diff --git a/src/Mono.Android/Xamarin.Android.Net/AndroidClientHandler.Legacy.cs b/src/Mono.Android/Xamarin.Android.Net/AndroidClientHandler.Legacy.cs
index 542d85e2bd7..7e802c5966a 100644
--- a/src/Mono.Android/Xamarin.Android.Net/AndroidClientHandler.Legacy.cs
+++ b/src/Mono.Android/Xamarin.Android.Net/AndroidClientHandler.Legacy.cs
@@ -361,7 +361,13 @@ Task ConnectAsync (HttpURLConnection httpConnection, CancellationToken ct)
 		protected virtual async Task WriteRequestContentToOutput (HttpRequestMessage request, HttpURLConnection httpConnection, CancellationToken cancellationToken)
 		{
 			using (var stream = await request.Content.ReadAsStreamAsync ().ConfigureAwait (false)) {
-				await stream.CopyToAsync(httpConnection.OutputStream!, 4096, cancellationToken).ConfigureAwait(false);
+				cancellationToken.ThrowIfCancellationRequested ();
+				try {
+					await stream.CopyToAsync(httpConnection.OutputStream!, 4096, cancellationToken).ConfigureAwait(false);
+				} catch (ObjectDisposedException ex) {
+					Logger.Log (LogLevel.Error, LOG_APP, $"Stream disposed while copying the content stream to output: {ex}");
+					cancellationToken.ThrowIfCancellationRequested ();
+				}
 
 				//
 				// Rewind the stream to beginning in case the HttpContent implementation
@@ -381,8 +387,15 @@ protected virtual async Task WriteRequestContentToOutput (HttpRequestMessage req
 				//
 				// See https://bugzilla.xamarin.com/show_bug.cgi?id=55477
 				//
-				if (stream.CanSeek)
-					stream.Seek (0, SeekOrigin.Begin);
+				if (stream.CanSeek) {
+					cancellationToken.ThrowIfCancellationRequested ();
+					try {
+						stream.Seek (0, SeekOrigin.Begin);
+					} catch (ObjectDisposedException ex) {
+						Logger.Log (LogLevel.Error, LOG_APP, $"Stream disposed while seeking to the beginning of the content stream: {ex}");
+						cancellationToken.ThrowIfCancellationRequested ();
+					}
+				}
 			}
 		}
 
diff --git a/src/Mono.Android/Xamarin.Android.Net/AndroidMessageHandler.cs b/src/Mono.Android/Xamarin.Android.Net/AndroidMessageHandler.cs
index e5218687ae7..7f0caae20b8 100644
--- a/src/Mono.Android/Xamarin.Android.Net/AndroidMessageHandler.cs
+++ b/src/Mono.Android/Xamarin.Android.Net/AndroidMessageHandler.cs
@@ -569,29 +569,43 @@ protected virtual async Task WriteRequestContentToOutput (HttpRequestMessage req
 			if (request.Content is null)
 				return;
 
-			var stream = await request.Content.ReadAsStreamAsync ().ConfigureAwait (false);
-			await stream.CopyToAsync(httpConnection.OutputStream!, 4096, cancellationToken).ConfigureAwait(false);
-
-			//
-			// Rewind the stream to beginning in case the HttpContent implementation
-			// will be accessed again (e.g. after redirect) and it keeps its stream
-			// open behind the scenes instead of recreating it on the next call to
-			// ReadAsStreamAsync. If we don't rewind it, the ReadAsStreamAsync
-			// call above will throw an exception as we'd be attempting to read an
-			// already "closed" stream (that is one whose Position is set to its
-			// end).
-			//
-			// This is not a perfect solution since the HttpContent may do weird
-			// things in its implementation, but it's better than copying the
-			// content into a buffer since we have no way of knowing how the data is
-			// read or generated and also we don't want to keep potentially large
-			// amounts of data in memory (which would happen if we read the content
-			// into a byte[] buffer and kept it cached for re-use on redirect).
-			//
-			// See https://bugzilla.xamarin.com/show_bug.cgi?id=55477
-			//
-			if (stream.CanSeek)
-				stream.Seek (0, SeekOrigin.Begin);
+			using (var stream = await request.Content.ReadAsStreamAsync ().ConfigureAwait (false)) {
+				cancellationToken.ThrowIfCancellationRequested ();
+				try {
+					await stream.CopyToAsync(httpConnection.OutputStream!, 4096, cancellationToken).ConfigureAwait(false);
+				} catch (ObjectDisposedException ex) {
+					Logger.Log (LogLevel.Error, LOG_APP, $"Stream disposed while copying the content stream to output: {ex}");
+					cancellationToken.ThrowIfCancellationRequested ();
+				}
+
+				//
+				// Rewind the stream to beginning in case the HttpContent implementation
+				// will be accessed again (e.g. after redirect) and it keeps its stream
+				// open behind the scenes instead of recreating it on the next call to
+				// ReadAsStreamAsync. If we don't rewind it, the ReadAsStreamAsync
+				// call above will throw an exception as we'd be attempting to read an
+				// already "closed" stream (that is one whose Position is set to its
+				// end).
+				//
+				// This is not a perfect solution since the HttpContent may do weird
+				// things in its implementation, but it's better than copying the
+				// content into a buffer since we have no way of knowing how the data is
+				// read or generated and also we don't want to keep potentially large
+				// amounts of data in memory (which would happen if we read the content
+				// into a byte[] buffer and kept it cached for re-use on redirect).
+				//
+				// See https://bugzilla.xamarin.com/show_bug.cgi?id=55477
+				//
+				if (stream.CanSeek) {
+					cancellationToken.ThrowIfCancellationRequested ();
+					try {
+						stream.Seek (0, SeekOrigin.Begin);
+					} catch (ObjectDisposedException ex) {
+						Logger.Log (LogLevel.Error, LOG_APP, $"Stream disposed while seeking to the beginning of the content stream: {ex}");
+						cancellationToken.ThrowIfCancellationRequested ();
+					}
+				}
+			}
 		}
 
 		internal Task WriteRequestContentToOutputInternal (HttpRequestMessage request, HttpURLConnection httpConnection, CancellationToken cancellationToken)