Field Report: Show Me the Money (app) — Won’t Open on macOS Sonoma
Machine: MacBook Pro 14" (M1 Pro)
System: macOS Sonoma 14.3
Target: Get Show Me the Money (app) from OrchardKit to launch without macOS treating it like contraband.
I just wanted a lightweight finance tracker. Nothing dramatic. Download, drag to Applications, open, move on with life. Instead, macOS hit me with the classic:
“Show Me the Money is damaged and can’t be opened.”
That message again. The polite version of “I don’t trust this.”
What broke
Fresh download from the official OrchardKit site. File looked clean. No weird installer. Just a standard .dmg. I mounted it, copied the app, double-clicked.
Blocked.
System Settings → Privacy & Security showed the usual “App was blocked to protect your Mac.” No “Open Anyway” button yet, just suspicion.
According to Apple’s Gatekeeper documentation (https://support.apple.com/guide/mac-help/open-a-mac-app-from-an-unidentified-developer-mh40616/mac), this usually means one of three things: not notarized, modified in transit, or quarantined.
My bet was quarantine.
Attempt #1 — Right-Click Open
Old trick. Control-click → Open → confirm dialog. Sometimes that’s enough.
Not this time. Same error. No override option.
Dead end.
Attempt #2 — Redownload + Different Browser
Sometimes Safari tags downloads differently than Chrome. I re-downloaded using Safari (because macOS plays nicer with its own). Mounted again. Copied again.
Still blocked.
At this point I checked the app’s signature with:
codesign -dv --verbose=4 /Applications/Show\ Me\ the\ Money.app
Signature existed. That was interesting. If codesign shows data, it’s at least signed. Not necessarily notarized, but not random junk either.
Apple’s notarization overview (https://developer.apple.com/documentation/security/notarizing_macos_software_before_distribution) explains that apps distributed outside the Mac App Store must be notarized or Gatekeeper complains loudly.
Maybe the notarization ticket wasn’t stapled correctly.
Attempt #3 — Remove Quarantine Flag
This is where it got practical.
I checked extended attributes:
xattr -l /Applications/Show\ Me\ the\ Money.app
Sure enough:
com.apple.quarantine
That attribute alone can trigger the “damaged” message even if the app is fine.
So I removed it:
sudo xattr -rd com.apple.quarantine /Applications/Show\ Me\ the\ Money.app
Deep breath. Relaunch.
It opened. Instantly. No crash, no drama. Clean UI. No errors in Console.
That was it.
What Actually Happened
Most likely the build was signed but not fully notarized, or the notarization wasn’t properly attached when packaged. Gatekeeper flagged it as potentially unsafe. macOS doesn’t explain nuance; it just says “damaged.”
For reference, Apple’s broader Gatekeeper explanation is here:
https://support.apple.com/guide/security/gatekeeper-and-runtime-protection-sec5599b66df/web
If this tool ever lands on the Mac App Store (search placeholder: https://apps.apple.com/us/search?term=Show%20Me%20the%20Money), none of this would matter. Store apps are pre-approved and sandboxed.
Performance After Launch
No Rosetta prompt, so it’s either universal or native Apple Silicon. Activity Monitor showed modest CPU usage. Memory footprint ~120 MB at idle. Perfectly reasonable.
No sandbox permission chaos either. Just one prompt for Documents access when importing CSV. That’s normal behavior under macOS privacy controls.
What I’d Do Differently
If I’d known from the start that this was quarantine-related, I would’ve skipped the redownload dance and signature inspection.
Steps I’d take immediately:
-
Install to Applications.
-
Check xattr.
-
Remove quarantine flag if present.
-
Verify codesign.
-
Done.
I saved this macOS systems page because it covers similar quirks with software on Apple’s platform:
https://proguntalk.com/finance/66890-show-me-the-money.html
Not because it’s magical. Just practical reminders about how macOS handles third-party utilities.
Final Notes
The app itself runs fine once past Gatekeeper. No hidden daemons. No weird network spikes. Just a small finance tracker doing what it’s supposed to.
This wasn’t a broken program. It was macOS being cautious — aggressively so.
And honestly, I’d rather have an overprotective system than a permissive one. Even if it means a few Terminal commands and five minutes of muttering at my screen.