If you're running FW >= 5.4.5: install the bridge. That could be summed up as such: if you're currently running FW 5.0.x to 5.4.4.2: reinstall the JB.

Additionally, be aware that a reset to factory defaults will break certain key aspects of the JailBreak, so make sure to re-apply the JailBreak (by following the very instructions in this notice) if you've reset your device to factory defaults (if you're unsure of that fact: better be safe than sorry ).

On the other hand, on FW versions the jailbreak method handles, simply reinstalling the JailBreak will do the trick just fine too, and in a faster manner, since you won't need to suffer through a reboot.

As such, it can always be used to upgrade your currently installed jailbreak.

That usually means previously jailbroken devices running a FW version unsupported by the current jailbreak method. The bridge (the Update_jailbreak_bridge_*_install.bin update package in the JailBreak archive, as well as the one in the JB hotfix archive, see the relevant section in #2 for more historical details) exists solely as a means to deploy the jailbreak in circumstances where the current jailbreak method is unusable, but custom packages are still usable.

What you should know about how best to proceed to update the JailBreak itself:

TablePlus 5.4.2 for windows instal