I had the same problem. In my case I did a test by moving my WP site to another server for testing (with All In On Migration plugin). It worked perfectly fine. So I was down to server configuration issue.
Looking closer I checked the root of my website and found there was no .htaccess file. I checked my permalink settings and re-saved the settings. Then I checked and there was still no .htaccess file.
I tried a reinstall of WordPress was prompted for FTP info so this indicated WordPress doesn’t have access to change files in my WordPress Installation folder. I had to check that permissions were set correctly. For me that would be running in linux via ssh 1) cd /var/www 2) chown -R apache:apache html This is because my wordpress install is in /var/www/html. You would have to do it on your WordPress install folder.
After setting permissions correctly go to the Permalink settings and click save to re-generate the .htaccess file. Then try turning on Jetpack features. For me this worked and now I’m living the life.
