Here is a very peculiar, interesting, and obscure issue/behavior in Visual Studio that you will rarely find. But if you do, this post will save you time!
The time in the Visual Studio machine was incorrect.
1. Ensure that both machines have the “Automatically adjust for clock Daylight Saving Time” in the Time Zone either checked or unchecked.
2. Select the correct time zone and time for both machines
3. Restart Visual Studio and connect to the test run
Important: Even though the display time may be the same, ensure that the actual time (difference from UTC) is correct. Keep reading for the details.
In my case the Visual Studio client machine was not automatically adjusting for daylight savings. At one moment I noticed that the time in the controller and the client was not the same, I changed the time in the client to match the controller and it still did not work *&#*^$# (because even though the “displayed time” was the same, the difference from UTC time was different). A few hours later a coworker and I restarted the machine and noticed that the time was out of synch again. That is when we decided to look at the daylight saving option, checked the option, synched the time, and solved the problem!