diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 16e982bfff38b..35b37c23910af 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -762,6 +762,7 @@ import {
     JSDocSatisfiesTag,
     JSDocSignature,
     JSDocTemplateTag,
+    JSDocTypeAssertion,
     JSDocTypedefTag,
     JSDocTypeExpression,
     JSDocTypeLiteral,
@@ -1037,7 +1038,6 @@ import {
     TypeReferenceSerializationKind,
     TypeReferenceType,
     TypeVariable,
-    UnaryExpression,
     unescapeLeadingUnderscores,
     UnionOrIntersectionType,
     UnionOrIntersectionTypeNode,
@@ -34267,14 +34267,14 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return getReturnTypeOfSignature(signature);
     }
 
-    function checkAssertion(node: AssertionExpression) {
+    function checkAssertion(node: AssertionExpression, checkMode: CheckMode | undefined) {
         if (node.kind === SyntaxKind.TypeAssertionExpression) {
             const file = getSourceFileOfNode(node);
             if (file && fileExtensionIsOneOf(file.fileName, [Extension.Cts, Extension.Mts])) {
                 grammarErrorOnNode(node, Diagnostics.This_syntax_is_reserved_in_files_with_the_mts_or_cts_extension_Use_an_as_expression_instead);
             }
         }
-        return checkAssertionWorker(node, node.type, node.expression);
+        return checkAssertionWorker(node, checkMode);
     }
 
     function isValidConstAssertionArgument(node: Node): boolean {
@@ -34305,8 +34305,9 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return false;
     }
 
-    function checkAssertionWorker(errNode: Node, type: TypeNode, expression: UnaryExpression | Expression, checkMode?: CheckMode) {
-        let exprType = checkExpression(expression, checkMode);
+    function checkAssertionWorker(node: JSDocTypeAssertion | AssertionExpression, checkMode: CheckMode | undefined) {
+        const { type, expression } = getAssertionTypeAndExpression(node);
+        const exprType = checkExpression(expression, checkMode);
         if (isConstTypeReference(type)) {
             if (!isValidConstAssertionArgument(expression)) {
                 error(expression, Diagnostics.A_const_assertions_can_only_be_applied_to_references_to_enum_members_or_string_number_boolean_array_or_object_literals);
@@ -34314,7 +34315,32 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             return getRegularTypeOfLiteralType(exprType);
         }
         checkSourceElement(type);
-        exprType = getRegularTypeOfObjectLiteral(getBaseTypeOfLiteralType(exprType));
+        checkNodeDeferred(node);
+        return getTypeFromTypeNode(type);
+    }
+
+    function getAssertionTypeAndExpression(node: JSDocTypeAssertion | AssertionExpression) {
+        let type: TypeNode;
+        let expression: Expression;
+        switch (node.kind) {
+            case SyntaxKind.AsExpression:
+            case SyntaxKind.TypeAssertionExpression:
+                type = node.type;
+                expression = node.expression;
+                break;
+            case SyntaxKind.ParenthesizedExpression:
+                type = getJSDocTypeAssertionType(node);
+                expression = node.expression;
+                break;
+        }
+
+        return { type, expression };
+    }
+
+    function checkAssertionDeferred(node: JSDocTypeAssertion | AssertionExpression) {
+        const { type, expression } = getAssertionTypeAndExpression(node);
+        const errNode = isParenthesizedExpression(node) ? type : node;
+        const exprType = getRegularTypeOfObjectLiteral(getBaseTypeOfLiteralType(checkExpression(expression)));
         const targetType = getTypeFromTypeNode(type);
         if (!isErrorType(targetType)) {
             addLazyDiagnostic(() => {
@@ -34325,7 +34351,6 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 }
             });
         }
-        return targetType;
     }
 
     function checkNonNullChain(node: NonNullChain) {
@@ -37554,8 +37579,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 return checkSatisfiesExpressionWorker(node.expression, getJSDocSatisfiesExpressionType(node), checkMode);
