diff --git a/internal/forge/github/github.go b/internal/forge/github/github.go
index 2a44aed083..dd80a73a40 100644
--- a/internal/forge/github/github.go
+++ b/internal/forge/github/github.go
@@ -199,7 +199,7 @@ func (c *LiveClient) do(ctx context.Context, method, path string, body any) (*ht
 			}
 			// HTTP client timeout (Client.Timeout exceeded): retry
 			// with exponential backoff, same as transient server errors.
-			if isTimeoutError(err) {
+			if isTimeoutError(ctx, err) {
 				if attempt == maxRetries-1 {
 					return nil, fmt.Errorf("http %s %s: %w (after %d attempts)", method, path, err, maxRetries)
 				}
@@ -289,10 +289,20 @@ func isRetryable(resp *http.Response) (bool, []byte) {
 }
 
 // isTimeoutError reports whether err is an HTTP client timeout (e.g.
-// Client.Timeout exceeded) as opposed to a caller-context cancellation.
-// Callers must check ctx.Err() first — this function only distinguishes
-// timeout transport errors from other transport errors.
-func isTimeoutError(err error) bool {
+// Client.Timeout exceeded) as opposed to a caller-context cancellation
+// or deadline. It checks ctx.Err() internally so callers do not need
+// to guard against context errors before calling this function.
+//
+// The context check is necessary because Go's net/http client timeout
+// wraps context.DeadlineExceeded internally, making error-only
+// introspection unable to distinguish caller deadlines from transport
+// timeouts. Checking the caller's context disambiguates: if ctx.Err()
+// is non-nil, the caller's context expired; otherwise, any Timeout()
+// error is a transport-level timeout worth retrying.
+func isTimeoutError(ctx context.Context, err error) bool {
+	if ctx.Err() != nil {
+		return false
+	}
 	var te interface{ Timeout() bool }
 	return errors.As(err, &te) && te.Timeout()
 }
diff --git a/internal/forge/github/github_test.go b/internal/forge/github/github_test.go
index 499105a1ad..4ea5226e75 100644
--- a/internal/forge/github/github_test.go
+++ b/internal/forge/github/github_test.go
@@ -2934,41 +2934,69 @@ func TestDoDoesNotRetryOnCallerContextCancel(t *testing.T) {
 }
 
 func TestIsTimeoutError(t *testing.T) {
+	// Create an already-cancelled context for testing the context guard.
+	cancelledCtx, cancel := context.WithCancel(context.Background())
+	cancel()
+
 	tests := []struct {
 		name string
+		ctx  context.Context
 		err  error
 		want bool
 	}{
 		{
 			name: "nil error",
+			ctx:  context.Background(),
 			err:  nil,
 			want: false,
 		},
 		{
 			name: "generic error",
+			ctx:  context.Background(),
 			err:  fmt.Errorf("connection refused"),
 			want: false,
 		},
 		{
-			name: "context.DeadlineExceeded",
+			name: "context.DeadlineExceeded with active context",
+			ctx:  context.Background(),
 			err:  context.DeadlineExceeded,
 			want: true,
 		},
 		{
-			name: "wrapped context.DeadlineExceeded",
+			name: "context.DeadlineExceeded with cancelled context",
+			ctx:  cancelledCtx,
+			err:  context.DeadlineExceeded,
+			want: false,
+		},
+		{
+			name: "wrapped context.DeadlineExceeded with cancelled context",
+			ctx:  cancelledCtx,
 			err:  fmt.Errorf("request failed: %w", context.DeadlineExceeded),
-			want: true,
+			want: false,
 		},
 		{
-			name: "context.Canceled is not a timeout",
+			name: "context.Canceled with active context",
+			ctx:  context.Background(),
 			err:  context.Canceled,
 			want: false,
 		},
+		{
+			name: "context.Canceled with cancelled context",
+			ctx:  cancelledCtx,
+			err:  context.Canceled,
+			want: false,
+		},
+		{
+			name: "timeout error with cancelled context returns false",
+			ctx:  cancelledCtx,
+			err:  context.DeadlineExceeded,
+			want: false,
+		},
 	}
 
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
-			assert.Equal(t, tt.want, isTimeoutError(tt.err))
+			assert.Equal(t, tt.want, isTimeoutError(tt.ctx, tt.err))
 		})
 	}
 }