their systems based on their point of view, morals and opinions.

* Quotas – Sorry, that mailbox is full – many service providers will limit the size of your inbox. The reasons for this are obvious… storage costs money.

* Daily delivery… not so much! -The fact that his message has arrived today does not mean that he will tomorrow. Content and virus filters are often updated daily. Also, the little geek behind the server admin console may decide to add an extra filter or click on a new feature just to try it out (I know, I’ve done that)… again, it’s the Wild West.

So how can I fix this? What I can do?

* Above all, keep this in mind.

* Request a delivery receipt.” Most email clients support this, however most email clients also provide the option to ignore them when received. Still, it doesn’t hurt to ask!

* Request confirmation. Ask the recipient of the message to reply with confirmation that they received it. This is probably the most reliable method to ensure that the message was received.

* Don’t assume anything: never just assume the message was received. You know what makes you think… It makes a fool of you and me!

*Follow up. If the message is critical, follow up with an additional phone call or email requesting confirmation.

The result and my recommendation:

Email is great and very convenient for everyday communications, but be aware of the pitfalls and don’t rely too much on email for critical communications. And please… Do not send your critical business files via email. FTP or burn to CD and send overnight.

Leave a Reply

Your email address will not be published. Required fields are marked *