Many times when I'm stuck, I seem to draw the conclusion that this is because the documentation is lacking. It might be me scapegoating, but many times I find that it is because there is a lack of documentation that I spend hours on hours trying to figure something out.

Debugging on Windows, is a prime example. If you take someone from the normal Visual Studio give give them a PDB file, the compiled executable, limited / no source code, a crash report and a minidump, they're going to be stumped looking on the internet for some resources and instructions on how to debug the program.

Others include debugging in general, making the switch to and working in a *NIX environment (ie. sans IDE) from Windows, adding functionality to a large enterprise application that doesn't have comments or documentation (so essentially you're stuck for 3 hours trying to find this interface to that will execute a command), and so on.