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Created attachment 16681 [details]
Very simple example:
var request = (HttpWebRequest) WebRequest.Create("http://localhost:4567/timeout"); // Some very slow endpoint
request.Timeout = 1000000; // More than 16 minutes
The above will time out after approximately 2 minutes 20 seconds (well, unless the server responds before that).
Attached is a very simple C# solution and a simple Sinatra web server for reproducing. The server sleeps for 2 minutes 40 seconds before responding, the client times out after 2 minutes 20 seconds.
Running the same example from .NET on Windows (towards the same server) works fine - waits for 2 minutes 40 seconds, doesn't throw any exceptions.
Running Mono 4.4.1 on OS X 10.11.5.
MonoMac, and Xamarin.Mac are products that allow you to target desktop OS X (Cocoa). Since this issue appears unrelated, and only deals with HttpWebRequest, I've moved it to the right section.
Thanks Chris! I sure did ponder about the Product/Component, but wasn't able to find anything better... Thanks for doing that!
It works fine with Mono master and Mono 4.6. I get a response after 160 seconds
This was a mono 4.4 regression that Ludovic fixed.
The current version on the alpha channel should fix the issue.