diff --git a/src/compiler/expressionToTypeNode.ts b/src/compiler/expressionToTypeNode.ts
index 30a154f636960..83f0a0f0d9a6b 100644
--- a/src/compiler/expressionToTypeNode.ts
+++ b/src/compiler/expressionToTypeNode.ts
@@ -706,12 +706,12 @@ export function createSyntacticTypeNodeBuilder(
         }
         if (!result && node.kind === SyntaxKind.PropertyAssignment) {
             const initializer = node.initializer;
-            const type = isJSDocTypeAssertion(initializer) ? getJSDocTypeAssertionType(initializer) :
+            const assertionNode = isJSDocTypeAssertion(initializer) ? getJSDocTypeAssertionType(initializer) :
                 initializer.kind === SyntaxKind.AsExpression || initializer.kind === SyntaxKind.TypeAssertionExpression ? (initializer as AsExpression | TypeAssertion).type :
                 undefined;
 
-            if (type && !isConstTypeReference(type)) {
-                result = serializeExistingTypeNode(type, context);
+            if (assertionNode && !isConstTypeReference(assertionNode) && resolver.canReuseTypeNodeAnnotation(context, node, assertionNode, symbol)) {
+                result = serializeExistingTypeNode(assertionNode, context);
             }
         }
         return result ?? inferTypeOfDeclaration(node, symbol, context, /*reportFallback*/ false);
diff --git a/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.js b/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.js
new file mode 100644
index 0000000000000..dc81a99aa63d7
--- /dev/null
+++ b/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.js
@@ -0,0 +1,34 @@
+//// [tests/cases/compiler/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts] ////
+
+//// [declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts]
+type Wrapper<T> = {
+  _type: T;
+};
+
+declare function stringWrapper(): Wrapper<string>;
+
+declare function objWrapper<T extends Record<string, Wrapper<any>>>(
+  obj: T,
+): Wrapper<T>;
+
+const value = objWrapper({
+  prop1: stringWrapper() as Wrapper<"hello">,
+});
+
+type Unwrap<T> = T extends Wrapper<any>
+  ? T["_type"] extends Record<string, Wrapper<any>>
+    ? { [Key in keyof T["_type"]]: Unwrap<T["_type"][Key]> }
+    : T["_type"]
+  : never;
+
+declare function unwrap<T>(wrapper: T): Unwrap<T>;
+
+export const unwrapped = unwrap(value);
+
+
+
+
+//// [declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.d.ts]
+export declare const unwrapped: {
+    prop1: "hello";
+};
diff --git a/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.symbols b/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.symbols
new file mode 100644
index 0000000000000..fcfc2f0f54962
--- /dev/null
+++ b/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.symbols
@@ -0,0 +1,78 @@
+//// [tests/cases/compiler/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts] ////
+
+=== declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts ===
+type Wrapper<T> = {
+>Wrapper : Symbol(Wrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 0))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 13))
+
+  _type: T;
+>_type : Symbol(_type, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 19))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 13))
+
+};
+
+declare function stringWrapper(): Wrapper<string>;
+>stringWrapper : Symbol(stringWrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 2, 2))
+>Wrapper : Symbol(Wrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 0))
+
+declare function objWrapper<T extends Record<string, Wrapper<any>>>(
+>objWrapper : Symbol(objWrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 4, 50))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 6, 28))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+>Wrapper : Symbol(Wrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 0))
+
+  obj: T,
