diff --git a/go.mod b/go.mod
index 402d3bf2662..eda5236aa67 100644
--- a/go.mod
+++ b/go.mod
@@ -12,6 +12,7 @@ require (
 	golang.org/x/oauth2 v0.0.0-20211104180415-d3ed0bb246c8
 	golang.org/x/sync v0.0.0-20210220032951-036812b2e83c
 	golang.org/x/sys v0.0.0-20211210111614-af8b64212486
+	golang.org/x/xerrors v0.0.0-20200804184101-5ec99f83aff1
 	google.golang.org/appengine v1.6.7
 	google.golang.org/genproto v0.0.0-20211208223120-3a66f561d7aa
 	google.golang.org/grpc v1.40.1
diff --git a/internal/gensupport/send.go b/internal/gensupport/send.go
index dab64aef367..dd50cc20a58 100644
--- a/internal/gensupport/send.go
+++ b/internal/gensupport/send.go
@@ -99,6 +99,17 @@ func sendAndRetry(ctx context.Context, client *http.Client, req *http.Request, r
 		case <-time.After(pause):
 		}
 
+		if ctx.Err() != nil {
+			// Check for context cancellation once more. If more than one case in a
+			// select is satisfied at the same time, Go will choose one arbitrarily.
+			// That can cause an operation to go through even if the context was
+			// canceled before.
+			if err == nil {
+				err = ctx.Err()
+			}
+			return resp, err
+		}
+
 		resp, err = client.Do(req.WithContext(ctx))
 
 		var status int
diff --git a/internal/gensupport/send_test.go b/internal/gensupport/send_test.go
index d6af483e66e..b4ce4cfde2f 100644
--- a/internal/gensupport/send_test.go
+++ b/internal/gensupport/send_test.go
@@ -8,6 +8,8 @@ import (
 	"context"
 	"net/http"
 	"testing"
+
+	"golang.org/x/xerrors"
 )
 
 func TestSendRequest(t *testing.T) {
@@ -29,3 +31,24 @@ func TestSendRequestWithRetry(t *testing.T) {
 		t.Error("got nil, want error")
 	}
 }
+
+type brokenRoundTripper struct{}
+
+func (t *brokenRoundTripper) RoundTrip(r *http.Request) (*http.Response, error) {
+	return nil, xerrors.New("this should not happen")
+}
+
+func TestCanceledContextDoesNotPerformRequest(t *testing.T) {
+	client := http.Client{
+		Transport: &brokenRoundTripper{},
+	}
+	for i := 0; i < 1000; i++ {
+		req, _ := http.NewRequest("GET", "url", nil)
+		ctx, cancel := context.WithCancel(context.Background())
+		cancel()
+		_, err := SendRequestWithRetry(ctx, &client, req, nil)
+		if !xerrors.Is(err, context.Canceled) {
+			t.Fatalf("got %v, want %v", err, context.Canceled)
+		}
+	}
+}