diff --git a/compiler/fir/fir2ir/tests-gen/org/jetbrains/kotlin/test/runners/codegen/FirBlackBoxCodegenTestGenerated.java b/compiler/fir/fir2ir/tests-gen/org/jetbrains/kotlin/test/runners/codegen/FirBlackBoxCodegenTestGenerated.java
index e57692aff42..ff0782803c6 100644
--- a/compiler/fir/fir2ir/tests-gen/org/jetbrains/kotlin/test/runners/codegen/FirBlackBoxCodegenTestGenerated.java
+++ b/compiler/fir/fir2ir/tests-gen/org/jetbrains/kotlin/test/runners/codegen/FirBlackBoxCodegenTestGenerated.java
@@ -52,6 +52,12 @@ public class FirBlackBoxCodegenTestGenerated extends AbstractFirBlackBoxCodegenT
             runTest("compiler/testData/codegen/box/annotations/annotatedObjectLiteral.kt");
         }
 
+        @Test
+        @TestMetadata("annotationOnWhen.kt")
+        public void testAnnotationOnWhen() throws Exception {
+            runTest("compiler/testData/codegen/box/annotations/annotationOnWhen.kt");
+        }
+
         @Test
         @TestMetadata("annotationProperty.kt")
         public void testAnnotationProperty() throws Exception {
diff --git a/compiler/fir/resolve/src/org/jetbrains/kotlin/fir/resolve/transformers/body/resolve/FirExpressionsResolveTransformer.kt b/compiler/fir/resolve/src/org/jetbrains/kotlin/fir/resolve/transformers/body/resolve/FirExpressionsResolveTransformer.kt
index 083121efb21..1878ab11080 100644
--- a/compiler/fir/resolve/src/org/jetbrains/kotlin/fir/resolve/transformers/body/resolve/FirExpressionsResolveTransformer.kt
+++ b/compiler/fir/resolve/src/org/jetbrains/kotlin/fir/resolve/transformers/body/resolve/FirExpressionsResolveTransformer.kt
@@ -639,6 +639,7 @@ open class FirExpressionsResolveTransformer(transformer: FirBodyResolveTransform
         }
 
         checkNotNullCall.argumentList.transformArguments(transformer, ResolutionMode.ContextDependent)
+        checkNotNullCall.transformAnnotations(transformer, ResolutionMode.ContextIndependent)
 
         var callCompleted = false
         val result = components.syntheticCallGenerator.generateCalleeForCheckNotNullCall(checkNotNullCall, resolutionContext)?.let {
diff --git a/compiler/testData/codegen/box/annotations/annotationOnWhen.kt b/compiler/testData/codegen/box/annotations/annotationOnWhen.kt
new file mode 100644
index 00000000000..2acd8d99853
--- /dev/null
+++ b/compiler/testData/codegen/box/annotations/annotationOnWhen.kt
@@ -0,0 +1,16 @@
+// TARGET_BACKEND: JVM
+
+enum class SomeEnum {
+    A, B
+}
+
+@Suppress("SOMETHING")
+fun box():String {
+    val someVal = SomeEnum.A
+    @Suppress("UNNECESSARY_NOT_NULL_ASSERTION")
+    when (someVal) {
+        SomeEnum.A -> {}
+        SomeEnum.B -> {}
+    }!! // !! is used to force compile-time exhaustiveness
+    return "OK"
+}
\ No newline at end of file
diff --git a/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/codegen/BlackBoxCodegenTestGenerated.java b/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/codegen/BlackBoxCodegenTestGenerated.java
index 87d71ed0a68..e65e5008e14 100644
--- a/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/codegen/BlackBoxCodegenTestGenerated.java
+++ b/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/codegen/BlackBoxCodegenTestGenerated.java
@@ -52,6 +52,12 @@ public class BlackBoxCodegenTestGenerated extends AbstractBlackBoxCodegenTest {
             runTest("compiler/testData/codegen/box/annotations/annotatedObjectLiteral.kt");
         }
 
+        @Test
+        @TestMetadata("annotationOnWhen.kt")
+        public void testAnnotationOnWhen() throws Exception {
+            runTest("compiler/testData/codegen/box/annotations/annotationOnWhen.kt");
+        }
+
         @Test
         @TestMetadata("annotationProperty.kt")
         public void testAnnotationProperty() throws Exception {
diff --git a/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/codegen/IrBlackBoxCodegenTestGenerated.java b/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/codegen/IrBlackBoxCodegenTestGenerated.java
index ca528f650ae..52e7e661251 100644
--- a/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/codegen/IrBlackBoxCodegenTestGenerated.java
+++ b/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/codegen/IrBlackBoxCodegenTestGenerated.java
@@ -52,6 +52,12 @@ public class IrBlackBoxCodegenTestGenerated extends AbstractIrBlackBoxCodegenTes
             runTest("compiler/testData/codegen/box/annotations/annotatedObjectLiteral.kt");
         }
 
+        @Test
+        @TestMetadata("annotationOnWhen.kt")
+        public void testAnnotationOnWhen() throws Exception {
+            runTest("compiler/testData/codegen/box/annotations/annotationOnWhen.kt");
+        }
+
         @Test
         @TestMetadata("annotationProperty.kt")
         public void testAnnotationProperty() throws Exception {
diff --git a/compiler/tests-gen/org/jetbrains/kotlin/codegen/LightAnalysisModeTestGenerated.java b/compiler/tests-gen/org/jetbrains/kotlin/codegen/LightAnalysisModeTestGenerated.java
index 5796606ac7b..3a6a627c381 100644
--- a/compiler/tests-gen/org/jetbrains/kotlin/codegen/LightAnalysisModeTestGenerated.java
+++ b/compiler/tests-gen/org/jetbrains/kotlin/codegen/LightAnalysisModeTestGenerated.java
@@ -57,6 +57,11 @@ public class LightAnalysisModeTestGenerated extends AbstractLightAnalysisModeTes
             runTest("compiler/testData/codegen/box/annotations/annotatedObjectLiteral.kt");
         }
 
+        @TestMetadata("annotationOnWhen.kt")
+        public void testAnnotationOnWhen() throws Exception {
+            runTest("compiler/testData/codegen/box/annotations/annotationOnWhen.kt");
+        }
+
         @TestMetadata("annotationProperty.kt")
         public void testAnnotationProperty() throws Exception {
             runTest("compiler/testData/codegen/box/annotations/annotationProperty.kt");