KACE Product Support

I noticed on our most recent patching job, we got a lot of "error (Log Upload Failed)" status codes. Reran the job again with the same result. Long story short I ended up rebooting some servers and they would go into "update in progress" taking 10-30 minutes to update and restart. What I found from this was that a large Cumulative Update was installed kb4507459 but the server NEVER REBOOTED after the update was installed. The job says to reboot the server but KACE did not and the servers are just stuck in limbo until we manually go in and reboot them. After rebooting and maybe rebooting again, servers we tested would finally scan ok and report back as normal.

Next, we have kb4512495 (1.5gb) for August 2019 and its the same thing. Ran a job on a few servers w/ this patch. The job fails again, and rerunning the job ends in fail or succeed but its still reporting the patch missing even though its installed. Once rebooting the server, the patch finishes installing as above and it seems to clear up and report back to kace all is good. 

Is this just a case of setting the job time out to 5 hours? (Max) Currently they are set at 3 which you would think its enough time. If the job times out, will the reboot not take place? And if setting it to 5 and we still have this happen, then what?