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  1. OpenProject
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  4. SMTP configuration

SMTP configuration

Added by Mitchell Laframboise 7 months ago

Hi there,

     I have tried to setup the SMTP server in OpenProject but am getting an ssl error that there is a self signed certificate in the chain.  

I've verified that the smtp server is using a trusted certificate and my synology nas is using a LetsEncrypt certifcate for the OpenProject Container.  I wouldn't be able to connect to OpenProject without it.

Can anyone help me figure this out? or have any insight in to what I may be overlooking.



Replies (5)

RE: SMTP configuration - Added by Mitchell Laframboise 7 months ago

Update:  I have figured out the ssl error, but now I'm having an issue with timeout errors.  I've tried turning the firewall off and updating dns.  I'm not sure where else to look

RE: SMTP configuration - Added by Mitchell Laframboise 7 months ago

Heres a screenshot of the error


RE: SMTP configuration - Added by Alexander Pieber about 2 months ago

Hello there!

I experience the same issue with a offline exchange server.
Specifically I see (Net::ReadTimeout with #<TCPSocket:(closed)>).
If I were to go with SSL I get a strange error:
An error occurred while sending mail (SSL_connect returned=1 errno=0 peeraddr=xxx.xx.x.xx:587 state=error: wrong version number)

Which leads me and my coworker believe that there is issue with TLS/SSL versions. But I have no issue performing TLS Handshakes or connecting to the SMTP from the machine. I run Openproject native on Ubuntu. Currently I am at a loss. And it is rather unclear where this problem specifically should be logged.

I should add the server uses a ACME cert with automatic renewal. The OpenProject website works fine as expected and uses the certificate.

I welcome any suggestions.

RE: SMTP configuration - Added by Alexander Pieber about 2 months ago

In bash I ran this oneliner:
echo -n -e "EHLO $(hostname)\nAUTH LOGIN\n$(echo -n 'openproject@domain.com' | base64)\n$(echo -n 'Password' | base64)\nQUIT\n" | openssl s_client -starttls smtp -crlf -quiet -connect smtp.domain.com:587
"Didn't find STARTTLS in server response, trying anyway..."
This is certainly a first for me. 

In the end we went without login. Since we use Starttls basically everywhere I am surprised by this specific issue.

RE: SMTP configuration - Added by Alexander Pieber about 2 months ago

I have a update.
We had a cert that ran out on Exchange which caused this issue specifically.
So now we got security again.

BR

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