How to Fix: KB4056892, KB4058258 Won't Install; Other Updates Stuck

Infopackets Reader Jeff W. writes:

I am having a problem with Windows 10 not updating - it keeps telling me that KB4058258 and KB4074595 won't install. It will attempt to install the updates, then when I check Windows Update again those two updates are there again. KB4058258 is a cumulative update for Windows 10 whereas KB4074595 is a security update for Adobe Flash update. Can you help? "

My response:

I asked Jeff if he would like me to connect to his system using my remote desktop support service, and he agreed.

I have been receiving a lot of inquiries about this lately and it seems that KB4056892 as well as KB4058258 in particular are causing Windows Update to jam and not allow other updates to pass through. According to Microsoft, both KB4056892 and KB4058258 are cumulative updates (and large ones at that); KB4056892 brings Windows 10 to OS Build 16299.192, whereas KB4058258 is 16299.214.

You can tell which version of Windows 10 you are running by clicking on the Start menu, then type in "winver" (no quotes) and press Enter on the keyboard.

How to Fix: KB4056892, KB4058258 Won't Install; Other Updates Stuck

If a Windows Update is getting stuck, there are a few things you can try to clear it out of the Windows Update queue so that other updates will install. There is no guarantee you will be able to install KB4056892 or KB4058258 as they both seem to be problematic for a lot of people and I suspect Microsoft will need to release a proper fix. That said I have had success in burrowing my way through to the point of allowing other updates to install using the method below and in some cases, updating to the latest cumulative update.

The first thing you need to do is run chkdsk on the drive to make sure there are no file system errors. To do so: click Start, type in "cmd" (no quotes); wait for "CMD.EXE" or "Command Prompt" to appear in the list, then right click and select "Run as Administrator". If chkdsk reports you have errors, enter in "chkdsk /f" and then press Enter, then reboot the machine to have it fix the errors. You will have to run chkdsk again after rebooting (without the /f parameter) to make sure you have no errors.
Assuming chkdsk completes, you will want to run "sfc /scannow" using an administrative command prompt. To do so: once again - click Start, type in "cmd" (no quotes); wait for "CMD.EXE" or "Command Prompt" to appear in the list, then right click and select "Run as Administrator".

Next, type in "sfc /scannow" on the command line and press Enter. This will take a while to complete and should report "No integrity violations". If you have errors and "sfc was not able to fix them" then it means your Windows is corrupt and needs to be repaired. This is beyond the scope of the article (it is a big fix), however you are welcome to contact me for 1-on-1 support using my remote desktop service, and I can look into this for you.
Assuming "sfc /scannow" has passed, you can now move toward clearing out the Windows Update queue. Highlight the text below using your mouse

net stop wuauserv
c:
cd \windows
rename softwaredistribution softwaredistribution.old
echo this is a dummy line

Right click over the above text and select "Copy" from the dialogue menu, then place your mouse in the middle of the command prompt window and select "Paste" from the dialogue menu. The text you copied above should be output to the command line. Your Windows Update queue should now be clear.
The next thing you want to do is to check to see if KB4056892 or KB4058258 have beeninstalled. Use your mouse to highlight the text below:

SYSTEMINFO.exe | findstr -i KB4056892
echo this is a dummy line

SYSTEMINFO.exe | findstr -i KB4058258
echo this is a dummy line

Right click the above text, then select "Copy" from the dialogue menu. Next, right click in the middle of your command prompt window to Paste and execute the command. If you see something like " [##]: KB4056892" as the response, then KB4056892 has in fact been installed. The response will be similar for KB4058258. If you don't get any response except for the command prompt, then the update was not installed.
If KB4056892 or KB4058258 have not been installed then you can go to the Windows Update catalogue website and download KB4056892 and/or KB4058258 manually and apply it. Make sure you select the proper download - use x64 if your Windows 10 is 64 bit and x86 if it's 32 bit. Note that updates are cumulative so technically speaking you can jump straight to KB4058258, though if that doesn't apply you might want to try KB4056892 first.

IMPORTANT: If you have other updates that aren't installing, you will want to follow this same procedure - using the Windows Update catalogue website - to search and download the appropriate update in order to 'push' the updates through manually. It is recommended you use Internet Explorer to connect to this website or it may not work properly.
Once the update(s) have been downloaded and installed, reboot the machine, log back in,then click Start -> Settings, then Updates and Security, then on the "Windows Update" tab on the left, click "Windows Update" and then "Check for updates". It should say your device is up to date. As I mentioned earlier you can also click Start and type in "winver" to see which OS Build you are on.

Further Troubleshooting KB4056892 and KB4058258

I have had some success in getting other updates to apply - however, both KB4056892 and KB4058258 keep reappearing in the Windows Update on some systems, stating it is still not applied. Some systems have allowed me to push through both updates.

If the above method does not work for you then I suggest you try it again a few times because, as they say, "3 times is a charm" and that may very well be the case for you. If still no dice then you may have no other option but to wait for Microsoft to release a proper fix. In the mean time the above method should at least clear your Windows Update queue to allow other important updates through.