Making progress on getting my personal site up-to-snuff, I installed JetPack and ran into some strange issues trying to enable features. I kept getting errors such as “Failed to fetch” when toggling settings in JetPack. Using Chrome’s developer tools, I noticed Chrome was blocking admin.js from being called due to mixed-content errors. I immediately suspected SSL as being the culprit. My site runs on SSL – WordPress was loading on SSL – so why the errors?
Turns out I did too good of a job on my nginx config. By forcing SSL for my entire domain within nginx, WordPress was “tolerating” running under SSL, but because JetPack was utilizing the URL from my wp-config.php, it was attempting to make calls against the non-SSL domain and thus chrome was throwing errors. Thankfully a quick fix, swap the URL on my WordPress config to https and all was well!