diff --git a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosticCompilerTestFE10TestdataTestGenerated.java b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosticCompilerTestFE10TestdataTestGenerated.java
index f9b80c1e453..d36e5e04170 100644
--- a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosticCompilerTestFE10TestdataTestGenerated.java
+++ b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosticCompilerTestFE10TestdataTestGenerated.java
@@ -711,6 +711,12 @@ public class DiagnosticCompilerTestFE10TestdataTestGenerated extends AbstractDia
             runTest("compiler/testData/diagnostics/tests/missingIteratorMissing.kt");
         }
 
+        @Test
+        @TestMetadata("missingWrongAnnotationTarget.kt")
+        public void testMissingWrongAnnotationTarget() throws Exception {
+            runTest("compiler/testData/diagnostics/tests/missingWrongAnnotationTarget.kt");
+        }
+
         @Test
         @TestMetadata("MultilineStringTemplates.kt")
         public void testMultilineStringTemplates() throws Exception {
diff --git a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated.java b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated.java
index 078709b44f2..621942bbff5 100644
--- a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated.java
+++ b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated.java
@@ -711,6 +711,12 @@ public class LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated
             runTest("compiler/testData/diagnostics/tests/missingIteratorMissing.kt");
         }
 
+        @Test
+        @TestMetadata("missingWrongAnnotationTarget.kt")
+        public void testMissingWrongAnnotationTarget() throws Exception {
+            runTest("compiler/testData/diagnostics/tests/missingWrongAnnotationTarget.kt");
+        }
+
         @Test
         @TestMetadata("MultilineStringTemplates.kt")
         public void testMultilineStringTemplates() throws Exception {
diff --git a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirLightTreeOldFrontendDiagnosticsTestGenerated.java b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirLightTreeOldFrontendDiagnosticsTestGenerated.java
index 28cee641e89..76e8e6a499c 100644
--- a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirLightTreeOldFrontendDiagnosticsTestGenerated.java
+++ b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirLightTreeOldFrontendDiagnosticsTestGenerated.java
@@ -711,6 +711,12 @@ public class FirLightTreeOldFrontendDiagnosticsTestGenerated extends AbstractFir
             runTest("compiler/testData/diagnostics/tests/missingIteratorMissing.kt");
         }
 
+        @Test
+        @TestMetadata("missingWrongAnnotationTarget.kt")
+        public void testMissingWrongAnnotationTarget() throws Exception {
+            runTest("compiler/testData/diagnostics/tests/missingWrongAnnotationTarget.kt");
+        }
+
         @Test
         @TestMetadata("MultilineStringTemplates.kt")
         public void testMultilineStringTemplates() throws Exception {
diff --git a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirPsiOldFrontendDiagnosticsTestGenerated.java b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirPsiOldFrontendDiagnosticsTestGenerated.java
index 2ca3a9815cc..afef44f5525 100644
--- a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirPsiOldFrontendDiagnosticsTestGenerated.java
+++ b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirPsiOldFrontendDiagnosticsTestGenerated.java
@@ -711,6 +711,12 @@ public class FirPsiOldFrontendDiagnosticsTestGenerated extends AbstractFirPsiDia
             runTest("compiler/testData/diagnostics/tests/missingIteratorMissing.kt");
         }
 
+        @Test
+        @TestMetadata("missingWrongAnnotationTarget.kt")
+        public void testMissingWrongAnnotationTarget() throws Exception {
+            runTest("compiler/testData/diagnostics/tests/missingWrongAnnotationTarget.kt");
+        }
+
         @Test
         @TestMetadata("MultilineStringTemplates.kt")
         public void testMultilineStringTemplates() throws Exception {
diff --git a/compiler/fir/raw-fir/light-tree2fir/src/org/jetbrains/kotlin/fir/lightTree/converter/LightTreeRawFirExpressionBuilder.kt b/compiler/fir/raw-fir/light-tree2fir/src/org/jetbrains/kotlin/fir/lightTree/converter/LightTreeRawFirExpressionBuilder.kt
index 395fc3552a2..29c7e7db361 100644
--- a/compiler/fir/raw-fir/light-tree2fir/src/org/jetbrains/kotlin/fir/lightTree/converter/LightTreeRawFirExpressionBuilder.kt
+++ b/compiler/fir/raw-fir/light-tree2fir/src/org/jetbrains/kotlin/fir/lightTree/converter/LightTreeRawFirExpressionBuilder.kt
@@ -728,6 +728,7 @@ class LightTreeRawFirExpressionBuilder(
                         symbol = FirPropertySymbol(variable.name)
                         isLocal = true
                         status = FirDeclarationStatusImpl(Visibilities.Local, Modality.FINAL)
+                        annotations += variable.annotations
                     }
                 }
                 DESTRUCTURING_DECLARATION -> subjectExpression =
diff --git a/compiler/fir/raw-fir/psi2fir/src/org/jetbrains/kotlin/fir/builder/PsiRawFirBuilder.kt b/compiler/fir/raw-fir/psi2fir/src/org/jetbrains/kotlin/fir/builder/PsiRawFirBuilder.kt
index 9ad409539c1..c1144787149 100644
--- a/compiler/fir/raw-fir/psi2fir/src/org/jetbrains/kotlin/fir/builder/PsiRawFirBuilder.kt
+++ b/compiler/fir/raw-fir/psi2fir/src/org/jetbrains/kotlin/fir/builder/PsiRawFirBuilder.kt
@@ -2384,6 +2384,7 @@ open class PsiRawFirBuilder(
                         symbol = FirPropertySymbol(name)
                         isLocal = true
                         status = FirDeclarationStatusImpl(Visibilities.Local, Modality.FINAL)
+                        ktSubjectExpression.extractAnnotationsTo(this)
                     }
                 }
                 else -> null
diff --git a/compiler/testData/diagnostics/tests/missingWrongAnnotationTarget.kt b/compiler/testData/diagnostics/tests/missingWrongAnnotationTarget.kt
new file mode 100644
index 00000000000..48b19b9f85c
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/missingWrongAnnotationTarget.kt
@@ -0,0 +1,12 @@
+// FIR_IDENTICAL
+// ISSUE: KT-53565
+
+@Target(AnnotationTarget.CLASS)
+annotation class InvalidAnn
+
+fun wrongAnnotationTargetInWhenSubject() {
+    // Error expected on annotation
+    when(<!WRONG_ANNOTATION_TARGET!>@InvalidAnn<!> val x = 0) {
+        0 -> {}
+    }
+}
diff --git a/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/DiagnosticTestGenerated.java b/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/DiagnosticTestGenerated.java
index b7eeea80914..5fdd6a41f75 100644
--- a/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/DiagnosticTestGenerated.java
+++ b/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/DiagnosticTestGenerated.java
@@ -711,6 +711,12 @@ public class DiagnosticTestGenerated extends AbstractDiagnosticTest {
             runTest("compiler/testData/diagnostics/tests/missingIteratorMissing.kt");
         }
 
+        @Test
+        @TestMetadata("missingWrongAnnotationTarget.kt")
+        public void testMissingWrongAnnotationTarget() throws Exception {
+            runTest("compiler/testData/diagnostics/tests/missingWrongAnnotationTarget.kt");
+        }
+
         @Test
         @TestMetadata("MultilineStringTemplates.kt")
         public void testMultilineStringTemplates() throws Exception {