diff --git a/src/crypto/tls/handshake_client_test.go b/src/crypto/tls/handshake_client_test.go
index 693f9686a79..f499cf3970d 100644
--- a/src/crypto/tls/handshake_client_test.go
+++ b/src/crypto/tls/handshake_client_test.go
@@ -6,6 +6,7 @@ package tls
 
 import (
 	"bytes"
+	"context"
 	"crypto/rsa"
 	"crypto/x509"
 	"encoding/base64"
@@ -20,6 +21,7 @@ import (
 	"os/exec"
 	"path/filepath"
 	"reflect"
+	"runtime"
 	"strconv"
 	"strings"
 	"testing"
@@ -2511,3 +2513,35 @@ func testResumptionKeepsOCSPAndSCT(t *testing.T, ver uint16) {
 			serverConfig.Certificates[0].SignedCertificateTimestamps, ccs.SignedCertificateTimestamps)
 	}
 }
+
+// TestClientHandshakeContextCancellation tests that cancelling
+// the context given to the client side conn.HandshakeContext
+// interrupts the in-progress handshake.
+func TestClientHandshakeContextCancellation(t *testing.T) {
+	c, s := localPipe(t)
+	ctx, cancel := context.WithCancel(context.Background())
+	unblockServer := make(chan struct{})
+	defer close(unblockServer)
+	go func() {
+		cancel()
+		<-unblockServer
+		_ = s.Close()
+	}()
+	cli := Client(c, testConfig)
+	// Initiates client side handshake, which will block until the client hello is read
+	// by the server, unless the cancellation works.
+	err := cli.HandshakeContext(ctx)
+	if err == nil {
+		t.Fatal("Client handshake did not error when the context was canceled")
+	}
+	if err != context.Canceled {
+		t.Errorf("Unexpected client handshake error: %v", err)
+	}
+	if runtime.GOARCH == "wasm" {
+		t.Skip("conn.Close does not error as expected when called multiple times on WASM")
+	}
+	err = cli.Close()
+	if err == nil {
+		t.Error("Client connection was not closed when the context was canceled")
+	}
+}
diff --git a/src/crypto/tls/handshake_server_test.go b/src/crypto/tls/handshake_server_test.go
index 756d288cb35..4c2d319fb1a 100644
--- a/src/crypto/tls/handshake_server_test.go
+++ b/src/crypto/tls/handshake_server_test.go
@@ -1946,27 +1946,22 @@ func TestAESCipherReordering13(t *testing.T) {
 	}
 }
 
+// TestServerHandshakeContextCancellation tests that cancelling
+// the context given to the server side conn.HandshakeContext
+// interrupts the in-progress handshake.
 func TestServerHandshakeContextCancellation(t *testing.T) {
 	c, s := localPipe(t)
-	clientConfig := testConfig.Clone()
-	clientErr := make(chan error, 1)
 	ctx, cancel := context.WithCancel(context.Background())
-	defer cancel()
+	unblockClient := make(chan struct{})
+	defer close(unblockClient)
 	go func() {
-		defer close(clientErr)
-		defer c.Close()
-		clientHello := &clientHelloMsg{
-			vers:               VersionTLS10,
-			random:             make([]byte, 32),
-			cipherSuites:       []uint16{TLS_RSA_WITH_RC4_128_SHA},
-			compressionMethods: []uint8{compressionNone},
-		}
-		cli := Client(c, clientConfig)
-		_, err := cli.writeRecord(recordTypeHandshake, clientHello.marshal())
 		cancel()
-		clientErr <- err
+		<-unblockClient
+		_ = c.Close()
 	}()
 	conn := Server(s, testConfig)
+	// Initiates server side handshake, which will block until a client hello is read
+	// unless the cancellation works.
 	err := conn.HandshakeContext(ctx)
 	if err == nil {
 		t.Fatal("Server handshake did not error when the context was canceled")
@@ -1974,9 +1969,6 @@ func TestServerHandshakeContextCancellation(t *testing.T) {
 	if err != context.Canceled {
 		t.Errorf("Unexpected server handshake error: %v", err)
 	}
-	if err := <-clientErr; err != nil {
-		t.Errorf("Unexpected client error: %v", err)
-	}
 	if runtime.GOARCH == "wasm" {
 		t.Skip("conn.Close does not error as expected when called multiple times on WASM")
 	}