Are they the same thing? Or are they different?
I'd read this SO post and this but they are comparing HttpContext.Current.Session and Session not Context.Session. What am I missing/misunderstanding?
HttpApplication's Session property exhibits different behaviour than does that of the proporty HttpContext.Current.Session. They will both return a reference to the same HttpSessionState instance if one is available. They differ in what they do when there is no instance of HttpSessionState available for the current request.
On this answer you have the complete response:
Difference between Session and HttpContext.Current.Session
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