SSL connect fails

Dear all,

after an update of our Ubuntu Server (and maybe, but not necessarily related), I am facing the problem that my Foswiki installation is not able to send mails anymore. Trying to send a test email in the mail configuration settings ends with the following error:

Sending email to "Wiki Administrator" ERROR: Failed to initialize SSL with {IP-adress of my smtp server}:587 - SSL connect attempt failed error:14161044:SSL routines:state_machine:internal error

What might be the problem?

Kind regards and thanks in advance for any help with this issue!

-- HcR - 03 Sep 2021

I'm guessing something changed with your OS update if it was working before that. Did you try enabling "Debug SMTP" under the Advanced tab in the Mail configuration? That might give you some additional info. Personally, I have had better luck in Ubuntu to configure ssmtp as default sendmail and then in Foswiki, simply use the sendmail option for outgoing emails.

-- LynnwoodBrown - 04 Sep 2021

Thanks for the very quick reply! Yes, I used the debug SMTP option but I could not figure out what exactly the problem is. I attached an anonymized version of the error log. It seems as if it succeeds to establish an unencrypted SMTP connection between the server on which I have my foswiki installation and my SMTP server. However, when SSL comes into play, something seems to go wrong.

Sendmail might be a good option as well, but as far as I understood (correct me if I am wrong) this would require saving my SMTP password in clear-text. As I am using the account also for other purposes, I would prefer to avoid the latter.

-- HcR - 07 Sep 2021

I'm afraid I can't see solution for connection from your log. You're correct that the ssmtp module stores the password in config file. You might also check out msmtp module which appears to have alternative options for retrieving the password.

-- LynnwoodBrown - 07 Sep 2021