diff --git a/java/java-analysis-impl/src/com/intellij/codeInspection/dataFlow/java/ControlFlowAnalyzer.java b/java/java-analysis-impl/src/com/intellij/codeInspection/dataFlow/java/ControlFlowAnalyzer.java
index a2e77b1ec866..c01dc8e760b1 100644
--- a/java/java-analysis-impl/src/com/intellij/codeInspection/dataFlow/java/ControlFlowAnalyzer.java
+++ b/java/java-analysis-impl/src/com/intellij/codeInspection/dataFlow/java/ControlFlowAnalyzer.java
@@ -1076,6 +1076,7 @@ public class ControlFlowAnalyzer extends JavaElementVisitor {
             addInstruction(new GotoInstruction(endGuardOffset));
             ((DeferredOffset)targetOffset).setOffset(getInstructionCount());
             guard.accept(this);
+            generateBoxingUnboxingInstructionFor(guard, PsiTypes.booleanType());
             addInstruction(new ResultOfInstruction(new JavaSwitchLabelTakenAnchor(guard)));
             addInstruction(new ConditionalGotoInstruction(offset, DfTypes.TRUE));
             endGuardOffset.setOffset(getInstructionCount());
diff --git a/java/java-tests/testData/inspection/dataFlow/fixture/SwitchBooleanWhen.java b/java/java-tests/testData/inspection/dataFlow/fixture/SwitchBooleanWhen.java
new file mode 100644
index 000000000000..0b8e77422913
--- /dev/null
+++ b/java/java-tests/testData/inspection/dataFlow/fixture/SwitchBooleanWhen.java
@@ -0,0 +1,13 @@
+import org.jetbrains.annotations.Nullable;
+
+// IDEA-363270
+public class SwitchBooleanWhen {
+  private String testBooleanValue(Object value) {
+    return switch (value) {
+      case Boolean booleanValue when booleanValue -> "true";
+      case Boolean booleanValue when <warning descr="Condition '!booleanValue' is always 'true'">!booleanValue</warning> -> "false";
+      case null -> "null";
+      default -> "unknown";
+    };
+  }
+}
\ No newline at end of file
diff --git a/java/java-tests/testSrc/com/intellij/java/codeInspection/DataFlowInspection21Test.java b/java/java-tests/testSrc/com/intellij/java/codeInspection/DataFlowInspection21Test.java
index d3d134ea0249..76b7d37beede 100644
--- a/java/java-tests/testSrc/com/intellij/java/codeInspection/DataFlowInspection21Test.java
+++ b/java/java-tests/testSrc/com/intellij/java/codeInspection/DataFlowInspection21Test.java
@@ -135,6 +135,8 @@ public class DataFlowInspection21Test extends DataFlowInspectionTestCase {
   public void testInstanceOfPatternAffectNullity() { doTest(); }
 
   public void testNullabilityInEnumSwitch() { doTest(); }
+  
+  public void testSwitchBooleanWhen() { doTest(); }
 
   public void testJetBrainsNotNullByDefault() {
     addJetBrainsNotNullByDefault(myFixture);