Sub-subdomains on different servers do not resolve

Just set-up a CloudFlare free account and now evaluating the service for a web-based application. So far everything seems to work great apart from one particular issue that I lack the know-how to resolve.

The account on CF is for an integrated application that consists of a website, a number of webapps under a subdomain ‘app.’, an api available on ‘api.’, and a subdomain static. for static content.

Before CloudFlare, my DNS configuration on the registrar had settings for all of the subdomains on the-application.com (e.g. A record for app, A record for api and so on). Since there are three release channels for the application – development, stage and production – I had duplicate DNS settings for each release channel; e.g. app.dev and app.stage, api.dev and api.stage, and so on. The dev and stage release channels are hosted on a different server.

While everything else works great, the sub-subdomains *.dev and *.stage do not work. I added A records on CloudFlare’s DNS configuration page but no luck so far, as only the “top-level” subdomains dev.the-application.com and stage.the-application.com work; app.dev.the-application.com doesn’t work due to some sort of DNS resolution failure. I read somewhere that even if I get the sub-subdomains to work, SSL may not due to CF not supporting sub-subdomains.

My DNS-fu is super limited and I would appreciate some assistance with this!

This sounds like an SSL issue, as Cloudflare SSL only covers subdomains, but not sub-subdomains.

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