This one was stupid and annoying and shouldn’t even have been a thing.

If you are already running a HTTPS enabled website that’s WordPress then you may find that by switching to CloudFlare and their Free plan that you get 500 error. Specifically the error being “Too many redirects.” A quick check in the CloudFlare settings under “Crypto” that they have “SSL = Flexible” as their default.

The Solution: You actually want SSL = Full (Strict) as this gives the best protection and also fixes this annoyance.