diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 2fbdccba85bbf..bdfa33e4277e2 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -21491,7 +21491,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                     eachTypeRelatedToType(source as UnionType, target, reportErrors && !(source.flags & TypeFlags.Primitive), intersectionState);
             }
             if (target.flags & TypeFlags.Union) {
-                return typeRelatedToSomeType(getRegularTypeOfObjectLiteral(source), target as UnionType, reportErrors && !(source.flags & TypeFlags.Primitive) && !(target.flags & TypeFlags.Primitive));
+                return typeRelatedToSomeType(getRegularTypeOfObjectLiteral(source), target as UnionType, reportErrors && !(source.flags & TypeFlags.Primitive) && !(target.flags & TypeFlags.Primitive), intersectionState);
             }
             if (target.flags & TypeFlags.Intersection) {
                 return typeRelatedToEachType(source, target as IntersectionType, reportErrors, IntersectionState.Target);
@@ -21525,7 +21525,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             let result = Ternary.True;
             const sourceTypes = source.types;
             for (const sourceType of sourceTypes) {
-                const related = typeRelatedToSomeType(sourceType, target, /*reportErrors*/ false);
+                const related = typeRelatedToSomeType(sourceType, target, /*reportErrors*/ false, IntersectionState.None);
                 if (!related) {
                     return Ternary.False;
                 }
@@ -21534,7 +21534,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             return result;
         }
 
-        function typeRelatedToSomeType(source: Type, target: UnionOrIntersectionType, reportErrors: boolean): Ternary {
+        function typeRelatedToSomeType(source: Type, target: UnionOrIntersectionType, reportErrors: boolean, intersectionState: IntersectionState): Ternary {
             const targetTypes = target.types;
             if (target.flags & TypeFlags.Union) {
                 if (containsType(targetTypes, source)) {
@@ -21561,14 +21561,14 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 }
                 const match = getMatchingUnionConstituentForType(target as UnionType, source);
                 if (match) {
-                    const related = isRelatedTo(source, match, RecursionFlags.Target, /*reportErrors*/ false);
+                    const related = isRelatedTo(source, match, RecursionFlags.Target, /*reportErrors*/ false, /*headMessage*/ undefined, intersectionState);
                     if (related) {
                         return related;
                     }
                 }
             }
             for (const type of targetTypes) {
-                const related = isRelatedTo(source, type, RecursionFlags.Target, /*reportErrors*/ false);
+                const related = isRelatedTo(source, type, RecursionFlags.Target, /*reportErrors*/ false, /*headMessage*/ undefined, intersectionState);
                 if (related) {
                     return related;
                 }
@@ -21577,7 +21577,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 // Elaborate only if we can find a best matching type in the target union
                 const bestMatchingType = getBestMatchingType(source, target, isRelatedTo);
                 if (bestMatchingType) {
-                    isRelatedTo(source, bestMatchingType, RecursionFlags.Target, /*reportErrors*/ true);
+                    isRelatedTo(source, bestMatchingType, RecursionFlags.Target, /*reportErrors*/ true, /*headMessage*/ undefined, intersectionState);
                 }
             }
             return Ternary.False;
diff --git a/tests/baselines/reference/nestedExcessPropertyChecking.errors.txt b/tests/baselines/reference/nestedExcessPropertyChecking.errors.txt
index 393c2d1e35b0e..7c131d020aa34 100644
--- a/tests/baselines/reference/nestedExcessPropertyChecking.errors.txt
+++ b/tests/baselines/reference/nestedExcessPropertyChecking.errors.txt
@@ -88,4 +88,29 @@ nestedExcessPropertyChecking.ts(40,9): error TS2559: Type 'false' has no propert
             },
         },
     };
+    
+    // Repro from #53412
+    
+    type BaseItem = {
+        id: number;
+    }
+    type ExtendedItem = BaseItem & {
+        description: string | null
+    };
+      
+    type BaseValue = {
+        // there are other fields
+        items: BaseItem[];
+    }
+    type ExtendedValue = BaseValue & {
+        // there are other fields
+        items: ExtendedItem[];
+    }
+    
+    const TEST_VALUE: ExtendedValue = {
+        items: [
+            {id: 1, description: null},
+            {id: 2, description: 'wigglytubble'},
+        ]
+    };
     
