No matter how much storage I get in a device, one thing about me is that I'll somehow still manage to run out of it. Keeping aside the fact that I have an image hoarding problem and refuse to delete screenshots I’ll likely never look at again, the bigger problem is that cleaning it up is so tedious that I'd rather just live with the “disk is almost full” warning. And frankly, I don't even know where to start! Ever since I got my M2 MacBook Air, I haven't bothered doing a proper cleanup.

A few weeks back, I used Claude Cowork to organize my extremely messy Mac, and it hit me: if it can sort through all that chaos and make it easier to navigate, it could probably help me actually clear things out. Of course, that's exactly what I decided to do, and I ended up freeing nearly 60GB of space from files I didn't even remember existed (classic me behavior, though).

So, what is Claude Cowork?

It's Claude, but it can actually touch your files

Cowork is a fairly new Anthropic feature that bridges the gap between Claude Code and non-technical users. If you haven't explored Claude Code just yet, it's Anthropic's popular developer tool that brings agentic AI right to your terminal. It can read your codebase, write files, run files, and essentially do anything a developer would do manually. Since Claude Code can access all of your files, people have been using it to do things far beyond coding, like organizing folders, batch renaming files, compiling research, and more. Developers realized pretty quickly that a tool with file system access and the ability to execute commands is useful for everything and for everyone.

Claude Code is largely limited to people who are comfortable working in a terminal. While it certainly isn't just for developers and there are ways to work around that limitation, it's still not the most intuitive experience for many. Anthropic noticed this too, and that's where Claude Cowork comes in.

It takes the same underlying agentic architecture of Claude Code and puts it inside the Claude Desktop app. With Cowork, you grant Claude access to any folder on your computer and describe what you'd like it to do. Since Cowork enables Claude to read, edit, create, and organize files directly on your behalf, it'll then go ahead and perform those actions for you automatically. Claude breaks each task into steps and works through them right in front of you.

While Cowork was previously only available on macOS, it's now available for Windows too. However, keep in mind that this feature is currently in research preview, and Anthropic is still working on agent safety. The feature is also exclusive to Claude's paid plans for now, so you won't be able to use it on the free tier.

Here's how Cowork helped me reclaim 60GB of storage

Three years of I'll organize this later finally caught up with me

Given that Claude can access folders and files on your local machine with Cowork, all I really needed to do was point the tool to my file system. Rather than picking the folder myself though, I started off with a simple prompt detailing what I wanted to do (i.e., clear up storage) to see what it would suggest.

I told it to go through my MacBook and find duplicate files, old installers, large files I don't need, and anything that looked like clutter. Here's the exact prompt I used:

Hey! Go through my MacBook. Find duplicate files, old installers, large files I probably don't need, and anything that looks like clutter. List everything you'd recommend deleting with file sizes, but DO NOT delete anything. Just give me the report.

The last part of the prompt is especially important. Given that Cowork is in research preview and that it's an AI feature at the end of the day, the risk of it deleting something important in the process is very real. So, throughout this entire process, I strictly instructed Claude to not delete anything and give me reports.

Right after I sent the first prompt, it asked me to give it access to my home folder, which would let it check common clutter spots like Downloads, Desktop, caches, and more. It then ran a bunch of scans in parallel and identified 17 GB of reclaimable space across my Downloads, Desktop, and Caches.

This included DMG and PKG files, duplicate downloads (I have no idea why I installed Zoom and Logi Options seven separate times), app caches, and large media files. It listed its findings in an HTML file, which I found a unique and convenient way to review everything before deciding what to delete.

Now, this was just the first pass. I then sent the following prompt:

Look through my Documents, Desktop, and Downloads folders. Find any files or folders I haven't opened or modified in over 2 months. Group them by size and tell me what they are, but don't delete anything.

I then had yet another HTML report with even more files that were doing nothing but consuming space. Then, I sent the prompt below:

Give me a complete breakdown of my Downloads and Documents folder by file type. How much total space is taken up by .dmg, .pkg, .zip, .pdf, .png, .mov, .wav, and everything else? I want to know where every GB is going. DO NOT DELETE ANYTHING!

All of the prompts above were focused primarily on the Documents and Downloads folders. I was sure a lot of storage was being taken up by the Applications folder as well, so I created a new prompt asking Claude to scan that area too.

What about Applications? I bet there's some stuff I haven't touched in days.

Claude pointed out apps like Norton Neo (a browser I installed for testing and haven't used since), old Google Chrome data, Steam (last opened in December 2023), and more.

I still thought there's a lot more data that could be cleaned up, so I sent the following prompt to Claude:

I'm sure there must be more stuff hoarding space! Unboxing videos and stuff? Or have I deleted those already?

It then found a folder that was taking 5.5 GB with months-old unboxing footage, a 2.4 GB folder of images I had transferred from my iPhone, 1.5 GB of random press kits, and more.

Yet again, I still felt like Claude was missing something. So, I told it that I was sure there was even more. It then asked for access to the following directories: ~/Library/Logs, ~/Library/Mail, ~/Library/Messages, ~/Library/Group Containers, ~/Library/Containers, ~/Library/Developer, ~/.Trash, ~/Movies, ~/Music, and ~/Pictures. It found a lot more applications and folders taking up space that I could consider deleting.

This included the WhatsApp desktop app taking up 6.1 GB (an app I barely open), Xcode Simulators worth 2.9 GB, which I also don’t use, CapCut taking up 1.1 GB just in cached data, and more.

All of the above combined added up to roughly 60 GB! I, unfortunately, have a MacBook with 256 GB of internal storage, so this was around a quarter of my entire drive.

This would have taken me forever

Could I have done this myself? Absolutely. Would I have done it myself? Likely no. Knowing myself, I'd have kept putting it off, letting files pile up, and ignoring those “disk is almost full” warnings by deleting apps I didn't need at that moment while leaving all the hidden clutter untouched.