+>obj : Symbol(obj, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 6, 68))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 6, 28))
+
+): Wrapper<T>;
+>Wrapper : Symbol(Wrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 0))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 6, 28))
+
+const value = objWrapper({
+>value : Symbol(value, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 10, 5))
+>objWrapper : Symbol(objWrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 4, 50))
+
+  prop1: stringWrapper() as Wrapper<"hello">,
+>prop1 : Symbol(prop1, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 10, 26))
+>stringWrapper : Symbol(stringWrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 2, 2))
+>Wrapper : Symbol(Wrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 0))
+
+});
+
+type Unwrap<T> = T extends Wrapper<any>
+>Unwrap : Symbol(Unwrap, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 12, 3))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 14, 12))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 14, 12))
+>Wrapper : Symbol(Wrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 0))
+
+  ? T["_type"] extends Record<string, Wrapper<any>>
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 14, 12))
+>Record : Symbol(Record, Decl(lib.es5.d.ts, --, --))
+>Wrapper : Symbol(Wrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 0, 0))
+
+    ? { [Key in keyof T["_type"]]: Unwrap<T["_type"][Key]> }
+>Key : Symbol(Key, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 16, 9))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 14, 12))
+>Unwrap : Symbol(Unwrap, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 12, 3))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 14, 12))
+>Key : Symbol(Key, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 16, 9))
+
+    : T["_type"]
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 14, 12))
+
+  : never;
+
+declare function unwrap<T>(wrapper: T): Unwrap<T>;
+>unwrap : Symbol(unwrap, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 18, 10))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 20, 24))
+>wrapper : Symbol(wrapper, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 20, 27))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 20, 24))
+>Unwrap : Symbol(Unwrap, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 12, 3))
+>T : Symbol(T, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 20, 24))
+
+export const unwrapped = unwrap(value);
+>unwrapped : Symbol(unwrapped, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 22, 12))
+>unwrap : Symbol(unwrap, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 18, 10))
+>value : Symbol(value, Decl(declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts, 10, 5))
+
diff --git a/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.types b/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.types
new file mode 100644
index 0000000000000..d432618693d4f
--- /dev/null
+++ b/tests/baselines/reference/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.types
@@ -0,0 +1,74 @@
+//// [tests/cases/compiler/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts] ////
+
+=== declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts ===
+type Wrapper<T> = {
+>Wrapper : Wrapper<T>
+>        : ^^^^^^^^^^
+
+  _type: T;
+>_type : T
+>      : ^
+
+};
+
+declare function stringWrapper(): Wrapper<string>;
+>stringWrapper : () => Wrapper<string>
+>              : ^^^^^^               
+
+declare function objWrapper<T extends Record<string, Wrapper<any>>>(
+>objWrapper : <T extends Record<string, Wrapper<any>>>(obj: T) => Wrapper<T>
+>           : ^ ^^^^^^^^^                            ^^   ^^ ^^^^^          
+
+  obj: T,
+>obj : T
+>    : ^
+
+): Wrapper<T>;
+
+const value = objWrapper({
+>value : Wrapper<{ prop1: Wrapper<"hello">; }>