             }
             if (isJSDocTypeAssertion(node)) {
-                const type = getJSDocTypeAssertionType(node);
-                return checkAssertionWorker(type, type, node.expression, checkMode);
+                return checkAssertionWorker(node, checkMode);
             }
         }
         return checkExpression(node.expression, checkMode);
@@ -37636,7 +37660,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 return checkTypeOfExpression(node as TypeOfExpression);
             case SyntaxKind.TypeAssertionExpression:
             case SyntaxKind.AsExpression:
-                return checkAssertion(node as AssertionExpression);
+                return checkAssertion(node as AssertionExpression, checkMode);
             case SyntaxKind.NonNullExpression:
                 return checkNonNullAssertion(node as NonNullExpression);
             case SyntaxKind.ExpressionWithTypeArguments:
@@ -44736,6 +44760,10 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
             case SyntaxKind.JsxElement:
                 checkJsxElementDeferred(node as JsxElement);
                 break;
+            case SyntaxKind.TypeAssertionExpression:
+            case SyntaxKind.AsExpression:
+            case SyntaxKind.ParenthesizedExpression:
+                checkAssertionDeferred(node as AssertionExpression | JSDocTypeAssertion);
         }
         currentNode = saveCurrentNode;
         tracing?.pop();
diff --git a/tests/baselines/reference/classVarianceCircularity.js b/tests/baselines/reference/classVarianceCircularity.js
new file mode 100644
index 0000000000000..60b4dd2995aab
--- /dev/null
+++ b/tests/baselines/reference/classVarianceCircularity.js
@@ -0,0 +1,32 @@
+//// [classVarianceCircularity.ts]
+// Issue #52813
+
+function f() {
+    const b = new Bar();
+    // Uncomment to create error
+    console.log(b.Value);
+}
+
+class Bar<T> {
+    num!: number;
+    // Or swap these two lines
+    Field: number = (this as Bar<any>).num;
+    Value = (this as Bar<any>).num;
+}
+
+//// [classVarianceCircularity.js]
+"use strict";
+// Issue #52813
+function f() {
+    var b = new Bar();
+    // Uncomment to create error
+    console.log(b.Value);
+}
+var Bar = /** @class */ (function () {
+    function Bar() {
+        // Or swap these two lines
+        this.Field = this.num;
+        this.Value = this.num;
+    }
+    return Bar;
+}());
diff --git a/tests/baselines/reference/classVarianceCircularity.symbols b/tests/baselines/reference/classVarianceCircularity.symbols
new file mode 100644
index 0000000000000..c0c3085755311
--- /dev/null
+++ b/tests/baselines/reference/classVarianceCircularity.symbols
@@ -0,0 +1,42 @@
+=== tests/cases/compiler/classVarianceCircularity.ts ===
+// Issue #52813
+
+function f() {
+>f : Symbol(f, Decl(classVarianceCircularity.ts, 0, 0))
+
+    const b = new Bar();
+>b : Symbol(b, Decl(classVarianceCircularity.ts, 3, 9))
+>Bar : Symbol(Bar, Decl(classVarianceCircularity.ts, 6, 1))
+
+    // Uncomment to create error
+    console.log(b.Value);
+>console.log : Symbol(Console.log, Decl(lib.dom.d.ts, --, --))
+>console : Symbol(console, Decl(lib.dom.d.ts, --, --))
+>log : Symbol(Console.log, Decl(lib.dom.d.ts, --, --))
+>b.Value : Symbol(Bar.Value, Decl(classVarianceCircularity.ts, 11, 43))
+>b : Symbol(b, Decl(classVarianceCircularity.ts, 3, 9))
+>Value : Symbol(Bar.Value, Decl(classVarianceCircularity.ts, 11, 43))
+}
+
+class Bar<T> {
+>Bar : Symbol(Bar, Decl(classVarianceCircularity.ts, 6, 1))
+>T : Symbol(T, Decl(classVarianceCircularity.ts, 8, 10))
+
+    num!: number;
+>num : Symbol(Bar.num, Decl(classVarianceCircularity.ts, 8, 14))
+
+    // Or swap these two lines
+    Field: number = (this as Bar<any>).num;
+>Field : Symbol(Bar.Field, Decl(classVarianceCircularity.ts, 9, 17))
+>(this as Bar<any>).num : Symbol(Bar.num, Decl(classVarianceCircularity.ts, 8, 14))
+>this : Symbol(Bar, Decl(classVarianceCircularity.ts, 6, 1))
+>Bar : Symbol(Bar, Decl(classVarianceCircularity.ts, 6, 1))
