Are you using agents right now? If agentless, there is no retry if the machine can't be reached at the time of the scan or deployment.
For Agents: All agent Patch Tasks will only run at the scheduled time. If an machine is offline or not on the network for a long time, the most if will do is check-in, obtain Policy changes, renew the license, send results. It will still wait for the next occurrence of the Patch Task.
There is an option to run on boot if the schedule is missed.
That might be show stopping for me.
I suppose I could maybe run a deployment schedule hourly to try to catch computers that apply to this scenario.