diff --git a/clwb/src/META-INF/clwb.xml b/clwb/src/META-INF/clwb.xml
index 9782a007564..8d84ef90e4c 100644
--- a/clwb/src/META-INF/clwb.xml
+++ b/clwb/src/META-INF/clwb.xml
@@ -33,6 +33,7 @@
     <actionConfigurationCustomizer implementation="com.google.idea.blaze.plugin.ClwbHideMakeActions"/>
     <registryKey defaultValue="false" description="Disable the extra debug flags in debug C/C++ builds" key="bazel.clwb.debug.extraflags.disabled"/>
     <registryKey defaultValue="false" description="Disable the fission flag in debug C/C++ builds" key="bazel.clwb.debug.fission.disabled"/>
+    <registryKey defaultValue="true" description="Enforce dbg compilation mode for debug runs" key="bazel.clwb.debug.enforce.dbg.compilation.mode"/>
     <registryKey defaultValue="true" description="Use GDB-Server instead of bundled GDB version" key="bazel.clwb.debug.use.gdb.server"/>
     <registryKey defaultValue="false" description="Use the debugger selected in the default toolchain" key="bazel.clwb.debug.use.default.toolchain"/>
   </extensions>
diff --git a/clwb/src/com/google/idea/blaze/clwb/run/BlazeCidrRunConfigurationRunner.java b/clwb/src/com/google/idea/blaze/clwb/run/BlazeCidrRunConfigurationRunner.java
index 3429fd59d15..2ce3cc1841f 100644
--- a/clwb/src/com/google/idea/blaze/clwb/run/BlazeCidrRunConfigurationRunner.java
+++ b/clwb/src/com/google/idea/blaze/clwb/run/BlazeCidrRunConfigurationRunner.java
@@ -44,6 +44,10 @@
 import com.intellij.util.PathUtil;
 import com.jetbrains.cidr.execution.CidrCommandLineState;
 
+import com.jetbrains.cidr.lang.toolchains.CidrSwitchBuilder;
+import com.jetbrains.cidr.lang.workspace.compiler.ClangClCompilerKind;
+import com.jetbrains.cidr.lang.workspace.compiler.ClangCompilerKind;
+import com.jetbrains.cidr.lang.workspace.compiler.MSVCCompilerKind;
 import javax.annotation.Nullable;
 import java.io.File;
 import java.util.List;
@@ -110,22 +114,39 @@ private ImmutableList<String> getExtraDebugFlags(ExecutionEnvironment env) {
     }
 
     final var flagsBuilder = ImmutableList.<String>builder();
-
-    if (debuggerKind == BlazeDebuggerKind.BUNDLED_LLDB && !Registry.is("bazel.trim.absolute.path.disabled")) {
-      flagsBuilder.add("--copt=-fdebug-compilation-dir=" + WorkspaceRoot.fromProject(env.getProject()));
-
-      if (SystemInfo.isMac) {
-        flagsBuilder.add("--linkopt=-Wl,-oso_prefix,.");
-      }
+    if (Registry.is("bazel.clwb.debug.enforce.dbg.compilation.mode")) {
+      flagsBuilder.add("--compilation_mode=dbg");
+      flagsBuilder.add("--strip=never");
+      flagsBuilder.add("--dynamic_mode=off");
     }
 
-    flagsBuilder.add("--compilation_mode=dbg");
-    flagsBuilder.add("--copt=-O0");
-    flagsBuilder.add("--copt=-g");
-    flagsBuilder.add("--strip=never");
-    flagsBuilder.add("--dynamic_mode=off");
-    flagsBuilder.addAll(BlazeGDBServerProvider.getOptionalFissionArguments());
+    var compilerKind = RunConfigurationUtils.getCompilerKind(configuration);
+    if (compilerKind == ClangClCompilerKind.INSTANCE || compilerKind == MSVCCompilerKind.INSTANCE) {
+      var sb = new CidrSwitchBuilder();
+      var sb2 = compilerKind.getSwitchBuilder(sb);
+      sb2
+          .withDebugInfo(-1) // ignored for msvc/clangcl
+          .withDisableOptimization();
+
+      sb2.buildRaw().forEach((opt) -> {
+        flagsBuilder.add("--copt=" + opt);
+      });
+
+    } else {
+      if (debuggerKind == BlazeDebuggerKind.BUNDLED_LLDB && !Registry.is(
+          "bazel.trim.absolute.path.disabled")) {
+        flagsBuilder.add(
+            "--copt=-fdebug-compilation-dir=" + WorkspaceRoot.fromProject(env.getProject()));
+
+        if (SystemInfo.isMac) {
+          flagsBuilder.add("--linkopt=-Wl,-oso_prefix,.");
+        }
+      }
 
