diff --git a/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/checkers/EnumDeclaringClassDeprecationChecker.kt b/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/checkers/EnumDeclaringClassDeprecationChecker.kt
new file mode 100644
index 00000000000..e971ce38408
--- /dev/null
+++ b/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/checkers/EnumDeclaringClassDeprecationChecker.kt
@@ -0,0 +1,29 @@
+/*
+ * Copyright 2010-2022 JetBrains s.r.o. and Kotlin Programming Language contributors.
+ * Use of this source code is governed by the Apache 2.0 license that can be found in the license/LICENSE.txt file.
+ */
+
+package org.jetbrains.kotlin.resolve.jvm.checkers
+
+import com.intellij.psi.PsiElement
+import org.jetbrains.kotlin.descriptors.CallableMemberDescriptor
+import org.jetbrains.kotlin.descriptors.PropertyDescriptor
+import org.jetbrains.kotlin.name.FqName
+import org.jetbrains.kotlin.name.StandardClassIds
+import org.jetbrains.kotlin.resolve.calls.checkers.CallChecker
+import org.jetbrains.kotlin.resolve.calls.checkers.CallCheckerContext
+import org.jetbrains.kotlin.resolve.calls.model.ResolvedCall
+import org.jetbrains.kotlin.resolve.descriptorUtil.classId
+import org.jetbrains.kotlin.resolve.jvm.diagnostics.ErrorsJvm
+import org.jetbrains.kotlin.resolve.scopes.receivers.ExtensionReceiver
+
+object EnumDeclaringClassDeprecationChecker : CallChecker {
+    override fun check(resolvedCall: ResolvedCall<*>, reportOn: PsiElement, context: CallCheckerContext) {
+        val resultingDescriptor = resolvedCall.resultingDescriptor
+        if (resultingDescriptor !is PropertyDescriptor || resultingDescriptor.kind != CallableMemberDescriptor.Kind.SYNTHESIZED) return
+        val extensionReceiver = resultingDescriptor.extensionReceiverParameter?.value as? ExtensionReceiver ?: return
+        if (resultingDescriptor.name.asString() != "declaringClass") return
+        if (extensionReceiver.type.constructor.declarationDescriptor.classId != StandardClassIds.Enum) return
+        context.trace.report(ErrorsJvm.ENUM_DECLARING_CLASS_DEPRECATED.on(context.languageVersionSettings, reportOn))
+    }
+}
\ No newline at end of file
diff --git a/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/diagnostics/DefaultErrorMessagesJvm.java b/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/diagnostics/DefaultErrorMessagesJvm.java
index 1933996b5f7..0bb4313d47e 100644
--- a/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/diagnostics/DefaultErrorMessagesJvm.java
+++ b/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/diagnostics/DefaultErrorMessagesJvm.java
@@ -228,6 +228,7 @@ public class DefaultErrorMessagesJvm implements DefaultErrorMessages.Extension {
         MAP.put(TYPEOF_NON_REIFIED_TYPE_PARAMETER_WITH_RECURSIVE_BOUND, "Non-reified type parameters with recursive bounds are not supported yet: {0}", STRING);
 
         MAP.put(JAVA_SAM_INTERFACE_CONSTRUCTOR_REFERENCE, "Java SAM interface constructor references are prohibited");
+        MAP.put(ENUM_DECLARING_CLASS_DEPRECATED, "Enum.declaringClass is deprecated, use javaDeclaringClass instead");
     }
 
     @NotNull
diff --git a/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/diagnostics/ErrorsJvm.java b/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/diagnostics/ErrorsJvm.java
index 67029b7f10a..34dea8aa1ac 100644
--- a/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/diagnostics/ErrorsJvm.java
+++ b/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/diagnostics/ErrorsJvm.java
@@ -206,6 +206,8 @@ public interface ErrorsJvm {
     DiagnosticFactory1<PsiElement, String> TYPEOF_NON_REIFIED_TYPE_PARAMETER_WITH_RECURSIVE_BOUND = DiagnosticFactory1.create(ERROR);
 
