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 8b7f3bd0746..1c7ce921cbb 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
@@ -22294,6 +22294,12 @@ public class DiagnosticCompilerTestFE10TestdataTestGenerated extends AbstractDia
         runTest("compiler/testData/diagnostics/tests/j+k/kjkPropertyAndExtensionProperty.kt");
       }
 
+      @Test
+      @TestMetadata("kjkRawTypeWithKotlinUpperBound.kt")
+      public void testKjkRawTypeWithKotlinUpperBound() {
+        runTest("compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.kt");
+      }
+
       @Test
       @TestMetadata("kt1402.kt")
       public void testKt1402() {
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 3c5ec07e069..58cb0d03613 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
@@ -22294,6 +22294,12 @@ public class LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated
         runTest("compiler/testData/diagnostics/tests/j+k/kjkPropertyAndExtensionProperty.kt");
       }
 
+      @Test
+      @TestMetadata("kjkRawTypeWithKotlinUpperBound.kt")
+      public void testKjkRawTypeWithKotlinUpperBound() {
+        runTest("compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.kt");
+      }
+
       @Test
       @TestMetadata("kt1402.kt")
       public void testKt1402() {
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 fecd4274410..93a5bdb8592 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
@@ -22288,6 +22288,12 @@ public class FirLightTreeOldFrontendDiagnosticsTestGenerated extends AbstractFir
         runTest("compiler/testData/diagnostics/tests/j+k/kjkPropertyAndExtensionProperty.kt");
       }
 
+      @Test
+      @TestMetadata("kjkRawTypeWithKotlinUpperBound.kt")
+      public void testKjkRawTypeWithKotlinUpperBound() {
+        runTest("compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.kt");
+      }
+
       @Test
       @TestMetadata("kt1402.kt")
       public void testKt1402() {
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 0ea4edd3d78..76a5ff18383 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
@@ -22294,6 +22294,12 @@ public class FirPsiOldFrontendDiagnosticsTestGenerated extends AbstractFirPsiDia
         runTest("compiler/testData/diagnostics/tests/j+k/kjkPropertyAndExtensionProperty.kt");
       }
 
+      @Test
+      @TestMetadata("kjkRawTypeWithKotlinUpperBound.kt")
+      public void testKjkRawTypeWithKotlinUpperBound() {
+        runTest("compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.kt");
+      }
+
       @Test
       @TestMetadata("kt1402.kt")
       public void testKt1402() {
diff --git a/compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.fir.kt b/compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.fir.kt
new file mode 100644
index 00000000000..928c205b1d5
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.fir.kt
@@ -0,0 +1,16 @@
+// ISSUE: KT-66158
+// FILE: Java1.java
+public class Java1 extends KotlinClass { }
+
+// FILE: 1.kt
+open class KotlinClass<T : Number> {
+    open fun bar(): T? {
+        return null!!
+    }
+}
+
+class A : Java1()
+
+fun test(a: A) {
+    val k: Number = <!INITIALIZER_TYPE_MISMATCH, TYPE_MISMATCH!>a.bar()<!>
+}
\ No newline at end of file
diff --git a/compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.kt b/compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.kt
new file mode 100644
index 00000000000..605b4e0f978
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.kt
@@ -0,0 +1,16 @@
+// ISSUE: KT-66158
+// FILE: Java1.java
+public class Java1 extends KotlinClass { }
+
+// FILE: 1.kt
+open class KotlinClass<T : Number> {
+    open fun bar(): T? {
+        return null!!
+    }
+}
+
+class A : Java1()
+
+fun test(a: A) {
+    val k: Number = <!TYPE_MISMATCH!>a.bar()<!>
+}
\ No newline at end of file
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 bd8c5b4c9db..ef09852d34d 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
@@ -22294,6 +22294,12 @@ public class DiagnosticTestGenerated extends AbstractDiagnosticTest {
         runTest("compiler/testData/diagnostics/tests/j+k/kjkPropertyAndExtensionProperty.kt");
       }
 
+      @Test
+      @TestMetadata("kjkRawTypeWithKotlinUpperBound.kt")
+      public void testKjkRawTypeWithKotlinUpperBound() {
+        runTest("compiler/testData/diagnostics/tests/j+k/kjkRawTypeWithKotlinUpperBound.kt");
+      }
+
       @Test
       @TestMetadata("kt1402.kt")
       public void testKt1402() {