Original poster here!
Update: I've done extensive troubleshooting and found the root cause:
/Applications/calibre.app/Contents/MacOS/calibre (Terminal) : 2-3 seconds
/Applications/calibre.app (or Finder) : 30+ minutes
The bottleneck:
spctl -a -vv /Applications/calibre.app hangs for 10+ seconds (should be <1 sec). System logs show syspolicyd stuck in a progress callback loop during trust evaluation. Console trace shows 15-second gap when loading QtCore framework.
What I've tried (all failed):
Removed quarantine, cleared all trust/policy caches
Safe Mode + SIP disable: deleted SystemPolicy*, gkopaque, TCC, certificate stores
Fresh Calibre install
syspolicyd restart/reset
NVRAM reset
Verification:
Other Qt apps (like Telegram Desktop) start instantly via Finder
codesign --verify --deep: valid
Calibre has 85 frameworks vs Telegram's 33
Something in Calibre's bundle structure triggers a macOS LaunchServices/syspolicyd evaluation loop that doesn't occur with Terminal launch. I have detailed logs if helpful.
Is there a known issue with large Qt bundles or embedded Python frameworks?