There are levels to it. As things get more complex the problems get infinitely more strange. As you learn a particular technology the strange things you encounter are often because of a misunderstanding about that technology or the way it works.

Once you hit professional level software engineering (think distributed systems), things are strange in large part because the system you're working on has hundreds of thousands of man hours poured into it, and is often very complex with 10 different technologies backing it to do various things.

The more strange things you encounter though the more you're learning!