FB13825638 (iOS 18 REGRESSION: Mail no longer accepts a self-signed certificate from my mail server (AGAIN))

Question

tkmcintosh OP

Created Jun ’24

Replies 14

Boosts 9

Views 3.3k

Participants 6

The same problem encountered with iOS 17 beta 1 and beta 2 is back:

Unable to create a secure connection to the server ("bad certificate format" -9,808).

Answered by tkmcintosh in 815823022

As of iOS 18.0.1, this issue remains unresolved. I've ultimately had to switch to a certificate from Let's Encrypt, as I can't wait forever for my e-mail to be accessible from my iOS devices. While this meets my current needs, it requires more maintenance than my previous setup, which had been stable for years.

I noticed that this issue sparked a discussion on Hacker News a while back (https://news.ycombinator.com/item?id=41583689), where many people chimed in debating the pros and cons of running a server with a self-signed certificate, using an internal CA, a public CA like Let's Encrypt, or other solutions. However, this largely missed the point:

This is a regression in iOS 18+.
macOS 15+ still handles this correctly, suggesting the change was an unintended regression rather than a deliberate policy shift.
Users shouldn't have to disrupt their stable, working configurations without good reason.

While this configuration might only impact a minority, it’s crucial to highlight such issues. Apple’s focus is understandably on the majority, but raising these concerns can sometimes lead to resolutions.

Boost

Answer 1

DTS Engineer OP

Apple

Jun ’24

link

1

Answer 2

tkmcintosh OP

Jun ’24

Problem remains in iOS 18.0 beta 2 (22A5297f). No change.

0

Answer 3

tkmcintosh OP

Jul ’24

Still occurs on iOS 18.0 beta 3 (22A5307f).

0

Answer 4

tkmcintosh OP

Jul ’24

Problem remains in iOS 18 beta 4 (22A5316j). No change.

0

Answer 5

tkmcintosh OP

Jul ’24

Problem remains on iOS 18 beta 4 v2 (22A5316k). No change.

0

Answer 6

Davidchill79 OP

Aug ’24

Just hit this as well...

0

Answer 7

Davidchill79 OP

Aug ’24

I got the same with 22A5326f ... I even reinstalled the profiles and hit the "trust" button but nothing solves it.

1

Answer 8

tkmcintosh OP

Aug ’24

As you said, behavior is still regressed in iOS 18.0 beta 5 (22A5326f)! Added more comments in the thread linked by DTS above about the similar problem that occurred in iOS 17.0 betas.

0

Answer 9

tkmcintosh OP

Aug ’24

Still broken in iOS 18.0 beta 6 (22A5338b)!

Haven't been able to use mail on my iPhone since WWDC :(

1

Answer 10

tkmcintosh OP

Sep ’24

Sadly, this regression has shipped in iOS 18.0 (22A3354). I am not optimistic that we will see a fix going forward. :(

3

Answer 11

jsmoriss OP

Sep ’24

I just experienced this problem after updating to iOS 18 - can't access my email - "bad certificate format". :-/

js.

2

Answer 12

Chepser OP

Oct ’24

Our certificate isn’t self-signed but we use TLS 1.0. Ihave same trouble with iOS18. 18.0.1 (22A3370) also with it.

0

Answer 13

faCADe OP

Oct ’24

On 8 October client reported that latest iPhone iOS 18 Beta has fixed the problem but then same day reported that it had broken again! Hopefully trying iOS 18.1 RC later today, fingers crossed.

0

Answer 14

tkmcintosh OP

Nov ’24

Accepted Answer

As of iOS 18.0.1, this issue remains unresolved. I've ultimately had to switch to a certificate from Let's Encrypt, as I can't wait forever for my e-mail to be accessible from my iOS devices. While this meets my current needs, it requires more maintenance than my previous setup, which had been stable for years.

I noticed that this issue sparked a discussion on Hacker News a while back (https://news.ycombinator.com/item?id=41583689), where many people chimed in debating the pros and cons of running a server with a self-signed certificate, using an internal CA, a public CA like Let's Encrypt, or other solutions. However, this largely missed the point:

This is a regression in iOS 18+.
macOS 15+ still handles this correctly, suggesting the change was an unintended regression rather than a deliberate policy shift.
Users shouldn't have to disrupt their stable, working configurations without good reason.

While this configuration might only impact a minority, it’s crucial to highlight such issues. Apple’s focus is understandably on the majority, but raising these concerns can sometimes lead to resolutions.

0