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iOS 18 breaks IMAPS self-signed certs

forums.developer.apple.com

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Re: iOS 18 breaks IMAPS self-signed certs

#101
post #88
post #86

Earlier quoted context omitted.

why should I require some third party's permission to do encryption between one of my computers and another one of my computers?

Because you chose to use a program that doesn't accept self-signed certificates. Use a different program or a different computer that actually respects your freedom to tinker with it. Problem solved.

No. He noted that it's a REGRESSION. So he chose one that DID accept them.

Running away from defects doesn't get them fixed.

Re: iOS 18 breaks IMAPS self-signed certs

#102
post #86

Earlier quoted context omitted.

Uh what is a mitm cert? You're the custodian of the private key associated with the certificate, not LetsEncrypt. And any CA can generate a certificate to MITM anything. That's why it's pretty much a requirement to submit all certs issued to Certificate Transparency, and if you're found to be misbehaving expect to receive ire from CA/B.

why should I require some third party's permission to do encryption between one of my computers and another one of my computers?

There are many other questions to ask until you come to this question. One of them is; why iOS doesn't let me play my own mp3s?

Re: iOS 18 breaks IMAPS self-signed certs

#103
I think I've seen this before, in previous versions of iOS. You used to be able to just force a trust, but it would ask you again sometimes. I ended up just using LetsEncrypt certs, the one I use on the main website. Then I have a hook that also copies it to mailu.

Re: iOS 18 breaks IMAPS self-signed certs

#104
post #98

Earlier quoted context omitted.

Pretty sure most people's threat model doesn't really care about the scenarios you mention. And for most people, that's fine.

A threat model which people using self-signed certificates especially care about. The idea of certificate authorities, certificate chains and intermediary certificates is common - and based on top down security. That is the reason why it is so dangerous. There is a “lock” and people believe everything is “good” but actually DigiNotar, TurkTrust or the bad government issued a certificate. Google tried more than once t…

why use a self signed certificate, why not create your own signer cert install that into IOS and then its no longer a "self signed" cert, but just a private cert org.

IOS does allow you to install private signer certs, right? (right?)

Re: iOS 18 breaks IMAPS self-signed certs

#105

I wish they could break Snapchat, Facebook etcs ‘s self-signed certs. I own the device, why can’t I see the traffic to and from all of these apps if I add my self-signed cert and approve to use a MITM-proxy. Most apps work, but not everyone. Often called certificate pinning.

Ownership philosophy aside, it's funny that you pick those two companies as examples.

The former enabled cert pinning (partially) as a response to a MITM[1] from the latter.

[1]: https://arstechnica.com/tech-policy/2024/03/facebook-secretl...

Re: iOS 18 breaks IMAPS self-signed certs

#106
post #41

Earlier quoted context omitted.

Apple could say "If you wanna talk HTTPS, you have to use our HTTPSClient class, and that only supports using the system certificate store and does not support pinning". Or they could say "All apps that don't support custom certificates for https will be denied app store approval".

While you're at it, make sure to have them prohibit any encryption on top of HTTPS, or apps might just be hiding things in application-level encryption schemes! Banning certificate pinning... Do we really need mandated insecurity by prohibiting apps from doing better than trusting all Apple-trusted CAs around the world?

They already do that to some extent, actually. Not as you mention, but because of US export compliance laws.

Re: iOS 18 breaks IMAPS self-signed certs

#107

I wish they could break Snapchat, Facebook etcs ‘s self-signed certs. I own the device, why can’t I see the traffic to and from all of these apps if I add my self-signed cert and approve to use a MITM-proxy. Most apps work, but not everyone. Often called certificate pinning.

If you jailbreak your phone then you are able to remove certificate pinning. If you just want to do this for research purposes then you can buy an old iPhone6s, iPhone8 or iPhoneX and use checkra1n which uses a bug early in the bootchain in order to jailbreak the phone. I think palera1n is based on checkra1n and might have better support for newer iOS versions: https://palera.in/

No need to jailbreak to remove pinning; you just need to patch the app itself (for example, by replacing the certificate it verifies against or the code that does the verification).

Re: iOS 18 breaks IMAPS self-signed certs

#108
post #98

Earlier quoted context omitted.

Pretty sure most people's threat model doesn't really care about the scenarios you mention. And for most people, that's fine.

A threat model which people using self-signed certificates especially care about. The idea of certificate authorities, certificate chains and intermediary certificates is common - and based on top down security. That is the reason why it is so dangerous. There is a “lock” and people believe everything is “good” but actually DigiNotar, TurkTrust or the bad government issued a certificate. Google tried more than once t…

There are or were two kinds of people using self-signed certificates. The vast majority used to be "I don't know how or can't afford to get a certificate chain cert."

Now, with letsencrypt, what's left of the "can't afford group" is "I can't be arsed to update my config yet".

Re: iOS 18 breaks IMAPS self-signed certs

#109
post #74
post #3

I switched to letsencrypt certs for my imap server. Works well, IMO better than the self-signed ones I used before.

That adds a lot of attack surface vs. issuing a self-signed cert and confirming it was securely verified by your imap client. Not only could let’s encrypt issue a mitm cert for your imap connections, so could other CAs, and any cloud providers / dns providers you use.

iOS never supported this configuration regardless, a change in SSL certificate does not cause any kind of notification to the user.

Also, you're basically objecting to the entire idea of PKI for use in IMAP which is incredibly hard to justify. Perhaps you wish to use a different model for your own personal reasons but the default being PKI should not be controversial, and if you want to use your own model you should use a different mail client.

Re: iOS 18 breaks IMAPS self-signed certs

#110
post #66

Earlier quoted context omitted.

In that case the NAS company should, at a minimum, be loading their NAS with a certificate signed by a CA owned by the NAS company, where the trust chain for their NAS's certificates are easily available for users to grab and install. In an ideal world they would load a letencrypt certificate and set up the tooling required to automatically pull down a new one when required. A NAS company owned CA doesn't offer much…

My point is precisely that current browsers and OSes make it impossible to ship a secure-by-default device running a local web server, NAS or otherwise. Requiring users to install a globally trusted CA is a disaster from a security point of view (now my NAS vendor or anyone that hacks them can pose as google.com!), and for this reason doesn’t even work with modern Android apps anymore, for example.

Offering a layperson NAS buyer a self-signed cert is not "secure by default" even if browsers did accept it.
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