iMessage leaks I know about:
- iCloud backups. While I appreciate Advanced Data Protection, I still count this because it’s not available everywhere, most people have it off, and most people with it off are unaware of it backdooring the E2EE marketing they still saw.
- Recipients’ copies, and all the ways their copies get copied. Yes, tricky to address, that’s the comment. While no app can guarantee no unencrypted recipient copies, privacy focused apps do make it not happen unintentionally and by default.
- APN leaks the timestamp, sender, and recipient of every message. Especially powerful in combination with recipient copies.
- Apple controls the key directory and can MITM at will. As usual, see Signal for a high profile attempt at a centralized key directory that’s resistant to controller abuse.
- Contacts, Siri, and Apple Intelligence all ingest then upload iMessage data.
- No source code or reproducible builds. Obvious reasons, still a real hole.
Avanced Data Security keeps your copy in iCloud safe, but doesn't help with the people you are messaging's copy.