I just submitted SmartFiler to the Mac App Store, and I’m pretty excited about this one. It’s a file organization tool for macOS that I built because every alternative I tried was either too complicated, too aggressive with your files, or just didn’t fit the way I actually work.

Here’s what it does.

Find Duplicates — by Name or by Content

SmartFiler can scan a folder and find duplicate files two ways: matching filenames, or matching actual file content using SHA-256 hashing. The content match is the one you want — it catches files that got renamed but are still identical copies taking up space. You review everything before anything gets deleted, and when you do delete, it goes to Trash, not gone forever.

Smart Buckets

This is my favorite feature. You define rules — by filename, path, or extension — and SmartFiler sorts your files into named folders automatically. Set up a bucket for invoices, one for screenshots, one for project files. You drag to reorder priority, toggle buckets on and off, and nothing moves until you say go.

Similar Files

Fuzzy filename matching that surfaces files that are probably related — like report_2025.pdf and report_2026.pdf. You control how loose or strict the matching is with a slider. Useful for cleaning up versioned files that accumulated over time.

Auto-Organize by Pattern

Point SmartFiler at a messy folder and it analyzes the files and suggests groupings — by file type, date, numbered sequences, or common name prefixes. You review the suggested groups, check or uncheck what you want, preview the changes, then organize. No surprises.

Filename Cleaner

Batch rename files to strip out special characters, fix spacing, change case, or apply a regex pattern. If you’ve ever downloaded a folder of files with names like IMG_20240315_094512_FINAL_v2 (1).jpg, you know why this exists.

Built Around Preview First

Every operation in SmartFiler shows you what’s going to happen before it happens. You can cancel long-running scans at any time. Deletions go to Trash. I built it this way on purpose — file operations are the kind of thing where you really don’t want surprises.

SmartFiler is currently under review at the Mac App Store. I’ll post the link here as soon as it’s live. In the meantime, you can check out the product page for more details.

If you’ve got feedback or questions, drop me a line at contact@robroy.online.