diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 79d6a2fbcdd..0a2d154b449 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -23682,10 +23682,12 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         return false;
     }
 
-    function isTypeParameterAtTopLevel(type: Type, typeParameter: TypeParameter): boolean {
-        return !!(type === typeParameter ||
-            type.flags & TypeFlags.UnionOrIntersection && some((type as UnionOrIntersectionType).types, t => isTypeParameterAtTopLevel(t, typeParameter)) ||
-            type.flags & TypeFlags.Conditional && (getTrueTypeFromConditionalType(type as ConditionalType) === typeParameter || getFalseTypeFromConditionalType(type as ConditionalType) === typeParameter));
+    function isTypeParameterAtTopLevel(type: Type, tp: TypeParameter, depth = 0): boolean {
+        return !!(type === tp ||
+            type.flags & TypeFlags.UnionOrIntersection && some((type as UnionOrIntersectionType).types, t => isTypeParameterAtTopLevel(t, tp, depth)) ||
+            depth < 3 && type.flags & TypeFlags.Conditional && (
+                isTypeParameterAtTopLevel(getTrueTypeFromConditionalType(type as ConditionalType), tp, depth + 1) ||
+                isTypeParameterAtTopLevel(getFalseTypeFromConditionalType(type as ConditionalType), tp, depth + 1)));
     }
 
     function isTypeParameterAtTopLevelInReturnType(signature: Signature, typeParameter: TypeParameter) {
diff --git a/tests/baselines/reference/wideningWithTopLevelTypeParameter.symbols b/tests/baselines/reference/wideningWithTopLevelTypeParameter.symbols
new file mode 100644
index 00000000000..7eb9498cf21
--- /dev/null
+++ b/tests/baselines/reference/wideningWithTopLevelTypeParameter.symbols
@@ -0,0 +1,133 @@
+=== tests/cases/compiler/wideningWithTopLevelTypeParameter.ts ===
+type C1<T> = T extends unknown ? T | undefined : never;
+>C1 : Symbol(C1, Decl(wideningWithTopLevelTypeParameter.ts, 0, 0))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 0, 8))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 0, 8))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 0, 8))
+
+type C2<T> = T extends unknown ? T | undefined : never;
+>C2 : Symbol(C2, Decl(wideningWithTopLevelTypeParameter.ts, 0, 55))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 1, 8))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 1, 8))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 1, 8))
+
+type C3<T> = T extends unknown ? T | undefined : never;
+>C3 : Symbol(C3, Decl(wideningWithTopLevelTypeParameter.ts, 1, 55))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 2, 8))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 2, 8))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 2, 8))
+
+type C4<T> = T extends unknown ? T | undefined : never;
+>C4 : Symbol(C4, Decl(wideningWithTopLevelTypeParameter.ts, 2, 55))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 3, 8))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 3, 8))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 3, 8))
+
+declare function f0<T>(x: T): [T];
+>f0 : Symbol(f0, Decl(wideningWithTopLevelTypeParameter.ts, 3, 55))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 5, 20))
+>x : Symbol(x, Decl(wideningWithTopLevelTypeParameter.ts, 5, 23))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 5, 20))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 5, 20))
+
+declare function f1<T>(x: C1<T>): [T];
+>f1 : Symbol(f1, Decl(wideningWithTopLevelTypeParameter.ts, 5, 34))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 6, 20))
+>x : Symbol(x, Decl(wideningWithTopLevelTypeParameter.ts, 6, 23))
+>C1 : Symbol(C1, Decl(wideningWithTopLevelTypeParameter.ts, 0, 0))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 6, 20))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 6, 20))
+
+declare function f2<T>(x: C1<C2<T>>): [T];
+>f2 : Symbol(f2, Decl(wideningWithTopLevelTypeParameter.ts, 6, 38))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 7, 20))
+>x : Symbol(x, Decl(wideningWithTopLevelTypeParameter.ts, 7, 23))
+>C1 : Symbol(C1, Decl(wideningWithTopLevelTypeParameter.ts, 0, 0))
