Windows: The Psiphon for Windows client will download and install updates as they are available.
If the psiphon doesn't connect (can't connect for any reason) and there is an update at that moment, can the Psiphon Windows client download and install that update?
If your Psiphon client cannot connect then the usual reason is that your Psiphon version is too old. In that case, the auto-update feature might or might not work. It depends on your location, how you connect to the Internet, and whether Psiphon servers are being blocked.
An easy thing to do is to download Psiphon fresh if it is more than a month old. This way you always have a relatively newer copy of Psiphon with working servers list.
Here is a simple batch script for always downloading fresh Psiphon3 and launching it:
@echo off
curl "https://www.psiphon3.com/psiphon3.exe" --output psiphon3.exe
psiphon3.exe
exit