diff --git a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendMPPDiagnosticsWithLightTreeTestGenerated.java b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendMPPDiagnosticsWithLightTreeTestGenerated.java
index df0608137fc..654666d009a 100644
--- a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendMPPDiagnosticsWithLightTreeTestGenerated.java
+++ b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendMPPDiagnosticsWithLightTreeTestGenerated.java
@@ -758,6 +758,12 @@ public class FirOldFrontendMPPDiagnosticsWithLightTreeTestGenerated extends Abst
             runTest("compiler/testData/diagnostics/tests/multiplatform/annotationMatching/differentOrder.kt");
         }
 
+        @Test
+        @TestMetadata("enumEntries.kt")
+        public void testEnumEntries() throws Exception {
+            runTest("compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.kt");
+        }
+
         @Test
         @TestMetadata("fakeOverrides.kt")
         public void testFakeOverrides() throws Exception {
diff --git a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendMPPDiagnosticsWithPsiTestGenerated.java b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendMPPDiagnosticsWithPsiTestGenerated.java
index 113dd96bc21..0907f1cfa8b 100644
--- a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendMPPDiagnosticsWithPsiTestGenerated.java
+++ b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirOldFrontendMPPDiagnosticsWithPsiTestGenerated.java
@@ -758,6 +758,12 @@ public class FirOldFrontendMPPDiagnosticsWithPsiTestGenerated extends AbstractFi
             runTest("compiler/testData/diagnostics/tests/multiplatform/annotationMatching/differentOrder.kt");
         }
 
+        @Test
+        @TestMetadata("enumEntries.kt")
+        public void testEnumEntries() throws Exception {
+            runTest("compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.kt");
+        }
+
         @Test
         @TestMetadata("fakeOverrides.kt")
         public void testFakeOverrides() throws Exception {
diff --git a/compiler/fir/resolve/src/org/jetbrains/kotlin/fir/resolve/transformers/mpp/FirExpectActualMatchingContextImpl.kt b/compiler/fir/resolve/src/org/jetbrains/kotlin/fir/resolve/transformers/mpp/FirExpectActualMatchingContextImpl.kt
index f6ca6b5bb0b..728c4d7cc52 100644
--- a/compiler/fir/resolve/src/org/jetbrains/kotlin/fir/resolve/transformers/mpp/FirExpectActualMatchingContextImpl.kt
+++ b/compiler/fir/resolve/src/org/jetbrains/kotlin/fir/resolve/transformers/mpp/FirExpectActualMatchingContextImpl.kt
@@ -238,6 +238,10 @@ class FirExpectActualMatchingContextImpl private constructor(
         return asSymbol().fir.collectEnumEntries().map { it.name }
     }
 
+    override fun RegularClassSymbolMarker.collectEnumEntries(): List<DeclarationSymbolMarker> {
+        return asSymbol().fir.collectEnumEntries().map { it.symbol }
+    }
+
     override val CallableSymbolMarker.dispatchReceiverType: SimpleTypeMarker?
         get() = asSymbol().dispatchReceiverType
     override val CallableSymbolMarker.extensionReceiverType: KotlinTypeMarker?
diff --git a/compiler/ir/backend.common/src/org/jetbrains/kotlin/backend/common/actualizer/IrExpectActualMatchingContext.kt b/compiler/ir/backend.common/src/org/jetbrains/kotlin/backend/common/actualizer/IrExpectActualMatchingContext.kt
index 538182bca31..5dccfd2cd45 100644
--- a/compiler/ir/backend.common/src/org/jetbrains/kotlin/backend/common/actualizer/IrExpectActualMatchingContext.kt
+++ b/compiler/ir/backend.common/src/org/jetbrains/kotlin/backend/common/actualizer/IrExpectActualMatchingContext.kt
@@ -267,6 +267,10 @@ internal abstract class IrExpectActualMatchingContext(
         return asIr().declarations.filterIsInstance<IrEnumEntry>().map { it.name }
     }
 
