Hey — quick story from last night. I was setting up an old test environment for NimbusApps and thought it would be funny (and slightly nostalgic) to install iWork ’05 Installer (app) on my MacBook Pro M1 running macOS Sonoma 14.5. You can already see where this is going.
What I wanted: just get the legacy Pages/Keynote versions running in a sandboxed user account for compatibility testing. Nothing production-critical. Just curiosity and some file conversion checks.
What happened instead: the installer wouldn’t even launch. macOS threw the classic line — “This app can’t be opened because it is from an unidentified developer.” On the second attempt, it escalated to “is damaged and can’t be opened.”
At first I did the predictable thing. Double-click. Right-click → Open. Same result. Then I went into System Settings → Privacy & Security expecting the usual “Open Anyway” button to appear. Apple documents that behavior here: https://support.apple.com/guide/mac-help/open-a-mac-app-from-an-unidentified-developer-mh40616/mac
Except it didn’t show up.
That’s when I realized this wasn’t just a basic Gatekeeper warning. This is a 2005 installer. Pre-notarization. Pre-modern code signing rules. macOS basically sees it as an artifact from another era.
For context, I found the installer while digging through resources and saved this page because it had the macOS notes in one place — I found this page useful while cross-checking compatibility info: https://treadmillreviews.online/office-and-productivity/92209-iwork-05-installer.html
The download itself wasn’t corrupted. The issue was trust and architecture.
First mistake: I tried launching it directly from Downloads. On modern macOS, that triggers App Translocation. The system runs the app from a randomized read-only path, which breaks some older installers immediately.
So I moved it to /Applications and tried again.
Still blocked.
At that point I checked extended attributes. Opened Terminal:
xattr /Applications/iWork\ ’05\ Installer.app
Sure enough — com.apple.quarantine.
Apple’s Gatekeeper overview explains why this flag exists: https://support.apple.com/en-us/HT202491
So I removed it:
xattr -dr com.apple.quarantine /Applications/iWork\ ’05\ Installer.app
Relaunched.
Now the message changed. Instead of “damaged,” I got the standard unidentified developer warning. And finally, the “Open Anyway” button appeared in Privacy & Security. Progress.
Clicked it. Confirmed.
And then… new problem. The installer bounced in the Dock and immediately quit.
That’s when the second layer became obvious: this is a PowerPC-era installer. My M1 Mac can translate Intel code via Rosetta 2, but it cannot run PowerPC binaries at all.
Apple explains Rosetta 2 here: https://support.apple.com/en-us/HT211861
Rosetta handles x86_64. It does not resurrect PowerPC. That bridge burned years ago.
So what I learned: Gatekeeper wasn’t the only barrier. Even after clearing quarantine, the architecture simply isn’t supported on Apple Silicon.
Out of curiosity, I tried running it inside a macOS virtual machine (older Intel build). That worked. The installer launched fine under an Intel Ventura VM, though even there it required the quarantine removal first.
So the actual solution depends on what you’re trying to achieve:
If the goal is just to use Pages/Keynote today, obviously use the modern versions via the Mac App Store: https://apps.apple.com/us/search?term=Pages
If the goal is archival or file conversion testing, you need either: – an older Intel Mac – or a virtual machine running an older macOS version
Trying to force it onto Apple Silicon natively isn’t realistic.
Here’s the short checklist I’m keeping for myself:
- Move legacy apps into
/Applicationsbefore launch. - Check and remove
com.apple.quarantineif blocked. - Verify architecture with
filecommand before assuming it will run. - Accept that PowerPC binaries won’t run on M-series Macs.
What I did wrong initially was treating it like a normal unsigned modern app. It’s not. It predates the entire notarization model. Expecting Sonoma to welcome it politely was optimistic.
After all that, I ended up doing the actual compatibility testing inside a VM. Slightly slower, but stable. The installer ran, apps launched, and I could open some ancient .key files we had archived.
So yeah — if you ever feel tempted to spin up a 2005 installer on a 2024 Mac, now you know the layers you’re dealing with. Gatekeeper is just the first gate. Architecture is the real one.
And honestly, part of me respects macOS for not blindly executing 20-year-old binaries. It’s annoying when you’re tinkering, but it makes sense.
Anyway, figured you’d appreciate the shortcut instead of losing an evening like I did.