No Stupid Questions

I always presumed they got his passwords and simply logged into his accounts.

The catch with everything that implements E2EE is that, at the end of the day, the humans at each end of the message have to decrypt the message to read it. And that process can leave trails, with the most sophisticated being variations of Van Eck phreaking (spying on a CRT monitor by detecting EM waves), and the least sophisticated being someone that glances over the person's shoulder and sees the messages on their phone.

In the middle would be cache files left on a phone or from a web browser, and these are the most damning because they will just be laying there, unknown, waiting to be discovered. Whereas the techniques above are active attacks, which require good timing to get even one message.

The other avenue is if anyone in the conversation has screenshots of the convo, or if they're old-school and actually print out each conversation into paper. Especially if they're an informant or want to catalog some blackmail for later use.

In short, opsec is hard to do 100% of the time. And it's the 1% of slip-ups that can give away the game.

Many ways people implement that E2EE email service, is smoke and mirrors that still puts your data on to foreign servers -- and if it touches/remains in a cloud space, even encrypted, I'd say there's still the opportunity for the leak to occur (encryption algorithms require updates periodically for very good reason!). However, back around the time period this stuff was happening, I imagine that if they'd used a properly setup E2EE service that they controlled, the comms would not have leaked in this volume. Like it used to be common for even smaller/medium sized businesses to maintain their own Email and Blackberry messaging service servers in the 2005-2015 period, which kept comms internal to the company (barring hackers of course).

If they had that setup properly and with retention periods set for things like backups / old messages and so on, this sort of leak, I imagine, would not have happened.

IT Operations type roles in companies are less common these days, as most just dump things into the cloud (and options like BB went poof!), but there is a reason that such departments exist, and why some industries place a high premium on things like data retention (and getting rid of data when you legally can, to minimize this very sort of risk). Most of the people involved in these scandals, appear to be incredibly wealthy / business people etc -- I mean, Bill Gates should've known for sure that this shit was highly leakable.

*Edit to add an obvious caveat, that if Epstein had been saving / retaining tons of information explicitly for future blackmail purposes or sale to foreign powers, then I mean... he was hoping to intentionally leak it, so if feds got access to wherever he was holding on to it, they'd likely get access. I'm also not totally sure where the sources for all of it came from, as I've not bothered to go through what all they collected -- but I'd guess with the volume, it's likely across various devices/accounts/media.

This is the reason Jim Balsillie, the co-CEO of RIM (BlackBerry), was never charged for stock manipulation while he was running the company. All the incriminating evidence would be in his emails, which are encrypted on his BlackBerry and he has never agreed to decrypt them.

Remind me if a device was obtained and cracked to uncover any of these docs.

E2EE isn't a magic defense against a court order.