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Description
Proposal
I propose an unexported context.Context field is added to the ClientHelloInfo and CertificateRequestInfo crypto/tls types. We should also add a Context() context.Context method to these types to access this context. Further, we should add a new method, HandshakeContext(context.Context) error to the tls.Conn struct, which will be used to propagate a context down the handshake call stack. The existing Handshake() error would call to the new method with a context.Background() context.
Standard library uses of (*tls.Conn).Handshake() should be moved over to the new method, where appropriate. For example, it is not clear that it is appropriate to change the existing Read and Write methods on the *tls.Conn to use the new handshake method, but in (*net/http.Server).serve, it is clear that moving to the new function would enhance the request lifetime control in the function.
The context.Context provided to HandshakeContext would only be used for cancellation of the handshake itself, and once the handshake has completed, cancelling the context will have no effect. This is in line with the predecent set by (*net.Dialer).DialContext.
Motivation
In recent Go releases, we've been able to use the handy GetCertificate and GetClientCertificate methods of the *tls.Config to dynamically control certificate management in Go apps. This is fantastic, and has lead to things like https://godoc.org/golang.org/x/crypto/acme/autocert and https://github.com/johanbrandhorst/certify which are somewhat unique to the Go ecosystem.
Unfortunately, one glaring omission from the API is a connection context for cancellation and request scoped variable propagation. This means users have to implement custom timeouts or block their TLS connections forever in case of problems. It also means powerful observability tools like tracing and metrics that make use of the context cannot be used.
Interaction with net/http
net/http.Server provide BaseContext, which is used to set a global context for the duration of (*http.Server).Serve, and ConnContext, which is used on every new connection. The context passed to (*tls.Conn).HandshakeContext would necessarily be a child of these contexts, as the existing Handshake call is made after these contexts are created. See