diff --git a/mcp/streamable.go b/mcp/streamable.go
index 708b1326..b49822e6 100644
--- a/mcp/streamable.go
+++ b/mcp/streamable.go
@@ -37,6 +37,7 @@ import (
 	"github.com/modelcontextprotocol/go-sdk/internal/util"
 	"github.com/modelcontextprotocol/go-sdk/internal/xcontext"
 	"github.com/modelcontextprotocol/go-sdk/jsonrpc"
+	"golang.org/x/oauth2"
 )
 
 // A StreamableHTTPHandler is an http.Handler that serves streamable MCP
@@ -1803,6 +1804,7 @@ func (c *streamableClientConn) Write(ctx context.Context, msg jsonrpc.Message) e
 		}
 		req.Header.Set("Content-Type", "application/json")
 		req.Header.Set("Accept", "application/json, text/event-stream")
+
 		if err := c.setMCPHeaders(req); err != nil {
 			// Failure to set headers means that the request was not sent.
 			// Wrap with ErrRejected so the jsonrpc2 connection doesn't set writeErr
@@ -1934,9 +1936,20 @@ func (c *streamableClientConn) setMCPHeaders(req *http.Request) error {
 		if ts != nil {
 			token, err := ts.Token()
 			if err != nil {
-				return err
-			}
-			if token != nil {
+				// If the error is an invalid_grant oauth2.RetrieveError it indicates
+				// that the token source doesn't have valid authorization for the token
+				// endpoint, per RFC 6749 section 5.2. For example, the refresh token
+				// may be expired or invalid.
+				//
+				// In that case, ignore the error, skip setting the Authorization
+				// header, and proceed with the request. Callers that support
+				// authorization flows get a 401/403 response and trigger the
+				// Authorize() flow to refresh their token.
+				var retrieveErr *oauth2.RetrieveError
+				if !errors.As(err, &retrieveErr) || retrieveErr.ErrorCode != "invalid_grant" {
+					return err
+				}
+			} else if token != nil {
 				req.Header.Set("Authorization", "Bearer "+token.AccessToken)
 			}
 		}
diff --git a/mcp/streamable_client_test.go b/mcp/streamable_client_test.go
index 96c5e75f..517e51af 100644
--- a/mcp/streamable_client_test.go
+++ b/mcp/streamable_client_test.go
@@ -6,6 +6,7 @@ package mcp
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"io"
 	"net/http"
@@ -1156,3 +1157,58 @@ func TestTokenInfo(t *testing.T) {
 		t.Errorf("got %q, want %q", g, w)
 	}
 }
+
+// errTestAuthorizeFailed is a sentinel error returned by
+// retrieveErrorOAuthHandler.Authorize().
+var errTestAuthorizeFailed = errors.New("authorize intentionally failed for test")
+
+// retrieveErrorOAuthHandler is a mock OAuthHandler that always returns
+// an oauth2.RetrieveError from its TokenSource's Token() method.
+type retrieveErrorOAuthHandler struct{}
+
+func (h *retrieveErrorOAuthHandler) TokenSource(ctx context.Context) (oauth2.TokenSource, error) {
+	return h, nil
+}
+
+func (h *retrieveErrorOAuthHandler) Token() (*oauth2.Token, error) {
+	return nil, &oauth2.RetrieveError{
+		Response:  &http.Response{StatusCode: http.StatusBadRequest},
+		Body:      []byte("test retrieve error"),
+		ErrorCode: "invalid_grant",
+	}
+}
+
+func (h *retrieveErrorOAuthHandler) Authorize(ctx context.Context, req *http.Request, resp *http.Response) error {
+	return errTestAuthorizeFailed
+}
+
+// TestStreamableClientOAuth_RetrieveError verifies that an invalid_grant RetrieveError
+// from the OAuth token source correctly skips sending Authorization header and relies on
+// the server's 401 response to trigger the Authorize fallback flow.
+func TestStreamableClientOAuth_RetrieveError(t *testing.T) {
+	ctx := context.Background()
+	oauthHandler := &retrieveErrorOAuthHandler{}
+
+	// Mock MCP server returns 401 Unauthorized to simulate a server rejecting
+	// the request that omitted the Authorization header.
+	httpServer := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusUnauthorized)
+	}))
+	t.Cleanup(httpServer.Close)
+
+	transport := &StreamableClientTransport{
+		Endpoint:     httpServer.URL,
+		OAuthHandler: oauthHandler,
+	}
+	client := NewClient(testImpl, nil)
+
+	// Attempt to connect. The Connect call will trigger the initialization request,
+	// which will fail to retrieve the token and proceed without auth header, receive 401,
+	// and invoke Authorize().
+	_, err := client.Connect(ctx, transport, nil)
+
+	// Expect the connection to fail with the sentinel error, not the RetrieveError.
+	if !errors.Is(err, errTestAuthorizeFailed) {
+		t.Fatalf("client.Connect() error = %v, want %v", err, errTestAuthorizeFailed)
+	}
+}