\ No newline at end of file
diff --git a/tests/baselines/reference/nestedExcessPropertyChecking.js b/tests/baselines/reference/nestedExcessPropertyChecking.js
index 9d37f3d75425f..bd52494fc3d7c 100644
--- a/tests/baselines/reference/nestedExcessPropertyChecking.js
+++ b/tests/baselines/reference/nestedExcessPropertyChecking.js
@@ -64,6 +64,31 @@ const response: Query = {
         },
     },
 };
+
+// Repro from #53412
+
+type BaseItem = {
+    id: number;
+}
+type ExtendedItem = BaseItem & {
+    description: string | null
+};
+  
+type BaseValue = {
+    // there are other fields
+    items: BaseItem[];
+}
+type ExtendedValue = BaseValue & {
+    // there are other fields
+    items: ExtendedItem[];
+}
+
+const TEST_VALUE: ExtendedValue = {
+    items: [
+        {id: 1, description: null},
+        {id: 2, description: 'wigglytubble'},
+    ]
+};
 
 
 //// [nestedExcessPropertyChecking.js]
@@ -90,3 +115,9 @@ var response = {
         },
     },
 };
+var TEST_VALUE = {
+    items: [
+        { id: 1, description: null },
+        { id: 2, description: 'wigglytubble' },
+    ]
+};
diff --git a/tests/baselines/reference/nestedExcessPropertyChecking.symbols b/tests/baselines/reference/nestedExcessPropertyChecking.symbols
index dbd83126cc5e6..1700d41c45548 100644
--- a/tests/baselines/reference/nestedExcessPropertyChecking.symbols
+++ b/tests/baselines/reference/nestedExcessPropertyChecking.symbols
@@ -165,3 +165,56 @@ const response: Query = {
     },
 };
 
+// Repro from #53412
+
+type BaseItem = {
+>BaseItem : Symbol(BaseItem, Decl(nestedExcessPropertyChecking.ts, 62, 2))
+
+    id: number;
+>id : Symbol(id, Decl(nestedExcessPropertyChecking.ts, 66, 17))
+}
+type ExtendedItem = BaseItem & {
+>ExtendedItem : Symbol(ExtendedItem, Decl(nestedExcessPropertyChecking.ts, 68, 1))
+>BaseItem : Symbol(BaseItem, Decl(nestedExcessPropertyChecking.ts, 62, 2))
+
+    description: string | null
+>description : Symbol(description, Decl(nestedExcessPropertyChecking.ts, 69, 32))
+
+};
+  
+type BaseValue = {
+>BaseValue : Symbol(BaseValue, Decl(nestedExcessPropertyChecking.ts, 71, 2))
+
+    // there are other fields
+    items: BaseItem[];
+>items : Symbol(items, Decl(nestedExcessPropertyChecking.ts, 73, 18))
+>BaseItem : Symbol(BaseItem, Decl(nestedExcessPropertyChecking.ts, 62, 2))
+}
+type ExtendedValue = BaseValue & {
+>ExtendedValue : Symbol(ExtendedValue, Decl(nestedExcessPropertyChecking.ts, 76, 1))
+>BaseValue : Symbol(BaseValue, Decl(nestedExcessPropertyChecking.ts, 71, 2))
+
+    // there are other fields
+    items: ExtendedItem[];
+>items : Symbol(items, Decl(nestedExcessPropertyChecking.ts, 77, 34))
+>ExtendedItem : Symbol(ExtendedItem, Decl(nestedExcessPropertyChecking.ts, 68, 1))
+}
+
+const TEST_VALUE: ExtendedValue = {
+>TEST_VALUE : Symbol(TEST_VALUE, Decl(nestedExcessPropertyChecking.ts, 82, 5))
+>ExtendedValue : Symbol(ExtendedValue, Decl(nestedExcessPropertyChecking.ts, 76, 1))
+
+    items: [
+>items : Symbol(items, Decl(nestedExcessPropertyChecking.ts, 82, 35))
+
+        {id: 1, description: null},
+>id : Symbol(id, Decl(nestedExcessPropertyChecking.ts, 84, 9))
+>description : Symbol(description, Decl(nestedExcessPropertyChecking.ts, 84, 15))
+
+        {id: 2, description: 'wigglytubble'},
+>id : Symbol(id, Decl(nestedExcessPropertyChecking.ts, 85, 9))
+>description : Symbol(description, Decl(nestedExcessPropertyChecking.ts, 85, 15))
+
+    ]
+};
+
diff --git a/tests/baselines/reference/nestedExcessPropertyChecking.types b/tests/baselines/reference/nestedExcessPropertyChecking.types
index abed36ba6fa06..f5f74489d2259 100644
--- a/tests/baselines/reference/nestedExcessPropertyChecking.types
+++ b/tests/baselines/reference/nestedExcessPropertyChecking.types
@@ -160,3 +160,58 @@ const response: Query = {
     },
 };
 
