On Windows.

The problem

Deeply nested directories are sometimes created during the course of software development. Imagine NPM packages, or C# solution with bin\debug directories and dlls named after project name. It quickly adds up. Issue is exacerbated with tendency of (some) development tools to suggest user dir as a home for new stuff. As a result we get a file path like C:\Users\user.name\source\project\MyAwesomeCompany.MyAwesomeProduct\MyAwesomeCompany.MyAwesomeProduct.Repository.Interface\bin\debug\MyAwesomeCompany.MyAwesomeProduct.Repository.Interface.dll

With even more creative names hitting the maximum path length of 260 characters is within reach :)

Deleting such path can prove difficult as doing it from Windows Explorer fails. Sometimes, a directory near the root can be renamed to one character which then helps with the delete. Sometimes, that does not work either.

Robocopy

One approach that consistently works and does not depend on third party utilities is using robocopy:

1. create an empty directory, e.g. c:\temp
2. open command prompt
3. copy and paste the following command, replacing the example directory with the one you want to delete:

robocopy c:\temp C:\Users\user.name\source\project\MyAwesomeCompany.MyAwesomeProduct /mir

Essentially, it tells robocopy to mirror the source directory onto the destination. Since the source is empty, it will delete everything in the destination. And it will do that quickly.

Bonus tip - if there is space somewhere in problem directory path, double quotes can be used:

robocopy c:\temp "C:\Users\user with a space\source\project\MyAwesomeCompany.My Awesome Product" /mir