I am totally baffled at this point. We have updates set to deploy via ADRs to servers. The ADRs create deployments that make the Updates available ASAP with deadline ASAP. We then use maintenance windows to tell the servers when to install and reboot.  Sound good?  Then when the maintenance window occurs, nothing happens.  Collected details below:

Deployment Settings:

General:
 Deployment Name: Microsoft Software Updates - 2015-09-01 04:00:29 PM
 Collection: MTW-Test
 Deployment Settings:
 Send wake-up packets: No
 Verbosity Level: Only success and error messages
 Scheduling:
 Deployment schedules will be based on: Computer local time
 Available to target computers: 9/1/2015 4:01:00 PM
 Deadline for software update installation: 9/1/2015 4:01:00 PM
 User Experience:
 User Notifications: Display in Software Center and show all notifications
 Install software updates outside the maintenance window when deadline is reached: No
 Restart system outside the maintenance window when deadline is reached: Suppressed
 If a restart is required it will be: Allowed
 Commit changes at deadline or during a maintenance window (requires restarts): Yes
 Alerts:
 On software update installation error generate a Window Event: No
 Disable Window Event while software updates install: No
 Download Settings:
 Computers can retrieve content from remote distribution points: No
 Download and install software updates from the fallback content source location: Yes

Maintenance windows are already applied to the collection and computers are aware of them.  The maintenance windows are set to occur after the deployment deadline (ASAP). Then next maintenance window is at 3:45 PM, to align with logs below.

UpdatesDeployment.log:

No current service window available to run updates assignment with time required = 600	UpdatesDeploymentAgent	9/1/2015 3:39:40 PM	24196 (0x5E84)
No service window available to run updates assignment	UpdatesDeploymentAgent	9/1/2015 3:39:40 PM	24196 (0x5E84)
This assignment ({9CCAB21E-8CA3-48FA-842F-97E1B1FAEF8F}) will be retried once the service window is available.	UpdatesDeploymentAgent	9/1/2015 3:39:40 PM	24196 (0x5E84)
EnumerateUpdates for action (UpdateActionInstall) - Total actionable updates = 32	UpdatesDeploymentAgent	9/1/2015 3:40:13 PM	25684 (0x6454)
EnumerateUpdates for action (UpdateActionInstall) - Total actionable updates = 32	UpdatesDeploymentAgent	9/1/2015 3:40:16 PM	25684 (0x6454)
EnumerateUpdates for action (UpdateActionInstall) - Total actionable updates = 32	UpdatesDeploymentAgent	9/1/2015 3:40:16 PM	25684 (0x6454)
EnumerateUpdates for action (UpdateActionInstall) - Total actionable updates = 32	UpdatesDeploymentAgent	9/1/2015 3:44:07 PM	21368 (0x5378)
EnumerateUpdates for action (UpdateActionInstall) - Total actionable updates = 32	UpdatesDeploymentAgent	9/1/2015 3:44:08 PM	21368 (0x5378)
CUpdateAssignmentsManager received a SERVICEWINDOWEVENT START Event	UpdatesDeploymentAgent	9/1/2015 3:45:00 PM	25504 (0x63A0)
No current service window available to run updates assignment with time required = 1	UpdatesDeploymentAgent	9/1/2015 3:45:00 PM	25504 (0x63A0)
No current service window available to run updates assignment with time required = 1	UpdatesDeploymentAgent	9/1/2015 3:45:00 PM	25504 (0x63A0)

