diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index ebb2b79af90..4ed611a4663 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -13547,17 +13547,17 @@ namespace ts {
                 constraint;
         }
 
-        // Ordinarily we reduce a keyof M where M is a mapped type { [P in K as N<P>]: X } to simply N<K>. This however presumes
-        // that N distributes over union types, i.e. that N<A | B | C> is equivalent to N<A> | N<B> | N<C>. That presumption is
-        // generally true, except when N is a non-distributive conditional type or an instantiable type with non-distributive
-        // conditional type as a constituent. In those cases, we cannot reduce keyof M and need to preserve it as is.
-        function isNonDistributiveNameType(type: Type | undefined): boolean {
+        // Ordinarily we reduce a keyof M, where M is a mapped type { [P in K as N<P>]: X }, to simply N<K>. This however presumes
+        // that N distributes over union types, i.e. that N<A | B | C> is equivalent to N<A> | N<B> | N<C>. That presumption may not
+        // be true when N is a non-distributive conditional type or an instantiable type with a non-distributive conditional type as
+        // a constituent. In those cases, we cannot reduce keyof M and need to preserve it as is.
+        function maybeNonDistributiveNameType(type: Type | undefined): boolean {
             return !!(type && (
-                type.flags & TypeFlags.Conditional && !(<ConditionalType>type).root.isDistributive ||
-                type.flags & (TypeFlags.UnionOrIntersection | TypeFlags.TemplateLiteral) && some((<UnionOrIntersectionType | TemplateLiteralType>type).types, isNonDistributiveNameType) ||
-                type.flags & (TypeFlags.Index | TypeFlags.StringMapping) && isNonDistributiveNameType((<IndexType | StringMappingType>type).type) ||
-                type.flags & TypeFlags.IndexedAccess && isNonDistributiveNameType((<IndexedAccessType>type).indexType) ||
-                type.flags & TypeFlags.Substitution && isNonDistributiveNameType((<SubstitutionType>type).substitute)));
+                type.flags & TypeFlags.Conditional && (!(<ConditionalType>type).root.isDistributive || maybeNonDistributiveNameType((<ConditionalType>type).checkType)) ||
+                type.flags & (TypeFlags.UnionOrIntersection | TypeFlags.TemplateLiteral) && some((<UnionOrIntersectionType | TemplateLiteralType>type).types, maybeNonDistributiveNameType) ||
+                type.flags & (TypeFlags.Index | TypeFlags.StringMapping) && maybeNonDistributiveNameType((<IndexType | StringMappingType>type).type) ||
+                type.flags & TypeFlags.IndexedAccess && maybeNonDistributiveNameType((<IndexedAccessType>type).indexType) ||
+                type.flags & TypeFlags.Substitution && maybeNonDistributiveNameType((<SubstitutionType>type).substitute)));
         }
 
         function getLiteralTypeFromPropertyName(name: PropertyName) {
@@ -13607,7 +13607,7 @@ namespace ts {
             type = getReducedType(type);
             return type.flags & TypeFlags.Union ? getIntersectionType(map((<IntersectionType>type).types, t => getIndexType(t, stringsOnly, noIndexSignatures))) :
                 type.flags & TypeFlags.Intersection ? getUnionType(map((<IntersectionType>type).types, t => getIndexType(t, stringsOnly, noIndexSignatures))) :
-                type.flags & TypeFlags.InstantiableNonPrimitive || isGenericTupleType(type) || isGenericMappedType(type) && isNonDistributiveNameType(getNameTypeFromMappedType(type)) ? getIndexTypeForGenericType(<InstantiableType | UnionOrIntersectionType>type, stringsOnly) :
+                type.flags & TypeFlags.InstantiableNonPrimitive || isGenericTupleType(type) || isGenericMappedType(type) && maybeNonDistributiveNameType(getNameTypeFromMappedType(type)) ? getIndexTypeForGenericType(<InstantiableType | UnionOrIntersectionType>type, stringsOnly) :
                 getObjectFlags(type) & ObjectFlags.Mapped ? getIndexTypeForMappedType(<MappedType>type, noIndexSignatures) :
                 type === wildcardType ? wildcardType :
                 type.flags & TypeFlags.Unknown ? neverType :
diff --git a/tests/baselines/reference/mappedTypeAsClauses.js b/tests/baselines/reference/mappedTypeAsClauses.js
index 1940283e299..e5e15d8e6b2 100644
--- a/tests/baselines/reference/mappedTypeAsClauses.js
+++ b/tests/baselines/reference/mappedTypeAsClauses.js
@@ -86,6 +86,34 @@ let keys: keyof OnlyPrimitives<Car>;  //  "name" | "seats"
 type KeysOfPrimitives<T> = keyof OnlyPrimitives<T>;
 
 let carKeys: KeysOfPrimitives<Car>;  // "name" | "seats"
+
+// Repro from #41453
+
+type Equal<A, B> = (<T>() => T extends A ? 1 : 2) extends (<T>() => T extends B ? 1 : 2) ? true : false;
+
+type If<Cond extends boolean, Then, Else> = Cond extends true ? Then : Else;
+
+type GetKey<S, V> = keyof { [TP in keyof S as Equal<S[TP], V> extends true ? TP : never]: any };
+
+type GetKeyWithIf<S, V> = keyof { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any };
+
+type GetObjWithIf<S, V> = { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any };
+
+type Task = {
+  isDone: boolean;
+};
+
+type Schema = {
+  root: {
+    title: string;
+    task: Task;
+  }
+  Task: Task;
+};
+
+type Res1 = GetKey<Schema, Schema['root']['task']>;  // "Task"
+type Res2 = GetKeyWithIf<Schema, Schema['root']['task']>;  // "Task"
+type Res3 = keyof GetObjWithIf<Schema, Schema['root']['task']>;  // "Task"
 
