Hey — listen, I spent a good chunk of yesterday evening poking at FreeSection (app) on macOS, and I figured I’d dump this here the same way I’d explain it to you in Slack. No polish, no promo tone. Just what broke, what I misunderstood, and what actually fixed it.
The task itself was boring in a good way. I wanted a small utility to split and reorganize large text and CSV files before importing them into another tool. Nothing heavy. I grabbed the app, dropped it into Applications on my M1 MacBook Air running macOS Sonoma 14.2, clicked the icon… and immediately got hit with the classic macOS dialog: “FreeSection can’t be opened because Apple cannot check it for malicious software.”
At first, I shrugged. Gatekeeper again. This is OrchardKit territory — useful tools, often unsigned or lightly notarized, assuming the user knows how macOS security works.
What I tried first (and why it didn’t help)
My first move was the lazy one: right-click → Open → Open Anyway. The dialog disappeared, Finder looked satisfied… and then nothing. No window. No error. The Dock icon bounced once and vanished. That’s always the worst state — not crashing loudly, just quietly opting out of existence.
I rebooted (because muscle memory). Same result.
Next stop was System Settings → Privacy & Security, scrolling down to see if macOS had left me an “Open Anyway” button. Nothing. The system behaved like the app had never tried to launch. At this point, it was clear this wasn’t just Gatekeeper being dramatic.
Apple’s own explanation of this behavior exists, but it’s very Apple about it — technically correct, emotionally distant: https://support.apple.com/guide/mac-help/open-a-mac-app-from-an-unidentified-developer-mh40616/mac
The wrong assumption
I assumed the binary itself was the problem — broken build, incompatible architecture, maybe Intel-only. I checked the app with file and codesign in Terminal. Signature wasn’t perfect, but it wasn’t garbage either. Clearing the quarantine flag helped Gatekeeper shut up, but the silent exit remained.
That’s when it clicked: this wasn’t a launch problem. It was a permissions problem happening before the UI even had a chance to exist.
What actually worked
Instead of launching it from Finder, I ran it directly from Terminal. That changed everything. Suddenly, the process didn’t die instantly. Instead, macOS threw up a delayed system prompt asking for file system access. That prompt had never appeared before.
Once I allowed file access, the app finally stayed alive — but still couldn’t open anything useful. The UI loaded, but selecting a file did nothing. No error. Just empty behavior.
The second missing piece turned out to be Full Disk Access. FreeSection needs to read and split files across arbitrary directories, and modern macOS treats that as a trust issue. After explicitly adding it under Privacy & Security → Full Disk Access, everything snapped into place.
Apple documents this model pretty clearly here: https://support.apple.com/guide/mac-help/control-access-to-your-mac-mh43185/mac and the underlying reasoning from the developer side: https://developer.apple.com/documentation/security/protecting_user_privacy
Once those permissions were set, the tool behaved exactly as advertised. Large files loaded instantly, sections split cleanly, no lag, no weird sandbox errors. Performance was solid — very much what you’d expect from a focused OrchardKit-style utility.
While double-checking that I wasn’t missing some known macOS quirk, I bookmarked this page because it matched the behavior I was seeing almost one-to-one and confirmed I wasn’t dealing with a bad build or unofficial fork: https://planetgpa.com/office-and-productivity/51917-freesection.html
What I’d do differently next time
If I had to compress the lesson for future me, it’d be this:
- If macOS blocks silently, launch from Terminal once.
- Gatekeeper is just the first filter; permissions come later.
- File utilities almost always need explicit disk access now.
- No error message doesn’t mean no error — it means macOS decided for you.
Once configured, FreeSection turned out to be exactly the quiet, dependable tool I wanted. The frustrating part wasn’t the app — it was convincing macOS to trust it enough to let it run.
Anyway. Writing this down while it’s still fresh. If you install it and it seems to ghost you on launch, you’re not losing it. It’s just macOS doing its thing again.