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May Updates for Windows Server 2016 requiring two passes? RRS feed

  • Question

  • I noticed this month that the May 2019 updates for Windows Server 2016 are not installing all in one pass.  According to WSUS, our Windows Server 2016 servers only needed two updates:

    1. Windows Malicious Software Removal Tool for May 2019

    2. 2019-05 Servicing Stack update.

    So our Win2016 servers installed the above two updates and then reported back to WSUS that they are 100% updated (i.e. green check-mark).  However, i was confused by this because i knew there was a 2019-05 Cumulative Update for Windows Server 2016 that was released as well.   So i manually remote to one of my servers, and pulled up the Windows Update setting.  Sure enough, it said "your computer is up to date".  Not believing it, i clicked "Check for Updates".  Shortly thereafter, i saw the 2019-05 Cumulative Update for Win2016 begin to install (just like i expected).

    Questions:

    1. Why didnt the 2019-05 CU install with the other two updates?  

    2. Why did WSUS think that the servers didnt even need the 2019-05 CU?  

    3. Why did WSUS tell me my servers were up to date when there was a pending 2019-05 CU in WSUS that had been downloaded?

    4. Why did the Windows Update setting ALSO say my computer was up to date when there was clearly another update needed.

    5. What can i do to prevent this in the future?

    6. Why did i have to manually install the 2019-05 CU??  That took a lot of time

    7. If certain updates require multiple install/reboots, shouldn't WSUS be able to detect that and handle it accordingly?  If not, what product can i get that WILL handle it correctly, and avoid giving me false information.

    Thank You!

    Sunday, May 19, 2019 4:47 PM

All replies

  • 1. Why didnt the 2019-05 CU install with the other two updates?  

    After the update is released in Microsoft Update, it will take some time to update to the WSUS update repository. As of now, the Cumulative Update (KB4494440) released on May 14 is already in WSUS.
      

    2. Why did WSUS think that the servers didnt even need the 2019-05 CU?  

    The servicing stack update (SSU) (KB4498947) must be installed before installing the latest cumulative update (LCU).
      

    3. Why did WSUS tell me my servers were up to date when there was a pending 2019-05 CU in WSUS that had been downloaded?

    If you are using Windows Update, the latest SSU (KB4498947) will be offered to you automatically. 
      

    4. Why did the Windows Update setting ALSO say my computer was up to date when there was clearly another update needed.

    This may be related to the instantaneous connection situation. As you said, after checking again, the Cumulative Update is checked.
      

    5. What can i do to prevent this in the future?

    If the client can report to the WSUS server on a regular basis, I think the required updates provided by WSUS are reliable.
     

    6. Why did i have to manually install the 2019-05 CU??  That took a lot of time

    As above, please complete the installation of the latest SSU (KB4498947).
     

    7. If certain updates require multiple install/reboots, shouldn't WSUS be able to detect that and handle it accordingly?  If not, what product can i get that WILL handle it correctly, and avoid giving me false information.

    As far as I understand it, WSUS analyzes the update requirements through the reports provided by the client. If the approved updates have been installed on the client by other means, the client's Windows Update will not repeatedly install the same update.
      

    Hope the above can help you.
      

    Regards,
    Yic

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    Monday, May 20, 2019 3:15 AM
  • Hi,
     

    Any update is welcome here.
    If the issue is resolved, share your solution or find the helpful response "Mark as Answer" to help other community members find the answer.
     

    Thank you for your cooperation, as always.
     

    Regards,
    Yic

    Please remember to mark as answers if they help.
    If you have feedback for TechNet Subscriber Support, contact tnmff@microsoft.com.

    Tuesday, May 28, 2019 1:57 AM