Looking for an app to organize files

Been through almost exactly this with a Synology full of backups of backups. Two things saved me. First, split the job in two: dedupe first, organize second. If you try to sort while duplicates are still in there you end up organizing the same file three times. For dupes with different filenames, dupeGuru or czkawka both compare actual file contents (hashes), so renamed copies still get caught. Both free. Run them, quarantine the dupes into a holding folder instead of deleting right away, and only trash it once you have lived without it for a couple weeks. Second, if the NAS connection is slow, pull one directory at a time to a local drive, clean it there, push it back. Working over SMB on thousands of small files is misery. And do not over-plan the folder tree. Two or three top level buckets (work, personal, media) beats a beautiful 40-folder taxonomy you will never maintain. For the actual sorting and renaming pass after dedupe, I use Sortio. You point it at a folder and describe what you want in plain English, like invoices by year in one place, photos by subject, installers in the trash pile, and it reads the file contents (including inside PDFs) to figure out where things go, then moves and renames them. It does not do deduplication, so it is only the organizing half. (disclosure: I work on it.) Works best in batches of a few thousand files, which fits the one-directory-at-a-time approach anyway.

You don't mention which NAS brand you have nor what overall file size we're talking about. But I would recommend doing at least the first steps in the file manager of your NAS directly, e.g. DSM with Synology (I own, so I only know about Synology's functionality). Working directly on the NAS is soooo much faster than pumping all files through the network to your Mac and back again. With DSM file manager, search through all your directories (all subfolders can be done at once) and move them to a temporary location named after each file type (e.g. "docx", "png", "jpg", "mp4", "mp3" - whatever you have). I'm sure it won't take all that long - probably even less long than reading through this reddit and think and rethink over how, what, where to start even ... ;) Then, look through what's left in the original folders. Now you can also delete all empty folders, and probably you already have a good overview of your files. By doing it manually, it's also much easier to gain a real overview and feel of what you have. If you do it all automatically, you will have a similar chaos afterwards. At some point, you must take a closer look at your files. Then I would use some sort of tools folder by folder. If you - for example - have large amounts of audio files, you can use a dedicated taggre (like MP3tag) to sort them all to dedicated folders (artist, album, etc.). With photo files, you can use Synology Photo to tag them. Of course, you can now also use dedicated file organization tools on your Mac. But also now, think of the file size such a locally running app would transfer from and to your NAS.

Here's a possibility for duplicate checks directly on a Synology NAS: https://mariushosting.com/how-to-find-duplicate-files-on-synology-nas/ I want to stress again that running any file apps outside of your NAS needs to transfer all files to your device (Mac) and then back. When wanting a duplicate check over all your files (you mentioned "not based on type rather than content"), you would need to have all files moved to where the app is running first! So, do it directly on your NAS. And as I forgot before: Backup your files first! When deleting any file you later miss, it's gone by then!

Leap 4 https://ironicsoftware.com/leap/ for looking through, organising and tagging your files. Gemini 2 for finding duplicates https://macpaw.com/gemini

Let claude do it for you

I’ve had Claude reorganize 20 years of videos, my music library, books and audiobooks, and video game ROMs. I ended up saving literally hundreds of gigs and everything is pristine now. It even re-wrote the ID3 tags on my mp3 files for consistency. 😃

I'd love a bit of a writeup on this. I'm sure having some guidelines and few personal stories behind it would help folks like me get over the mental hurdle with a project like this (even for a small-scale first attempt).

I’m following here, thank you

did a version of this last year - years of downloads, exports and backup-of-backup folders spread across two macs. the thing that actually moved the needle wasn't any app, it was deciding the destination structure first. for me that ended up being just two top-level trees (work and personal, different clouds) and nothing else allowed at root. until that decision existed, every tool was just helping me shuffle the graveyard around faster. then dedupe before organising, otherwise you file the same thing three times. and keep a quarantine folder rather than deleting anything on the first pass - two weeks later you'll want something back. the sorting itself is the boring easy part once the structure exists, hazel or even dumb scripts will do it.

This is too General. You can’t find App that works perfectly with all types of files You need multiple Apps for example Eager for assets

Sortio https://www.getsortio.com you can even run it using a local LLM if your mac is capable so no exfiltration to the cloud, I hope when macOS 27 is release they are able to leverage the Apple model foundations

A very easy way to do it manually is with FindAnyFile. You can define exact search locations, files, dates, etc. and you can drag/drop the finds to any location you want. Even so, while your files will be organized, I guess you will get an organized graveyard of files. What would be your next step after organizing your files?

A safer first pass is to use a read-only disk inventory tool, export the biggest folders/file types, and only then pick a duplicate cleaner. Moving everything automatically is where these cleanups usually go wrong.

I use organize (https://organize.readthedocs.io/en/latest/) to sort files by type, date and even names. It takes a bit of work to write the rules but then works well for me

Try to check it this project can fit your needs TagStudio

Maybe relevant https://devpost.com/software/llamafs

I like the PARA method for organizing. https://fortelabs.com/blog/para/

For the “same file, different name” thing you want content matching, not name matching. Gemini 2 (already said) does this well if you want a GUI. Free option is dupeGuru - open source, has a Music mode and a Picture mode, and it can match by content and even near-dupes, not just exact names. Works fine on a mounted NAS folder One thing from doing this on a NAS: use a cable if you can, not wifi. It has to read a ton of files over the network to hash them, and on wifi it’s super slow. Mount the share in Finder first (Go → Connect to Server, smb://your-nas-ip) so the app sees it like a local drive For sorting by year/type etc, Hazel is the usual one - you make rules and it files new stuff automatically. But it won’t clean up the existing mess in a smart way, and that’s the hard part imo. I ended up doing that part in a different way - can explain in a reply if anyone wants, it’s a bit more involved

have you thought about using claude cowork analyse everything and sort it. i did this for my business, i had lots of images, random documents all over the place and needed everything properly organised and structured so i could find anything exactly when i needed it. worked well for me

Honest take: AutoShelf handles 1-3 well but not #4. For organizing by type, size, and date, it's a good fit. You set up rules like "move PDFs older than 1 year to /NAS/Archives" or "trash files smaller than 1KB." It watches folders and runs automatically. You can grab it at https://useautoshelf.com But duplicate detection with different filenames is a different problem. AutoShelf doesn't do content analysis or hash comparison. For that, you'd want something like Gemini or Duplicate File Detective first, then use AutoShelf to keep things organized going forward. Worth noting: AutoShelf works with any folder a Mac can mount, including SMB/NFS network volumes. No special NAS setup needed. I'm the developer, happy to answer any questions.

Personnellement je me suis créer un widget pour mon Mac , des bulle style glass de projet ou tu insère tes fichier dossier pour trier tout ton bureau et que tout sois plus fluide. Si sa t’intéresse n’hésite pas je vais bientôt le publier

I would split this into two passes. First, use a dedicated duplicate tool for exact/near duplicates. That is a different job from organization, and it is where you want conservative matching, preview, and a delete log. Second, for the remaining files, I would avoid letting any AI move thousands of NAS files blindly. The safer workflow is: make a spreadsheet or dry-run list first preserve original path and filename group by obvious facts like type, date, size, camera/app/source when available only then use content-based naming or folder suggestions for the messy files keep a log of old path -> new path Disclosure: I built a Mac app called NameQuick for the content-based cleanup part. It reads files and suggests names/folders before applying changes, so a file like scan_0042.pdf can become something readable. But for true duplicate detection I would still use a purpose-built duplicate app first.