diff --git a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosisCompilerTestFE10TestdataTestGenerated.java b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosisCompilerTestFE10TestdataTestGenerated.java
index 1cde13a6d25..8b4690b87e1 100644
--- a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosisCompilerTestFE10TestdataTestGenerated.java
+++ b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosisCompilerTestFE10TestdataTestGenerated.java
@@ -11964,6 +11964,12 @@ public class DiagnosisCompilerTestFE10TestdataTestGenerated extends AbstractDiag
                 runTest("compiler/testData/diagnostics/tests/generics/kt34729.kt");
             }
 
+            @Test
+            @TestMetadata("kt53656.kt")
+            public void testKt53656() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/generics/kt53656.kt");
+            }
+
             @Test
             @TestMetadata("kt5508.kt")
             public void testKt5508() throws Exception {
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 624b3f405f6..87972d881e6 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
@@ -11964,6 +11964,12 @@ public class FirOldFrontendDiagnosticsTestGenerated extends AbstractFirDiagnosti
                 runTest("compiler/testData/diagnostics/tests/generics/kt34729.kt");
             }
 
+            @Test
+            @TestMetadata("kt53656.kt")
+            public void testKt53656() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/generics/kt53656.kt");
+            }
+
             @Test
             @TestMetadata("kt5508.kt")
             public void testKt5508() 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 c9efc79e2b6..499d38de77c 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
@@ -11964,6 +11964,12 @@ public class FirOldFrontendDiagnosticsWithLightTreeTestGenerated extends Abstrac
                 runTest("compiler/testData/diagnostics/tests/generics/kt34729.kt");
             }
 
+            @Test
+            @TestMetadata("kt53656.kt")
+            public void testKt53656() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/generics/kt53656.kt");
+            }
+
             @Test
             @TestMetadata("kt5508.kt")
             public void testKt5508() throws Exception {
diff --git a/compiler/testData/diagnostics/tests/generics/kt53656.fir.kt b/compiler/testData/diagnostics/tests/generics/kt53656.fir.kt
new file mode 100644
index 00000000000..bb429822a01
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/generics/kt53656.fir.kt
@@ -0,0 +1,15 @@
+interface One<T>
+fun <E, R> foo(): E where E : Number, E : One<R>, R : One<E> = null!!
+
+interface Entity<T>
+abstract class SecuredEntity<out E>(val entity: E) where E : Entity<Int>, E : SecurityCodeAware<*,*>
+interface SecurityCodeAware<out E, R : SecuredEntity<E>> where E : Entity<Int>, E : SecurityCodeAware<E, R>
+fun <E, R : SecuredEntity<E>> SecurityCodeAware<E, R>.secured() : R where E : Entity<Int>, E : SecurityCodeAware<E, R> = <!RETURN_TYPE_MISMATCH!>when(this) {
+    is Order -> SecuredOrder(this)
+    else -> null!!
+}<!>
+class Order : Entity<Int>
+class SecuredOrder(order: Order) : SecuredEntity<<!UPPER_BOUND_VIOLATED!>Order<!>>(<!ARGUMENT_TYPE_MISMATCH!>order<!>)
+fun main() {
+    val securedOrder = Order().<!UNRESOLVED_REFERENCE_WRONG_RECEIVER!>secured<!>()
+}
diff --git a/compiler/testData/diagnostics/tests/generics/kt53656.kt b/compiler/testData/diagnostics/tests/generics/kt53656.kt
new file mode 100644
index 00000000000..72ba7e7bb76
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/generics/kt53656.kt
@@ -0,0 +1,15 @@
+interface One<T>
+fun <E, R> foo(): E where E : Number, E : One<R>, R : One<E> = null!!
+
+interface Entity<T>
+abstract class SecuredEntity<out E>(val entity: E) where E : Entity<Int>, E : SecurityCodeAware<*,*>
+interface SecurityCodeAware<out E, R : SecuredEntity<E>> where E : Entity<Int>, E : SecurityCodeAware<E, R>
+fun <E, R : SecuredEntity<E>> SecurityCodeAware<E, R>.secured() : R where E : Entity<Int>, E : SecurityCodeAware<E, R> = when(this) {
+    is <!INCOMPATIBLE_TYPES!>Order<!> -> <!TYPE_MISMATCH!>SecuredOrder(<!DEBUG_INFO_SMARTCAST!>this<!>)<!>
+    else -> null!!
+}
+class Order : Entity<Int>
+class SecuredOrder(order: Order) : SecuredEntity<<!UPPER_BOUND_VIOLATED!>Order<!>>(order)
+fun main() {
+    val securedOrder = Order().<!UNRESOLVED_REFERENCE_WRONG_RECEIVER!>secured<!>()
+}
diff --git a/compiler/testData/diagnostics/tests/generics/kt53656.txt b/compiler/testData/diagnostics/tests/generics/kt53656.txt
new file mode 100644
index 00000000000..3aed662fc2d
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/generics/kt53656.txt
@@ -0,0 +1,46 @@
+package
+
+public fun </*0*/ E : kotlin.Number, /*1*/ R : One<E>> foo(): E where E : One<R>
+public fun main(): kotlin.Unit
+public fun </*0*/ E : Entity<kotlin.Int>, /*1*/ R : SecuredEntity<E>> SecurityCodeAware<E, R>.secured(): R where E : SecurityCodeAware<E, R>
+
+public interface Entity</*0*/ T> {
+    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
+}
+
+public interface One</*0*/ T> {
+    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
+}
+
+public final class Order : Entity<kotlin.Int> {
+    public constructor Order()
+    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
+}
+
+public abstract class SecuredEntity</*0*/ out E : Entity<kotlin.Int>> where E : SecurityCodeAware<*, *> {
+    public constructor SecuredEntity</*0*/ out E : Entity<kotlin.Int>>(/*0*/ entity: E) where E : SecurityCodeAware<*, *>
+    public final val entity: E
+    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
+}
+
+public final class SecuredOrder : SecuredEntity<Order> {
+    public constructor SecuredOrder(/*0*/ order: Order)
+    public final override /*1*/ /*fake_override*/ val entity: Order
+    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
+}
+
+public interface SecurityCodeAware</*0*/ out E : Entity<kotlin.Int>, /*1*/ R : SecuredEntity<E>> where E : SecurityCodeAware<E, R> {
+    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 f501e3a2a34..9a68f88f3a5 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
@@ -11970,6 +11970,12 @@ public class DiagnosticTestGenerated extends AbstractDiagnosticTest {
                 runTest("compiler/testData/diagnostics/tests/generics/kt34729.kt");
             }
 
+            @Test
+            @TestMetadata("kt53656.kt")
+            public void testKt53656() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/generics/kt53656.kt");
+            }
+
             @Test
             @TestMetadata("kt5508.kt")
             public void testKt5508() throws Exception {