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When Emails Fail to Send emails flying into brick wall

Sometimes you send out emails, but they don't make it to their recipient. Here's what you need to do to get your emails sent, and also to fix the underlying problem.

Sometimes emails fail to send. You get a message from your server explaining why the recipient rejected it. To fix the problem, you should understand the explanation. It is much easier to solve a problem when you know what it is! The resolution of this issue is usually simple and doesn't take long. There are two things you need to do:
  1. Send your email.
  2. Get the problem fixed
I will explain both.


Let's assume that your domain is hosted by BlueHost or InmotionHosting or GoDaddy, or any other website hosting company. They usually provide email service in addition to your website hosting.

These problems can occur with AOL or Comcast or Google or any other company, but they aren't as frequent. Here's why they occur.

How Email Works

Cop stopping with handYou give an email to your hosting company claiming to be from your company. Your host then sends that message. When the receiving server gets the message, it does some checks.
  1. Does this person have permission to send messages from this company?
  2. Is this company's email setup properly?
  3. Are they on any blocklist for being spammers?
  4. Can I be sure this is the correct person?
If any of these checks comes out negative, then a good email recipient will reject your email and it gets bounced back to you.

These failures occur frequently with less expensive web hosting services and they're beginning to occur more often as people are taking the fight against spam and phishing exploits more seriously. My web host explained to me that if I wanted to be sure my business emails went out, I should get another service. Their business is Web Hosting, not email. However, I've seen this happen to Comcast and Google as well. Things sometimes get screwed up.

If you absolutely need to get the message out right away, you need a second option. I normally send out my email from steveshank.com, but I have my Comcast account and a Gmail account available. I can send from either of them if necessary.

Setting Up a Second Email Account

Everyone should have a second email account. It's like having a second bathroom. You may not need it often, but it is awfully good to have when your primary bathroom isn't working. If you have your own domain, just add an account with your email client for your ISP.

For example, if you are using Thunderbird, then Tools > Account Settings will bring this menu.

Then Account Actions and select Add Mail Account...

You can then fill in your name, email address and password. Most email clients, like Thunderbird and Outlook will figure out all the other stuff for you. If you are already using your ISP as your primary email provider, then you can get a Gmail, Yahoo or other free account to have available if you should ever need it.

If you like using webmail, perhaps Gmail, get another webmail site in case you need it. Your ISP will have webmail available as part of your subscription.

When you write a message, just click the little v on the end of the "from" to pull down

That will let you select which account you'd like to send from. Choose the new account and you'll get your email out.

Get the Problem Fixed

Your email providers will fix most of these problems if you give them the necessary information. You'll usually get a message back from a "Mailer Daemon" or some such explaining that they couldn't deliver your email. Here are some sample error messages and what they mean. Be sure you forward this information to your email provider when you call them.

Sample 1: Failure to authenticate

: host Gmail-SMTP-in.l.google.com [] said:550-5.7.26 This message does not pass authentication checks (SPF and DKIM both 550-5.7.26 do not pass).

So, it is saying that when the message reached Gmail, they checked your email and returned it instead of delivering it to your recipient. Gmail checked with your domain and you weren't authorized to send messages in your company's name. SPF is sender policy framework and DKIM is Domain Keys Identified Mail. They are two protocols that email hosts use to check with the domain and make sure the email is legitimate. Your mail host needs to fix this.

The email host made many changes over the years, and they eventually missed updating my client. All that he needed to do was call the mail host and have them fix it.

Sample 2: Another authentication failure

: host Gmail-SMTP-in.l.google.com[] said:
550-5.7.25 [] The IP address sending this message does not have a 550-5.7.25 PTR record setup, or the corresponding forward DNS entry does not 550-5.7.25 point to the sending IP. As a policy, Gmail does not accept messages 550-5.7.25 from IPs with missing PTR records. Please visit
550-5.7.25 https://support.google.com/mail/answer/81126#ip-practices

Again, this was a screwed up mail record and the client needed to call his web host and have them fix it. The addresses resolve to either the recipient's servers or the sender's addresses. In this case, it was the PTR record that was no longer proper.

Sample 3: Blocked by a spam filter!

This one is a little different.

owner@clientcompany.com host mail.clientcompany.com [] SMTP error from remote mail server after RCPT TO:: 550-"JunkMail rejected - se3h-lax1.servconfig.com []:32769 is in 550-an RBL on rbl.websitewelcome.com, see Blocked - see 550 http://www.spamcop.net/w3m?action=checkblock&ip="
Here someone was sending out spam from the email servers I was sharing and got the server on a blocklist from Spamcop. My mail host needed to remove that IP address and negotiate with Spamcop. Again, let your email provider know, and maybe you'll send out from another server in the server farm next time.

Sample 4: Slowed due to bad conduct

client@msn.com host MSN-com.olc.protection.outlook.com [] Delay reason: SMTP error from remote mail server after pipelined end of data:
451 4.7.650 The mail server [] has been temporarily rate limited due to IP reputation. For e-mail delivery information, see https://postmaster.live.com (S775) [VI1EUR05FT057.eop-eur05.prod.protection.outlook.com]

Here, they're not an a blocklist yet, but there have been complaints, so they are processing emails from those servers more slowly and may or may not get to yours.

The Solution

My web host was having so many problems, for so long, that I gave up and purchased an email host separate from my web host. I use Runbox.com, but Fastmail.com and Mailbox.org are also good options. In general, inexpensive Web hosts aren't very good at email, but can handle websites just fine. When their only business is email, they are good at it and the service is inexpensive. I reviewed three services here. All three of these services protect your privacy as well and give you a more secure option than your web host is likely to provide.

You should always have a second email account you can use to send emails out in an emergency. This is just part of life in the modern age. But you should also try and provide your email service with the complete messages regarding the reason your email was rejected.

Date: March 2023

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