ServiceWindowManager.log

OnIsServiceWindowAvailable called with: Runtime:600, Type:4	ServiceWindowManager	9/1/2015 3:39:40 PM	24196 (0x5E84)
        Biggest Active Service Window for Type=4 not found	ServiceWindowManager	9/1/2015 3:39:40 PM	24196 (0x5E84)
Program cannot Run! Setting *canProgramRun to FALSE	ServiceWindowManager	9/1/2015 3:39:40 PM	24196 (0x5E84)
WillProgramRun called with: Runtime:600, Type:4	ServiceWindowManager	9/1/2015 3:39:40 PM	24196 (0x5E84)
A Service Window of this type exists.	ServiceWindowManager	9/1/2015 3:39:40 PM	24196 (0x5E84)
There exists a Service Window of this Type, for this duration. The Program will run eventually.	ServiceWindowManager	9/1/2015 3:39:40 PM	24196 (0x5E84)
ServiceWindowManager	9/1/2015 3:39:40 PM	24196 (0x5E84)
ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
A Timer Event has occurred	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
    Sending Message SERVICEWINDOWEVENT:START event	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
    The Service Window={115D36D4-C22D-4D22-8FFE-CFECB2778EDD} has started at 9/1/2015 3:45:00 PM	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
Checking Service Windows to find Next Event.....	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
    Next Event Time is at 9/1/2015 10:00:00 PM. Service Window with ID:49fd80be-ac4b-4877-974d-ecd09958926d. Is the next event the beginning of the window? Yes	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
    Scheduling the Timer Task	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
    Scheduled the timer to fire on 9/1/2015 10:00:00 PM	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
OnIsServiceWindowAvailable called with: Runtime:1, Type:4	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
        Biggest Active Service Window for Type=4 not found	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
Program cannot Run! Setting *canProgramRun to FALSE	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
WillProgramRun called with: Runtime:1, Type:4	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
This is a One Shot Service Window. Returning true	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
A Service Window of this type exists.	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
There exists a Service Window of this Type, for this duration. The Program will run eventually.	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
OnIsServiceWindowAvailable called with: Runtime:1, Type:6	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
        Biggest Active Service Window for Type=6 not found	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
Program cannot Run! Setting *canProgramRun to FALSE	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
WillProgramRun called with: Runtime:1, Type:6	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
This is a One Shot Service Window. Returning true	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
A Service Window of this type exists.	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
There exists a Service Window of this Type, for this duration. The Program will run eventually.	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
OnIsServiceWindowAvailable called with: Runtime:900, Type:2	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
No Service Windows exist for this type. Will check if the program can run in the All Programs window...	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
        Biggest Active Service Window has ID = {115D36D4-C22D-4D22-8FFE-CFECB2778EDD} having Starttime=9/1/2015 3:45:00 PM	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
            Duration is 0 days, 12 hours, 15 mins, 00 secs	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
ActiveServiceWindow has 44100 seconds left	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
Program can run! Setting *canProgramRun to TRUE	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
OnIsServiceWindowAvailable called with: Runtime:900, Type:6	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
        Biggest Active Service Window for Type=6 not found	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)
Program cannot Run! Setting *canProgramRun to FALSE	ServiceWindowManager	9/1/2015 3:45:00 PM	25504 (0x63A0)

RebootCoordinator.log

Reboot Coordinator received a SERVICEWINDOWEVENT START Event	RebootCoordinator	9/1/2015 3:45:00 PM	25504 (0x63A0)

Found these, but don't seem to provide additional clues.

http://henkhoogendoorn.blogspot.com/2011/04/maintenance-windows-in-configmgr-2012.html

http://www.systemcentercentral.com/forums-archive/topic/software-updates-not-deploying/

This one seemed interesting as I did have the available time set to a few days in the future initially (maintence window still after deadline though).  But have since removed all deployments to the test collection and applied all of them with ASAP/ASAP.

To make it even more strange, I have a lab that deploys updates to maintenance windows using the same settings without any issues.

Any thoughts??

Thanks!

I know this sounds strange BUT.....

When you create your deployment, do NOT use the ASAP setting. Give it an exact date and time.  Let the maintenance window mange the delivery, not the scheduled (ASAP) time. My server team had the same issue and while they were used to using ASAP, we have a much more aggressive maint window these days. Once I suggested this change, it resolved there issue.

