Error: System.Net.WebException: The operation has timed out

If this is happening randomly (sometimes it works, sometimes it doesn't), it is possible you have another .NET application running on your GP client machine that is hogging up open web request sockets. See this blog post for an example of how to recreate this issue:

http://www.wadewegner.com/2007/08/systemnetwebexception-when-issuing-more-than-two-concurrent-webrequests/

The recommended solution is to add the following to your machine.config to increase the number of available web request slots for .NET applications:

<system.net>
	<connectionManagement>
		<add address="*" maxconnection="100" />
	</connectionManagement>
</system.net>

Add that to the bottom just above the closing configuration tag.

 

Machine config locations per product:

GP2010:

C:\Windows\Microsoft.NET\Framework\v2.0.50727\CONFIG\machine.config

 

GP2013:

C:\Windows\Microsoft.NET\Framework\v4.0.30319\Config\machine.config

 

GP2015:

C:\Windows\Microsoft.NET\Framework\v4.0.30319\Config\machine.config

 

GP2016:

C:\Windows\Microsoft.NET\Framework\v4.0.30319\Config\machine.config

 

Additionally, if your traffic goes through a proxy server, you may need to add the following inside the system.net tags. Tailor for your settings:

<defaultProxy> 
       <proxy
         usesystemdefault="false"
         proxyaddress="http://yourproxyserver.net:8080"
         bypassonlocal="true"
       />
       <bypasslist>
         <add address="[a-z]+\.yourdomain\.com$" />
         <add address="[a-z]+\.otherdomain\.com$" />
         <add address="[a-z]+\.etcdomain\.net$" />
         <add address="10\.100\.105\.\d{1,3}" />
       </bypasslist>
</defaultProxy>

https://docs.microsoft.com/en-us/dotnet/framework/configure-apps/file-schema/network/defaultproxy-element-network-settings

 

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