Meaning of Leaky Abstraction?
Here's a meatspace example:
Automobiles have abstractions for drivers. In its purest form, there's a steering wheel, accelerator and brake. This abstraction hides a lot of detail about what's under the hood: engine, cams, timing belt, spark plugs, radiator, etc.
The neat thing about this abstraction is that we can replace parts of the implementation with improved parts without retraining the user. Let's say we replace the distributor cap with electronic ignition, and we replace the fixed cam with a variable cam. These changes improve performance but the user still steers with the wheel and uses the pedals to start and stop.
It's actually quite remarkable... a 16 year old or an 80 year old can operate this complicated piece of machinery without really knowing much about how it works inside!
But there are leaks. The transmission is a small leak. In an automatic transmission you can feel the car lose power for a moment as it switches gears, whereas in CVT you feel smooth torque all the way up.
There are bigger leaks, too. If you rev the engine too fast, you may do damage to it. If the engine block is too cold, the car may not start or it may have poor performance. And if you crank the radio, headlights, and AC all at the same time, you'll see your gas mileage go down.
It simply means that your abstraction exposes some of the implementation details, or that you need to be aware of the implementation details when using the abstraction. The term is attributed to Joel Spolsky, circa 2002. See the wikipedia article for more information.
A classic example are network libraries that allow you to treat remote files as local. The developer using this abstraction must be aware that network problems may cause this to fail in ways that local files do not. You then need to develop code to handle specifically errors outside the abstraction that the network library provides.
Wikipedia has a pretty good definition for this
A leaky abstraction refers to any implemented abstraction, intended to reduce (or hide) complexity, where the underlying details are not completely hidden
Or in other words for software it's when you can observe implementation details of a feature via limitations or side effects in the program.
A quick example would be C# / VB.Net closures and their inability to capture ref / out parameters. The reason they cannot be captured is due to an implementation detail of how the lifting process occurs. This is not to say though that there is a better way of doing this.