+>C2 : Symbol(C2, Decl(wideningWithTopLevelTypeParameter.ts, 0, 55))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 7, 20))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 7, 20))
+
+declare function f3<T>(x: C1<C2<C3<T>>>): [T];
+>f3 : Symbol(f3, Decl(wideningWithTopLevelTypeParameter.ts, 7, 42))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 8, 20))
+>x : Symbol(x, Decl(wideningWithTopLevelTypeParameter.ts, 8, 23))
+>C1 : Symbol(C1, Decl(wideningWithTopLevelTypeParameter.ts, 0, 0))
+>C2 : Symbol(C2, Decl(wideningWithTopLevelTypeParameter.ts, 0, 55))
+>C3 : Symbol(C3, Decl(wideningWithTopLevelTypeParameter.ts, 1, 55))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 8, 20))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 8, 20))
+
+declare function f4<T>(x: C1<C2<C3<C4<T>>>>): [T];
+>f4 : Symbol(f4, Decl(wideningWithTopLevelTypeParameter.ts, 8, 46))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 9, 20))
+>x : Symbol(x, Decl(wideningWithTopLevelTypeParameter.ts, 9, 23))
+>C1 : Symbol(C1, Decl(wideningWithTopLevelTypeParameter.ts, 0, 0))
+>C2 : Symbol(C2, Decl(wideningWithTopLevelTypeParameter.ts, 0, 55))
+>C3 : Symbol(C3, Decl(wideningWithTopLevelTypeParameter.ts, 1, 55))
+>C4 : Symbol(C4, Decl(wideningWithTopLevelTypeParameter.ts, 2, 55))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 9, 20))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 9, 20))
+
+const c0 = f0(7);  // [number]
+>c0 : Symbol(c0, Decl(wideningWithTopLevelTypeParameter.ts, 11, 5))
+>f0 : Symbol(f0, Decl(wideningWithTopLevelTypeParameter.ts, 3, 55))
+
+const c1 = f1(7);  // [number]
+>c1 : Symbol(c1, Decl(wideningWithTopLevelTypeParameter.ts, 12, 5))
+>f1 : Symbol(f1, Decl(wideningWithTopLevelTypeParameter.ts, 5, 34))
+
+const c2 = f2(7);  // [number]
+>c2 : Symbol(c2, Decl(wideningWithTopLevelTypeParameter.ts, 13, 5))
+>f2 : Symbol(f2, Decl(wideningWithTopLevelTypeParameter.ts, 6, 38))
+
+const c3 = f3(7);  // [number]
+>c3 : Symbol(c3, Decl(wideningWithTopLevelTypeParameter.ts, 14, 5))
+>f3 : Symbol(f3, Decl(wideningWithTopLevelTypeParameter.ts, 7, 42))
+
+const c4 = f4(7);  // [7] since we have an internal nesting limit of 3
+>c4 : Symbol(c4, Decl(wideningWithTopLevelTypeParameter.ts, 15, 5))
+>f4 : Symbol(f4, Decl(wideningWithTopLevelTypeParameter.ts, 8, 46))
+
+// Repro from #52620
+
+class FormControl<T> {
+>FormControl : Symbol(FormControl, Decl(wideningWithTopLevelTypeParameter.ts, 15, 17))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 19, 18))
+
+    constructor(t: T extends undefined ? never : T) {}
+>t : Symbol(t, Decl(wideningWithTopLevelTypeParameter.ts, 20, 16))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 19, 18))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 19, 18))
+}
+
+const a = new FormControl('');  // string
+>a : Symbol(a, Decl(wideningWithTopLevelTypeParameter.ts, 23, 5))
+>FormControl : Symbol(FormControl, Decl(wideningWithTopLevelTypeParameter.ts, 15, 17))
+
+class FormControl2<T> {
+>FormControl2 : Symbol(FormControl2, Decl(wideningWithTopLevelTypeParameter.ts, 23, 30))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 25, 19))
+
+    constructor(t: T | string) {}
+>t : Symbol(t, Decl(wideningWithTopLevelTypeParameter.ts, 26, 16))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 25, 19))
+}
+
+const b = new FormControl2('');  // string
+>b : Symbol(b, Decl(wideningWithTopLevelTypeParameter.ts, 29, 5))
+>FormControl2 : Symbol(FormControl2, Decl(wideningWithTopLevelTypeParameter.ts, 23, 30))
+
+class FormControl3<T> {
+>FormControl3 : Symbol(FormControl3, Decl(wideningWithTopLevelTypeParameter.ts, 29, 31))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 31, 19))
+
+    constructor(t: T extends undefined ? never : T | string) {}
+>t : Symbol(t, Decl(wideningWithTopLevelTypeParameter.ts, 32, 16))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 31, 19))
+>T : Symbol(T, Decl(wideningWithTopLevelTypeParameter.ts, 31, 19))
+}
+
+const c = new FormControl3('');  // string
+>c : Symbol(c, Decl(wideningWithTopLevelTypeParameter.ts, 35, 5))
