- You're implementing something complex (like an algorithm)
- You're implementing something stupid (typically a workaround for something that could not be done in a more elegant way, and you want to explain why it can't be refactored)
If the code is well written it is also self explanatory. This can be done by structuring / formatting the code well, into methods, classes, packages - and naming these constructs in a reasonable way. Naming variables is obviously also very important - and be consistent!
In my opinion comments only clutters the code, and in most cases reduces readability. Like mentioned before you cannot always trust that the comments are up-to-date, but the code certainly will - so I believe time should be spent making the code readable instead. "Look, there is what you intend and what you write" - those should be the same, there should be no in-between.
My primary language is Java by the way (about 10 years of experience).