You’re here because you read my previous blog post “Installing Ruby on Windows 10.”  If you haven’t read the previous post, you can do so here: https://dqfan2012.tumblr.com/post/153277721020/installing-ruby-on-windows-10. It’s an article that discusses installing Ruby on a Windows 10 machine.

You want to install an excellent Ruby Gem, like the newest version of Rails, but you’re getting an error similar to the one in the following screenshot, and you don’t know what to do. Never fear! I will explain the steps necessary to resolve this issue!

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You need to download the newest version of Ruby Gems and install it manually. Browse to https://rubygems.org. Click on the “Install RubyGems” button beneath the search bar. After the “Download RubyGems” page loads, click on the “GEM” button. This button will trigger the download of the latest version RubyGems, which is 2.6.8 as of this writing.

Updating RubyGems manually requires that you use the Command Prompt. Open the Command Prompt. I’m assuming you have some experience with the Command Prompt. If not, I suggest you use Google to learn more about it. Learning how to use Command Prompt is beyond the scope of this article.

Once you’ve opened Command Prompt, you want to browse to the RubyGem update download location. (My download location may differ from yours. If it does, there’s no reason to be alarmed. My setup is probably different than yours). The following screenshot provides an example.

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Now, all you have to do is manually install the RubyGems update, and you should be good to go. Run the following command to install the RubyGems update manually.

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Your Command Prompt should look similar to this once RubyGems has successfully updated.

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Next, run the command: update_rubygems to finish the update process.

Let’s make sure the RubyGems update solved our SSL certificate issue. I think updating all the installed RubyGems should prove that we resolved the problem. Enter the following command to update all installed gems. (Please Note: If you’re prompted to overwrite rake, select Yes. Same goes for rdoc)

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Gems have finished updating example screenshot:

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Now that we’ve fixed the SSL certificate issue and updated our RubyGems, it’s time to start programming with Ruby and Rails! Good Luck!