Would a canonical "Can X see my data over Wi-Fi/Work Internet?" question be helpful?

Question

I have noticed a lot of questions in this format being tossed around:

Can my employer see what I'm doing over Wi-Fi/Work Internet Connection?

Just searching for "Can my employer" on the Security Stack brings up tons of these types of questions.

Now it's not always exactly this question. Sometimes there are little variations like:

When I'm using App-X, can my employer see what I'm doing over Wi-Fi?

or

Can my roomates see what I'm doing on my home internet?

Would a canonical "Who can see my data over a network?" question be useful?

My thoughts are that there are only a few different circumstances in which the answer would differ (i.e. whether or not the application encrypts its data, whether or not there is a proxy in use etc...), and these could be covered in a single question/comprehensive answer.

OR would the idiosyncracies (like network configuration, application used, encryption standards) between questions of this type make it a poor candidate for a canonical question?

Answer 1

I think this could be a good canonical question that could often be used as a duplicate target. But for it to be useful it needs to be on a level that the kind of person who usually post about this can understand.

That means there should be no assumptions in the question that the novice could not verify if they apply. So I don't think we should mention proxies and installed certificates or asume that the computer has not been tampered with - I would say that is stuff for an answer.

And I think the question should explicitly state that it is trying to be canonical and aimed at the broad audience.

So here is my attempt at a question:

Can my employer see what I do on the internet when I am connected to the company network?

Lets say I browse the web and use different apps while connected to the network at work. Can my employer (who controls the network) see what websites I visit, what emails I send, my IM messages, what Spotify songs I listen to, etc?

Does it matter if I use my own computer or one provided for me by my employer? Does it matter what programs I use, or what websites I visit?

This is an attempt at a canonical question following this discussion on Meta. The aim is to produce basic answers that can be understood by the general audience.

That is my two cents. Feel free to copy paste if you want to, edit if you feel like, or throw in the bin if you prefer that. I have some bullet points for what I would like an answer to contain, but maybe I should save them for an actual answer...

Answer 2

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:

1. Is the "attacker" actively or passively listening in?
2. What measures are in place already? Is there a proxy?
3. What is the level of authority the "attacker" has on the network?
4. What sort of device is being used? What version?
5. 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:

1. The attacker should be actively looking for any information they can find
2. 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
3. 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)
4. 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
5. 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?

Assuming that:

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...