Windows Server 2008 R2 Standard – Cannot download Windows Updates

I'm attempting to update a production server that hasn't had a Windows Update installed in almost 3 years.

When I attempt to download any update, even if I select just one, the download hangs at 0% consistently. The first time I downloaded the updates (97 updates), it hung at 46% for 12+hrs.

I stopped the download, restarted the computer, restarted the Windows update, and ever since then, it hangs at 0%.

The event log is indicating that the installer, TrustedInstaller.exe, is crashing everytime I try to re-download the updates.

Faulting application name: TrustedInstaller.exe, version: 6.1.7600.16385, time stamp: 0x4a5bc4b0
Faulting module name: ntdll.dll, version: 6.1.7600.16385, time stamp: 0x4a5be02b
Exception code: 0xc00000fd
Fault offset: 0x0000000000055237
Faulting process id: 0x10b0
Faulting application start time: 0x01d23c2c67a04444
Faulting application path: C:\Windows\servicing\TrustedInstaller.exe
Faulting module path: C:\Windows\SYSTEM32\ntdll.dll
Report Id: a8423514-a81f-11e6-9286-b8ac6f92c237

Note: The other day, it let me know that I would need to download an update to the installer before installing Window's updates (humourous).

I ran this, and I'm not sure if it was successful or not, but I would assume so, since I was able to start downloading the updates up to 46%.

At this point I'm wondering if I should just install SP1 directly on the server. I assume it's a roll-up of all the major updates since, but I could be wrong.