I apologize if posting an answer to my own question is not preferred on Meta, but I couldn't have fit everything into a comment. TL;DR, check the block quote at the bottom of this post for the proposed question.
This is what I have come up with, and what I think the question should involve. Any and all input is appreciated.
The question should cover "Who can see my data over a network?" in a very general way, but will still need to address some specific concerns, these being:
- Is the "attacker" actively or passively listening in?
- What measures are in place already? Is there a proxy?
- What is the level of authority the "attacker" has on the network?
- What sort of device is being used? What version?
- What applications are being used?
Now, these questions are, generally, the reason why there are so many different variations of the "Who can see my data?" question on the network right now. In order to sharpen the question while still making it as general as possible, I believe the question should address these questions in the following way:
- The attacker should be actively looking for any information they can find
- The measures already in place should be of an unknown quantity, but we should assume there is no proxy, or the answer is pretty simple, but it should address what would happen if there was a proxy
- The attacker's level of authority should be that of a Sys Admin, someone with administrator privileges on the network but no sort of "illicit" access, i.e. they can't install a dedicated piece of malware on the target's machine or access their device without permission (if they brought in their own device, for example)
- As far as the device is concerned, any up-to-date device should be fair game for this question as we want it to cover a vast majority of the already existing questions
- The applications being used should fall into the category of either encrypted or not encrypted, finer granulation would make the question to broad
Now, how should the question be formulated? Here's my first swing:
Who can see my data when I am connected to an actively administered/monitored network, and what can they see?
No one has had any illicit or physical access to my devices. My OSs' are all
up to date. Some of my applications encrypt data, and others do not. There is a proxy, but I have not installed any certificates. There is very little other information about the network.
Any input is appreciated; please criticize, poke holes, call me names, etc...