The update always seems to arrive right before something important

A device asks to restart just as a meeting is about to begin, or an app changes its layout before a ticket needs to be shown. Updates matter, but the timing can make a routine change feel much more stressful than it needs to be. How do you plan around this without putting updates off forever? A reminder before travel or an important presentation might be useful. So might keeping a copy of essential documents available offline. What preparation has saved you from trying to fix a device with five minutes to spare?