Hope this helps.

Lavelle

• Proposed as answer by Lavelle Evans 9 hours 6 minutes ago

I know this sounds strange BUT.....

When you create your deployment, do NOT use the ASAP setting. Give it an exact date and time.  Let the maintenance window mange the delivery, not the scheduled (ASAP) time. My server team had the same issue and while they were used to using ASAP, we have a much more aggressive maint window these days. Once I suggested this change, it resolved there issue.

Hope this helps.

Lavelle

• Proposed as answer by Lavelle Evans Tuesday, September 01, 2015 10:43 PM
• Unproposed as answer by PaulWetter 19 hours 5 minutes ago

I'm not sure why this would matter.  As long as the updates are downloaded and distributed already.  And if the deadline isn't set to before the maintenance window, it will not install them anyway.  My understanding is that ASAP sets a deadline at the time of creation anyway so, why would setting it for 2 hours later, or something like that matter.

Also, I am following Kent's guidelines in his book as well with ASAP/ASAP and have maintenance window control install and reboot.  My lab is working flawlessly.

Any other ideas?

KENT is awesome and I don't know why it matters but I'm speaking from my own personal experience. Generally speaking, if it works in the lab, then it "should" work in production, but my lap is much smaller and has less dutiy cycles to content with.

I would make sure the SCCM client is the newest version. I had an issue where it would never reboot using the older client. This is when I was on SCCM R2 CU2 but the servers were on SCCM R2. (no CU installed)

How long is your maintenance window?  It could be to short.

• Edited by Lavelle Evans 16 hours 6 minutes ago

Paul,

FYI: In our case, we install software updates outside the maintenance window, our servers just wait for the window to perform the reboot.

This one jumps out at me:

No current service window available to run updates assignment with time required = 600	UpdatesDeploymentAgent	9/1/2015 3:39:40 PM	

So, SCCM wants 600 minutes for the install, or 10 hours.  I'm going to guess your maintenance windows is smaller than that, thus it's not kicking off.

You'll need to look at your restart counters and estimated runtimes of patches to figure out if SCCM is coming up with a valid estimate, get a large maintenance window, or break the patches up into smaller deployments.

More info: http://blogs.technet.com/b/csloyan/archive/2010/10/24/maintenance-window-calculations-explained.aspx

Double checked Client.  Both client and server in both lab and Prod are on 2012R2 CU4.  Good thought though.

Yah, I thought that the 600 was the issue as well and also saw that blog post.  But, I think the 600 is seconds.  and I also think that 2012R2 calculates based on the amount of time it says that the current patch can take.  By default, this is 10 minutes in SCCM 2012R2.  My lab for example, I had a test server that had less than an hour left in maintenance window.  Pushed group of over 30 updates to it.  They all installed in that time frame.  Then log showed at ~10 minutes remaining that it no longer had a maintenance window long enough to reboot.  So, all patches installed but it did not reboot.  This IS what I expected to see.  And, just to be sure, I set up a 24 hour maintenance window to test with as well.

I may have just found the problem...  I will post back after more testing.

Ok.  This is what I found.  It has to do with types of Maintenance windows and is either a bug or undocumented "feature".

When the system was originally set up (before me), to prevent servers from patching, they created a single maintenance window for all servers 10 years in the future so updates would not install until later maintenance windows were created.  This sounds fine but, there was the side effect I experienced.  They created that as a software update only maintenance window.  All of my maintenance windows were created as maintenance windows for all deployments.  Apparently this means all deployments unless there is a more specific maintenance window available for updates only.  So, the fact that Maintenance windows are cumulative has a big "IF" now, I guess.  If someone can find this documented, please pass it along.

Anyway, I excluded my test machines from this collection with the 10 year future Updates maintenance window.  Then did a policy update and it started installing immediately because I was in an active maintenance window. Eureka!

Thanks for all the input everyone!