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Thunderbird 91.6.0 SSL connection problems to Upgraded Dovecot server

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  • Last reply by bob.weeks

bob.weeks
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

Chosen solution

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

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All Replies (3)

Matt
Matt
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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

bob.weeks
bob.weeks Question owner
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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.

bob.weeks
bob.weeks Question owner
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Chosen Solution

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