Like with most useful tools, you have to use it more than "several times" to gain fluency.
I remember needing to learn Ruby and Rails on an existing closed codebase and having the debugger take me right to the core of Rails several times to understand why certain things were done in a certain way in the top level code. This allowed me to get acquainted with internals of Rails and how Ruby's inheritance system much faster as well as the existing codebase that was built on top.