diff --git a/src/Mono.Android/Xamarin.Android.Net/AndroidMessageHandler.cs b/src/Mono.Android/Xamarin.Android.Net/AndroidMessageHandler.cs
index 71d972d0a87..8971220b68b 100644
--- a/src/Mono.Android/Xamarin.Android.Net/AndroidMessageHandler.cs
+++ b/src/Mono.Android/Xamarin.Android.Net/AndroidMessageHandler.cs
@@ -494,7 +494,11 @@ Task ConnectAsync (HttpURLConnection httpConnection, CancellationToken ct)
 						Logger.Log (LogLevel.Info, LOG_APP, $"Exception caught while cancelling connection: {ex}");
 						ct.ThrowIfCancellationRequested ();
 					}
-					throw;
+
+					// All exceptions related to connectivity should be wrapped in HttpRequestException. In theory it is possible that the exception will be
+					// thrown for another reason above, but it's OK to wrap it in HttpRequestException anyway, since we're working in the context of
+					// `ConnectAsync` which, from the end user's point of view, is 100% related to connectivity.
+					throw new HttpRequestException ("Connection failure", ex);
 				}
 			}, ct);
 		}
diff --git a/tests/Mono.Android-Tests/Xamarin.Android.Net/AndroidMessageHandlerTests.cs b/tests/Mono.Android-Tests/Xamarin.Android.Net/AndroidMessageHandlerTests.cs
index 2f1517d57c6..c15b8292c36 100644
--- a/tests/Mono.Android-Tests/Xamarin.Android.Net/AndroidMessageHandlerTests.cs
+++ b/tests/Mono.Android-Tests/Xamarin.Android.Net/AndroidMessageHandlerTests.cs
@@ -139,10 +139,14 @@ private async Task AssertRejectsRemoteCertificate (Func<Task> makeRequest)
 				Assert.Fail ("The request wasn't rejected");
 			}
 #if NET
-			catch (System.Net.WebException ex) {}
+			// While technically we should be throwing only HttpRequestException (as per HttpClient.SendAsync docs), in reality
+			// we need to consider legacy code that migrated to .NET and may still expect WebException.  Thus, we throw both
+			// of these and we need to catch both here
+			catch (System.Net.WebException) {}
 #else
 			catch (Java.IO.IOException) {}
 #endif
+			catch (System.Net.Http.HttpRequestException) {}
 		}
 	}
 }