Hello,

I have managed to debug the problem a bit further. With libssl 1.0.2a I note that the following command gets stuck

 openssl s_client -connect imap.some.org:993

it outputs

 CONNECTED(00000003)

and hangs until there’s a timeout.

On the other hand, the following command successfully establishes a connection:

 openssl s_client -tls1 -connect imap.some.org:993

Part of the output is

New, TLSv1/SSLv3, Cipher is RC4-SHA
Server public key is 2048 bit
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated

Consequently, I tried forcing TLSv1 in mbsync by specifying in ~/.mbsyncrc

UseTLSv1 yes
UseTLSv1.1 no
UseTLSv1.2 no

But this doesn't seem to change anything, mbsync still gets stuck until there’s a timeout, just like I described in my previous message. This is not actually not surprising, at the above three lines are just mbsync’s defaults.

Finally, I was able to get it to work using the following in ~/.mbsyncrc

IMAPAccount some-remote-account
RequireSSL no
User myuser
Pass secret
CertificateFile /home/cwg/14-x509-certs/some.pem
Tunnel "/usr/bin/openssl s_client -CAfile /home/cwg/14-x509-certs/some.pem -tls1 -connect imap.some.org:993 -quiet"

I still do not understand which part of the software stack is responsible for this issue to which extent: isync, Microsoft’s IMAP server, or OpenSSL. It would be great if someone with understanding could tell me, so that I can report the issue appropriately (not that I see any chances in reporting to Microsoft…).

Thanks
Christoph

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