     DiagnosticFactory0<PsiElement> JAVA_SAM_INTERFACE_CONSTRUCTOR_REFERENCE = DiagnosticFactory0.create(ERROR);
+    DiagnosticFactoryForDeprecation0<PsiElement> ENUM_DECLARING_CLASS_DEPRECATED =
+            DiagnosticFactoryForDeprecation0.create(LanguageFeature.ProhibitEnumDeclaringClass);
 
     @SuppressWarnings("UnusedDeclaration")
     Object _initializer = new Object() {
diff --git a/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/platform/JvmPlatformConfigurator.kt b/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/platform/JvmPlatformConfigurator.kt
index 140edf81ee9..936846eb25f 100644
--- a/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/platform/JvmPlatformConfigurator.kt
+++ b/compiler/frontend.java/src/org/jetbrains/kotlin/resolve/jvm/platform/JvmPlatformConfigurator.kt
@@ -60,6 +60,7 @@ object JvmPlatformConfigurator : PlatformConfiguratorBase(
         InconsistentOperatorFromJavaCallChecker,
         PolymorphicSignatureCallChecker,
         SamInterfaceConstructorReferenceCallChecker,
+        EnumDeclaringClassDeprecationChecker,
     ),
 
     additionalTypeCheckers = listOf(
diff --git a/compiler/testData/diagnostics/tests/enum/declaringClass.fir.kt b/compiler/testData/diagnostics/tests/enum/declaringClass.fir.kt
index 7e3a26ceb51..679a5071d82 100644
--- a/compiler/testData/diagnostics/tests/enum/declaringClass.fir.kt
+++ b/compiler/testData/diagnostics/tests/enum/declaringClass.fir.kt
@@ -1,5 +1,6 @@
 // FULL_JDK
 // WITH_STDLIB
+// !LANGUAGE: -ProhibitEnumDeclaringClass
 
 import java.util.*
 
diff --git a/compiler/testData/diagnostics/tests/enum/declaringClass.kt b/compiler/testData/diagnostics/tests/enum/declaringClass.kt
index 19c864cff60..cbd1eac117d 100644
--- a/compiler/testData/diagnostics/tests/enum/declaringClass.kt
+++ b/compiler/testData/diagnostics/tests/enum/declaringClass.kt
@@ -1,9 +1,10 @@
 // FULL_JDK
 // WITH_STDLIB
+// !LANGUAGE: -ProhibitEnumDeclaringClass
 
 import java.util.*
 
 fun <E : Enum<E>> foo(values: Array<E>) {
-    EnumSet.noneOf(values.first().declaringClass)
+    EnumSet.noneOf(values.first().<!ENUM_DECLARING_CLASS_DEPRECATED_WARNING!>declaringClass<!>)
     EnumSet.noneOf(values.first().<!UNRESOLVED_REFERENCE!>getDeclaringClass<!>())
 }
diff --git a/compiler/util/src/org/jetbrains/kotlin/config/LanguageVersionSettings.kt b/compiler/util/src/org/jetbrains/kotlin/config/LanguageVersionSettings.kt
index 322b52e5348..34ca39bab7d 100644
--- a/compiler/util/src/org/jetbrains/kotlin/config/LanguageVersionSettings.kt
+++ b/compiler/util/src/org/jetbrains/kotlin/config/LanguageVersionSettings.kt
@@ -267,6 +267,7 @@ enum class LanguageFeature(
     ProhibitArrayLiteralsInCompanionOfAnnotation(KOTLIN_1_9, kind = BUG_FIX), // KT-39041
     ProhibitCyclesInAnnotations(KOTLIN_1_9, kind = BUG_FIX), // KT-47932
     ForbidExtensionFunctionTypeOnNonFunctionTypes(KOTLIN_1_9), // related to KT-43527
+    ProhibitEnumDeclaringClass(KOTLIN_1_9, kind = BUG_FIX), // KT-49653
 
     // Temporarily disabled, see KT-27084/KT-22379
     SoundSmartcastFromLoopConditionForLoopAssignedVariables(sinceVersion = null, kind = BUG_FIX),