+>FormControl3 : Symbol(FormControl3, Decl(wideningWithTopLevelTypeParameter.ts, 29, 31))
+
diff --git a/tests/baselines/reference/wideningWithTopLevelTypeParameter.types b/tests/baselines/reference/wideningWithTopLevelTypeParameter.types
new file mode 100644
index 00000000000..c29e4a80e20
--- /dev/null
+++ b/tests/baselines/reference/wideningWithTopLevelTypeParameter.types
@@ -0,0 +1,104 @@
+=== tests/cases/compiler/wideningWithTopLevelTypeParameter.ts ===
+type C1<T> = T extends unknown ? T | undefined : never;
+>C1 : C1<T>
+
+type C2<T> = T extends unknown ? T | undefined : never;
+>C2 : C2<T>
+
+type C3<T> = T extends unknown ? T | undefined : never;
+>C3 : C3<T>
+
+type C4<T> = T extends unknown ? T | undefined : never;
+>C4 : C4<T>
+
+declare function f0<T>(x: T): [T];
+>f0 : <T>(x: T) => [T]
+>x : T
+
+declare function f1<T>(x: C1<T>): [T];
+>f1 : <T>(x: C1<T>) => [T]
+>x : C1<T>
+
+declare function f2<T>(x: C1<C2<T>>): [T];
+>f2 : <T>(x: C1<C2<T>>) => [T]
+>x : C1<C2<T>>
+
+declare function f3<T>(x: C1<C2<C3<T>>>): [T];
+>f3 : <T>(x: C1<C2<C3<T>>>) => [T]
+>x : C1<C2<C3<T>>>
+
+declare function f4<T>(x: C1<C2<C3<C4<T>>>>): [T];
+>f4 : <T>(x: C1<C2<C3<C4<T>>>>) => [T]
+>x : C1<C2<C3<C4<T>>>>
+
+const c0 = f0(7);  // [number]
+>c0 : [number]
+>f0(7) : [number]
+>f0 : <T>(x: T) => [T]
+>7 : 7
+
+const c1 = f1(7);  // [number]
+>c1 : [number]
+>f1(7) : [number]
+>f1 : <T>(x: C1<T>) => [T]
+>7 : 7
+
+const c2 = f2(7);  // [number]
+>c2 : [number]
+>f2(7) : [number]
+>f2 : <T>(x: C1<C2<T>>) => [T]
+>7 : 7
+
+const c3 = f3(7);  // [number]
+>c3 : [number]
+>f3(7) : [number]
+>f3 : <T>(x: C1<C2<C3<T>>>) => [T]
+>7 : 7
+
+const c4 = f4(7);  // [7] since we have an internal nesting limit of 3
+>c4 : [7]
+>f4(7) : [7]
+>f4 : <T>(x: C1<C2<C3<C4<T>>>>) => [T]
+>7 : 7
+
+// Repro from #52620
+
+class FormControl<T> {
+>FormControl : FormControl<T>
+
+    constructor(t: T extends undefined ? never : T) {}
+>t : T extends undefined ? never : T
+}
+
+const a = new FormControl('');  // string
+>a : FormControl<string>
+>new FormControl('') : FormControl<string>
+>FormControl : typeof FormControl
+>'' : ""
+
+class FormControl2<T> {
+>FormControl2 : FormControl2<T>
+
+    constructor(t: T | string) {}
+>t : string | T
+}
+
+const b = new FormControl2('');  // string
+>b : FormControl2<string>
+>new FormControl2('') : FormControl2<string>
+>FormControl2 : typeof FormControl2
+>'' : ""
+
+class FormControl3<T> {
+>FormControl3 : FormControl3<T>
+
+    constructor(t: T extends undefined ? never : T | string) {}
+>t : T extends undefined ? never : string | T
+}
+
+const c = new FormControl3('');  // string
+>c : FormControl3<string>
+>new FormControl3('') : FormControl3<string>
+>FormControl3 : typeof FormControl3
+>'' : ""
+
diff --git a/tests/cases/compiler/wideningWithTopLevelTypeParameter.ts b/tests/cases/compiler/wideningWithTopLevelTypeParameter.ts
new file mode 100644
index 00000000000..061fab5d4ed
--- /dev/null
+++ b/tests/cases/compiler/wideningWithTopLevelTypeParameter.ts
@@ -0,0 +1,39 @@
+// @strict: true
+// @noEmit: true
+
+type C1<T> = T extends unknown ? T | undefined : never;
+type C2<T> = T extends unknown ? T | undefined : never;
+type C3<T> = T extends unknown ? T | undefined : never;
+type C4<T> = T extends unknown ? T | undefined : never;
+
+declare function f0<T>(x: T): [T];
+declare function f1<T>(x: C1<T>): [T];
+declare function f2<T>(x: C1<C2<T>>): [T];
+declare function f3<T>(x: C1<C2<C3<T>>>): [T];
+declare function f4<T>(x: C1<C2<C3<C4<T>>>>): [T];
+
+const c0 = f0(7);  // [number]
+const c1 = f1(7);  // [number]
+const c2 = f2(7);  // [number]
+const c3 = f3(7);  // [number]
+const c4 = f4(7);  // [7] since we have an internal nesting limit of 3
+
+// Repro from #52620
+
+class FormControl<T> {
+    constructor(t: T extends undefined ? never : T) {}
+}
+
+const a = new FormControl('');  // string
+
+class FormControl2<T> {
+    constructor(t: T | string) {}
+}
+
+const b = new FormControl2('');  // string
+
+class FormControl3<T> {
+    constructor(t: T extends undefined ? never : T | string) {}
+}
+
+const c = new FormControl3('');  // string