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Thunderbird 91.6.0 SSL connection problems to Upgraded Dovecot server

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  • Èsì tí ó kẹ́hìn lọ́wọ́ bob.weeks

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I am in the middle of migrating an Ubuntu 18 server to a new 20 server and I am having problems connecting with thunderbird imap 993 with an error of "Failed to initialize SSL server context: Couldn't parse private SSL key" on the mail log. I have successfully connected with Mac mail client using the inbuilt certificate in the keychain but I would rather use Thunderbird as all my other accounts are there.

I do not seen to be able to associate a certificate with the email settings. I have installed a number of certificates into Thunderbird prefs but no matter what setting I use it is always "Couldn't parse private SSL key" I can connect on No security 143 using normal password but switching to SSL/TLS fails.

If I select Authentication Method = TLS Certificate (Which is what I selected in Mac Mail Client. there is no option to select the certificate to us.

Please advise Bob

I am in the middle of migrating an Ubuntu 18 server to a new 20 server and I am having problems connecting with thunderbird imap 993 with an error of "Failed to initialize SSL server context: Couldn't parse private SSL key" on the mail log. I have successfully connected with Mac mail client using the inbuilt certificate in the keychain but I would rather use Thunderbird as all my other accounts are there. I do not seen to be able to associate a certificate with the email settings. I have installed a number of certificates into Thunderbird prefs but no matter what setting I use it is always "Couldn't parse private SSL key" I can connect on No security 143 using normal password but switching to SSL/TLS fails. If I select Authentication Method = TLS Certificate (Which is what I selected in Mac Mail Client. there is no option to select the certificate to us. Please advise Bob

Ọ̀nà àbáyọ tí a yàn

Looks like it isn't Thunderbird, Closer inspection of the logs and Mac mail was also reporting can't connect switching back to insecure connection. :( Right back to the drawing board Thanks for your input Bob

Ka ìdáhùn ni ìṣètò kíkà 👍 0

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The expectation is the certificate will be installed in the Thunderbird certificate manager and selected automatically if I read this bug correctly https://bugzilla.mozilla.org/show_bug.cgi?id=431819

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Not sure, the link talks about recurring popups. Switching to non-ssl the connection works as expected. however even though I have a number of certificates installed in the Thunderbird database selecting TLS Certificate Does nothing. Ive tried Encrypted password too but still nothing. As a side note to get the Mac mail to work I had to explicitly tell the server which certificate to use, which I didn't before I upgraded Dovecot.


The Dovecot error is Error: Failed to initialize SSL server context: Couldn't parse private SSL key: error:06065064: digital envelope routines: EVP_DecryptFinal_ex: bad decrypt, error: 0906A065:PEM routines

PEM_do_header:

bad decrypt: user=<>, rip=xxx.XXX.XXX.XXX, lip=192.168.1.161, session=<Hp0FadnX79ta/06M>

So I am guessing the cert is not being passed to the server

Thanks for your input. I'll keep looking.

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Ọ̀nà àbáyọ Tí a Yàn

Looks like it isn't Thunderbird, Closer inspection of the logs and Mac mail was also reporting can't connect switching back to insecure connection. :( Right back to the drawing board Thanks for your input Bob