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Let us assume that satisfaction can be derived from challenges, such as in games. Let us also also assume that the appeal of many websites or real-life experiences comes from incorporating gaming elements (think Jane McGonigal and gamification).
Be it through limited affordance (removing choices), incentives, or simply "good" UX design…
can some things be made to be too easy?
How would you draw the line?
If a user has some external task they need to perform with an application (e.g. buy tickets, place an order) then I don't see any way to make the UI - and process - too easy. Optimum situation could utilize a personal butler and have the user to do nothing.
However, if part of the appeal of the app/game is directly related to operating the app or to the difficulty and/or learning experiences, the easiest solution might not be fun or rewarding at all.
As an example of this, page 7 (numbered page 6) in Daniel Cook's presentation about mixing games and applications shows the easiest possible UI for a princess rescue game. By comparison, on page 3 (4) is somewhat more "business-flavoured" version of the same thing. If your daily work consisted eight hours with the app, which one would you prefer?
When considering whether individual actions (e.g. removing some entity) can be made too easy to cause problems I'd say that most of the times a careful planning (providing users with full undo history, preview of destructive action or such) will give best results. More about this can be read from Aza Raskin's ALA article Never Use a Warning When You Mean Undo.
I think you need to step back briefly and ask "what is the users aim?" If it is to achieve a task where the computer application is a necessary part of getting there (business-type activities), then the computer solution cannot really be made easy enough - it should be the simplest possible route to achieving a sucessfull conclusion.
If, however, the aim is engagement with a application - a more game-orientated approach - then the nature of the game should not be too simple, but the process of interacting with teh game should still be as simple as possible. Including puzzles in the game is fine, but making it difficult to interact with the game is wrong. So the UX should always be as simple as possible, which is not to say that the challenges within the task should always be made easy. It all depends on the users aim.
I assume you are talking about the experience of interacting with software applications, tools, devices, and machines because the experience of entertainment objects & systems is very different.
All of the aforementioned objects can be broadly defined as tools that we employ to simplify complex tasks, such as filing taxes, creating a collage of favorite pets, getting from point A to point B, or watching a movie. Thus, their very nature is to be as simple as possible and the goal in improving them is making them easier to use even further.
Usually, tools are simplified through automating and reducing steps in the process of reaching the final goal of the user. And this is precisely where the limit of simplification and the curse of experience design lie.
The secret to a good UX isn't in leaving a challenge to use the tool but in the perception & the availability of manual control to the user. We need to leave the option of manual override in some places and explain the 100% automated steps in other places. Otherwise, users may be left dissatisfied with the final result with no way to change it.
Therefore, a tool is too easy when the user loses the feeling of control over the produced result.
Of course a challenge can be made too easy.
With a game, it has been researched what would make it attractive to play and keep playing etc. Therefor the term "flow" was used which describes a state were there is .... high concentration, focus, challenge etc.
So different (implicit and explicit) factors are being applied for. It goes to far to go into depth here. When you search the internet for "game challenge difficulty flow" you will get enough to go from there.
Think of Tetris. A very simple game once you know how to control the blocks. Yet every time it is challenging to get more lines, more points, etc.
A racing game in advanced mode (e.g. F1 cars), the learning curve is higher and for some more challenging for them and not doable for others.
