Problem checking for updates - Code 80240442 - Windows Update ran into a problem

At least I now know I'm not alone with this. MS support had exactly the same issues with remote diagnostics and in the end "accidentally" terminated the remote session.

I'm having the same problem. I've been affected since upgrading to Window 8.1 late last year. Tagging as many of these posts as I can find in the hopes that someone on one of them finds a resolution one day. I have a work around. But it's not a permanent solution. 

If you haven't seen this elsewhere, open Internet Explorer, go to Tools - Options to open the Internet Options pop-up window.

Before making any of these changes, write down your current settings so that you can change them back later.

In Internet Options, click on the Connections tab. Click the LAN Settings button. Under Proxy Server, check the box for 'Use a proxy server...'. None of the other boxes or fields on this window are filled in. Click the Advanced button to open the Proxy Settings pop-up window. For HTTP and Secure, set proxy address to 127.0.0.1 and set Port to 8888. Under Exceptions, enter exactly: <-loopback>

Click OK to close the Proxy Settings window. Click OK to close the LAN Settings window. Click OK to close Internet Options.

Check for Updates. If you're lucky, it will work. However, with the settings as they are you won't be able to use IE and some programs may not work. Install all updates, and then change the LAN Settings back to the original settings.

Hopefully Microsoft gets this fixed soon. This is a big security flaw impacting a large number of people.

I sympathize with your predicament. There's a long running thread whereby a Finnish user by the name of Mika Hirvonen who's Profile shows him to be s senior software engineer experienced the same difficulties installing the update which you can read about here: http://answers.microsoft.com/en-us/windows/forum/windows8_1-windows_update/windows-update-error-80244fff/16f1c7d7-f0e2-4e76-b656-c749287d9713?page=11&msgId=6f74002f-f1aa-4aba-bc33-25d6cfebaa45

I actually referred him to Andy's post since I was under the impression that it had been marked as Answer by him.

But the user eventually gave up and reinstalled the OS.

But it's a bit disconcerting if Microsoft is marking threads as "Answered" just to give the impression that "all is well" with 8.1 when that isn't the case at all.

At least I now know I'm not alone with this. MS support had exactly the same issues with remote diagnostics and in the end "accidentally" terminated the remote session.

Ok, I was just wanting to add my name to the list of people still with the problem.  I've given up on Microsoft Support actually fixing the issue.  It seems like certain machines eventually get kicked to some bad update servers.  I spent MANY hours before with the old code. Different Windows keys, install/upgrade paths, network hardware, network settings, and now system drives don't stop the issue from eventually popping back up on my machine.  Their tier 1 support spent an hour or so remotely trying all the fixes that I tried from the forums.  Tier 2 and 3 basically just kept running Chkdsk on my SSD system drive, along with a couple commands that they had trouble pasting to my command prompt correctly..  I sent them packet captures from that machine trying to check for updates and 2 other machines with the same type of software installed that don't have the issue, but never heard back.  It sounded like they might have actually fixed it with update 1, but it looks like they just have a new code for it now.. :(