SSL 525 Failed Handshake

I have a wordpress site hosted on wp engine and an application hosted on digital ocean. The application is under a subdomain of the wordpress site pointing to the digital ocean server. Im currently getting a 525 ssl handshake failure when trying to access the application and cant figure out where the problem lies. I’ve tried both a LetsEncrypt and a Cloudflare Origin Cert and I cant get either to work for some reason. I’ve contacted wp engine and they said it was a Cloudflare problem. Thanks for the help!

Are you sure Cloudflare is enabled for this sub domain? It looks like not.

We just switched it to Go daddy to see if that would change anything. We are registering it back to Cloudflare now

It’s looking good now. Tested it with curl and Firefox.

So the homepage is secured but then when i log into the application it isn’t anymore.

It now looks like wordpress is creating a redirect loop. Be sure your blog is set up to use https://… as the home.

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