I like the direction this is headed. I have a few questions and observations:

There seem to be some constraints for support of sipsec that I didn't see mentioned explicitly:
- The UAC and each proxy must ensure that the transport used
  for the next hop is a connection-oriented, congestion-controlled
  transport. That is mentioned in the overview, but not specifically
  for the UAC and Proxy.

- For the tunneling to work I don't think there can be shared use
  of the connection. That is something special here. (In case of
  SCTP, I guess it would be sufficient to reserve a stream.)

There are some things that is is desirable to do that may be hard with sipsec, or at least need to be figured out. A couple that come to mind are:
- best effort security
- forking

For best effort security, one option seems to be to delay the CONNECT until you know the capabilities of the callee. For instance, a session could be established with SIP or SIPS, including supported:sipsec. If the session is established, then it could be followed up with a CONNECT/Replaces.

If you want to call an AOR that results in forking, CONNECT doesn't seem to work very well. I This may be a good reason to replace forking at a proxy with redirect. The proxy could return 3xx with the alternatives, which might be either SIP, SIPS, or SIPSEC. There are a lot of details to work our for this.

        Thanks,
        Paul



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