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 f51b02d90b6..59847a43942 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
@@ -12940,6 +12940,24 @@ public class DiagnosisCompilerTestFE10TestdataTestGenerated extends AbstractDiag
                 runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity.kt");
             }
 
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity2.kt")
+            public void testEnumEntryVsStaticAmbiguity2() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.kt");
+            }
+
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity3.kt")
+            public void testEnumEntryVsStaticAmbiguity3() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.kt");
+            }
+
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity4.kt")
+            public void testEnumEntryVsStaticAmbiguity4() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.kt");
+            }
+
             @Test
             @TestMetadata("ExplicitImportsAmbiguity.kt")
             public void testExplicitImportsAmbiguity() 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 e986b1bfd40..59394aeb9fb 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
@@ -12940,6 +12940,24 @@ public class FirOldFrontendDiagnosticsTestGenerated extends AbstractFirDiagnosti
                 runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity.kt");
             }
 
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity2.kt")
+            public void testEnumEntryVsStaticAmbiguity2() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.kt");
+            }
+
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity3.kt")
+            public void testEnumEntryVsStaticAmbiguity3() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.kt");
+            }
+
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity4.kt")
+            public void testEnumEntryVsStaticAmbiguity4() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.kt");
+            }
+
             @Test
             @TestMetadata("ExplicitImportsAmbiguity.kt")
             public void testExplicitImportsAmbiguity() 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 aa0fd212a51..d839e7d7d22 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
@@ -12940,6 +12940,24 @@ public class FirOldFrontendDiagnosticsWithLightTreeTestGenerated extends Abstrac
                 runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity.kt");
             }
 
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity2.kt")
+            public void testEnumEntryVsStaticAmbiguity2() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.kt");
+            }
+
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity3.kt")
+            public void testEnumEntryVsStaticAmbiguity3() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.kt");
+            }
+
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity4.kt")
+            public void testEnumEntryVsStaticAmbiguity4() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.kt");
+            }
+
             @Test
             @TestMetadata("ExplicitImportsAmbiguity.kt")
             public void testExplicitImportsAmbiguity() throws Exception {
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.fir.kt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.fir.kt
new file mode 100644
index 00000000000..4d37b5dc026
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.fir.kt
@@ -0,0 +1,37 @@
+// KT-49200
+// FILE: first/KtNodeTypes.java
+
+package first;
+
+public interface KtNodeTypes {
+    String SOME = "Some";
+}
+
+// FILE: SomeEnum.kt
+
+package second
+
+enum class SomeEnum {
+    SOME;
+}
+
+// FILE: OtherEnum.kt
+
+package third
+
+enum class SomeEnum {
+    SOME;
+}
+
+// FILE: test.kt
+
+import first.KtNodeTypes.*
+import second.SomeEnum.*
+import third.SomeEnum.*
+
+fun test(arg: String): Boolean {
+    return when (arg) {
+        <!OVERLOAD_RESOLUTION_AMBIGUITY!>SOME<!> -> true
+        else -> false
+    }
+}
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.kt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.kt
new file mode 100644
index 00000000000..9c0ed43d34d
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.kt
@@ -0,0 +1,37 @@
+// KT-49200
+// FILE: first/KtNodeTypes.java
+
+package first;
+
+public interface KtNodeTypes {
+    String SOME = "Some";
+}
+
+// FILE: SomeEnum.kt
+
+package second
+
+enum class SomeEnum {
+    SOME;
+}
+
+// FILE: OtherEnum.kt
+
+package third
+
+enum class SomeEnum {
+    SOME;
+}
+
+// FILE: test.kt
+
+import first.KtNodeTypes.*
+import second.SomeEnum.*
+import third.SomeEnum.*
+
+fun test(arg: String): Boolean {
+    return when (arg) {
+        SOME -> true
+        else -> false
+    }
+}
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.txt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.txt
new file mode 100644
index 00000000000..b79831712b1
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.txt
@@ -0,0 +1,59 @@
+package
+
+public fun test(/*0*/ arg: kotlin.String): kotlin.Boolean
+
+package first {
+
+    public interface KtNodeTypes {
+        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
+
+        // Static members
+        public const final val SOME: kotlin.String = "Some"
+    }
+}
+
+package second {
+
+    public final enum class SomeEnum : kotlin.Enum<second.SomeEnum> {
+        enum entry SOME
+
+        private constructor SomeEnum()
+        @kotlin.internal.IntrinsicConstEvaluation public final override /*1*/ /*fake_override*/ val name: kotlin.String
+        public final override /*1*/ /*fake_override*/ val ordinal: kotlin.Int
+        protected final override /*1*/ /*fake_override*/ fun clone(): kotlin.Any
+        public final override /*1*/ /*fake_override*/ fun compareTo(/*0*/ other: second.SomeEnum): kotlin.Int
+        public final override /*1*/ /*fake_override*/ fun equals(/*0*/ other: kotlin.Any?): kotlin.Boolean
+        protected/*protected and package*/ final override /*1*/ /*fake_override*/ /*isHiddenForResolutionEverywhereBesideSupercalls*/ fun finalize(): kotlin.Unit
+        public final override /*1*/ /*fake_override*/ /*isHiddenForResolutionEverywhereBesideSupercalls*/ fun getDeclaringClass(): java.lang.Class<second.SomeEnum!>!
