I've opened a bug report upstream https://bugzilla.mindrot.org/show_bug.cgi?id=2918 because friends not using Ubuntu confirmed the same erratic behavior even with newer OpenSSH versions (7.8)
** Bug watch added: OpenSSH Portable Bugzilla #2918 https://bugzilla.mindrot.org/show_bug.cgi?id=2918 -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1798049 Title: ssh ConnectTimeout is obeyed only on 1st ConnectionAttempt To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1798049/+subscriptions -- ubuntu-bugs mailing list [email protected] https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs
