diff --git a/mcp/streamable.go b/mcp/streamable.go
index 76f2b0e4..f4dd21f3 100644
--- a/mcp/streamable.go
+++ b/mcp/streamable.go
@@ -1801,6 +1801,22 @@ func (c *streamableClientConn) Write(ctx context.Context, msg jsonrpc.Message) e
 
 	if (resp.StatusCode == http.StatusUnauthorized || resp.StatusCode == http.StatusForbidden) && c.oauthHandler != nil {
 		if err := c.oauthHandler.Authorize(ctx, req, resp); err != nil {
+			// If the caller's context was cancelled while we were running the
+			// authorization flow, treat the connection as failed so subsequent
+			// operations on it (e.g. the cancellation notify the call layer
+			// sends in response to ctx cancellation) short-circuit instead of
+			// re-invoking the OAuth handler. Otherwise the user gets prompted
+			// to authorize a request they have already abandoned. See #882.
+			//
+			// We check ctx.Err() rather than the error returned by Authorize,
+			// because the handler is user-implemented and may return an error
+			// that does not wrap context.Canceled (e.g. a custom sentinel or
+			// a fmt.Errorf with %v). The context itself is the authoritative
+			// source for whether the caller abandoned the request.
+			ctxErr := ctx.Err()
+			if errors.Is(ctxErr, context.Canceled) || errors.Is(ctxErr, context.DeadlineExceeded) {
+				c.fail(fmt.Errorf("%s: authorization cancelled: %w", requestSummary, err))
+			}
 			// Wrap with ErrRejected so the jsonrpc2 connection doesn't set writeErr
 			// and permanently break the connection.
 			// Wrap the authorization error as well for client inspection.
diff --git a/mcp/streamable_client_test.go b/mcp/streamable_client_test.go
index 43564fd3..719cb580 100644
--- a/mcp/streamable_client_test.go
+++ b/mcp/streamable_client_test.go
@@ -1016,6 +1016,94 @@ func TestStreamableClientOAuth_401(t *testing.T) {
 	}
 }
 
+// blockingCountingOAuthHandler is an OAuthHandler that blocks inside
+// Authorize until the caller's context is cancelled, then returns a custom
+// error that does NOT wrap context.Canceled. This mirrors real-world OAuth
+// handlers that catch the cancellation internally and surface their own
+// error type. The fix for #882 checks ctx.Err() directly rather than
+// relying on the error from Authorize, so this must still trigger c.fail().
+// It records how many times Authorize is invoked.
+type blockingCountingOAuthHandler struct {
+	mu        sync.Mutex
+	callCount int
+}
+
+func (h *blockingCountingOAuthHandler) TokenSource(ctx context.Context) (oauth2.TokenSource, error) {
+	return nil, nil
+}
+
+func (h *blockingCountingOAuthHandler) Authorize(ctx context.Context, req *http.Request, resp *http.Response) error {
+	h.mu.Lock()
+	h.callCount++
+	h.mu.Unlock()
+	// Block until the caller's context is cancelled, mirroring an
+	// interactive OAuth flow that the user has abandoned.
+	<-ctx.Done()
+	// Return a custom error that does not wrap context.Canceled, as a
+	// real-world handler might. The code under test must check ctx.Err()
+	// to detect the cancellation, not this error.
+	return fmt.Errorf("oauth flow interrupted")
+}
+
+func (h *blockingCountingOAuthHandler) Calls() int {
+	h.mu.Lock()
+	defer h.mu.Unlock()
+	return h.callCount
+}
+
+// TestStreamableClientOAuth_CancelledAuthorize_NoReprompt is a regression
+// test for #882. When OAuthHandler.Authorize returns a context-cancelled
+// error, the connection must enter a failed state so that the cancellation
+// notification the call layer sends in response to ctx cancellation does
+// not flow back through the same broken auth path and re-invoke Authorize.
+func TestStreamableClientOAuth_CancelledAuthorize_NoReprompt(t *testing.T) {
+	handler := &blockingCountingOAuthHandler{}
+
+	fake := &fakeStreamableServer{
+		t: t,
+		responses: fakeResponses{
+			{"POST", "", methodInitialize, ""}: {
+				header: header{
+					"Content-Type":  "application/json",
+					sessionIDHeader: "123",
+				},
+				body: jsonBody(t, initResp),
+			},
+		},
+	}
+	verifier := func(ctx context.Context, token string, req *http.Request) (*auth.TokenInfo, error) {
+		return &auth.TokenInfo{Expiration: time.Now().Add(time.Hour)}, nil
+	}
+	httpServer := httptest.NewServer(auth.RequireBearerToken(verifier, nil)(fake))
+	t.Cleanup(httpServer.Close)
+
+	transport := &StreamableClientTransport{
+		Endpoint:     httpServer.URL,
+		OAuthHandler: handler,
+	}
+	client := NewClient(testImpl, nil)
+
+	// Use a context with a tight deadline so the cancellation path runs
+	// while the auth flow is in progress.
+	ctx, cancel := context.WithTimeout(context.Background(), 200*time.Millisecond)
+	defer cancel()
+
+	_, err := client.Connect(ctx, transport, nil)
+	if err == nil {
+		t.Fatal("expected client.Connect to fail")
+	}
+
+	// Give the cancellation Notify path a moment to (try to) run.
+	time.Sleep(50 * time.Millisecond)
+
+	// Authorize should be invoked exactly once. The bug in #882 caused
+	// it to be invoked a second time when the call layer sent the
+	// cancellation notification through the same auth-broken connection.
+	if got := handler.Calls(); got != 1 {
+		t.Errorf("expected Authorize to be called exactly 1 time, got %d", got)
+	}
+}
+
 func TestTokenInfo(t *testing.T) {
 	ctx := context.Background()
 
