Hi Matt,

If the initial "Checking for updates..." phase of Windows Update runs for long periods of time, you can try the below fixes to get it resolved.

Fix 1: Enable automatic Windows Updates

1. Select the Start button. In the search box, enter Update, and then, in the list of results, select Windows Update.
2. In the left pane, select Change settings, and then under Important updates, select Install updates automatically (recommended).
3. Under Recommended updates, select the Give me recommended updates the same way I receive important updates check box, and then select OK.

Fix 2: Use below mentioned methods one by one:

• Make sure that your PC is connected to the Internet. Some updates can’t be installed if you’re using a metered Internet connection.
• If you’re connected the Internet and updates aren’t installed automatically, wait a few minutes and then try to install the updates manually.
• Use the Windows Update Troubleshooter to try to fix the problem.

Fix 3: Use the system update readiness tool
Download the System Readiness Tool.The System Update Readiness Tool checks your computer and tries to resolve certain conditions that could interfere with the installation of updates or other software.

Here is a link to download System Readiness Tool; you may do it according to the exact configuration of the computer:

http://support.microsoft.com/kb/947821

I hope this helps in fixing the update issue.

Regards,
Lokesh