BitBucket Server - Encrypted email not working

[Darrel Anthony]

Hi

We have BitBucket Server installed locally (on a Windows server) and I have set up the mail server settings so that notification emails can be sent to users from BitBucket Server (i.e. reset password emails, etc). It works fine until I tick the 'Use SSL/TLS if available' box at which point the emails stop getting sent. 

On the 'Mail server configuration' page there is a 'Send a test email' section. The test email works fine with the 'Use SSL/TLS if available' box unticked and fails when it is ticked so I am certain that's the problem.

The BitBucket system states the following (for the 'Use SSL/TLS if available' option):

If the SMTP server supports the STARTTLS extension this will be used to encrypt mail with SSL/TLS otherwise plaintext will be used.

I contacted the people that host our mail server about it and their response was the following:

It should work fine, your server supports SSL/TLS/STARTTLS so it shouldn't have any issues connecting with that option enabled. As it may be using a self-signed certificate then you may need to tell it to accept potentially invalid certificates but normally that's the default.

I don't know how to do what they are suggesting. Can anyone point me in the right direction here?

Thanks

[Rodrigo M]

Hello Darrel

My recommendation is to check all the steps mentioned in the Setting up your mail server.

Under Securing email notifications section, it states the below:

Note that if you use either SMTP with STARTTLS, or SMTPS, and connect to a self-signed mail server, you may need to import the server's cert ificate and set up a custom cacerts file for Bitbucket Server (just as you do for any outbound SSL/TLS connection to a self-signed server). See this Bitbucket Server knowledge base article for information about how to do that.

The information brought by your mail server hosting company it's related to the sentence above. You will need to import the certificate from the mail server into Bitbucket Server.

More information on how to import the certificate from one app server to the JAVA trustore that Bitbucket is running here.

Regards
Rodrigo