[dstjean]

I don't think NOT performing packet inspection due to privacy concern is a good idea. (Good security controls should exist over its administration)

One reason why organizations use packet inspection is to protect its staffs, customers and vendors from malicious actors who could cause data breaches leading to huge privacy issues.

Privacy over Security? The right balance must be found

[pjc50]

Of course, this means the packet inspection host and the organisation's internal CA are now great targets to attack. This approach puts all the eggs in a single central basket.

[dstjean]

IMO relying 100% on the end devices to protect themselves is too risky. Layered security seems to work best. Also I prefer to heavily monitor/secure two appliances/systems than heavily monitor thousands of end devices

[zrm]

> Layered security seems to work best. Also I prefer to heavily monitor/secure two appliances/systems than heavily monitor thousands of end devices

It can't be both at once. Either you have multiple layers because both the appliance and the endpoints are independently secure and the attacker has to compromise both, or you don't monitor/secure the individual endpoints and the appliances become a single layer / single point of compromise.

And if the appliances can see all the plaintext of everything then they're a single point of compromise even if the endpoints are otherwise secure, because the attacker can still read all the secrets through the man-in-the-middlebox.

What works is to leave each thing to what it's good at. The endpoints are good at inspecting the plaintext, because they inherently have to have it anyway and they have the context to understand what it's supposed to look like. So you don't end up interfering with a newer, more secure protocol because the middlebox doesn't understand it. And plaintext is sensitive data so the fewer things that have access to it the fewer things you can compromise to get access to it.

What middleboxes are really good at is certain types of access control, e.g. blacklisting malicious IP addresses for outgoing connections, or whitelisting source and destination addresses and ports for incoming connections. They keep your local IP cameras off the internet even if the cameras "should" be secure on their own.

[LeifCarrotson]

A user has no way of knowing whether a packet inspection will be performed by benevolent actors seeking to protect their security or by malicious actors seeking to invade their privacy.

As in the good old post "What colour are your bits" [1] regarding the subject of copyright, the computer is colorblind when it comes to privacy vs. security tradeoffs. You seem to see color, believing compromise for security to be acceptable, and hoping you can allow your lawful and good security inspections to occur while disallowing nasty privacy invasion.

The computer doesn't see color. It is impossible to build a security protocol that will distinguish between good third parties and malicious third parties. "Good security controls" come down to trusting people to do the right thing, and when there's big money coercing companies to do the wrong thing, the right thing too often loses.

[1]: https://ansuz.sooke.bc.ca/entry/23/

[rocqua]

It could be shown client-side whether an SSL connection uses a locally installed root CA or a globally trusted CA.

This way, an employee could see whether their employer is MitM-ing their connection to FB / reddit.com / pornhub / their bank. Based on this, they could complain to their employer for unreasonable MitMing, and serve as a weak detection point for compromise of the company root CA.

[jrockway]

You can't trust your client. The IT department will just push a browser that says "you're using the root CA for this connection" while actually using the MITM CA.

Maybe you'll download your own Chrome, but that silently gives you their hacked version. The SHA256sum on their website has also been tampered with. Fine, you say, you'll download the source code and compile it yourself. But the compiler has been tampered with to detect when it's compiling Chromium, and adds the IT department's hacks.

You cannot trust a client you do not fully control.

[Dylan16807]

That's a separate issue, because a completely custom browser can intercept even without a MitM on the connection.

Sometimes you either have your own device or you trust your employer to not directly lie to you.