I'm not sure the exact scenario required to trigger this, but attempting to connect to the VM Service of a frontend_server snapshot was sufficient to reproduce it. Debugging from the Observatory works.
To get the Observatory to print out:
diff --git a/packages/flutter_tools/lib/src/compile.dart b/packages/flutter_tools/lib/src/compile.dart
index 76ba6793b8..bc681ee8c9 100644
--- a/packages/flutter_tools/lib/src/compile.dart
+++ b/packages/flutter_tools/lib/src/compile.dart
@@ -696,11 +696,13 @@ class DefaultResidentCompiler implements ResidentCompiler {
);
final List<String> command = <String>[
_artifacts.getHostArtifact(HostArtifact.engineDartBinary).path,
+ '--observe',
'--disable-dart-dev',
frontendServer,
'--sdk-root',
sdkRoot,
'--incremental',
+ '--verbose',
if (testCompilation)
'--no-print-incremental-dependencies',
'--target=$targetModel',
To trigger the crash I'm trying to debug (requires running a flutter web app)
diff --git a/packages/flutter_tools/lib/src/resident_runner.dart b/packages/flutter_tools/lib/src/resident_runner.dart
index 0342a56138..786db092cd 100644
--- a/packages/flutter_tools/lib/src/resident_runner.dart
+++ b/packages/flutter_tools/lib/src/resident_runner.dart
@@ -116,6 +116,7 @@ class FlutterDevice {
} else {
assert(false);
}
+ extraFrontEndOptions.add('--enable-experiment=alternative-invalidation-strategy');
generator = ResidentCompiler(
globals.artifacts.getHostArtifact(HostArtifact.flutterWebSdk).path,
Note that it says it is paused in the debugger, but there is no debugger pane and hitting step doesn't seem to do anything.

I'm not sure the exact scenario required to trigger this, but attempting to connect to the VM Service of a frontend_server snapshot was sufficient to reproduce it. Debugging from the Observatory works.
To get the Observatory to print out:
To trigger the crash I'm trying to debug (requires running a flutter web app)
Note that it says it is paused in the debugger, but there is no debugger pane and hitting step doesn't seem to do anything.