The most backdoor-looking feature for me in supposedly encrypted systems are cloud backups. They are “optional” yet most users will agree (especially when given software constantly nags about it until you give up) and their backups will leak both sides of conversations, despite all end-to-end encryption attempts.
This is something i don't understand (at least for me/my use case): Are historic chats that important to have them backed up? To me, if there's anything of value, i'll save it via other means...
I made a card for my girlfriend on our 5th anniversary by going back and finding our first messages to each other on WhatsApp, and putting a screenshot of them on the front of the card with some corny message. She balled up and was crying for quite some time. Anyway we are broken up now, but that's not the point!
These things really do have sentimental value, and it's not always obvious at the time.