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ZDNET’s key takeaways
- Agentic file management shows real productivity promise.
- Security, scale, and trust remain major open questions.
- At $100 per month, Cowork is for early adopters only.
“With great power comes great responsibility.” So said wise old Uncle Ben to a young Peter Parker. With Claude Cowork, you’re granting the AI enormous power, but the responsibility of what it does falls entirely on your shoulders.
Claude Cowork is basically agentic AI for your file system. Here’s a view of its main screen.
You can see that Claude recommends six task categories (at 1). In this first hands-on article, we’ll look at the Organize Files option and crunch some data. That will give us a good head start on what this new beastie can do for us.
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Like most chatbots, there’s a prompt entry area (at 2). But the real key to Cowork’s power is the Work in a Folder option (at 3). Here is where you specify what folder on your local computer Claude is going to dig through and process.
It may seem dangerous to let an AI loose in your computer’s files (and it is). However, Anthropic has been doing this for quite a while with its Claude Code capability. In order to code, the AI has to work on all the files related to a programming project. The iPhone app I had Claude build (and the Mac and Watch apps I’m working on) take 946 files. Claude Code has access to all of them.
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There are some differences. Most programmers use something called source code control, which is a way of dynamically tracking and backing up every change to every file. I use GitHub for that. So I can revert any change Claude makes, going all the way back to the beginning of the project.
Claude Cowork does not have this capability (although if you’re geeky enough, you can certainly set it up). But Anthropic wants regular non-programmer users to be able to use Cowork, so some of the power coder features Claude Code has, by the nature of being a coding tool, don’t exist in Cowork.
Research preview
Let’s talk about some of the other things you need to use Cowork right now, just days after its initial release. Anthropic calls this a “research preview,” from which you can infer that it’s experimental, don’t bet your life on it, and anything could happen. This is somewhere between beta and alpha code.
Also: How to install and configure Claude Code, step by step
Cowork is currently only available to Mac users with Apple Silicon processors. It’s an app you can download and install. You can use some Cowork features from within the browser, but clearly you won’t be able to do the sort of file system manipulations I’m going to show you today.
Finally, Cowork is only available to those on the Anthropic Max plan, which starts at $100 per month. Right now, the folks spending that much are almost exclusively programmers. That’s why I have access to it. I’m using the Max plan to build my apps, so Claude Cowork is an added bonus, not a substantial extra expense.
While some users will undoubtedly find the features of Cowork worth the $100-per-month price, most won’t. I suspect that once this gets out of preview, Anthropic will open it up to a wider (and more thrifty) audience.
You should also have a very strong and reliable (and tested) backup strategy in place, so you can recover files if Claude decides to nuke them during some random AI hissy fit or misinterpretation of your instructions.
Test configuration
I installed Claude Cowork on my M4 Max Mac Studio. I have 128GB RAM on this machine, so it’s a fairly powerful machine. I created a folder on an external drive and did all my testing there.
To test, I made copies of three active folders:
- A large folder of random PDF file scans
- A folder of Home Depot credit card statements going back to 2017
- A folder containing all the PDFs I’ve downloaded and left in my Downloads folder
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To be clear, I didn’t want to let Cowork run loose on my main files or folders. So, by duplicating these folders, I was able to work with the AI without worrying it would destroy something important.
Random PDF scans
My wife and I have long made it a practice of scanning in all important (or even possibly important) documents, which then get stored on our Synology file server. Before they get assigned to their eventual homes, the files are dumped into a folder called ScanSnap Scans, named thusly because we use a ScanSnap scanner to capture the paper documents.
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My first big test was to have it scan this folder. I gave it the prompt, “Examine this folder and read each file. Create a list of master categories that would organize the files. Also create a list of subcategories under each master category. Do not modify or change any files. Just report back.”
Cowork did a surprisingly good job with that analysis, but it became immediately clear that I didn’t want Claude to have that much information about us. I certainly wasn’t going to be able to use it as an example for this article. Here’s a heavily redacted screenshot.
Home Depot statements
On the other hand, it will come as a surprise to absolutely no one that I shop at Home Depot. According to a Notion AI scan of my ZDNET blog drafts, I’ve mentioned Home Depot at least 10 times. I’ve also mentioned it numerous times on my YouTube channel.
I set Cowork loose on my directory of Home Depot statements to see what it would do. I told it to, “Examine all spending at Home Depot. I want an overall understanding of what was purchased, for how much, when, and where (Oregon or Florida).”
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At first, Cowork got a bit confused. Although my folder had data from 2017-2025, Cowork decided to stop at 2022. It wasn’t as useful as I wanted. So, I prompted it with an error report, using pretty much the same style I’ve used with Claude Code.
Here’s what I told it: “This is incomplete. You appear to have stopped in 2021-2022. Redo completely and account all through the beginning to the end of 2025.”
Interestingly, part of the way through, it exceeded its processing context and had to do a compaction.
In Claude Code, this usually doesn’t happen until hours into coding, but this capacity overload happened about a half hour into our session. Once the compaction completed (where, basically, the AI does a memory flush and garbage collection), Cowork was back in action.
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After another multi-minute wait, Cowork returned with an overview.
Unfortunately, the credit card statements list purchases in broad categories. So while I could know that tools were purchased, the data doesn’t tell us what tools.
Finally, although I didn’t request it, Cowork appeared to generate a report in a more traditional Word document format. Unfortunately, attempts to open it resulted in, “Failed to load local file.”
This is a research preview, after all.
