Timey 2 (app) on macOS Sonoma: When a Simple Timer Refused to Start
I needed a lightweight focus timer. Nothing fancy — just something minimal to run alongside Xcode and a dozen Safari tabs. The slug pointed to Timey 2, clearly a productivity utility, and since OrchardKit was mentioned around it, I assumed it’s a small indie release packaged outside the Mac App Store.
My setup: MacBook Air M2, macOS Sonoma 14.4.1. Clean install, no beta profiles, no weird security tweaks.
The plan was simple. Download, drag to Applications, launch, start 25-minute sessions. Instead, I got hit with:
“Timey 2 can’t be opened because Apple cannot check it for malicious software.”
Classic Gatekeeper.
First Attempt: The Usual Right-Click Trick
The obvious workaround on macOS is right-click → Open → confirm. Apple documents this flow clearly here: https://support.apple.com/en-us/HT202491
I did that. It launched once. Closed it. Tried reopening normally.
Blocked again.
That was odd. Usually once you approve it, the system remembers.
I checked whether there was an official Mac App Store build to avoid the whole notarization dance. Searched here: https://apps.apple.com/us/search?term=Timey%202
Nothing definitive showed up for this exact utility. So this build was clearly distributed independently — meaning full Gatekeeper scrutiny.
What Was Actually Happening
The error message wasn’t about malware. It was about notarization.
Since macOS Catalina, Apple requires distributed apps to be notarized. Developer documentation explains the process here: https://developer.apple.com/documentation/security/notarizing_macos_software_before_distribution
If an app is unsigned or improperly notarized, Gatekeeper flags it. But here’s the nuance: sometimes the outer bundle is signed, but a nested helper binary is not.
So I checked the signature:
codesign --verify --deep --strict --verbose=2 /Applications/Timey\ 2.app
There it was — a signature warning tied to an embedded framework. Not fatal, but enough to make Sonoma nervous.
At this point I made a wrong assumption: I thought clearing quarantine would solve it permanently.
xattr -dr com.apple.quarantine /Applications/Timey\ 2.app
It launched once. Then macOS blocked it again after a reboot.
So quarantine wasn’t the root cause. It was signature validation combined with the app requesting system-level permissions.
The Real Culprit: Accessibility Permission
This timer overlays on screen and optionally pauses when certain apps become active. That means it hooks into Accessibility APIs.
And macOS does not grant that silently.
When the tool first launched, I noticed a quick system prompt flash and disappear behind other windows. After that, it failed to relaunch properly. That’s when it clicked: it probably requested Accessibility access but never received explicit approval.
Apple explains these privacy controls here: https://support.apple.com/guide/security/privacy-controls-secddd1d86a6/web
I went to:
System Settings → Privacy & Security → Accessibility
Timey 2 wasn’t listed.
That’s when I realized something subtle: if the app fails signature checks, macOS may not register it correctly in TCC (Transparency, Consent, and Control). So the permission prompt can misfire.
What Actually Worked
I did this sequence cleanly:
- Removed the app entirely from Applications.
- Re-downloaded the build.
- Moved it to /Applications before first launch.
- Cleared quarantine once.
- Launched it via Terminal directly:
/Applications/Timey\ 2.app/Contents/MacOS/Timey\ 2
Launching via Terminal ensured I saw every console message. Sure enough, it printed a permission-related warning.
After that launch, it finally appeared in the Accessibility list. I enabled it manually.
Closed. Reopened normally from Finder.
No more warnings. No more blocks. Stable launch every time.
CPU usage stayed under 1–2%, overlay behaved properly, and it resumed timers correctly after sleep — which is usually where small timer utilities break.
I saved this page because it helped confirm how modern macOS systems treat small productivity apps that request system permissions: https://technotafastore.xyz/office-and-productivity/76979-timey-2.html
It aligned with what I was seeing on Sonoma — the security model is stricter, especially with unsigned helpers.
If I Had to Do It Again
I wouldn’t waste time fighting Gatekeeper repeatedly. I’d do it clean from the start:
- Install into /Applications first.
- Clear quarantine once.
- Launch via Terminal to watch permission logs.
- Immediately check Accessibility and other privacy panes.
Most “can’t be opened” issues aren’t corruption. They’re permission mismatches or incomplete notarization.
The irony is that the app itself is simple and lightweight. Once macOS trusts it properly, it behaves perfectly fine. The friction comes from the operating system trying to protect you — and doing it a little aggressively.
OrchardKit didn’t ship something broken. It’s just that Sonoma is unforgiving with small independent builds that request system hooks.
End result: fully working focus timer, clean launches, no security compromises.
And a reminder that on modern macOS, if something “won’t open,” it’s almost never random. It’s usually Gatekeeper, notarization, or privacy controls quietly standing in the way.