+>      : ^^^^^^^^^^^^^^^^^                ^^^^
+>objWrapper({  prop1: stringWrapper() as Wrapper<"hello">,}) : Wrapper<{ prop1: Wrapper<"hello">; }>
+>                                                            : ^^^^^^^^^^^^^^^^^                ^^^^
+>objWrapper : <T extends Record<string, Wrapper<any>>>(obj: T) => Wrapper<T>
+>           : ^ ^^^^^^^^^                            ^^   ^^ ^^^^^          
+>{  prop1: stringWrapper() as Wrapper<"hello">,} : { prop1: Wrapper<"hello">; }
+>                                                : ^^^^^^^^^                ^^^
+
+  prop1: stringWrapper() as Wrapper<"hello">,
+>prop1 : Wrapper<"hello">
+>      : ^^^^^^^^^^^^^^^^
+>stringWrapper() as Wrapper<"hello"> : Wrapper<"hello">
+>                                    : ^^^^^^^^^^^^^^^^
+>stringWrapper() : Wrapper<string>
+>                : ^^^^^^^^^^^^^^^
+>stringWrapper : () => Wrapper<string>
+>              : ^^^^^^               
+
+});
+
+type Unwrap<T> = T extends Wrapper<any>
+>Unwrap : Unwrap<T>
+>       : ^^^^^^^^^
+
+  ? T["_type"] extends Record<string, Wrapper<any>>
+    ? { [Key in keyof T["_type"]]: Unwrap<T["_type"][Key]> }
+    : T["_type"]
+  : never;
+
+declare function unwrap<T>(wrapper: T): Unwrap<T>;
+>unwrap : <T>(wrapper: T) => Unwrap<T>
+>       : ^ ^^       ^^ ^^^^^         
+>wrapper : T
+>        : ^
+
+export const unwrapped = unwrap(value);
+>unwrapped : { prop1: "hello"; }
+>          : ^^^^^^^^^^^^^^^^^^^
+>unwrap(value) : { prop1: "hello"; }
+>              : ^^^^^^^^^^^^^^^^^^^
+>unwrap : <T>(wrapper: T) => Unwrap<T>
+>       : ^ ^^       ^^ ^^^^^         
+>value : Wrapper<{ prop1: Wrapper<"hello">; }>
+>      : ^^^^^^^^^^^^^^^^^                ^^^^
+
diff --git a/tests/cases/compiler/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts b/tests/cases/compiler/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts
new file mode 100644
index 0000000000000..05cedc8b10aba
--- /dev/null
+++ b/tests/cases/compiler/declarationAssertionNodeNotReusedWhenTypeNotEquivalent1.ts
@@ -0,0 +1,27 @@
+// @strict: true
+// @declaration: true
+// @emitDeclarationOnly: true
+
+type Wrapper<T> = {
+  _type: T;
+};
+
+declare function stringWrapper(): Wrapper<string>;
+
+declare function objWrapper<T extends Record<string, Wrapper<any>>>(
+  obj: T,
+): Wrapper<T>;
+
+const value = objWrapper({
+  prop1: stringWrapper() as Wrapper<"hello">,
+});
+
+type Unwrap<T> = T extends Wrapper<any>
+  ? T["_type"] extends Record<string, Wrapper<any>>
+    ? { [Key in keyof T["_type"]]: Unwrap<T["_type"][Key]> }
+    : T["_type"]
+  : never;
+
+declare function unwrap<T>(wrapper: T): Unwrap<T>;
+
+export const unwrapped = unwrap(value);
diff --git a/tests/cases/fourslash/quickInfoAssertionNodeNotReusedWhenTypeNotEquivalent1.ts b/tests/cases/fourslash/quickInfoAssertionNodeNotReusedWhenTypeNotEquivalent1.ts
new file mode 100644
index 0000000000000..aa14e0fa5eb1b
--- /dev/null
+++ b/tests/cases/fourslash/quickInfoAssertionNodeNotReusedWhenTypeNotEquivalent1.ts
@@ -0,0 +1,36 @@
+/// <reference path="fourslash.ts" />
+
+// https://github.com/microsoft/TypeScript/issues/60573
+
+// @strict: true
+
+//// type Wrapper<T> = {
+////   _type: T;
+//// };
+////
+//// function stringWrapper(): Wrapper<string> {
+////   return { _type: "" };
+//// }
+////
+//// function objWrapper<T extends Record<string, Wrapper<any>>>(
+////   obj: T,
+//// ): Wrapper<T> {
+////   return { _type: obj };
+//// }
+////
+//// const value = objWrapper({
+////   prop1: stringWrapper() as Wrapper<"hello">,
+//// });
+////
+//// type Unwrap<T extends Wrapper<any>> = T["_type"] extends Record<
+////   string,
+////   Wrapper<any>
+//// >
+////   ? { [Key in keyof T["_type"]]: Unwrap<T["_type"][Key]> }
+////   : T["_type"];
+////
+//// type Test/*1*/ = Unwrap<typeof value>;
+
+verify.quickInfoAt("1", `type Test = {
+    prop1: "hello";
+}`)