Packaging Pitfalls, Part 3: Jamf Deployments Pass — But Apps Still Fail

Jamf has become the go-to solution for deploying software across macOS fleets. From enterprise environments to education and government, it’s widely trusted to push configurations, enforce policies, and – most importantly – install applications. Jamf is widely used, but Jamf deployment issues often emerge not from the tool, but from the package itself.

And Jamf won’t tell you that.

You’ll see a green “completed” status in the policy log. Everything looks fine, until someone checks the Mac and realizes: the app isn’t there, it’s broken, or it’s silently failed. That’s when the real troubleshooting begins.

The issue usually isn’t Jamf. It’s the package.

Improperly built packages cause many deployment failures — not the way they are delivered. And in the macOS world, that difference matters a lot more than most expect.

Let’s look at the most common (and costly) pitfalls.

Silent failure from missing notarization and signing

Since macOS Catalina, Apple requires that .pkg installers be both signed with a valid Developer ID and notarized. Skipping either step often leads Gatekeeper to block the installation. But it won’t show a warning. It won’t log an error in Jamf. It will simply do… nothing.

Locally, a test install might seem fine — especially if Gatekeeper has been disabled. But in real-world deployments, especially in secured environments, the install never completes.

Always sign your packages with a valid Developer ID certificate — this ensures they pass Gatekeeper checks and build user trust.

Here’s a basic example of how to sign a .pkg file:

productsign \
--sign "Developer ID Installer: Your Company (TEAMID)" \
YourApp.pkg \
YourApp-signed.pkg

Want to learn more about the notarization process? Check out our article: Notarization Process for macOS Installers. For official requirements and technical details, refer to Apple’s developer documentation

Wrong execution context in scripts

Jamf runs scripts as root, not as the logged-in user. This catches many packagers off guard.

Scripts that reference ~/Library or expect user-level preferences fail silently, because ~ for root points to /var/root, not the user’s actual home directory. Scripts that try to trigger UI prompts or launch agents may do nothing at all.

Use Jamf’s $3 variable to reliably reference the user context. Explicitly test scripts on real endpoints — don’t assume behavior will match your test VM.

Intel-only binaries on Apple Silicon devices

We’re well into the Apple Silicon era, but some packages still include Intel-only binaries that won’t execute properly on M1/M2 Macs — especially if Rosetta isn’t pre-installed.

Even shell scripts can behave differently, since system paths, default shell environments, and permissions vary across architectures.

Detect architecture explicitly (uname -m) and branch logic if needed. Build and test universal binaries wherever possible.

No Logging = Invisible Jamf Deployment Issues

One of the most frustrating Jamf deployment issues happens when the app doesn’t install, files are missing — yet the log says the job succeeded.

Without proper logging, you’re stuck guessing: was the package broken, did the script exit early, or did the target path not exist?

Log everything — especially in postinstall scripts. Write to predictable locations like /tmp/yourtool-install.log and use meaningful exit codes to flag problems.

Overreliance on snapshot-based packaging (Jamf Composer)

Composer — Jamf’s own packaging tool — is often a gateway into macOS software deployment. It’s simple: take a snapshot before and after installing an app, and Composer generates a .pkg file.

But simplicity can be dangerous.

Snapshot-based packages often:

• include unnecessary files like caches, logs, or temp content;
• place files in user-specific paths;
• fail to reproduce key install logic from the original installer (e.g., scripts, launch agents, permissions);
• behave inconsistently on other Macs — especially with different OS versions or hardware.

What works on your test device might completely fail when deployed to a wider fleet.

While Composer can be a great entry point into Mac packaging, it’s important to understand where manual snapshot methods may fall short.

For complex or large-scale deployments, consider a packaging solution like Apptimized Factory, which provides full control, quality assurance, and packages built for scalable macOS deployment. You can request ready-to-use .pkg, .dmg, .app, or .mpkg files — all signed, notarized, and tested across Apple Silicon and Intel devices.

Jamf only does what you tell it to do

Jamf doesn’t validate, fix, or warn. It pushes the package — and assumes you know what’s inside.

That’s why packaging matters just as much as deployment.

We create high-quality macOS packages that are signed, tested, architecture-aware, and ready for real-world deployment.