I have a maintenance window, a deadline and repeatidly machines do not install either during the maintenance window (which is 5 hours long) or during the day (the install during deadline period). I believe the maintenance window of 5 hours is continuously not long enough. SCCM may not fire off the update task until hour 4, calculate the 1 hour remaining is not enough and not install. I believe the reason the deadline install (anytime basically) does not work is because my business hours on the default windows setting is set to 5 am - 10 pm. It will never install no matter what SCCM wants. So from 5 am to 10 pm no install. The maintenance window in my case starts at midnight and goes till 5 a.m. and doesn't install because for whatever reason it decides there is not enoug time.
I just took a machine and adjusted by windows business time by unchecking s, m, t, w, th, f, s boxes. I also set the time to 8 pm - 9 pm (only one hour). Although the time doesn't matter because I unchecked the days of the week (but we are all superstitous right?). I restarted the sms agent host service on the client. Now the logs: 1) updates deployment show a need for patches; 2) WUAHandler shows "Async installation of updates started".
I do not see the software center beginning patches, I have only waited a few minutes during the deadline period. However as soon as I restarted the service (I cleared ccmcache earlier) I immediately saw patches download to the folder.
I manually started patches on this machine and it is patching.
This doesnt prove a resolution (other that the logs suggesting it). But I have gone around and around and around with patches not deploying. I have never turned off the business time on the windows machine. I think this setup on the machine is useless for most people.
Summary: if you are confident on the deployment package, the maintenance window, see "not enough time for maintenance window or no maintenance window found then: 1) turn off the business time; 2) shorten it and increase your maintenance window to have alot more time to run (although that will initiate a reboot huh?
I am going to verify the business window as the culprit and probably push out a GPO to turn it off on all machines. I will use the maintenance window basically to stop my deadline behaviour from rebooting the machines during work hours.