Free Digital Janitor Straightens Out Messy File Hierarchies

My Downloads folder can get messy. Before I started testing Digital Janitor (free), it contained over 150 different files, weighing in at over 700MB--and this is after a recent cleaning. Digital Janitor’s promise is to sort and tidy up any random bunch of files you throw at it, so my Downloads folder seemed like an ideal candidate.

Digital Janitor screenshot
Digital Janitor’s simple interface works, but leaves room for improvement.
When launching Digital Janitor, the first thing you do is select the folder you’d like to sort. Then, you set up “rules” for the sorting process. Each rule can match files per extension, “keyword” (a wildcard within the filename), or size. Once you set up your criteria, select a destination for those files. This can either be another folder (“Large ZIP Files”) or the Recycle Bin.

And then, before you click the “Add rule” button, pause for a moment and carefully consider what you’ve just configured. You need to do this, because once you add a rule, there’s no way to edit it--you can only delete it and write a new one instead, which would be added to the end of the list. Also, I should point out extensions are case-sensitive, so if your rule specifies what to do with “PDF” files, it will not apply to any “pdf” files.

What makes the rule-based system even trickier is that there is no way to sort the rules. If you’ve ever played with a rule-based system before (such as Windows’ built-in user permissions system), you may know that the order by which rules are applied is very important. For example, if I have one rule specifying “Delete all files over 100MB” and another rule specifying “Move all ZIP files to the Archives folder” and Folder Janitor meets a 150MB ZIP file--what will it do with it?

I tested this, and Digital Janitor was not quite ready to handle such a scenario: It prompted me with a dialog showing the conflicting file (the large ZIP) and offered me to replace or rename it. The message wasn’t about a rule conflict (which was the real issue), but about a naming conflict--it said the file already existed, when it didn’t. Then, no matter what I selected, it deleted the file, probably because the deletion rule came first on the list. That’s a sensible thing to do; but since there’s no way for you to sort the list or edit your existing rules, you must carefully plan ahead and avoid any conflicts.

Once you have a solid set of rules, Digital Janitor works as you would expect. Click Sort, and all the files neatly go where they belong. The result can be a satisfying list of subfolders--“Large ZIPs,” “Installers,” “PDFs,” etc. If you’re happy with your rule set after trying it out, you can save it and then load it next time you run the app, and just click Sort to repeat the same operation again.

Digital Janitor is also supposed to have scheduling support for running profiles automatically, but this failed abysmally on my test system. Setting up this feature required elevation (but failed to prompt for it), and once set, the schedule would run, but Digital Janitor would crash right after executing it. The developer was unable to replicate the error.

Digital Janitor has several other tricks up its sleeve, including sorting your MP3 files (but only if they’re well-tagged, perhaps with MusicBrainz Picard). With editable and sortable rules, it could be a real powerhouse.

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