Auddog007's picture

I've been using Redmine for 3.5 years using my office365 account as the smtp server.  I have recently purchased a new domain and move my office365 account from GoDaddy to Microsoft.  I have updated the configuration.yml to reflect the changes, but when I attempted to send emails from Redmine I was getting an authenication error.  I researched any additional settings as well as attempted to use my gmail account, but still was getting an authenication error.  I opened the Turnkey Configuration console and went through the advanced menu settings.  In the mail relay settings, I don't remember changing anything, but now when I attempt to send a test email, I get the following: An error occurred while sending mail (hostname "localhost" does not match the server certificate).  Nothing I change will get rid of this error.  I have done the 'deconfigure", but still the same error.  Is there file that was automatically written to or file that can be erased.

Here is my current configuration.yml file:

 delivery_method: :smtp

  enable_starttls_auto: true
  port: 587
  authentication: :login
  password: H0NotRealPasswordCR

  wkhtmltopdf_exe_path: '/usr/local/rbenv/shims/wkhtmltopdf'


Thanks for looking and any help that you can provide.


Jeremy Davis's picture

The Redmine app SMTP settings mean that Redmine will attempt to connect to your remote SMTP relay directly. That means that the TurnKey Confconsole Mail relay settings are somewhat irrelevant (it's still worth setting them IMO, but Redmine won't use them).

So you have 2 options. If you've setup the TurnKey system wide SMTP relay and wish to use that, then you can change the Redmine settings so that it uses the systemwide Postfix config (that you've done via the "Mail relay" config). For that you'll want to configure Redmine to use "sendmail" (Postfix provides a sendmail binary).

Alternatively, you'll need to troubleshoot why Redmine can not successfully authenticate. TBH, I have no experience with Redmine other than via the system Postfix but by my understanding what you've done looks ok. It certainly appears to match what Redmine have documented for Office 365. They do have a few troubleshooting steps noted there, although you didn't state your exact error message so I'm not sure if your specific issue is covered? Perhaps it's as simple as quoting your password?

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