Cloudflare Universal SSL limitations with multi-level subdomains

Mon, 13 Oct 2025 20:30:00 +0100

Universal SSL (free) doesn’t support multi-level subdomains

I’ve battled another Cloudflare issue recently which is almost certainly due to my lack of experience with Cloudflare! However, I’m documenting it here for my own benefit and hopefully others.

After migrating some of my applications that have staging versions of a backend API, I came across some domains that just wouldn’t resolve the SSL certificate. The error was simply ERR_SSL_VERSION_OR_CIPHER_MISMATCH.

Too many redirects with Cloudflare + Azure App Service

Sat, 25 Jan 2025 00:05:00 +0100

Too many redirects?! Why

I spent far too long troubleshooting why a perfectly good, HTTPS enabled Web Application hosted on an Azure App Service failed after moving the DNS (proxied) over to Cloudflare.

The App Service wasn’t doing anything I would consider non-standard. Simple site with a custom domain, correct SSL bindings and just a free “App Service Managed Certificate”.

Symptom was simply ERR_TOO_MANY_REDIRECTS like so:

Cloudflare on Dave Hogan

Cloudflare Universal SSL limitations with multi-level subdomains

Universal SSL (free) doesn’t support multi-level subdomains

Too many redirects with Cloudflare + Azure App Service

Too many redirects?! Why