It seems like a prerequisite is a certain level of world model and associated reasoning ability. Your examples are entirely dependent on the past context being relevant to the current situation. That's particularly tricky if you regularly ask about hypotheticals or problems that you're assisting someone else with. A human would probably ask clarifying questions such as "is this for the operations team at X? are they still size Y?" and "is this app proxied like the others you mentioned in the past?" rather than assuming.

There's also a noticable hierarchy to such context that needs to be correctly modeled - you could for example be involved with multiple teams of different sizes that are subject to different rules which is something a human would understand naturally.