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iOS 18 breaks IMAPS self-signed certs

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Re: iOS 18 breaks IMAPS self-signed certs

#151
post #134

Earlier quoted context omitted.

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

Would it be less secure than unencrypted HTTP?

No.

But if you want "secure by default" then neither one is acceptable.

Re: iOS 18 breaks IMAPS self-signed certs

#152
post #148
post #132

Earlier quoted context omitted.

But if you distrust the entire PKI ecosystem, how are you intending to use your email server? If someone is trying to send you an email, their admin definitely isn't going to set up an in-person meeting with you to exchange certificate signatures. Their server is either going to accept any certificate (which means MitM is trivial), or they're going to verify it against PKI (which you don't use because you don't trust…

IMAP is for reading your emails not sending, that means you could accept PKI for SMTP to communicate with untrustworthy clients, but want to ensure that your access to your emails are safe(r).

Of course, but all emails you could read have been sent at one point or another. Unless you only care about local email delivery, you're going to have to get involved with PKI.

And if your threat model is bad enough that PKI isn't good enough for IMAP, why aren't you using a VPN in the first place? Or even an airgapped network? Or PGP?

Re: iOS 18 breaks IMAPS self-signed certs

#153

Earlier quoted context omitted.

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…

It did support it. One had to trust the certificate manually. I gave up on self-signed cents about 6 years ago.

It supported using self signed certs, but if the server suddenly switched from a self signed to a trusted CA-signed certificate, no prompt would be given. So the idea that self signed certificates are somehow more secure for this specific purpose is incorrect.

Re: iOS 18 breaks IMAPS self-signed certs

#154
I use letsencrypt for my mail server and I have done so for years, but iOS 18 appears to have broken my configuration which has worked perfectly for as long as I can remember. I believe my certificates were all set up correctly because it never gave me a problem up until now and never asked for authorisation of any kind. At this stage MacOSX works just fine, but iOS 18 and iPadOS 18 just do nothing.

Re: iOS 18 breaks IMAPS self-signed certs

#155
post #113

Earlier quoted context omitted.

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.

Self-signed certs were a defect — people were used to just click OK and blackhats exploited that. OP wants support for the special case where only the cert issuer trusts the cert (he has his own self-signed cert). Apple and others do support that: You make a private CA, trust that CA in the device, and then use that CA to sign certs for your IMAP server. IIRC (and this is from vague memory) you may need to configure…

Interesting. I use self-signed certs for development, but haven't tried to use them for an E-mail server. After an article or two on here, I'm convinced that trying to run your own server is a futile time-suck.

Re: iOS 18 breaks IMAPS self-signed certs

#156

Earlier quoted context omitted.

It did support it. One had to trust the certificate manually. I gave up on self-signed cents about 6 years ago.

It supported using self signed certs, but if the server suddenly switched from a self signed to a trusted CA-signed certificate, no prompt would be given. So the idea that self signed certificates are somehow more secure for this specific purpose is incorrect.

It was a complex Trust relationship and Apple’s it just work was onerous to work around. When security is the top priority I would alway go with self-signed certificates.

Re: iOS 18 breaks IMAPS self-signed certs

#157
I had this issue with let's encrypt certificates. IMHO it's unreleated to the issue. IOS18 mail initially connected using TLSv1.3. Afer deleting and re-installing Mail, the connection falls back to TLSSv1.2 and another set of ciphers. Then downloading of mails works again.

Using dovecot 2.3/Ubuntu on the server.

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