diff --git a/mcp/transport.go b/mcp/transport.go
index 23dccf8e..426aa07e 100644
--- a/mcp/transport.go
+++ b/mcp/transport.go
@@ -14,13 +14,20 @@ import (
 	"net"
 	"os"
 	"sync"
+	"time"
 
 	internaljson "github.com/modelcontextprotocol/go-sdk/internal/json"
 	"github.com/modelcontextprotocol/go-sdk/internal/jsonrpc2"
-	"github.com/modelcontextprotocol/go-sdk/internal/xcontext"
 	"github.com/modelcontextprotocol/go-sdk/jsonrpc"
 )
 
+// notifyCancellationTimeout bounds the cancellation notification we send to
+// the peer when the caller's context is cancelled. The notification is
+// best-effort: a degraded connection (e.g. an OAuth flow that has been
+// abandoned) must not be able to block the caller's return path or
+// re-trigger expensive recovery on its behalf. See issue #882.
+const notifyCancellationTimeout = 5 * time.Second
+
 // ErrConnectionClosed is returned when sending a message to a connection that
 // is closed or in the process of closing.
 var ErrConnectionClosed = errors.New("connection closed")
@@ -216,8 +223,19 @@ func call(ctx context.Context, conn *jsonrpc2.Connection, method string, params
 	case errors.Is(err, jsonrpc2.ErrClientClosing), errors.Is(err, jsonrpc2.ErrServerClosing):
 		return fmt.Errorf("%w: calling %q: %v", ErrConnectionClosed, method, err)
 	case ctx.Err() != nil:
-		// Notify the peer of cancellation.
-		err := conn.Notify(xcontext.Detach(ctx), notificationCancelled, &CancelledParams{
+		// Best-effort notify the peer of cancellation. We deliberately bound
+		// this with a fresh, short-lived context derived from
+		// context.Background() rather than reusing (or merely detaching) the
+		// caller's already-cancelled context. The connection may be in a
+		// degraded state — for example, the original failure may have come
+		// from an OAuth flow whose handler context expired (see #882) — and
+		// reusing that context would either return immediately with an error
+		// or, worse, re-trigger expensive recovery (re-auth) on the caller's
+		// return path. The bounded background context lets the notification
+		// attempt to deliver but never blocks the caller indefinitely.
+		notifyCtx, cancelNotify := context.WithTimeout(context.Background(), notifyCancellationTimeout)
+		defer cancelNotify()
+		err := conn.Notify(notifyCtx, notificationCancelled, &CancelledParams{
 			Reason:    ctx.Err().Error(),
 			RequestID: call.ID().Raw(),
 		})