HttpContext and all its properties are not thread safe, so you have to be very careful. Reading data from different streams at the same time may not harm, but you must be sure that no write operations are occurring. However, even if you are sure that the Items property is not changed, I would prefer to make a copy and provide it to background threads. This clearly indicates intent and saves you from discussion during code reviews or people reevaluating whether this code is really thread safe.
Now about using HttpContext in asynchronous requests; Accessing the HttpContext from different threads would be dangerous, but in this case, ASP.NET manages the threads and ensures that only one thread processes the request. It would be different if, for example, you deployed a new thread manually (using the thread pool or new Thread() ) and supplying HttpContext for this thread, continuing execution.
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