+    override fun RegularClassSymbolMarker.collectEnumEntries(): List<DeclarationSymbolMarker> {
+        return asIr().declarations.filterIsInstance<IrEnumEntry>().map { it.symbol }
+    }
+
     override val CallableSymbolMarker.dispatchReceiverType: KotlinTypeMarker?
         get() = (asIr().parent as? IrClass)?.defaultType
 
diff --git a/compiler/resolution.common/src/org/jetbrains/kotlin/resolve/calls/mpp/AbstractExpectActualAnnotationMatchChecker.kt b/compiler/resolution.common/src/org/jetbrains/kotlin/resolve/calls/mpp/AbstractExpectActualAnnotationMatchChecker.kt
index 20b55765a0e..e499ab443c3 100644
--- a/compiler/resolution.common/src/org/jetbrains/kotlin/resolve/calls/mpp/AbstractExpectActualAnnotationMatchChecker.kt
+++ b/compiler/resolution.common/src/org/jetbrains/kotlin/resolve/calls/mpp/AbstractExpectActualAnnotationMatchChecker.kt
@@ -5,8 +5,10 @@
 
 package org.jetbrains.kotlin.resolve.calls.mpp
 
+import org.jetbrains.kotlin.descriptors.ClassKind
 import org.jetbrains.kotlin.mpp.*
 import org.jetbrains.kotlin.name.ClassId
+import org.jetbrains.kotlin.name.Name
 import org.jetbrains.kotlin.name.StandardClassIds
 import org.jetbrains.kotlin.resolve.checkers.OptInNames
 import org.jetbrains.kotlin.resolve.multiplatform.ExpectActualCompatibility
@@ -80,6 +82,9 @@ object AbstractExpectActualAnnotationMatchChecker {
         if (checkClassScopesForAnnotationCompatibility) {
             checkAnnotationsInClassMemberScope(expectSymbol, actualSymbol)?.let { return it }
         }
+        if (expectSymbol.classKind == ClassKind.ENUM_CLASS && actualSymbol.classKind == ClassKind.ENUM_CLASS) {
+            checkAnnotationsOnEnumEntries(expectSymbol, actualSymbol)?.let { return it }
+        }
 
         return null
     }
@@ -170,4 +175,27 @@ object AbstractExpectActualAnnotationMatchChecker {
         }
         return null
     }
+
+    context (ExpectActualMatchingContext<*>)
+    private fun checkAnnotationsOnEnumEntries(
+        expectClassSymbol: RegularClassSymbolMarker,
+        actualClassSymbol: RegularClassSymbolMarker,
+    ): Incompatibility? {
+        fun DeclarationSymbolMarker.getEnumEntryName(): Name =
+            when (this) {
+                is CallableSymbolMarker -> callableId.callableName
+                is RegularClassSymbolMarker -> classId.shortClassName
+                else -> error("Unexpected type $this")
+            }
+
+        val expectEnumEntries = expectClassSymbol.collectEnumEntries()
+        val actualEnumEntriesByName = actualClassSymbol.collectEnumEntries().associateBy { it.getEnumEntryName() }
+
+        for (expectEnumEntry in expectEnumEntries) {
+            val actualEnumEntry = actualEnumEntriesByName[expectEnumEntry.getEnumEntryName()] ?: continue
+            areAnnotationsSetOnDeclarationsCompatible(expectEnumEntry, actualEnumEntry)
+                ?.let { return it }
+        }
+        return null
+    }
 }
\ No newline at end of file
diff --git a/compiler/resolution.common/src/org/jetbrains/kotlin/resolve/calls/mpp/ExpectActualMatchingContext.kt b/compiler/resolution.common/src/org/jetbrains/kotlin/resolve/calls/mpp/ExpectActualMatchingContext.kt
index b790ee5d452..b1d17171544 100644
--- a/compiler/resolution.common/src/org/jetbrains/kotlin/resolve/calls/mpp/ExpectActualMatchingContext.kt
+++ b/compiler/resolution.common/src/org/jetbrains/kotlin/resolve/calls/mpp/ExpectActualMatchingContext.kt
@@ -111,6 +111,7 @@ interface ExpectActualMatchingContext<T : DeclarationSymbolMarker> : TypeSystemC
     fun RegularClassSymbolMarker.getMembersForExpectClass(name: Name): List<DeclarationSymbolMarker>
 
