For CONNECT, that's moot: you can't see what happens next. A HTTPS request running through a CONNECT proxy is invisible to that proxy.
It helps a bit to understand what is happening, with CONNECT. A client sends a request like this:
CONNECT example.com:443 HTTP/1.1
Host: example.com:443
This asks the server to establish a TCP connection to example.com on port 443. When that connection is established, the server responds with:
200 OK
Server: myserver
At this point, this connection can no longer be used for HTTP. When the server sends its 200 response, it is telling the client that from this point forward the server is no longer processing the bytes the client sends it. Instead, it is forwarding them on to example.com. In essence, the server has become a dumb pipe, just forwarding bytes back and forth.
This behaviour is required by the HTTP specifications. Quoting RFC 9110 (HTTP Semantics) § 9.3.6 (Connect):
The CONNECT method requests that the recipient establish a tunnel to the destination origin server identified by the request target and, if successful, thereafter restrict its behavior to blind forwarding of data, in both directions, until the tunnel is closed.
If you're only serving HTTPS requests through the proxy, what will happen next is that the client will send a TLS CLIENT_HELLO message, beginning a TLS handshake. This handshake is (by design) resistant to being intercepted. You cannot see what is going on inside that TLS tunnel, and so will not be able to decode any of the data, unless you are attempting to build a man-in-the-middle proxy.
No, glue will only be called once.
Before, we have a standard plaintext HTTP server pipeline followed by the ConnectHandler:
┌────────────────────────┐ ┌───────────────────────┐ ┌───────────────────────┐
│ │ │ │ │ │
│ HTTP Request Decoder │ │ HTTP Response Encoder │ │ Connect Handler │
│ │ │ │ │ │
└────────────────────────┘ └───────────────────────┘ └───────────────────────┘
After, all of the HTTP handlers are removed, and we have two Channel's that have been "glued" together by use of a pair of GlueHandlers:
│
┌───────────────────────┐ │ ┌───────────────────────┐
│ │ │ │
│ Glue Handler │ │ │ Glue Handler │
│ │ │ │
└───────────────────────┘ │ └───────────────────────┘
│