Getting Chrome onto Windows Server 2019

Photo by Lukas on Unsplash

A new Windows Server 2019 instance only ships with Internet Explorer, and IE's default security settings actively get in the way of downloading anything, including the browser you'd rather be using. Here's the sequence that gets Chrome installed without fighting it the whole way.

1. When IE opens for the first time, dismiss the initial pop-up with OK.
2. Open Internet Options from the settings menu.
3. Go to the Security tab.
4. Click Custom Level, find the Downloads section, and enable File Download.
5. Click OK and confirm the security-settings change when it asks.
6. Go to Trusted Sites and add https://www.google.com to the list.
7. Apply and confirm.
8. Open a new tab. Another pop-up will appear. Uncheck the highlighted box, choose Add to trust the site, and close the dialog.
9. Search "download chrome" and open the first result.
10. Click Download Chrome (refresh the page if the button doesn't show up).
11. When prompted, choose Save, then Run, to finish the install.

After that, Chrome installs normally and you can leave IE alone for good.

Practical guide: the checklist version

A condensed run-through of the exact steps, in order, for the next time you're stuck on a fresh box with only IE.

1. Dismiss the first-run pop-up. Click OK when IE opens for the first time so it stops blocking everything else.
2. Open Internet Options and go to Security. This is where the download-blocking settings live.
3. Enable File Download under Custom Level. Find the Downloads section and turn on File Download, then click OK and confirm the change.
4. Add google.com to Trusted Sites. Go to Trusted Sites, add https://www.google.com, then apply and confirm.
5. Trust the new tab pop-up too. Open a new tab, uncheck the highlighted box in the pop-up that appears, choose Add, and close the dialog.
6. Search for Chrome and open the first result. Search "download chrome" and click through to the official page.
7. Click Download Chrome. Refresh the page first if the button doesn't render.
8. Save, then Run, to finish the install. Choose Save when prompted, then Run the installer.
9. Leave IE alone for good. Once Chrome installs, there's no reason to go back.