[v15] Cache PIV connections to share across the program execution (#4…

…7953)

* Cache PIV connections to share across the program execution (#47091)

* Cache yubikey objects.

* Cache PIV connections to share across the program execution.

* Do not release the connection until `sign` returns

* Do not ignore errors

* Perform a "warm up" call to YubiKey

* Fix tests

* Use a specific interface to check if the key can be "warmed up"

* Allow abandoning `signer.Sign` call when context is canceled

* Make sure that the cached key is valid for the given private key policy

The reason for adding this check was failing `invalid key policies` test.

* Make `hardwareKeyWarmer` private

* Force callers to release connection

* Improve comments

* Fix lint

* Improve `connect` comment

* Fix race condition

* Simplify `release` logic

* Trigger license/cla

---------

Co-authored-by: joerger <[email protected]>

(cherry picked from commit bd6fdbf)

* Sign a hashed message in hardware key warmup call (#48206)

Otherwise, signing may fail with "input must be a hashed message" error.

(cherry picked from commit 47494db)

* Remove delayed closing of yubikey connection to prevent the connection from leaking after program execution. (#48414)

(cherry picked from commit b7c0e79)

---------

Co-authored-by: Brian Joerger <[email protected]>

api/client/proxy/client.go

@@ -82,7 +82,7 @@ type ClientConfig struct {
 
 // CheckAndSetDefaults ensures required options are present and
 // sets the default value of any that are omitted.
-func (c *ClientConfig) CheckAndSetDefaults() error {
+func (c *ClientConfig) CheckAndSetDefaults(ctx context.Context) error {
 	if c.ProxyAddress == "" {
 		return trace.BadParameter("missing required parameter ProxyAddress")
 	}
@@ -115,6 +115,21 @@ func (c *ClientConfig) CheckAndSetDefaults() error {
 			// not to send the client certificate by looking at certificate request.
 			if len(tlsCfg.Certificates) > 0 {
 				cert := tlsCfg.Certificates[0]
+
+				// When a hardware key is used to store the private key, the user may fail to provide
+				// a PIN or touch before a gRPC dial timeout occurs.
+				// The resulting "dial timeout" error is generic and doesn't indicate an issue with the
+				// hardware key itself (since YubiKey is treated like any other key).
+				// To avoid this, we perform a "warm-up" call to the key, ensuring it is ready
+				// before initiating the gRPC dial.
+				// This approach works because the connection is cached for a few seconds,
+				// allowing subsequent calls without requiring additional user action.
+				if priv, ok := cert.PrivateKey.(hardwareKeyWarmer); ok {
+					err := priv.WarmupHardwareKey(ctx)
+					if err != nil {
+						return nil, trace.Wrap(err)
+					}
+				}
 				tlsCfg.Certificates = nil
 				tlsCfg.GetClientCertificate = func(_ *tls.CertificateRequestInfo) (*tls.Certificate, error) {
 					return &cert, nil
@@ -183,7 +198,7 @@ const protocolProxySSHGRPC string = "teleport-proxy-ssh-grpc"
 // of the caller, then prefer to use NewSSHClient instead which omits
 // the gRPC dialing altogether.
 func NewClient(ctx context.Context, cfg ClientConfig) (*Client, error) {
-	if err := cfg.CheckAndSetDefaults(); err != nil {
+	if err := cfg.CheckAndSetDefaults(ctx); err != nil {
 		return nil, trace.Wrap(err)
 	}
 
@@ -439,3 +454,9 @@ func (c *Client) Ping(ctx context.Context) error {
 	_, _ = c.transport.ClusterDetails(ctx)
 	return nil
 }
+
+// hardwareKeyWarmer performs a bogus call to the hardware key,
+// to proactively prompt the user for a PIN/touch (if needed).
+type hardwareKeyWarmer interface {
+	WarmupHardwareKey(ctx context.Context) error
+}