Claude Cowork – First Impressions

I’ve just installed Claude Cowork on my Mac. The hype: “The Future of AI at Work: Introducing Cowork“. The reality – early stage agentic AI that can process your files and access some applications.

I’ve subscribed to Claude Pro – £18 a month, which gives access to the beta version, and I’ve decided to use it to try and tidy up my music Mac – an M1 Mac mini, and try and sort a whole bunch of boring things that I’ve never got round to, meaning I’m constantly fighting disk space, my backup approach isn’t as good as it should be, I can’t find files, and I miss emails and messages.

Let’s start with what I’ve got. My main music software is Cubase, and all my songs are in one place on a local drive. It’s backed up using Time Machine, and when I remember I copy files to iCloud. Everything I use is in the iCloud ecosystem, so Apple Mail, Calendar, Notes, and I’m writing this on Pages. I don’t use file management other than music and rely on search.

So let’s see if Cowork can handle the boring stuff I’ve been putting off for years.

Round 1 – A proper backup approach (Score: 10/10)

It starts off by suggesting zipping up my music folder and copying it to iCloud on a regular basis. It writes some scripts to do this, and tells me how to run them as it can’t do it itself, as it’s running in an isolated virtual machine. This works, but it didn’t calculate how much space I’d need, so we run out of disk space. It can’t see this itself, so I have to tell it.

It has another go, this time suggesting a file sync with Rsync and switching on Mac disk optimisation, so the files don’t stay on my hard disk but instead go to iCloud. Again it writes scripts and tells me how to run them. I test it, it works, so it writes a script to schedule it.

Why don’t I use proper backup software? Everything I’ve tried has either hammered disk storage or CPU when I’m recording. So for the first time in years I have a decent automated offsite backup that doesn’t interfere with my audio work.

Round 2 – Cleaning up my Downloads folder (Score – 10/10)

I ask it to move music downloads into a folder on iCloud, same for videos, and delete everything else. It asks me a couple of clarifying questions and then does it flawlessly.

Round 3 – Tidying up my mixes (Score – 10/10)

With Cubase, you mix your tracks down to a .wav file or MP3, depending if you want high quality or a compressed file just for sharing. I create a new file each time and never get round to deleting ones I don’t need. So I ask it to tidy things up.

It works out I have 64 music projects and can save me loads of storage. It figures out I don’t need the MP3s, and that I give them incremental numbers in the file names, so I only need the highest numbered one. It won’t delete them itself though – presumably a safety feature. So it creates me a script and gets me to review it to make sure the files I wanted to go were right. They were, so I ran it and cleared off around 25GB of files in two batches – it did the top 15 worst offenders first, then the rest.

This alone made the subscription worthwhile.

Round 4 – Tidying up my email (Score: 1/10)

So first, there is no connector to Apple Mail. It tells me it can use the web interface, but that seems like a stupid idea, so I test things on a semi-abandoned Gmail account, where there is a connector. I ask it to unsubscribe from all the junk. I’d assumed it could do that with the connector, but no, it wants to use the web interface. It plods along, eventually doing two, before telling me it was too much like hard work, and I should do it myself! I guess what it really meant was it would burn through all my tokens.

Round 5 – Find all my subscriptions (Score: 7/10)

I thought I’d give it another go, this time with Apple Mail, so I ask it to find my paid subscriptions. Again, it used the web interface, but it does a good job, and finds most of them, successfully figuring out what were subscriptions and giving me a report. As a bonus it also told me what I was spending on Switch games.

Round 6 – Answering iMessages (Score: 0/10)

There is an iMessage connector, and I’m rubbish at answering messages from my wife, so I have a cunning plan – get Cowork to give the initial answer and then bug me until I reply. I install the connector. But I can’t get it to work. It basically fails to even connect to iMessage. I try to debug it, but no joy.

Round 7 – Blogging (Score: 3/10)

There’s a WordPress connector, so I connect it to this blog. I try something trivial – get it to give me stats. I guess I should be amazed that it works, but it does.

I also have a go at getting it to write a version of this blog. I assume it can see all of the things we have done, so I ask it to write a blog about it. It turns out it can’t access its own chats, so I paste a few of them in. It writes an OK blog. I ask it to publish it for me, but it tells me the WordPress connector only has read permissions – it can’t create or publish posts.

I guess that might be for the best.

I show it this blog, and ask which is better, mine or it’s.  It just about concedes mine is better (or it’s being nice and tell me what I want to hear! “For a personal blog, yours is probably the better fit. It’s honest, funny, practical, and respects the reader’s time. Mine reads more like a tech review article. Want to publish yours instead?”

Round 8 – Gig booking (Score: 5/10)

I see a Trivago connector so I try this. I say I want to see The Twilight Sad in Manchester or Bristol so can it tell me the total cost including hotel. This starts off well. It finds the gig dates, then fires up the Trivago connector, and finds 3 hotel options for each (budget, mid, posh).

I ask if it can book it for me. It can navigate to booking sites, search for hotels, and fill in basic information, but it can’t enter credit card details, create accounts, or complete payment transactions. So I’d still have to do all the important bits myself.

It doesn’t seem worth the effort!

Summary

So what’s the takeaway? I actually achieved more than I expected. Sorting out the backup and disk space was a major win – the kind of tedious work that I’d been putting off for literally years because it was too much faff. Clearing 25GB of redundant mix files alone justified the subscription.

It couldn’t organise my iCloud files as they weren’t local, which was disappointing.

I was surprised how bad it was at email. Using the web browser instead of the Gmail connector seems nuts, and the iMessage connector simply didn’t work.

The connectors are at a very limited stage at the moment, which is understandable for a beta. They’ve clearly gone down the safe, read-only route. I imagine in time they’ll be able to post blogs, book hotels, and actually complete tasks rather than just helping you get 90% of the way there.

Would I recommend it? If you’ve got file management tasks you’ve been avoiding, absolutely. For everything else, it’s promising but not there yet. I’ll definitely keep using it for the file and backup stuff, but I won’t be asking it to manage my email or messages anytime soon.