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.
Topic:
Business & Education
SubTopic:
Device Management