CONNECT request to a forward HTTP proxy over an SSL connection?

Question

I am writing an HTTP proxy and I am having trouble understanding some details of making a CONNECT request over TLS. To get a better picture, I am experimenting with Apache

Answer 1

You're doing everything right. It's Apache that got things wrong. Support for CONNECT over TLS was only added recently (https://issues.apache.org/bugzilla/show_bug.cgi?id=29744) and there's still some things to be ironed out. The issue you're hitting is one of them.