Thank you, it looks like since I was calling setTaskCompleted right after calling my post function; and that caused it to not complete the URLSession call. I added a semaphore to wait til the URLSession task completes and thats did the trick.

By any chance did you ever find an answer to this?

Oh wow, thanks cant believe I have been doing it wrong all this time - SMH. Yes, my project has multiple command-line tools and a couple of .app applications. All of the project is compiled via a bash script. Each of them has it's own target and Xcode project which are all tied to a Xcode workspace.

Hi Quinn, Thanks for the reply. But it is signed, thats whats killing me. My project is a Xcode project and I compile it via xcodebuild. bash-3.2codesign -d -vv /private/var/tmp/MPUpdater  Executable=/private/var/tmp/MPUpdater Identifier=com.mp.updater Format=Mach-O universal (x86_64 arm64) CodeDirectory v=20500 size=11103 flags=0x10000(runtime) hashes=338+5 location=embedded Signature size=9048 Authority=Apple Development: Charles Heizer (W42PNHC2DS) Authority=Apple Worldwide Developer Relations Certification Authority Authority=Apple Root CA Timestamp=Apr 8, 2021 at 3:02:23 PM Info.plist entries=7 TeamIdentifier=BLZUAP2L36 Runtime Version=11.1.0 Sealed Resources=none Internal requirements count=1 size=184