+>num : Symbol(Bar.num, Decl(classVarianceCircularity.ts, 8, 14))
+
+    Value = (this as Bar<any>).num;
+>Value : Symbol(Bar.Value, Decl(classVarianceCircularity.ts, 11, 43))
+>(this as Bar<any>).num : Symbol(Bar.num, Decl(classVarianceCircularity.ts, 8, 14))
+>this : Symbol(Bar, Decl(classVarianceCircularity.ts, 6, 1))
+>Bar : Symbol(Bar, Decl(classVarianceCircularity.ts, 6, 1))
+>num : Symbol(Bar.num, Decl(classVarianceCircularity.ts, 8, 14))
+}
diff --git a/tests/baselines/reference/classVarianceCircularity.types b/tests/baselines/reference/classVarianceCircularity.types
new file mode 100644
index 0000000000000..664e5ef220490
--- /dev/null
+++ b/tests/baselines/reference/classVarianceCircularity.types
@@ -0,0 +1,45 @@
+=== tests/cases/compiler/classVarianceCircularity.ts ===
+// Issue #52813
+
+function f() {
+>f : () => void
+
+    const b = new Bar();
+>b : Bar<unknown>
+>new Bar() : Bar<unknown>
+>Bar : typeof Bar
+
+    // Uncomment to create error
+    console.log(b.Value);
+>console.log(b.Value) : void
+>console.log : (...data: any[]) => void
+>console : Console
+>log : (...data: any[]) => void
+>b.Value : number
+>b : Bar<unknown>
+>Value : number
+}
+
+class Bar<T> {
+>Bar : Bar<T>
+
+    num!: number;
+>num : number
+
+    // Or swap these two lines
+    Field: number = (this as Bar<any>).num;
+>Field : number
+>(this as Bar<any>).num : number
+>(this as Bar<any>) : Bar<any>
+>this as Bar<any> : Bar<any>
+>this : this
+>num : number
+
+    Value = (this as Bar<any>).num;
+>Value : number
+>(this as Bar<any>).num : number
+>(this as Bar<any>) : Bar<any>
+>this as Bar<any> : Bar<any>
+>this : this
+>num : number
+}
diff --git a/tests/baselines/reference/classVarianceResolveCircularity.errors.txt b/tests/baselines/reference/classVarianceResolveCircularity.errors.txt
new file mode 100644
index 0000000000000..faff1bf64260a
--- /dev/null
+++ b/tests/baselines/reference/classVarianceResolveCircularity.errors.txt
@@ -0,0 +1,15 @@
+tests/cases/compiler/classVarianceResolveCircularity.ts(5,5): error TS7022: 'Value' implicitly has type 'any' because it does not have a type annotation and is referenced directly or indirectly in its own initializer.
+
+
+==== tests/cases/compiler/classVarianceResolveCircularity.ts (1 errors) ====
+    // Issue #52813
+    
+    class Bar<T> {
+        num!: number;    // Swap to remove error
+        Value = callme(this).num;
+        ~~~~~
+!!! error TS7022: 'Value' implicitly has type 'any' because it does not have a type annotation and is referenced directly or indirectly in its own initializer.
+        Field: number = callme(this).num;
+    }
+    declare function callme(x: Bar<any>): Bar<any>;
+    declare function callme(x: object): string;
\ No newline at end of file
diff --git a/tests/baselines/reference/classVarianceResolveCircularity.js b/tests/baselines/reference/classVarianceResolveCircularity.js
new file mode 100644
index 0000000000000..2518fa84c7bdc
--- /dev/null
+++ b/tests/baselines/reference/classVarianceResolveCircularity.js
@@ -0,0 +1,21 @@
+//// [classVarianceResolveCircularity.ts]
+// Issue #52813
+
+class Bar<T> {
+    num!: number;    // Swap to remove error
+    Value = callme(this).num;
+    Field: number = callme(this).num;
+}
+declare function callme(x: Bar<any>): Bar<any>;
+declare function callme(x: object): string;
+
+//// [classVarianceResolveCircularity.js]
+"use strict";
+// Issue #52813
+var Bar = /** @class */ (function () {
+    function Bar() {
+        this.Value = callme(this).num;
+        this.Field = callme(this).num;
+    }
+    return Bar;
+}());
diff --git a/tests/baselines/reference/classVarianceResolveCircularity.symbols b/tests/baselines/reference/classVarianceResolveCircularity.symbols
new file mode 100644
index 0000000000000..a3bf2bc878ff6
--- /dev/null
+++ b/tests/baselines/reference/classVarianceResolveCircularity.symbols
@@ -0,0 +1,34 @@
+=== tests/cases/compiler/classVarianceResolveCircularity.ts ===
+// Issue #52813
+
+class Bar<T> {
