As someone who's a support engineer (in enterprise software) this part was interesting to me because it was obviously not written by someone who has spent a long time in a support or documentation environment.

> Similarly, a support agent might tell you to “Go to your cases” over webchat or a phone call. This is confusing if the UI says “My cases”.

The way that I would word it and would mentor people to say is "go to 'my cases' at the top"

Thats a thoughtful way of communicating. However I am not sure if the issue is that big. If someone tells me "I like your car", I also have to do the transfer that they are talking about "my" car. However I am not working in the support field, and communicating in a way that works around these pitfalls is probably the safer way.