Claude Relentlessly Got Nancy Drew (2007) to Run on My Mac

Claude does not discriminate between solving valuable problems or getting an old video game to work.

Either way, it is relentless.

A few days ago, my girlfriend and I were talking about early computer games, and she mentioned Nancy Drew. Immediately all these hazy memories came flooding back to me. Stressed about quickly getting cold outside the lodge, playing a board game against an NPC to solve a puzzle… and cooking a lot? I was a bit hazy on the details. I remember playing them together on the family computer in our kitchen.

I called my sister and she had more specific memories — we got Nancy Drew: The White Wolf of Icicle Creek for Christmas in 2008. She was 15, I was 12. You’re Nancy, investigating sabotage at a snowed-in Canadian lodge. There’s a wolf lurking outside. Guests keep having suspicious accidents. My sister’s most vivid memory was also flipping burgers for the lodge guests.

I hadn’t thought about these games in years. I wanted to replay it immediately.

The only problem: it’s a Windows XP game from 2007, I’m on an M1 Pro MacBook, and there is no Mac port.

I’ve used Porting Kit to play Age of Empires 2 on my Mac, so I’m not a total stranger to running old Windows games. I briefly considered setting up a VM for windows but it seemed like a hassle, so I found a Wineskin wrapper for a different Nancy Drew game (The Final Scene) and bought White Wolf on Big Fish Games for $10. I swapped out the game files, launched it, and… nothing. No error, no crash, just nothing.

Using Claude

I’m primarily a web engineer, so I have basically zero experience debugging Wine, Windows, etc. So I pointed Claude Code at the Wineskin wrapper. I instructed it to use vanilla Wine so Claude could mess with the configuration directly, and then just… watched it go.

The process was surprisingly hands-off. Claude would launch the game, capture the Wine debug logs (thousands of lines), read them, identify the error, suggest a fix, I would approve it, it would apply, and try again. Each loop took a couple minutes. I mostly observed. A few things I watched:

It ditched the version I paid for. The $10 Big Fish Games copy had kernel-level DRM. Claude tried a few ways around it, then just said “we should find a clean version” and pulled the original retail disc images from Internet Archive. Is this legal? I don’t know.

It made binary edits to DLLs. At one point Claude found an assertion crash in Wine’s Vulkan code, located the exact byte offset in a 32-bit DLL, and patched it — changed two bytes from 75 17 to 90 90 (a jump instruction to two NOPs). Needless to say, I would not have considered it. But it sort of fascinated me and I respected its commitment, so I let it keep running.

It tried a lot of graphics engine configurations. Vulkan, OpenGL, DXVK 2.7.1, DXVK 1.10.3, different MoltenVK versions, disabling multithreaded rendering. Probably a dozen different combinations. Here’s the funny thing: OpenGL was the first renderer it tried. It failed immediately and Wine said “Disabling 3D support,” so Claude switched to Vulkan and spent hours fighting assertion crashes and shader compilation failures. After exhausting every Vulkan approach, it switched back to OpenGL… and it worked. It fell back to an older OpenGL version, but everything rendered. The fix was going back to the thing that failed on day one, and it probably only worked because of all the other fixes (filesystem, DRM, config changes) that had accumulated along the way.

It fixed the virtual filesystem. The game hardcodes a Z:\Program Files path that doesn’t exist on macOS. Claude created a directory with symlinks to both macOS system folders and the game files, and pointed Wine’s Z: drive at it.

Frankly, I was never sure whether any of these moves were correct. But I trusted it enough (and looked at the commands before approving) and let it continue.

I had to nudge it to focus a couple times — it went down a few rabbit holes with DXVK that weren’t going anywhere. But generally I just let it run. About six hours of debugging total (spread across a few sessions over a week, whenever I had a spare moment), ~400 tool calls, 10 dead ends.

A Wine expert could have probably solved this very quickly. They’d know the right settings, recognize the DRM on sight, understand the stack limitations. I don’t know any of that. But Claude gave me a run loop, and the magic was that it could churn through approaches way faster than I could Google them.

Playing it

It ran beautifully. Smooth, no crashes, no glitches. (Yes the game is dark.)

And the game is so fun. It completely holds up. The mystery is genuinely well-written — multiple suspects, red herrings, great pacing. You DO cook A LOT of meals for the lodge guests (and they complain if you mess up). You snowshoe around the property. The puzzles are genuinely challenging. The art and atmosphere are perfect - so many amazing details and delightful moments. We even pulled up ancient forum posts and an “Arglefunk” video at one point to get past a particularly quirky puzzle that had us stuck for half an hour, all part of the charm of a 2007 point-and-click.

Reflecting

For me, this experience was almost a perfect example of the current AI paradigm. Claude was decently smart and likely had all of the Wine docs and forums somewhere in its training data. But it was surprisingly dumb too, mistaking an error and ignoring OpenGL for most of the investigation.

But most of all, it was relentless in a way that I’m not sure I would have been about getting this game to work, which made all the difference. Its ability to try so many things faster than I could have made this type of investigation possible.

Open Questions

1. Was it legal for Claude to use the iso it found on archive.org?
2. Is it legal for me to send the full .app to my sister?
3. What game should we try next? :)

Leave a comment below!

Full investigation timeline

I asked Claude to pull its full session history - here it is on a timeline.