PDFs in my Downloads folder
So far, Cowork didn’t do much more than I’ve been able to do with ChatGPT Deep Research. While ChatGPT wouldn’t read an entire directory, when I uploaded a zipped directory to ChatGPT, it was able to do analytics similar to what we saw above.
(Disclosure: Ziff Davis, ZDNET’s parent company, filed an April 2025 lawsuit against OpenAI, alleging it infringed Ziff Davis copyrights in training and operating its AI systems.)
Now, I wanted Cowork to clean up my files. I have a perfect candidate folder. I download a lot of PDFs. I drop them all into my Downloads folder. I use a Mac utility called Hazel, which keeps an eye on my Downloads folder and, based on file type, sorts files into subfolders. As of the writing of this article, my Downloads – PDFs subfolder has about 300 files in it.
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I wanted Cowork to organize that folder. Specifically, I have a lot of research documents and white papers I wanted to organize and be able to easily find. Could Claude Cowork do that for me?
Apparently not. At least not yet (spoiler: it will before this article is done). This is a research preview, after all.
And then things broke
So, I pointed Cowork at that folder and told it, “Examine all the files in this folder. Read the file contents. Present me with a list of categories that the files could be sorted into, but do not move any files.”
Also: You can use Anthropic’s popular Claude Code tool on the web now – how to get access
This was going to be my first step, to see what Cowork made of the documents. But there was a problem. This is a research preview, after all.
I wasn’t quite sure what it meant by “The prompt is too long,” so I asked more questions. That didn’t go well, either. This is a research preview, after all.
Eventually, I decided to simply restart the Claude Mac app, and that did the trick.
Optimizing downloaded PDFs
As you can see, my Downloads – PDFs folder is completely unorganized.
The first thing I had Cowork do was simply tell me what it could about the folder.
One thing I found interesting was its observation that there were a number of generically named files. I told Claude to examine the files and propose renames. As you can see, it spends quite a bit of time working through the process.
Once again, Claude ran out of context memory, but it eventually continued and proposed fairly good naming for those generic files.
At this point, I instructed Claude to go ahead and rename those files. This is the first time I actually gave Cowork permission to change the actual files on my computer. It completed the task successfully.
So, next I wanted it to categorize the files. I instructed, “Scan all the files (you’ll probably need to read at least the first page of each), list a set of categories that the files can be sorted into. Don’t move any files yet.”
Also: 10 things I wish I knew before trusting Claude Code to build my iPhone app
It came back with a set of proposed categories that were actually quite good. I liked how it separated the research reports from the press kits. Those were the two categories I was most interested in for future reference.
I told it, “I like it. Make it so. But do not use the / character in any file or folder names.” And it did what I asked. A few minutes later, I had a directory structure with category names. The only thing I didn’t like was that Claude put index numbers in front of each category name. So, I instructed, “Please eliminate the category numbers on the folders.”
Here’s the result.
This is pretty slick. Claude went through and reorganized hundreds of files into appropriate directories. Hazel can do that with file types, but Claude Cowork was able to do that based on the content of the files, which is far more relevant for my kind of work.
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I did try one more thing. I wanted Claude to identify the company or institution for each of the research files. That didn’t turn out quite the way I wanted.
This is a research preview, after all.
What’s it all mean?
There are a lot of boring and tedious computer tasks that AIs could help us with. But there are some serious hurdles to get over before we get there.
Security is obviously a big one. As soon as I realized Claude Cowork was going to be looking at a lot of my personal files, my red flags went up. I am fairly sure Anthropic knows to separate local data from data it uses to train, since its big focus is on security and transparency. But still, we hit a trust wall there.
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Capacity is another. I just asked Claude Cowork to reorganize a few hundred files, and there were at least two times when the AI ran out of resources and had to consolidate. That’s a lot more frequent than Claude Code. Is it because Claude Cowork uses a lot more resources than Claude Code, because Cowork is new and not optimized, or because of some other limitation? What happens when we want the AI to manage directories with 50,000 or 500,000 documents? Does it even stand a chance?
Flexibility is a third. I keep all my images for ZDNET articles in an image organizer called Eagle. Each article has its own folder, but those folders are poorly named. I’d love to have the AI go through those folders, match up the files with my ZDNET articles, and name them properly. But ZDNET blocks AI crawlers, and Claude Cowork knows nothing of how Eagle works. As long as AIs hit brick walls that limit their effectiveness, their effectiveness will be limited.
You might think the minimum $100-per-month price was also a limitation, but I expect that to relax over time. I’m much more concerned with the three issues outlined above, and whether and when tools like Cowork will be up to more general and more comprehensive tasks.
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As for me, will I use Claude Cowork on my live directory structure? No. But I might make a copy of a directory and let Cowork go to town on that, then review its work. I’ll keep digging, so stay tuned. I’ll let you know if Cowork seems to have more value over time.
AI is fast moving. I expect Claude Cowork to leave its research preview and hit prime time sometime in 2026. Stay tuned. Once it has some serious market traction, I may add it to my productivity stack.
Have you experimented with Claude Cowork or other AI tools that work directly on your file system? How comfortable are you letting an AI read, rename, or reorganize your files, even in a test folder? What use cases would make a tool like this worth the risk or the price for you, and what limitations or safeguards would you need before trusting it on real data? Let us know in the comments below.
You can follow my day-to-day project updates on social media. Be sure to subscribe to my weekly update newsletter, and follow me on Twitter/X at @DavidGewirtz, on Facebook at Facebook.com/DavidGewirtz, on Instagram at Instagram.com/DavidGewirtz, on Bluesky at @DavidGewirtz.com, and on YouTube at YouTube.com/DavidGewirtzTV.