AWS WorkMail Not Sending Emails – Credentials Working Fine in Other Web Apps

Hi all,

We’re having trouble with AWS WorkMail not sending emails from our Discourse instance. The same AWS WorkMail credentials work fine in another web app, so the issue isn’t with the credentials.

We tested Gmail SMTP, and emails send without issues, suggesting it’s specific to AWS WorkMail. We ran discourse-doctor and got an error (see attached screenshot).

Has anyone faced this issue with AWS WorkMail? Any help would be appreciated!

Thanks!

timeout means that your container can’t connect to the host and port that you’re sending it to. It’s likely a networking issue in Docker (sort of unlikely) or a networking/firewall issue with your VM and/or AWS (more likely and there are like 100,000 ways that you can do it wrong.)

Thanks for your response!

We initially thought it might be a networking issue too. However, we tested the connection using telnet from the Discourse instance, and it connects successfully to AWS WorkMail on the specified host and port. This suggests that the connection is being made, but the emails still aren’t sending through.

Given that other services like Gmail’s SMTP are working fine with the same setup, do you have any ideas on what else could be causing this? Could there be something specific to how Discourse handles AWS WorkMail?

Any further suggestions would be really appreciated!

Thanks again for your help.

From inside the container?

No, Please assist us to resolve this issue.

You’d need to enter the container and install telnet.

Thank you for the suggestion. I think the issue is that WorkMail operates on port 465, which may be causing the error. Do you have any other suggestions or workarounds for resolving this issue.
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I use ses. Maybe it’s the same config. Can i see what you have in the app.yml?

(of course, hide your password)

There’s a setting to turn off tls. I think it’s in the yml file commented out.