
I’m Steve and I’m a fileaholic. When I’m in my “flow” – I’m doing screenshots and downloading files to desktop or downloads folders like a maniac. I often will run across an problem when I need to refind a screenshot of file whose file name is “image.jpg” or “screenshot date.png” – Can’t ever find that. Also, it eats up a lot of space. I’ve tried to go through my files but looking at a file and then finding where to put it takes a lot of time.
Thus was born my next Claude Cowork project. Here’s my initial prompt:
Reading my prompt, it’s clear that I’m a negative person, OK? Claude Cowork blew me away. I thought it was strange that again, it was initially offering me to build a web application. This is pretty much just “Claude” at this point. I doublechecked and it said that the web was the best way because it offered you the interactivity I wanted and that couldn’t be done inside of Claude on the Mac.
Asking me questions has been a great way to work with our AI Overloards™ Here’s my first series of questions and answers:


It has assumed I would pre-select the folders before starting the file uploads. I suggested a change:


Here’s a demo:
I made additional feature requests including
- the ability to preview PDF
- move the buttons to the right side and extend them
- show the target folder name and below it, the enclosing folder name (to be sure about the target folder
- ability to support previewing for Microsoft files
- ability to rename files
- it was remembering skipped files, I asked it not to do that.
One thing I learned will be to ask Claude to version the outputs. I wanted to show initial versions and they were overwritten. They were able to recreate the original versions however so I could do the screenshots above. A very workable tool.