This is known as insider threat detection / User Behavior Analytics (UBA). It could also be considered part of Data Loss Prevention (DLP). Insider threats are probably the hardest things to reliably detect on a large corporate network (compared to all of the other types of information threats), especially at a company where most of the employees are very active users of technology. The field is still in its infancy, with lots of cool-looking "AI-driven / ML-powered / buzzword-optimized" products from startups which typically end up generating an absurd amount of anomaly detections per day, usually with a 99.9% false positive rate. Of course I'm generalizing and I imagine some companies have implemented a fairly effective UBA program, but I think they're rare.

It's just trying to find a needle in an extremely large haystack. When you're dealing with technology departments, normal behavior can easily be a modest amount of network traffic for a few days followed by a huge burst of downloads and uploads from/to internal services and databases and cloud storage and any number of things. Suspicious website browsing could be innocuous research and curiosity. That personal USB drive plugged in is probably some developer with a deadline who never got around to requesting a corporate drive and can't wait a few days for it to be approved and needs to physically transfer files ASAP.

It's just not an easy problem. There are probably hundreds of other instances of an Apple employee not looking at any prototype data for months and suddenly poring over tons of it. Maybe they're preparing for a presentation or a new project. Adding lots of red tape and restrictions and wasting time investigating employees who've done nothing wrong (or perhaps who violated policy but with no real bad intent or serious negligence) and telling people they can't do certain things which make their job more efficient takes a huge toll on everyone. It's a necessary evil, but trade-offs always have to be considered. Apple wants their autonomous car program developed as quickly as possible, and the more they restrict access and require lengthy approval processes, the slower things will get done.

And fundamentally, unless you're in a weird situation, probably ~0.1% of your employees are insider threats, and probably ~0.01% are significant insider threats which could actually affect your business. The odds are stacked against you.

Occasionally you'll run across a smoking gun that's easy to detect with basic logic like "email sent to webmail account with no subject and over 6 attachments", but if you're dealing with a smart insider threat - especially one working on behalf of a superpower government's intelligence apparatus - you're not going to find something so blatant. I have sometimes run across things like that, but it's usually something gray like a developer emailing themselves some code so they can continue to work on it at home. The worst thing I've ever found was a salesperson emailing themselves proprietary leads/contact lists shortly before their resignation date. A spy is never going to get caught from such low-hanging fruit detections.

You have to start with the basics: strict policy guidelines, least privilege principle, log everything, a good team of people to investigate anomalies and write up employees who are violating policy, and then finally you can shell out a lot of resources on automated detection and baseline and tune for a long time until you have a manageable number of dashboards and reports and alerts that the team can respond to. Apple will presumably restrict access more carefully after this incident, and implement some new statistical anomaly detection, but insider threats will always be hard to detect.

Dabbling in UBA also made me realize some of the issues faced by agencies like NSA. I'm sure they have strong policies against unauthorized data access (like looking up information about romantic partners), fully intend to enforce them, and have lots of manual and automated detections, but in reality the amount of data and number of daily data accesses is probably way too high to consistently catch bad actors. I think that's one of many strong practical arguments to not let them have have easy access to such a big trove of sensitive data, even if you make the assumption they're behaving completely ethically and responsibly.