Hi @agenciafun,
Thank you for your interest in Jetpack Boost and sorry to hear that you are having some trouble with it.
First, may I confirm you are running the latest version (v1.2.0) of the Jetpack Boost plugin. This latest version should provide a bit more detailed information regarding the HTTP 500 error such as on which page of your site it is occurring.
In order for Jetpack Boost to generate Critical CSS, it loads pre-selected posts and pages of your site in a hidden container. An HTTP 500 error means that while trying to load one of your site pages, the server returned an error. These types of errors can sometimes be temporary and if you try again generating the Critical CSS on your site using Jetpack Boost, it might work the second time around.
If it does not, making sure to run the latest version (v1.2.0) of Jetpack Boost, you could try purging any caches that you might have (WordPress cache, Cloudflare cache, etc) and trying to log into your site in an incognito window (to prevent browser cache from interfering) and try it out again.
If the above steps don’t change anything, can you take a screenshot of the DevTools Network tab and the Browser Console? Please make sure also to take a screenshot when you’re on the Jetpack Boost dashboard.
You can create and share screenshots using something like Snipboard or Imgur and post the link here.`
I am looking forward to your reply!
Best
— David
Jetpack Boost Developer