diff --git a/src/Foundation/NSUrlSessionHandler.cs b/src/Foundation/NSUrlSessionHandler.cs
index e34081682faa..fd63e033dadb 100644
--- a/src/Foundation/NSUrlSessionHandler.cs
+++ b/src/Foundation/NSUrlSessionHandler.cs
@@ -1493,8 +1493,14 @@ public override async Task<int> ReadAsync (byte [] buffer, int offset, int count
 					try {
 						await Task.Delay (50, cancellationToken).ConfigureAwait (false);
 					} catch (TaskCanceledException ex) {
-						// add a nicer exception for the user to catch, add the cancelation exception
-						// to have a decent stack
+						// If the caller's token triggered the cancellation, surface it
+						// as OperationCanceledException so callers can distinguish
+						// between a caller-requested cancellation and a request timeout.
+						if (cancellationToken.IsCancellationRequested)
+							throw new OperationCanceledException (ex.Message, ex, cancellationToken);
+						// If the caller's token is not cancelled, this is an internal
+						// cancellation (e.g. HttpClient.Timeout), so wrap it in a
+						// TimeoutException.
 						throw new TimeoutException ("The request timed out.", ex);
 					}
 				}
diff --git a/tests/monotouch-test/System.Net.Http/NSUrlSessionHandlerTest.cs b/tests/monotouch-test/System.Net.Http/NSUrlSessionHandlerTest.cs
index 79c787d387c1..31499a57e16b 100644
--- a/tests/monotouch-test/System.Net.Http/NSUrlSessionHandlerTest.cs
+++ b/tests/monotouch-test/System.Net.Http/NSUrlSessionHandlerTest.cs
@@ -5,6 +5,7 @@
 using System;
 using System.Net;
 using System.Net.Http;
+using System.Net.Sockets;
 using System.Text;
 using System.Threading;
 using System.Threading.Tasks;
@@ -321,6 +322,105 @@ public void BasicAuthWorksWhenBearerIsAdvertisedFirst ()
 			}
 		}
 
+		// https://github.com/dotnet/macios/issues/25667
+		[Test]
+		public void StreamReadAsyncCallerCancellationThrowsOperationCanceledException ()
+		{
+			// Use a raw TCP server so we have full control over when bytes are sent on the wire.
+			var tcpListener = new TcpListener (IPAddress.Loopback, 0);
+			tcpListener.Start ();
+			var port = ((IPEndPoint) tcpListener.LocalEndpoint).Port;
+
+			var serverReady = new SemaphoreSlim (0, 1);
+
+			// Server accepts the HTTP request, sends response headers and a large
+			// first body chunk, then stalls (never sends the rest of the declared body).
+			var serverTask = Task.Run (async () => {
+				try {
+					serverReady.Release ();
+					using var tcpClient = await tcpListener.AcceptTcpClientAsync ().ConfigureAwait (false);
+					tcpClient.NoDelay = true;
+					var stream = tcpClient.GetStream ();
+
+					// Wait for the full HTTP request (ends with \r\n\r\n)
+					var requestBytes = new byte [8192];
+					var totalRead = 0;
+					while (true) {
+						var n = await stream.ReadAsync (requestBytes, totalRead, requestBytes.Length - totalRead).ConfigureAwait (false);
+						if (n == 0)
+							return;
+						totalRead += n;
+						var requestSoFar = Encoding.ASCII.GetString (requestBytes, 0, totalRead);
+						if (requestSoFar.Contains ("\r\n\r\n"))
+							break;
+					}
+
+					// Declare a large Content-Length, send a smaller body, then stall.
+					// This ensures NSUrlSession delivers the initial body data via
+					// DidReceiveData while keeping the connection open for more.
+					var bodyChunk = new string ('A', 4096);
+					var responseText = "HTTP/1.1 200 OK\r\n" +
+						$"Content-Length: {bodyChunk.Length * 10}\r\n" +
+						"Content-Type: text/plain\r\n" +
+						"\r\n" +
+						bodyChunk;
+					var responseBytes = Encoding.ASCII.GetBytes (responseText);
+					await stream.WriteAsync (responseBytes, 0, responseBytes.Length).ConfigureAwait (false);
+					await stream.FlushAsync ().ConfigureAwait (false);
+
+					// Stall: never send the remaining body
+					await Task.Delay (TimeSpan.FromMinutes (5)).ConfigureAwait (false);
+				} catch (ObjectDisposedException) {
+					// listener was stopped
+				} catch (SocketException) {
+					// listener was stopped
+				}
+			});
+
+			Type caughtExceptionType = null;
+
+			try {
+				var done = TestRuntime.TryRunAsync (TimeSpan.FromSeconds (30), async () => {
+					await serverReady.WaitAsync ().ConfigureAwait (false);
+
+					using var handler = new NSUrlSessionHandler ();
+					using var httpClient = new HttpClient (handler);
+					httpClient.Timeout = TimeSpan.FromMinutes (5);
+
+					using var request = new HttpRequestMessage (HttpMethod.Get, $"http://127.0.0.1:{port}/stall");
+					var response = await httpClient.SendAsync (request, HttpCompletionOption.ResponseHeadersRead).ConfigureAwait (false);
+					var stream = await response.Content.ReadAsStreamAsync ().ConfigureAwait (false);
+
+					// First read succeeds (server sent 4KB of body data)
+					var buffer = new byte [8192];
+					var bytesRead = await stream.ReadAsync (buffer, 0, buffer.Length).ConfigureAwait (false);
+					Assert.That (bytesRead, Is.GreaterThan (0), "First read should return data");
+
+					// Second read: cancel after 250ms via caller token.
+					// The server declared a much larger Content-Length but stopped
+					// sending, so ReadAsync will block in the polling loop until
+					// the caller token fires.
+					using var cts = new CancellationTokenSource (TimeSpan.FromMilliseconds (250));
+					try {
+						await stream.ReadAsync (buffer, 0, buffer.Length, cts.Token).ConfigureAwait (false);
+						Assert.Fail ("Expected an exception from the cancelled ReadAsync");
+					} catch (Exception ex) {
+						caughtExceptionType = ex.GetType ();
+					}
+				}, out var ex2);
+
+				Assert.That (done, Is.True, "Test timed out");
+				Assert.That (ex2, Is.Null, $"Unexpected exception: {ex2}");
+
+				// Caller cancellation should surface as OperationCanceledException (or a subclass like TaskCanceledException),
+				// not as TimeoutException. TimeoutException should be reserved for actual request timeouts.
+				Assert.That (typeof (OperationCanceledException).IsAssignableFrom (caughtExceptionType), Is.True,
+					$"Expected OperationCanceledException but got {caughtExceptionType}");
+			} finally {
+				tcpListener.Stop ();
+			}
+		}
+
 		static HttpListener? StartListenerOnAvailablePort (out int listeningPort)
 		{
 			// IANA suggested range for dynamic or private ports