In Xamarin, there was an issue I was facing where the requests to my server would time out.
Requests to other servers (for example: https://api.ipify.org?format=json) were consistently succesful.
Additionally it only occured on Android. This issue was also exclusive to Xamarin/Visual Studio, the same request made through a test app built in Android Studio succeeded.
I finally found a solution by adjusting the settings described here:
My existing settings were 'default' for both options. Here is what I changed it to in order to resolve the problem:
HttpClient implementation: AndroidClientHandler
SSL/TLS Implementation: Native TLS 1.2+
I believe that the reason for the error was a non-native http client being utilized by Mono. Switching to the native client worked and is consistent with my testing in Android Studio!
I couldn't find any other resources which suggested this fix so I thought it best to post it.