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Stop Breaking TLS

markround.com

1–10 of 175 posts

Re: Stop Breaking TLS

#3
I remember at my first job, the internet stopped working at my workstation. I got on the phone with IT, and the guy said "looks like you don't have our new certificates." I asked why I would need my employer's certificates. He said "because we MITM every connection." I asked if that was even legal, and he said yes it's legal.

At another job I was handling a support ticket where a customer was asking, in so many words, "can I get HTTP headers of requests flowing through my Envoy TLS reverse proxy?" I said that they could terminate TLS at the proxy and redo things that way, but then that wouldn't be a TLS proxy it'd be a MITM or a gateway. They could log the downstream/upstream and duration of connections, but that wouldn't help.

Re: Stop Breaking TLS

#5
> Consider this - what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously? I’d wager that’s almost at the whatever is the statistics equivalent of the Planck length level of probability.

It doesn't matter if every certificate authority is compromised or just one. One is all that is needed to sign certificates for all websites.

Re: Stop Breaking TLS

#6
Lame on user machines, but sometimes needed in a server environment. Easier to detect if someone is hauling off with your database as that will be the one you can’t see what’s going on. Of course, solve one problem and introduce three more.

Re: Stop Breaking TLS

#7

> Consider this - what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously? I’d wager that’s almost at the whatever is the statistics equivalent of the Planck length level of probability. It doesn't matter if every certificate authority is compromised or just one. One is all that is needed to sign certificates for all websites.

Author here, hi! Was just venting last night, but that's a very good point, I'll update it later with your correction :)

Re: Stop Breaking TLS

#8
It's definitely annoying if you work in enterprise, but on the flip side: the fact that these enterprise requirements exist is the main reason that TLS certificate configurability is possible at all, without which it would be dramatically harder (or impossible) to reverse engineer or do security & privacy research on mobile apps, IoT, etc etc etc.

Enterprise control over company devices and user control over personal devices are not so different.

A few apps do use certificate pinning nowadays, which creates similar problems, but saying "you can never add your own MitM TLS cert" is not far from certificate pinning everything everywhere all the time. Good luck creating a new home assistant integration for your smart airfryer when you can't read any of the traffic from its app.

Imo: let's make it easier! Standardize TLS configuration for all tools, make easy cert configuration of devices a legal requirement (any smart device sold with hardcoded CA certificates is a device with a fixed end date, where the CA certs expire and it becomes a brick), guarantee user control over their own TLS trust, and provide good tools to check exactly who you're trusting (and expose that clearly to users). Not really practical of course (and opens all sorts of risky games with nation state interception as well) but there are upsides here as well.

Re: Stop Breaking TLS

#9

> Consider this - what is the likelihood of every certificate authority on the Internet having their private keys compromised simultaneously? I’d wager that’s almost at the whatever is the statistics equivalent of the Planck length level of probability. It doesn't matter if every certificate authority is compromised or just one. One is all that is needed to sign certificates for all websites.

Author here, hi! Was just venting last night, but that's a very good point, I'll update it later with your correction :)

You should make it about CT logs. I believe you need to compromise at least three of them.

Re: Stop Breaking TLS

#10
I agree with the sentiment, but I think it's a pretty naive view of the issue. Companies will want all info they can in case some of their workers does something illegal-inappropiate to deflect the blame. That's a much more palpable risk than "local CA certificates being compromised or something like that.

And some of the arguments are just very easily dismissed. You don't want your employer to see you medical records? Why were you browsing them during work hours and using your employers' device in the first place?

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