diff --git a/pgconn/pgconn.go b/pgconn/pgconn.go
index d425b5ad8..819380e3f 100644
--- a/pgconn/pgconn.go
+++ b/pgconn/pgconn.go
@@ -2250,3 +2250,55 @@ func (h *DeadlineContextWatcherHandler) HandleCancel(ctx context.Context) {
 func (h *DeadlineContextWatcherHandler) HandleUnwatchAfterCancel() {
 	h.Conn.SetDeadline(time.Time{})
 }
+
+// CancelRequestContextWatcherHandler handles canceled contexts by sending a cancel request to the server. It also sets
+// a deadline on a net.Conn as a fallback.
+type CancelRequestContextWatcherHandler struct {
+	Conn *PgConn
+
+	// CancelRequestDelay is the delay before sending the cancel request to the server.
+	CancelRequestDelay time.Duration
+
+	// DeadlineDelay is the delay to set on the deadline set on net.Conn when the context is canceled.
+	DeadlineDelay time.Duration
+
+	cancelFinishedChan             chan struct{}
+	handleUnwatchAfterCancelCalled func()
+}
+
+func (h *CancelRequestContextWatcherHandler) HandleCancel(context.Context) {
+	h.cancelFinishedChan = make(chan struct{})
+	var handleUnwatchedAfterCancelCalledCtx context.Context
+	handleUnwatchedAfterCancelCalledCtx, h.handleUnwatchAfterCancelCalled = context.WithCancel(context.Background())
+
+	deadline := time.Now().Add(h.DeadlineDelay)
+	h.Conn.conn.SetDeadline(deadline)
+
+	go func() {
+		defer close(h.cancelFinishedChan)
+
+		select {
+		case <-handleUnwatchedAfterCancelCalledCtx.Done():
+			return
+		case <-time.After(h.CancelRequestDelay):
+		}
+
+		cancelRequestCtx, cancel := context.WithDeadline(handleUnwatchedAfterCancelCalledCtx, deadline)
+		defer cancel()
+		h.Conn.CancelRequest(cancelRequestCtx)
+
+		// CancelRequest is inherently racy. Even though the cancel request has been received by the server at this point,
+		// it hasn't necessarily been delivered to the other connection. If we immediately return and the connection is
+		// immediately used then it is possible the CancelRequest will actually cancel our next query. The
+		// TestCancelRequestContextWatcherHandler Stress test can produce this error without the sleep below. The sleep time
+		// is arbitrary, but should be sufficient to prevent this error case.
+		time.Sleep(100 * time.Millisecond)
+	}()
+}
+
+func (h *CancelRequestContextWatcherHandler) HandleUnwatchAfterCancel() {
+	h.handleUnwatchAfterCancelCalled()
+	<-h.cancelFinishedChan
+
+	h.Conn.conn.SetDeadline(time.Time{})
+}
diff --git a/pgconn/pgconn_test.go b/pgconn/pgconn_test.go
index 704abe1cd..e91f699a4 100644
--- a/pgconn/pgconn_test.go
+++ b/pgconn/pgconn_test.go
@@ -3527,3 +3527,114 @@ func TestDeadlineContextWatcherHandler(t *testing.T) {
 		ensureConnValid(t, pgConn)
 	})
 }
+
+func TestCancelRequestContextWatcherHandler(t *testing.T) {
+	t.Parallel()
+
+	t.Run("DeadlineExceeded cancels request after CancelRequestDelay", func(t *testing.T) {
+		config, err := pgconn.ParseConfig(os.Getenv("PGX_TEST_DATABASE"))
+		require.NoError(t, err)
+		config.BuildContextWatcherHandler = func(conn *pgconn.PgConn) ctxwatch.Handler {
+			return &pgconn.CancelRequestContextWatcherHandler{
+				Conn:               conn,
+				CancelRequestDelay: 250 * time.Millisecond,
+				DeadlineDelay:      5000 * time.Millisecond,
+			}
+		}
+		config.ConnectTimeout = 5 * time.Second
+
