I encountered the same problem, but luckily was able to hit a different breakpoint at a later point in the same flow. I moused over the outlined breakpoint and saw the following tool tip:
Xcode won't pause at this breakpoint because it has not been resolved.
Resolving it requires that:
The line at the breakpoint is compiled.
The compiler generates debug information that is not stripped out (check the Build Settings).
The library for the breakpoint is loaded.
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I added the "Background Modes" Capability with "Location updates" checked on.
I verified that the backgroundRefreshStatus is available.
I have added the info.plist keys: NSLocationAlwaysAndWhenInUseUsageDescription, NSLocationWhenInUseUsageDescription, and NSLocationTemporaryUsageDescriptionDictionary with descriptions.
I have tried monitoring for a region, both with and without also invoking startMonitoringSignificantLocationChanges.
I show an alert for region changes while the app is foregrounded, and local notification for region changes when the app is in the background, both of those work. No notifications appear after a force-quit.