+        public final override /*1*/ /*fake_override*/ fun hashCode(): kotlin.Int
+        public open override /*1*/ /*fake_override*/ fun toString(): kotlin.String
+
+        // Static members
+        public final /*synthesized*/ fun valueOf(/*0*/ value: kotlin.String): second.SomeEnum
+        public final /*synthesized*/ fun values(): kotlin.Array<second.SomeEnum>
+    }
+}
+
+package third {
+
+    public final enum class SomeEnum : kotlin.Enum<third.SomeEnum> {
+        enum entry SOME
+
+        private constructor SomeEnum()
+        @kotlin.internal.IntrinsicConstEvaluation public final override /*1*/ /*fake_override*/ val name: kotlin.String
+        public final override /*1*/ /*fake_override*/ val ordinal: kotlin.Int
+        protected final override /*1*/ /*fake_override*/ fun clone(): kotlin.Any
+        public final override /*1*/ /*fake_override*/ fun compareTo(/*0*/ other: third.SomeEnum): kotlin.Int
+        public final override /*1*/ /*fake_override*/ fun equals(/*0*/ other: kotlin.Any?): kotlin.Boolean
+        protected/*protected and package*/ final override /*1*/ /*fake_override*/ /*isHiddenForResolutionEverywhereBesideSupercalls*/ fun finalize(): kotlin.Unit
+        public final override /*1*/ /*fake_override*/ /*isHiddenForResolutionEverywhereBesideSupercalls*/ fun getDeclaringClass(): java.lang.Class<third.SomeEnum!>!
+        public final override /*1*/ /*fake_override*/ fun hashCode(): kotlin.Int
+        public open override /*1*/ /*fake_override*/ fun toString(): kotlin.String
+
+        // Static members
+        public final /*synthesized*/ fun valueOf(/*0*/ value: kotlin.String): third.SomeEnum
+        public final /*synthesized*/ fun values(): kotlin.Array<third.SomeEnum>
+    }
+}
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.diag.txt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.diag.txt
new file mode 100644
index 00000000000..d997ff7a7e1
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.diag.txt
@@ -0,0 +1,3 @@
+/test.kt:26:9: warning: ambiguous access to property 'first.KtNodeTypes.SOME' is deprecated because similar enum entry 'second.SomeEnum.SOME' is available. Please add explicit named import or use fully qualified name
+        SOME -> true
+        ^
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.fir.kt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.fir.kt
new file mode 100644
index 00000000000..9b849dbee92
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.fir.kt
@@ -0,0 +1,29 @@
+// KT-49200
+// !RENDER_DIAGNOSTICS_FULL_TEXT
+// FILE: first/KtNodeTypes.java
+
+package first;
+
+public interface KtNodeTypes {
+    String SOME = "Some";
+}
+
+// FILE: SomeEnum.kt
+
+package second
+
+enum class SomeEnum {
+    SOME;
+}
+
+// FILE: test.kt
+
+import first.KtNodeTypes.SOME
+import second.SomeEnum.SOME
+
+fun test(arg: String): Boolean {
+    return when (arg) {
+        <!OVERLOAD_RESOLUTION_AMBIGUITY!>SOME<!> -> true
+        else -> false
+    }
+}
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.kt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.kt
new file mode 100644
index 00000000000..1edaaeda1da
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.kt
@@ -0,0 +1,29 @@
+// KT-49200
+// !RENDER_DIAGNOSTICS_FULL_TEXT
+// FILE: first/KtNodeTypes.java
+
+package first;
+
+public interface KtNodeTypes {
+    String SOME = "Some";
+}
+
+// FILE: SomeEnum.kt
+
+package second
+
+enum class SomeEnum {
+    SOME;
+}
+
+// FILE: test.kt
+
+import first.KtNodeTypes.SOME
+import second.SomeEnum.SOME
+
+fun test(arg: String): Boolean {
+    return when (arg) {
+        <!DEPRECATED_RESOLVE_WITH_AMBIGUOUS_ENUM_ENTRY!>SOME<!> -> true
+        else -> false
+    }
+}
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.txt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.txt
new file mode 100644
index 00000000000..9e2def9a15f
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.txt
@@ -0,0 +1,37 @@
+package
+
+public fun test(/*0*/ arg: kotlin.String): kotlin.Boolean
+
+package first {
+
+    public interface KtNodeTypes {
+        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
+
+        // Static members
+        public const final val SOME: kotlin.String = "Some"
+    }
+}
+
+package second {
+
+    public final enum class SomeEnum : kotlin.Enum<second.SomeEnum> {
+        enum entry SOME
+
+        private constructor SomeEnum()
+        @kotlin.internal.IntrinsicConstEvaluation public final override /*1*/ /*fake_override*/ val name: kotlin.String
+        public final override /*1*/ /*fake_override*/ val ordinal: kotlin.Int
+        protected final override /*1*/ /*fake_override*/ fun clone(): kotlin.Any
+        public final override /*1*/ /*fake_override*/ fun compareTo(/*0*/ other: second.SomeEnum): kotlin.Int
+        public final override /*1*/ /*fake_override*/ fun equals(/*0*/ other: kotlin.Any?): kotlin.Boolean
+        protected/*protected and package*/ final override /*1*/ /*fake_override*/ /*isHiddenForResolutionEverywhereBesideSupercalls*/ fun finalize(): kotlin.Unit
+        public final override /*1*/ /*fake_override*/ /*isHiddenForResolutionEverywhereBesideSupercalls*/ fun getDeclaringClass(): java.lang.Class<second.SomeEnum!>!
