I have been using SSH remotely, enabled it though sudo raspi-config, and then a week or so later I tried to connect through PuTTy and it timed out. Checked the config and it was disabled... Any ideas on how to keep it enabled permanently?
I set a static IP this way, it is configured to a t a dynamic IP address and when it changed I would be trying to use an outdated IP.
I think you can try to find your raspberry IP, you can find it in router control and connect again. If you connect with right IP and it still timeout or refuse you can connect Pi sd card to your PC and check in boot folder have ssh file. If not you must creat file name ssh and copy it to your SD card and start your PI again. In raspbian ver 2016-11-25 SSH disabled by default. It can be enabled by creating a file with name "ssh" in boot partition You can read release notes here