+		pgConn, err := pgconn.ConnectConfig(context.Background(), config)
+		require.NoError(t, err)
+		defer closeConn(t, pgConn)
+
+		ctx, cancel := context.WithTimeout(context.Background(), 50*time.Millisecond)
+		defer cancel()
+
+		_, err = pgConn.Exec(ctx, "select 1, pg_sleep(3)").ReadAll()
+		require.Error(t, err)
+		var pgErr *pgconn.PgError
+		require.ErrorAs(t, err, &pgErr)
+
+		ensureConnValid(t, pgConn)
+	})
+
+	t.Run("DeadlineExceeded - do not send cancel request when query finishes in grace period", func(t *testing.T) {
+		config, err := pgconn.ParseConfig(os.Getenv("PGX_TEST_DATABASE"))
+		require.NoError(t, err)
+		config.BuildContextWatcherHandler = func(conn *pgconn.PgConn) ctxwatch.Handler {
+			return &pgconn.CancelRequestContextWatcherHandler{
+				Conn:               conn,
+				CancelRequestDelay: 1000 * time.Millisecond,
+				DeadlineDelay:      5000 * time.Millisecond,
+			}
+		}
+		config.ConnectTimeout = 5 * time.Second
+
+		pgConn, err := pgconn.ConnectConfig(context.Background(), config)
+		require.NoError(t, err)
+		defer closeConn(t, pgConn)
+
+		ctx, cancel := context.WithTimeout(context.Background(), 100*time.Millisecond)
+		defer cancel()
+
+		_, err = pgConn.Exec(ctx, "select 1, pg_sleep(0.250)").ReadAll()
+		require.NoError(t, err)
+
+		ensureConnValid(t, pgConn)
+	})
+
+	t.Run("DeadlineExceeded sets conn deadline with DeadlineDelay", func(t *testing.T) {
+		config, err := pgconn.ParseConfig(os.Getenv("PGX_TEST_DATABASE"))
+		require.NoError(t, err)
+		config.BuildContextWatcherHandler = func(conn *pgconn.PgConn) ctxwatch.Handler {
+			return &pgconn.CancelRequestContextWatcherHandler{
+				Conn:               conn,
+				CancelRequestDelay: 5000 * time.Millisecond, // purposely setting this higher than DeadlineDelay to ensure the cancel request never happens.
+				DeadlineDelay:      250 * time.Millisecond,
+			}
+		}
+		config.ConnectTimeout = 5 * time.Second
+
+		pgConn, err := pgconn.ConnectConfig(context.Background(), config)
+		require.NoError(t, err)
+		defer closeConn(t, pgConn)
+
+		ctx, cancel := context.WithTimeout(context.Background(), 50*time.Millisecond)
+		defer cancel()
+
+		_, err = pgConn.Exec(ctx, "select 1, pg_sleep(1)").ReadAll()
+		require.Error(t, err)
+		require.ErrorIs(t, err, context.DeadlineExceeded)
+		require.True(t, pgConn.IsClosed())
+	})
+
+	for i := 0; i < 10; i++ {
+		t.Run(fmt.Sprintf("Stress %d", i), func(t *testing.T) {
+			t.Parallel()
+
+			config, err := pgconn.ParseConfig(os.Getenv("PGX_TEST_DATABASE"))
+			require.NoError(t, err)
+			config.BuildContextWatcherHandler = func(conn *pgconn.PgConn) ctxwatch.Handler {
+				return &pgconn.CancelRequestContextWatcherHandler{
+					Conn:               conn,
+					CancelRequestDelay: 5 * time.Millisecond,
+					DeadlineDelay:      1000 * time.Millisecond,
+				}
+			}
+			config.ConnectTimeout = 5 * time.Second
+
+			pgConn, err := pgconn.ConnectConfig(context.Background(), config)
+			require.NoError(t, err)
+			defer closeConn(t, pgConn)
+
+			for i := 0; i < 20; i++ {
+				func() {
+					ctx, cancel := context.WithTimeout(context.Background(), 4*time.Millisecond)
+					defer cancel()
+					pgConn.Exec(ctx, "select 1, pg_sleep(0.010)").ReadAll()
+					ensureConnValid(t, pgConn)
+				}()
+			}
+		})
+	}
+}