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I booted a server and (too late) I discovered that some breaking change had been made to /etc/ssh/sshd.conf. Can I be reasonably sure that restarting sshd keeps existing connections ? (this was on solaris, but question also applies to ubuntu)

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You can be (reasonably) sure that your current connection will not break when you restart sshd. If you want to be on the safe side, simply send a SIGHUP to your running instance and it will re-read its configuration file.

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