+>Bar : Symbol(Bar, Decl(classVarianceResolveCircularity.ts, 0, 0))
+>T : Symbol(T, Decl(classVarianceResolveCircularity.ts, 2, 10))
+
+    num!: number;    // Swap to remove error
+>num : Symbol(Bar.num, Decl(classVarianceResolveCircularity.ts, 2, 14))
+
+    Value = callme(this).num;
+>Value : Symbol(Bar.Value, Decl(classVarianceResolveCircularity.ts, 3, 17))
+>callme(this).num : Symbol(Bar.num, Decl(classVarianceResolveCircularity.ts, 2, 14))
+>callme : Symbol(callme, Decl(classVarianceResolveCircularity.ts, 6, 1), Decl(classVarianceResolveCircularity.ts, 7, 47))
+>this : Symbol(Bar, Decl(classVarianceResolveCircularity.ts, 0, 0))
+>num : Symbol(Bar.num, Decl(classVarianceResolveCircularity.ts, 2, 14))
+
+    Field: number = callme(this).num;
+>Field : Symbol(Bar.Field, Decl(classVarianceResolveCircularity.ts, 4, 29))
+>callme(this).num : Symbol(Bar.num, Decl(classVarianceResolveCircularity.ts, 2, 14))
+>callme : Symbol(callme, Decl(classVarianceResolveCircularity.ts, 6, 1), Decl(classVarianceResolveCircularity.ts, 7, 47))
+>this : Symbol(Bar, Decl(classVarianceResolveCircularity.ts, 0, 0))
+>num : Symbol(Bar.num, Decl(classVarianceResolveCircularity.ts, 2, 14))
+}
+declare function callme(x: Bar<any>): Bar<any>;
+>callme : Symbol(callme, Decl(classVarianceResolveCircularity.ts, 6, 1), Decl(classVarianceResolveCircularity.ts, 7, 47))
+>x : Symbol(x, Decl(classVarianceResolveCircularity.ts, 7, 24))
+>Bar : Symbol(Bar, Decl(classVarianceResolveCircularity.ts, 0, 0))
+>Bar : Symbol(Bar, Decl(classVarianceResolveCircularity.ts, 0, 0))
+
+declare function callme(x: object): string;
+>callme : Symbol(callme, Decl(classVarianceResolveCircularity.ts, 6, 1), Decl(classVarianceResolveCircularity.ts, 7, 47))
+>x : Symbol(x, Decl(classVarianceResolveCircularity.ts, 8, 24))
+
diff --git a/tests/baselines/reference/classVarianceResolveCircularity.types b/tests/baselines/reference/classVarianceResolveCircularity.types
new file mode 100644
index 0000000000000..d7e48dffe67df
--- /dev/null
+++ b/tests/baselines/reference/classVarianceResolveCircularity.types
@@ -0,0 +1,33 @@
+=== tests/cases/compiler/classVarianceResolveCircularity.ts ===
+// Issue #52813
+
+class Bar<T> {
+>Bar : Bar<T>
+
+    num!: number;    // Swap to remove error
+>num : number
+
+    Value = callme(this).num;
+>Value : any
+>callme(this).num : number
+>callme(this) : Bar<any>
+>callme : { (x: Bar<any>): Bar<any>; (x: object): string; }
+>this : this
+>num : number
+
+    Field: number = callme(this).num;
+>Field : number
+>callme(this).num : number
+>callme(this) : Bar<any>
+>callme : { (x: Bar<any>): Bar<any>; (x: object): string; }
+>this : this
+>num : number
+}
+declare function callme(x: Bar<any>): Bar<any>;
+>callme : { (x: Bar<any>): Bar<any>; (x: object): string; }
+>x : Bar<any>
+
+declare function callme(x: object): string;
+>callme : { (x: Bar<any>): Bar<any>; (x: object): string; }
+>x : object
+
diff --git a/tests/cases/compiler/classVarianceCircularity.ts b/tests/cases/compiler/classVarianceCircularity.ts
new file mode 100644
index 0000000000000..3c92600d4197d
--- /dev/null
+++ b/tests/cases/compiler/classVarianceCircularity.ts
@@ -0,0 +1,16 @@
+// @strict: true
+
+// Issue #52813
+
+function f() {
+    const b = new Bar();
+    // Uncomment to create error
+    console.log(b.Value);
+}
+
+class Bar<T> {
+    num!: number;
+    // Or swap these two lines
+    Field: number = (this as Bar<any>).num;
+    Value = (this as Bar<any>).num;
+}
\ No newline at end of file
diff --git a/tests/cases/compiler/classVarianceResolveCircularity.ts b/tests/cases/compiler/classVarianceResolveCircularity.ts
new file mode 100644
index 0000000000000..abff110eea799
--- /dev/null
+++ b/tests/cases/compiler/classVarianceResolveCircularity.ts
@@ -0,0 +1,11 @@
+// @strict: true
+
+// Issue #52813
+
+class Bar<T> {
+    num!: number;    // Swap to remove error
+    Value = callme(this).num;
+    Field: number = callme(this).num;
+}
+declare function callme(x: Bar<any>): Bar<any>;
+declare function callme(x: object): string;
\ No newline at end of file