+// Repro from #53412
+
+type BaseItem = {
+>BaseItem : { id: number; }
+
+    id: number;
+>id : number
+}
+type ExtendedItem = BaseItem & {
+>ExtendedItem : BaseItem & { description: string | null; }
+
+    description: string | null
+>description : string | null
+
+};
+  
+type BaseValue = {
+>BaseValue : { items: BaseItem[]; }
+
+    // there are other fields
+    items: BaseItem[];
+>items : BaseItem[]
+}
+type ExtendedValue = BaseValue & {
+>ExtendedValue : BaseValue & { items: ExtendedItem[]; }
+
+    // there are other fields
+    items: ExtendedItem[];
+>items : ExtendedItem[]
+}
+
+const TEST_VALUE: ExtendedValue = {
+>TEST_VALUE : ExtendedValue
+>{    items: [        {id: 1, description: null},        {id: 2, description: 'wigglytubble'},    ]} : { items: ({ id: number; description: null; } | { id: number; description: string; })[]; }
+
+    items: [
+>items : ({ id: number; description: null; } | { id: number; description: string; })[]
+>[        {id: 1, description: null},        {id: 2, description: 'wigglytubble'},    ] : ({ id: number; description: null; } | { id: number; description: string; })[]
+
+        {id: 1, description: null},
+>{id: 1, description: null} : { id: number; description: null; }
+>id : number
+>1 : 1
+>description : null
+
+        {id: 2, description: 'wigglytubble'},
+>{id: 2, description: 'wigglytubble'} : { id: number; description: string; }
+>id : number
+>2 : 2
+>description : string
+>'wigglytubble' : "wigglytubble"
+
+    ]
+};
+
diff --git a/tests/cases/compiler/nestedExcessPropertyChecking.ts b/tests/cases/compiler/nestedExcessPropertyChecking.ts
index 9e7c808b5e0ec..35caf37d7d13c 100644
--- a/tests/cases/compiler/nestedExcessPropertyChecking.ts
+++ b/tests/cases/compiler/nestedExcessPropertyChecking.ts
@@ -63,3 +63,28 @@ const response: Query = {
         },
     },
 };
+
+// Repro from #53412
+
+type BaseItem = {
+    id: number;
+}
+type ExtendedItem = BaseItem & {
+    description: string | null
+};
+  
+type BaseValue = {
+    // there are other fields
+    items: BaseItem[];
+}
+type ExtendedValue = BaseValue & {
+    // there are other fields
+    items: ExtendedItem[];
+}
+
+const TEST_VALUE: ExtendedValue = {
+    items: [
+        {id: 1, description: null},
+        {id: 2, description: 'wigglytubble'},
+    ]
+};