For Windows users who manage their own system updates, the patching process is a bit like going to the dentist — you really hope it’ll be pain-free.

For making that twice-monthly chore a little easier, here are some simple tips and tricks to avoid patching woes.

Make the updating task a regular routine

If you’re a Windows user who handles updates manually, you might still be slogging through the most-recent Patch Tuesday releases of .NET, Windows, Office, and Silverlight fixes. My first tip for installing updates is to set aside a specific time each month to review and install them. Although new batches of patches typically come out the second and fourth Tuesdays of the month, in most cases it’s safe to tackle updates just once a month. (On rare occasions, an especially critical patch might require your immediate attention.) I tend to wait until the weekend following an update’s release.

Reboot your system more often — not less

Yes, I know it’s a pain to reboot your machine; but when it comes to patching, rebooting often is better. In fact, I recommend rebooting PCs right before installing updates. It reduces the likelihood that some unrelated issue is the cause of problems cropping up during the update process.

I’ve had computers fail to reboot right after an update was installed, and I eventually discovered that the root cause was something completely separate — such as a failing power supply, motherboard, or hard drive. Rebooting before patching might have revealed those types of problems and saved time wasted on troubleshooting a perfectly good patch. (It’s always a bit surprising that PCs can run continuously for months, then fail when rebooted.)

Expect 32-bit updates on 64-bit Windows systems

If you have Windows 7 x64, you’re used to seeing 64-bit patches. But what about those 32-bit Office updates constantly being offered up? It’s both common and perfectly normal to have 32-bit programs running on 64-bit systems. Windows x64 has a built-in emulator that makes 32-bit apps assume they’re running on a 32-bit OS. (The primary advantage of a 64-bit OS, as you probably know, is to allow access to more than 4GB of RAM on a system — especially useful for running virtual machines.)

You can tell whether an app is 32-bit or 64-bit. During installation, 64-bit software is automatically placed in the Program Files folder; 32-bit software is placed in Program Files (x86). (Windows makes this a bit more confusing than it should be. C:\Windows\System32 is the 64-bit Windows system folder, and C:\Windows\Syswow64 is the system folder handling 32-bit programs.)

The most prominent 32-bit application you’re likely to see on a 64-bit Windows system is Office. For most users, 32-bit Office is the safer choice; add-ins for Office need to have a matching bittedness, and not all add-ins have been recoded to support 64-bit Office. Fortunately, making the choice is usually easy. When purchasing Office, the package usually includes both 32-bit and 64-bit versions.

Bottom line: If a 32-bit patch is offered for your 64-bit system, approve the update (unless there is some unrelated potential problem with the patch).

Windows Genuine Advantage during patching?

On a few occasions, Windows Secrets readers have asked us about a genuine Windows validation alert that pops up after updating. Their immediate worry is that Microsoft believes they’re using unauthorized software. There’s no reason to panic. As long as you have the original installation keys or there’s that tiny little Microsoft application sticker on your computer, you’re the authorized user and Windows won’t suddenly stop working.

Microsoft Security Essentials seems to be a culprit in many of these false alerts. In one case, I added additional RAM memory to a machine and MSE triggered the genuine Windows warning. Checking the information in Start/Control Panel/System confirmed that the OS was indeed genuine. To fix the problem, I had MSE check the Windows Genuine Advantage (WGA) status — and the PC was back to normal.

Typically, the problem is not with WGA but with MSE’s inability to read parts of the Windows Registry properly. Again, simply telling MSE to recheck usually makes the alerts disappear.

Does your system know what time it really is?

Oddly, updates can fail if the computer is set to an incorrect time. Microsoft’s laundry list of things to check when Windows Update problems pop up (see MS Support article 818018) includes making sure that the system is set to the right date and time.

It may seem hard to believe, but I know of standalone PC users who have used the computer’s date and time function as a fast calendar look-up — and accidentally changed the date set on the PC. In such cases, the computer seems to boot and run normally; it’s easy to overlook that some Windows components (such as the Event Viewer) or software (such as IM clients) isn’t working perfectly — and neither is Windows Update.

Install an update using Windows’ Safe Mode

When all else fails, rebooting a system in Safe Mode and manually installing the update can solve the problem. More often than not, it’s an antivirus app keeping a critical file open — and the update won’t install with the file running in another process. Booting into Safe Mode ensures that the file is closed.

Watch out for those Registry cleaners

Recently, while tracking KB 2686509 installation issues (see my companion story, “Patch Watch Update: Duqu-patch install problems”), I found a forum post in which someone recommended using a Registry cleaner before and after patching.

I’m not a fan of that technique. In a few instances, when helping users with patching problems, I’ve discovered that an overly aggressive Registry cleaner was the source of the trouble. The cleaner had removed some needed registry keys.

Cleaning up and thinning down the OS with an app such as nLite (info page) can also cause updating issues. A much-viewed Windows Answers post mentions nLite as the trigger for some KB 2686509 patch failures.

Bottom line: More rebooting and less-aggressive cleaning tend to make my machines patch better. I recommend staying away from tools that strip off parts of the operating system. Installing updates as you would any other app should ensure your patching process goes as well as it can.