+      flagsBuilder.add("--copt=-O0");
+      flagsBuilder.add("--copt=-g");
+      flagsBuilder.addAll(BlazeGDBServerProvider.getOptionalFissionArguments());
+    }
     return flagsBuilder.build();
   }
 
diff --git a/clwb/tests/headlesstests/com/google/idea/blaze/clwb/ExecutionTest.java b/clwb/tests/headlesstests/com/google/idea/blaze/clwb/ExecutionTest.java
index 8051c1e7403..d2841043553 100644
--- a/clwb/tests/headlesstests/com/google/idea/blaze/clwb/ExecutionTest.java
+++ b/clwb/tests/headlesstests/com/google/idea/blaze/clwb/ExecutionTest.java
@@ -3,6 +3,7 @@
 import static com.google.common.truth.Truth.assertThat;
 
 import com.google.idea.blaze.base.run.producers.BlazeBuildFileRunConfigurationProducer;
+import com.google.idea.blaze.clwb.base.AllowedVfsRoot;
 import com.google.idea.blaze.clwb.base.ClwbHeadlessTestCase;
 import com.google.idea.blaze.common.Label;
 import com.intellij.execution.ExecutionListener;
@@ -12,6 +13,7 @@
 import com.intellij.execution.PsiLocation;
 import com.intellij.execution.actions.ConfigurationContext;
 import com.intellij.execution.actions.RunConfigurationProducer;
+import com.intellij.execution.executors.DefaultDebugExecutor;
 import com.intellij.execution.executors.DefaultRunExecutor;
 import com.intellij.execution.impl.ExecutionManagerImpl;
 import com.intellij.execution.process.ProcessHandler;
@@ -22,7 +24,10 @@
 import com.intellij.openapi.actionSystem.PlatformCoreDataKeys;
 import com.intellij.openapi.actionSystem.impl.SimpleDataContext;
 import com.intellij.openapi.module.ModuleUtilCore;
+import com.intellij.openapi.util.SystemInfo;
 import com.intellij.testFramework.PlatformTestUtil;
+import com.intellij.util.system.OS;
+import java.util.ArrayList;
 import java.util.concurrent.CompletableFuture;
 import java.util.concurrent.TimeUnit;
 import org.jetbrains.annotations.NotNull;
@@ -33,12 +38,30 @@
 @RunWith(JUnit4.class)
 public class ExecutionTest extends ClwbHeadlessTestCase {
 
+  @Override
+  protected void addAllowedVfsRoots(ArrayList<AllowedVfsRoot> roots) {
+    super.addAllowedVfsRoots(roots);
+
+    // use flat?
+    String path;
+    if (SystemInfo.isWindows) {
+      path = "main/hello-world.exe";
+    } else {
+      path = "main/hello-world";
+    }
+
+    var fastBuildRoot = AllowedVfsRoot.bazelBinRecursive(myBazelInfo, path);
+    var debugBuildRoot = AllowedVfsRoot.recursive(fastBuildRoot.toString().replace("fastbuild", "dbg"));
+    roots.add(debugBuildRoot);
+  }
+
   @Test
   public void testClwb() throws Exception {
     final var errors = runSync(defaultSyncParams().build());
     errors.assertNoErrors();
 
     checkRun();
+    checkDebug();
     checkTest();
   }
 
@@ -47,6 +70,11 @@ private void checkRun() throws Exception {
     assertThat(result).isEqualTo(0);
   }
 
+  private void checkDebug() throws Exception {
+    final var result = execute(Label.of("//main:hello-world"), DefaultDebugExecutor.EXECUTOR_ID);
+    assertThat(result).isEqualTo(0);
+  }
+
   private void checkTest() throws Exception {
     final var result = execute(Label.of("//main:test"), DefaultRunExecutor.EXECUTOR_ID);
     assertThat(result).isEqualTo(0);
@@ -61,7 +89,7 @@ private int execute(Label label, String executorId) throws Exception {
         .add(Location.DATA_KEY, PsiLocation.fromPsiElement(element))
         .build(), ActionPlaces.UNKNOWN);
 
-    final var executor = ExecutorRegistry.getInstance().getExecutorById(DefaultRunExecutor.EXECUTOR_ID);
+    final var executor = ExecutorRegistry.getInstance().getExecutorById(executorId);
     assertThat(executor).isNotNull();
 
     final var producer = RunConfigurationProducer.getInstance(BlazeBuildFileRunConfigurationProducer.class);