OSX El Captian SMTP Timeouts caused by...

Markus's Avatar


20 Dec, 2015 10:55 PM


I just want to post an interesting fact regarding https://gpgtools.tenderapp.com/discussions/problems/47326-os-x-el-c... ... I had the same issue on an MBP2014 w/ OSX 10.11.2 but I currently have no 3rd party mailbundles activated or any version of GPGTools installed :-)

After some further troubleshooting I can confirm that this issue is not caused by
-GPGTools -wrong firewall or routing configuration (or just "bad voodoo" as mentioned in the link above) -your mail-configuration (eg. 3rd party bundles or the mailprovider's smtp service availability) It seems like that this "bug" occurs ONLY if you connect to your mail-provider via some kind of VPN and/or have some kind of antivirus web-traffic protection (..https: packetinspection / SSL certs.. ) activated - (I can't lock out the antivirus completely)

If I am connected via VPN and try to receive mails via OSX Mail.app the same issue occurs.
If I am connected via VPN and try to receive mails via Unibox.app the same issue occurs - the corresponding log file entry would be
hostname: smtp.gmail.com, port: 465, security layer: kCFStreamSocketSecurityLevelTLSv1 (Error Domain=NSPOSIXErrorDomain Code=60 "Operation timed out")

seems like the big data players don't like the mixture of VPN + TLS + apps like GPGTools etc etc etc

  1. Support Staff 1 Posted by Steve on 13 Jan, 2016 11:29 AM

    Steve's Avatar

    Hi Markus,

    thanks for the input. I've cross-linked this new discussion in the old discussion for reference.

    Kind regards,

  2. Steve closed this discussion on 13 Jan, 2016 11:29 AM.

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