Remi Chauveau Notes
Troubleshooting 🛠

Why Are My Emails Not Sending and How to Fix it

30 January 2024
Undelivered emails are frustrating. It’s hard enough to manage your deliverability strategy and focus on your engagement, but none of that is possible if your emails don’t make it to the inbox. If you’re at a loss for why your emails won’t send, we’ve got you covered.

Let’s say you’ve integrated your app with email functionality, designed some great email content, developed a marketing strategy, and you think you’re good to go. But then you hit send from your email client, and you see one of the following error messages from your mail delivery subsystem:

-Message not delivered.

-Email failed to send.

-Failed to send email.


You’ve probably thought long and hard about emails failing to get delivered, but what’s this about emails failing to send? In this article, we discuss some of the reasons for undelivered emails. Then, here are some ways to fix the issue and leave you with five tips for smoother future email sends.

What does the ‘Email failed to send’ message mean?

Simply put, this message is as it says: your email is currently not deliverable. Email delivery failure can feel really complicated but the first place to look is at your SMTP server, the mail server that’s responsible for sending, receiving, and transferring your email via the Simple Mail Transfer Protocol (SMTP) protocol. SMTP then uses TLS/SSL to secure the network connection between your email client and your mail server.

Email sending failures often occur if you self-manage your own SMTP server, which comes with large technical overhead and security requirements.

Why do emails fail to send, and how can I fix it?

Don’t give up too easily – just because your email failed to send this time doesn’t mean you’ve stumbled into an unfixable situation. The reasons your email failed to send can vary from the pretty mundane (a bad internet connection) to technically complex issues (your SMTP server connection).

Here are some common reasons your email failed to send:

1. You’re not connected to the internet.

2. You’ve set up your email client with the wrong SMTP parameters.

3. Your SMTP server connection is malfunctioning.

4. You’re using the wrong SMTP port.

5. Your firewall settings are getting in the way.

Let’s unpack each of these below and walk through some troubleshooting steps.

1. You’re not connected to the internet

Have you tried turning it off and on? Okay, we don’t mean to make light of the situation, but sometimes this happens. Check your internet connection first before tearing apart your SMTP server setup. Sometimes, the issue really is just that simple.

2. You’ve set up your email client with the wrong SMTP parameters

Are your emails not sending in Microsoft Outlook or Gmail via your app integration? Chances are you’ve set up your webmail client with the wrong SMTP authentication or made a few typos.



3. Your SMTP server connection is malfunctioning

Okay, this is where it gets tricky. Your SMTP server connection may be malfunctioning. If your SMTP parameters are correctly set up, your email server may be down or not functioning.

How to fix: Here’s a list of common SMTP response codes and some SMTP commands to help you troubleshoot.

4. You’re using the wrong SMTP port

The old school convention states that your outgoing mail server should use port 25. However, some inbox service providers (ISPs) block port 25 because of spam issues.

5. Your firewall settings are getting in the way

That’s right, check your antivirus or firewall settings. Sometimes, outgoing mail can be blocked by your own privacy protection protocols.

How to fix: Set up a proper exception rule for your firewall or antivirus program.

4 tips to avoid the ‘email failed to send’ message

The best way to fix a problem is to prevent it. With that being said, here are five ways to avoid that dreaded “email failed to send” message:

1. Check your internet connection and email password

Typos and human errors are easy. Save yourself a few headaches by making sure your Wi-Fi connection works and that your authentication protocols are all properly set up before you hit send.

2. Check your SMTP server details

Ensure you’ve correctly entered the right parameters and that your mail server is functioning as intended.

3. Use the correct SMTP port

Port 587 is considered the default SMTP port for mail transfer, and it’s what you should use unless you’re blocked by your network or internet provider.

4. Use an ESP that provides an SMTP relay service

ESPs, like Mailgun, provide an SMTP relay service that helps you circumvent all the headaches associated with running your own SMTP server. Leave delivery failures in the dust while the pros manage your email delivery.

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Did You Know

People are more likely to open emails with emoji

A significant proportion of Google’s trillions of annual searches have never been searched before. Many email marketers are finding that using emoji in their subject lines increases open rates. An Experian report from 2023 found that 68 percent of companies using emoji in their subject lines had more unique opens than those who didn’t. Unfortunately, that doesn’t mean you should use emoji in all of your emails all the time. Forbes reports that using emoji in work emails might lower your colleagues’ opinions of you.

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