     fun RegularClassSymbolMarker.collectEnumEntryNames(): List<Name>
+    fun RegularClassSymbolMarker.collectEnumEntries(): List<DeclarationSymbolMarker>
 
     val CallableSymbolMarker.dispatchReceiverType: KotlinTypeMarker?
     val CallableSymbolMarker.extensionReceiverType: KotlinTypeMarker?
diff --git a/compiler/resolution/src/org/jetbrains/kotlin/resolve/multiplatform/ClassicExpectActualMatchingContext.kt b/compiler/resolution/src/org/jetbrains/kotlin/resolve/multiplatform/ClassicExpectActualMatchingContext.kt
index b35ff1a079e..79648708387 100644
--- a/compiler/resolution/src/org/jetbrains/kotlin/resolve/multiplatform/ClassicExpectActualMatchingContext.kt
+++ b/compiler/resolution/src/org/jetbrains/kotlin/resolve/multiplatform/ClassicExpectActualMatchingContext.kt
@@ -176,11 +176,14 @@ class ClassicExpectActualMatchingContext(
     }
 
     override fun RegularClassSymbolMarker.collectEnumEntryNames(): List<Name> {
+        return collectEnumEntries().map { it.name }
+    }
+
+    override fun RegularClassSymbolMarker.collectEnumEntries(): List<DeclarationDescriptor> {
         return asDescriptor()
             .unsubstitutedMemberScope
             .getDescriptorsFiltered()
             .filter(DescriptorUtils::isEnumEntry)
-            .map { it.name }
     }
 
     override val CallableSymbolMarker.dispatchReceiverType: KotlinTypeMarker?
diff --git a/compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.fir.kt b/compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.fir.kt
new file mode 100644
index 00000000000..9a8b1622a30
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.fir.kt
@@ -0,0 +1,15 @@
+// MODULE: m1-common
+// FILE: common.kt
+annotation class Ann
+
+<!INCOMPATIBLE_MATCHING{JVM}!>expect enum class E {
+    @Ann
+    FOO,
+    <!NO_ACTUAL_FOR_EXPECT{JVM}!>MISSING_ON_ACTUAL<!>
+}<!>
+
+// MODULE: m1-jvm()()(m1-common)
+// FILE: jvm.kt
+actual enum class <!ACTUAL_ANNOTATIONS_NOT_MATCH_EXPECT, ACTUAL_WITHOUT_EXPECT!>E<!> {
+    <!ACTUAL_ANNOTATIONS_NOT_MATCH_EXPECT!>FOO<!>
+}
diff --git a/compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.kt b/compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.kt
new file mode 100644
index 00000000000..a0a413b35c9
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.kt
@@ -0,0 +1,15 @@
+// MODULE: m1-common
+// FILE: common.kt
+annotation class Ann
+
+expect enum class E {
+    @Ann
+    FOO,
+    MISSING_ON_ACTUAL
+}
+
+// MODULE: m1-jvm()()(m1-common)
+// FILE: jvm.kt
+actual enum class <!ACTUAL_ANNOTATIONS_NOT_MATCH_EXPECT, ACTUAL_WITHOUT_EXPECT!>E<!> {
+    FOO
+}
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 29503239e0a..404b19e8936 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
@@ -23527,6 +23527,12 @@ public class DiagnosticTestGenerated extends AbstractDiagnosticTest {
                     runTest("compiler/testData/diagnostics/tests/multiplatform/annotationMatching/differentOrder.kt");
                 }
 
+                @Test
+                @TestMetadata("enumEntries.kt")
+                public void testEnumEntries() throws Exception {
+                    runTest("compiler/testData/diagnostics/tests/multiplatform/annotationMatching/enumEntries.kt");
+                }
+
                 @Test
                 @TestMetadata("fakeOverrides.kt")
                 public void testFakeOverrides() throws Exception {