Why didn't my email get delivered?

We expect every valid email to be delivered and when that doesn't happen, it is very frustrating to all involved.  At YachtCloser, we send around 150,000 emails per month, and generally have problems with only a handful. Unfortunately, if your email is one that has a problem, those numbers are not very comforting.

How does YachtCloser send email?

When we send an email, we package it up and transmit to an email server, complete with the intended recipient's address. The outbound email service we use is provided by and managed by a third-party vendor who specializes in high volume email delivery. They ensure their servers have a high sending reputation, because email server sending reputation affects deliverability. We also have a published "approved sending server" list, i.e. a list of what email servers are allowed to send for us, enabling receiving servers to verify an email came from YachtCloser appropriately.

Those third party email servers work out the actual delivery of each individual email by contacting the recipient's receiving email server and delivering it to that email server. Once the email has been sent, our ability to affect the process further is completely stopped.  Also, our ability to see what is happening is extremely limited and totally dependent on information sent back from the receiving email server, which sometimes is absolutely nothing.

What happens on the receiving end for an email?

It is normal in the current technology world for servers to receive messages, even invalid ones, and never actually report an error. These servers look at the sending server's reputation, the published approved sending server list, any digital signatures, and then the message itself. They also look at one or more “black lists”, i.e. black list services located around the world that track reports of servers or addresses that spend spam. If our sending email servers end up on a black list, which can happen (e.g. accidental “spam” button clicks), it can be devastating. These black lists, while intended to provide a public service, also create a mine field for email senders. Each has their own rules and policies. Even when you comply, it can take 48 hours or more before they will remove an entry from their list. Which black lists are used depends on the receiving email server that hosts an individual user's mailbox. Based on all of these factors, the receiving email server software tries to “guess” if the message is spam or not. Unfortunately, both black lists and email service providers change their rules, guidelines, and tools regularly.

Email Service Providers vs. Spammers

Those who send spam of course know about all of this, and have access to all the same tools and technologies, and work tireless to find ways to get past all of these obstacles. The result is that people who just want to use email are caught in the middle of a genuine arms race between email service providers and spammers. It is virtually impossible for software that does this analysis to be correct 100% of the time. And when it is wrong, you either get spam, or don’t get valid email that isn’t spam. Most providers tend to be aggressive, and are willing to accept more false positives (blocking what should be allowed) than spam. 

What if your email is not received?

If your email is not received, there are a few options:

1. Many people have more than one email address and changing to an alternative email address can sometimes be a quick fix.

2. Please contact us. We know that every single email sent matters. We will dig in, research it, and resolve it as quickly as we can. We can manually forward to you an original copy of the email so that you can manually forward to your clients.  Oftentimes this is the best workaround, though manually forwarded emails are not foolproof.  Please understand that some of these email deliverability problems are an uphill battle.

Please know that we work very hard to ensure YachtCloser delivers as many emails as possible.  We are very proud of an extremely high average delivery rate (over 99%).

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