Upgrading Windows 7

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Windows 7 is the most advanced and stable Windows NT 6.1-based operating system. However, updating the system from a vanilla RTM or SP1 install can be a bit of a nightmare. People have made custom ISOs with tons of updates and drivers slipstreamed in, but I don't trust those. Thankfully, installing updates manually is super easy with the Convenience Rollup!

Pre-Requisites

As far as I'm aware, Windows only shipped as either RTM or with Service Pack 1. This makes it really easy to figure out which you have!

Open winver with whatever means you like. Next to "Version 6.1", you'll see either "(Build 7600)" or "(Build 7601: Service Pack 1)". If you're on Build 7600, you'll need to install Service Pack 1 (KB976932: x64, x32) before you install the Convenience Rollup.[TODO —Screenshot of winver?]

Convenience Rollup

Now this is where things get good. At some point, Microsoft realized nobody wanted to install hundreds of updates every time they brought a new system online, and not everybody knows what slipstreaming is—let alone who was responsible for that term. The Convenience Update is basically an "SP2 Lite" for Windows 7, rolling up every update from SP2 to 2016 into one .msu file. And moving onward, Monthly Rollups were provided that made it easy to get all of the future updates at once.

How To Install

The below table lists all updates you'll need, and where to get them. Make sure to update them in order!

KB Number Download Links Notes
KB4490628 x64, x32 Servicing Stack Update for March 2019. This is the latest SSU available for stock Win7.
KB3125574 x64, x32 Convenience Rollup! I recommend rebooting after you install this, if it doesn't force you to.
KB4474419 x64, x32 Adds SHA-2 code signing support to Windows 7. You'll definitely need to restart after this, the 2020 rollups use SHA-2 signing.
KB4539601 x64, x32 Monthly Rollup for January 31, 2020. Technically a Preview Rollup, but this fixes an issue in the Jan 14 Rollup where your wallpaper won't appear.[TODO —Link to MS KB]

What about ESU?

Say what you will about C&Ds, but I'm just not a fan.