diff --git a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendDiagnosticsTestGenerated.java b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendDiagnosticsTestGenerated.java
index 368b4d4b5da..5615e3818ea 100644
--- a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendDiagnosticsTestGenerated.java
+++ b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendDiagnosticsTestGenerated.java
@@ -1098,6 +1098,12 @@ public class FirOldFrontendDiagnosticsTestGenerated extends AbstractFirDiagnosti
                 runTest("compiler/testData/diagnostics/tests/annotations/AnnotatedLoop.kt");
             }
 
+            @Test
+            @TestMetadata("AnnotatedNullableTypes.kt")
+            public void testAnnotatedNullableTypes() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.kt");
+            }
+
             @Test
             @TestMetadata("AnnotatedResultType.kt")
             public void testAnnotatedResultType() throws Exception {
diff --git a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendDiagnosticsWithLightTreeTestGenerated.java b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendDiagnosticsWithLightTreeTestGenerated.java
index 932a845ebed..6df47289d8f 100644
--- a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendDiagnosticsWithLightTreeTestGenerated.java
+++ b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendDiagnosticsWithLightTreeTestGenerated.java
@@ -1098,6 +1098,12 @@ public class FirOldFrontendDiagnosticsWithLightTreeTestGenerated extends Abstrac
                 runTest("compiler/testData/diagnostics/tests/annotations/AnnotatedLoop.kt");
             }
 
+            @Test
+            @TestMetadata("AnnotatedNullableTypes.kt")
+            public void testAnnotatedNullableTypes() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.kt");
+            }
+
             @Test
             @TestMetadata("AnnotatedResultType.kt")
             public void testAnnotatedResultType() throws Exception {
diff --git a/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.fir.kt b/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.fir.kt
new file mode 100644
index 00000000000..61d329fa0bf
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.fir.kt
@@ -0,0 +1,10 @@
+annotation class Ann
+
+val a: <!WRONG_ANNOTATION_TARGET!>@Ann<!> String? = ""
+val b: (<!WRONG_ANNOTATION_TARGET!>@Ann<!> String)? = "" // false negative in K1, OK in K2
+
+@Target(AnnotationTarget.TYPE)
+annotation class TypeAnn
+
+val c: @TypeAnn String? = ""
+val d: (@TypeAnn String)? = ""
diff --git a/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.kt b/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.kt
new file mode 100644
index 00000000000..d42f4c42552
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.kt
@@ -0,0 +1,10 @@
+annotation class Ann
+
+val a: <!WRONG_ANNOTATION_TARGET!>@Ann<!> String? = ""
+val b: (@Ann String)? = "" // false negative in K1, OK in K2
+
+@Target(AnnotationTarget.TYPE)
+annotation class TypeAnn
+
+val c: @TypeAnn String? = ""
+val d: (@TypeAnn String)? = ""
diff --git a/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.txt b/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.txt
new file mode 100644
index 00000000000..134e7a061f7
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.txt
@@ -0,0 +1,20 @@
+package
+
+public val a: @Ann kotlin.String? = ""
+public val b: @Ann kotlin.String? = ""
+public val c: @TypeAnn kotlin.String? = ""
+public val d: @TypeAnn kotlin.String? = ""
+
+public final annotation class Ann : kotlin.Annotation {
+    public constructor Ann()
+    public open override /*1*/ /*fake_override*/ fun equals(/*0*/ other: kotlin.Any?): kotlin.Boolean
+    public open override /*1*/ /*fake_override*/ fun hashCode(): kotlin.Int
+    public open override /*1*/ /*fake_override*/ fun toString(): kotlin.String
+}
+
+@kotlin.annotation.Target(allowedTargets = {AnnotationTarget.TYPE}) public final annotation class TypeAnn : kotlin.Annotation {
+    public constructor TypeAnn()
+    public open override /*1*/ /*fake_override*/ fun equals(/*0*/ other: kotlin.Any?): kotlin.Boolean
+    public open override /*1*/ /*fake_override*/ fun hashCode(): kotlin.Int
+    public open override /*1*/ /*fake_override*/ fun toString(): kotlin.String
+}
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 d9a780547ce..bf16bc1297b 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
@@ -1098,6 +1098,12 @@ public class DiagnosticTestGenerated extends AbstractDiagnosticTest {
                 runTest("compiler/testData/diagnostics/tests/annotations/AnnotatedLoop.kt");
             }
 
+            @Test
+            @TestMetadata("AnnotatedNullableTypes.kt")
+            public void testAnnotatedNullableTypes() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/annotations/AnnotatedNullableTypes.kt");
+            }
+
             @Test
             @TestMetadata("AnnotatedResultType.kt")
             public void testAnnotatedResultType() throws Exception {