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Keep Folder Organization feature on macOS explained and clarified.

Death by 1000 Cuts

In the article Death by 1000 Cuts, I summarized the current state of software quality. I mentioned that we are all experiencing issues on a daily basis and it’s wearing us down.

This is the first in a series of deadly cuts that I have experienced and a proposed solution.

Software Documentation Gaps

My go-to way of getting documentation is a Google search. It would be ideal if we could rely on clicking help and getting the answers we’re looking for. Unfortunately most of the time the thing we are trying to do is not documented.

Keep folder Organization

Click to see the full Apple Photos screen for context

I’ve been trying out Apple’s Photos app. I searched the documentation to find what Keep Folder Organization means when importing pictures with the keyword Keep Folder Organization. I thought this would help me move on with my life with a better understanding.

Unfortunately using the documentation did not immediately pay dividends. I then searched the documentation for Import and landed at what looked like the right place.

I chose Import photos and movies from your camera to Mac which was not what I was trying to do. Unfortunately, this was the best documentation I could find at that moment. The article did not mention anything about keeping a folder organized.

So I went to Google and found an article on Apple’s discussion forum and this feature was not what I thought it was at all. I thought the feature would move files around and put files into folders or something of that nature. The real purpose is to create albums based on your folder structure.

Keep folder organization explained
Keep File Organization Option Details

The worst part of this common problem is that people are afraid to present their problems. I expect someone to correct me and say I’m dumb for not knowing how to do this. This behavior is not productive. Shutting people down does not help improve user experiences for anyone.

Software Documentation Gaps
Bridge the gap in your software documentation


  • Use whatever godforsaken help system the software framework has available to it
  • Add context-sensitive help alongside controls to save people time
  • Do whatever it takes to avoid making people dig through incomplete documentation
  • Take a community-centric approach. Allow people to make comments that relate to the control in question
  • If laziness sets in then at least provide a link to a Google search page

Death by 1000 Cuts

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