Hi, Moving the thread to bugs@ has it seems to be an issue with libssl.
When connecting with nc(1) to outlook.office365.com:993, on older system is able to connect and verify the connection. On a recent system, the handshake failed due to "invalid digest length". on "old" -current (snapshot): OpenBSD 6.4-current (GENERIC.MP) #419: Wed Oct 31 18:14:06 MDT 2018 $ nc -vvc outlook.office365.com 993 Connection to outlook.office365.com 993 port [tcp/imaps] succeeded! TLS handshake negotiated TLSv1.2/ECDHE-RSA-AES256-GCM-SHA384 with host outlook.office365.com Peer name: outlook.office365.com Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=outlook.com Issuer: /C=US/O=DigiCert Inc/CN=DigiCert Cloud Services CA-1 Valid From: Wed Aug 1 02:00:00 2018 Valid Until: Sat Aug 1 14:00:00 2020 Cert Hash: SHA256:47be4a2af4d726b98ad723eed11ec6cb7b58a9cae90d5638e96fb2b037f21fcd OCSP URL: http://ocspx.digicert.com OCSP Stapling: good response_status=0 cert_status=0 crl_reason=0 this update: Tue Nov 13 00:24:08 2018 next update: Mon Nov 19 23:39:08 2018 revocation: * OK The Microsoft Exchange IMAP4 service is ready. [QQBNADUAUABSADAANAAwADIAQwBBADAAMAAwADMALgBlAHUAcgBwAHIAZAAwADQALgBwAHIAbwBkAC4AbwB1AHQAbABvAG8AawAuAGMAbwBtAA==] but on more recent system (manually built system): OpenBSD 6.4-current (GENERIC.MP) #18: Sun Nov 11 15:45:56 CET 2018 $ nc -vvc outlook.office365.com 993 Connection to outlook.office365.com 993 port [tcp/imaps] succeeded! nc: tls handshake failed (handshake failed: error:04FFF08F:rsa routines:CRYPTO_internal:invalid digest length) Something changed. Thanks. -- Sebastien Marie On Tue, Nov 13, 2018 at 07:58:00AM +0000, Mikolaj Kucharski wrote: > Hi, > > I just upgraded base system to: > > OpenBSD 6.4-current (GENERIC.MP) #437: Mon Nov 12 20:06:01 MST 2018 > dera...@amd64.openbsd.org:/usr/src/sys/arch/amd64/compile/GENERIC.MP > > and all packages to the latest snapshot at the time: > > $ pkg_info -f quirks | awk -F: '/digital-signature/ {print $2}' > 2018-11-11T21 > > $ pkg_info -qI offlineimap > offlineimap-7.2.1 > > I'm seeing this while OfflineIMAP 7.2.1 talks to outlook.office365.com: > > > Establishing connection to outlook.office365.com:993 (Remote) > ERROR: Unknown SSL protocol connecting to host 'outlook.office365.com' for > repository 'Remote'. OpenSSL responded: > [SSL: BAD_SIGNATURE] bad signature (_ssl.c:730) > > ..and connection closes. Is this known problem? I don't see this problem > when OfflineIMAP talks to Google. > > Regards, > Mikolaj > -- Sebastien Marie