+        public final override /*1*/ /*fake_override*/ fun hashCode(): kotlin.Int
+        public open override /*1*/ /*fake_override*/ fun toString(): kotlin.String
+
+        // Static members
+        public final /*synthesized*/ fun valueOf(/*0*/ value: kotlin.String): second.SomeEnum
+        public final /*synthesized*/ fun values(): kotlin.Array<second.SomeEnum>
+    }
+}
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.kt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.kt
new file mode 100644
index 00000000000..ee0f4f37e19
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.kt
@@ -0,0 +1,38 @@
+// FIR_IDENTICAL
+// KT-49200
+// FILE: first/KtNodeTypes.java
+
+package first;
+
+public interface KtNodeTypes {
+    String SOME = "Some";
+}
+
+// FILE: SomeEnum.kt
+
+package second
+
+enum class SomeEnum {
+    SOME;
+}
+
+// FILE: third/OtherTypes.java
+
+package third
+
+public interface OtherTypes {
+    String SOME = "Other";
+}
+
+// FILE: test.kt
+
+import first.KtNodeTypes.*
+import second.SomeEnum.*
+import third.OtherTypes.*
+
+fun test(arg: String): Boolean {
+    return when (arg) {
+        <!OVERLOAD_RESOLUTION_AMBIGUITY!>SOME<!> -> true
+        else -> false
+    }
+}
diff --git a/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.txt b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.txt
new file mode 100644
index 00000000000..52a55219f01
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.txt
@@ -0,0 +1,49 @@
+package
+
+public fun test(/*0*/ arg: kotlin.String): kotlin.Boolean
+
+package first {
+
+    public interface KtNodeTypes {
+        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
+
+        // Static members
+        public const final val SOME: kotlin.String = "Some"
+    }
+}
+
+package second {
+
+    public final enum class SomeEnum : kotlin.Enum<second.SomeEnum> {
+        enum entry SOME
+
+        private constructor SomeEnum()
+        @kotlin.internal.IntrinsicConstEvaluation public final override /*1*/ /*fake_override*/ val name: kotlin.String
+        public final override /*1*/ /*fake_override*/ val ordinal: kotlin.Int
+        protected final override /*1*/ /*fake_override*/ fun clone(): kotlin.Any
+        public final override /*1*/ /*fake_override*/ fun compareTo(/*0*/ other: second.SomeEnum): kotlin.Int
+        public final override /*1*/ /*fake_override*/ fun equals(/*0*/ other: kotlin.Any?): kotlin.Boolean
+        protected/*protected and package*/ final override /*1*/ /*fake_override*/ /*isHiddenForResolutionEverywhereBesideSupercalls*/ fun finalize(): kotlin.Unit
+        public final override /*1*/ /*fake_override*/ /*isHiddenForResolutionEverywhereBesideSupercalls*/ fun getDeclaringClass(): java.lang.Class<second.SomeEnum!>!
+        public final override /*1*/ /*fake_override*/ fun hashCode(): kotlin.Int
+        public open override /*1*/ /*fake_override*/ fun toString(): kotlin.String
+
+        // Static members
+        public final /*synthesized*/ fun valueOf(/*0*/ value: kotlin.String): second.SomeEnum
+        public final /*synthesized*/ fun values(): kotlin.Array<second.SomeEnum>
+    }
+}
+
+package third {
+
+    public interface OtherTypes {
+        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
+
+        // Static members
+        public const final val SOME: kotlin.String = "Other"
+    }
+}
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 48ed0783eb0..c8a629058f7 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
@@ -12946,6 +12946,24 @@ public class DiagnosticTestGenerated extends AbstractDiagnosticTest {
                 runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity.kt");
             }
 
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity2.kt")
+            public void testEnumEntryVsStaticAmbiguity2() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity2.kt");
+            }
+
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity3.kt")
+            public void testEnumEntryVsStaticAmbiguity3() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity3.kt");
+            }
+
+            @Test
+            @TestMetadata("EnumEntryVsStaticAmbiguity4.kt")
+            public void testEnumEntryVsStaticAmbiguity4() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/imports/EnumEntryVsStaticAmbiguity4.kt");
+            }
+
             @Test
             @TestMetadata("ExplicitImportsAmbiguity.kt")
             public void testExplicitImportsAmbiguity() throws Exception {