Windows file organizers compared

DropIt vs File Juggler
(and a third option).

DropIt and File Juggler are two of the best-known ways to sort files automatically on Windows. They take quite different approaches, and one of them hasn't been updated in years. Here's how they compare, honestly, including where TidyFile fits.

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At a glance

DropItFile JugglerTidyFile
PriceFree, open sourceOne-time licence, 30-day trialSubscription, 7-day trial
Latest version8.5.1, from 2018MaintainedMaintained
How it sortsDrop files on a target, or monitor foldersWatches folders automaticallyWatches folders automatically
Reads text inside documents—Yes, e.g. PDFsNo
Preview before tidying——Yes
Undo moves——One click

Pick DropIt if…

You want something free and you like sorting by dragging files onto a target, or you need actions like compressing and extracting archives. Bear in mind its last release was 8.5.1 in 2018, before Windows 11, so you're on your own if something breaks. More in our DropIt alternative comparison.

Pick File Juggler if…

You need rules based on what's written inside documents, such as filing scanned invoices by the supplier name or date on the page. That's File Juggler's strength, and it's maintained, with a one-time licence. More in our File Juggler alternative comparison.

Or pick TidyFile if…

You want simple rules (file type, name, size or age) that you can set up in a minute, and a safety net: a preview of exactly what will move before it tidies existing files, and one-click undo afterwards. It installs from the Microsoft Store and runs quietly in the tray. It doesn't read inside documents, so if you need that, File Juggler is the better fit.

The TidyFile rule

Documents out of Downloads

When a file
in Downloads · type is pdf, docx, xlsx
Then
move to Documents\{year}

Tip: folders like Documents or Pictures mean your own folders. In TidyFile, click Browse to pick the folder, then add the rest, such as \{year}. A folder typed without a drive letter is created inside the watched folder instead.

Set it up once and TidyFile applies it in the background, to new files the moment they arrive. Preview what it'll do to the files already there, and undo anything from the activity log.

Questions

Is DropIt or File Juggler better?+

It depends what you need. DropIt is free and flexible but hasn't had a release since 2018. File Juggler is paid and maintained, and stands out for rules that read the text inside documents. If you want simple rules with a preview and undo, TidyFile is the third option.

Is File Juggler free?+

No. File Juggler has a 30-day trial with every feature, then needs a licence, which covers future upgrades. DropIt is free.

Can DropIt sort files automatically?+

Yes. As well as its drag-and-drop target, DropIt can monitor folders and process new files on a timer or when the folder changes.