 
 //// [mappedTypeAsClauses.js]
@@ -189,3 +217,27 @@ declare let primitiveCar: OnlyPrimitives<Car>;
 declare let keys: keyof OnlyPrimitives<Car>;
 declare type KeysOfPrimitives<T> = keyof OnlyPrimitives<T>;
 declare let carKeys: KeysOfPrimitives<Car>;
+declare type Equal<A, B> = (<T>() => T extends A ? 1 : 2) extends (<T>() => T extends B ? 1 : 2) ? true : false;
+declare type If<Cond extends boolean, Then, Else> = Cond extends true ? Then : Else;
+declare type GetKey<S, V> = keyof {
+    [TP in keyof S as Equal<S[TP], V> extends true ? TP : never]: any;
+};
+declare type GetKeyWithIf<S, V> = keyof {
+    [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any;
+};
+declare type GetObjWithIf<S, V> = {
+    [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any;
+};
+declare type Task = {
+    isDone: boolean;
+};
+declare type Schema = {
+    root: {
+        title: string;
+        task: Task;
+    };
+    Task: Task;
+};
+declare type Res1 = GetKey<Schema, Schema['root']['task']>;
+declare type Res2 = GetKeyWithIf<Schema, Schema['root']['task']>;
+declare type Res3 = keyof GetObjWithIf<Schema, Schema['root']['task']>;
diff --git a/tests/baselines/reference/mappedTypeAsClauses.symbols b/tests/baselines/reference/mappedTypeAsClauses.symbols
index 77ca6856b10..1de577a5fd5 100644
--- a/tests/baselines/reference/mappedTypeAsClauses.symbols
+++ b/tests/baselines/reference/mappedTypeAsClauses.symbols
@@ -264,3 +264,108 @@ let carKeys: KeysOfPrimitives<Car>;  // "name" | "seats"
 >KeysOfPrimitives : Symbol(KeysOfPrimitives, Decl(mappedTypeAsClauses.ts, 82, 36))
 >Car : Symbol(Car, Decl(mappedTypeAsClauses.ts, 57, 21))
 
+// Repro from #41453
+
+type Equal<A, B> = (<T>() => T extends A ? 1 : 2) extends (<T>() => T extends B ? 1 : 2) ? true : false;
+>Equal : Symbol(Equal, Decl(mappedTypeAsClauses.ts, 86, 35))
+>A : Symbol(A, Decl(mappedTypeAsClauses.ts, 90, 11))
+>B : Symbol(B, Decl(mappedTypeAsClauses.ts, 90, 13))
+>T : Symbol(T, Decl(mappedTypeAsClauses.ts, 90, 21))
+>T : Symbol(T, Decl(mappedTypeAsClauses.ts, 90, 21))
+>A : Symbol(A, Decl(mappedTypeAsClauses.ts, 90, 11))
+>T : Symbol(T, Decl(mappedTypeAsClauses.ts, 90, 60))
+>T : Symbol(T, Decl(mappedTypeAsClauses.ts, 90, 60))
+>B : Symbol(B, Decl(mappedTypeAsClauses.ts, 90, 13))
+
+type If<Cond extends boolean, Then, Else> = Cond extends true ? Then : Else;
+>If : Symbol(If, Decl(mappedTypeAsClauses.ts, 90, 104))
+>Cond : Symbol(Cond, Decl(mappedTypeAsClauses.ts, 92, 8))
+>Then : Symbol(Then, Decl(mappedTypeAsClauses.ts, 92, 29))
+>Else : Symbol(Else, Decl(mappedTypeAsClauses.ts, 92, 35))
+>Cond : Symbol(Cond, Decl(mappedTypeAsClauses.ts, 92, 8))
+>Then : Symbol(Then, Decl(mappedTypeAsClauses.ts, 92, 29))
+>Else : Symbol(Else, Decl(mappedTypeAsClauses.ts, 92, 35))
+
+type GetKey<S, V> = keyof { [TP in keyof S as Equal<S[TP], V> extends true ? TP : never]: any };
+>GetKey : Symbol(GetKey, Decl(mappedTypeAsClauses.ts, 92, 76))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 94, 12))
+>V : Symbol(V, Decl(mappedTypeAsClauses.ts, 94, 14))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 94, 29))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 94, 12))
+>Equal : Symbol(Equal, Decl(mappedTypeAsClauses.ts, 86, 35))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 94, 12))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 94, 29))
+>V : Symbol(V, Decl(mappedTypeAsClauses.ts, 94, 14))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 94, 29))
+
+type GetKeyWithIf<S, V> = keyof { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any };
+>GetKeyWithIf : Symbol(GetKeyWithIf, Decl(mappedTypeAsClauses.ts, 94, 96))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 96, 18))
+>V : Symbol(V, Decl(mappedTypeAsClauses.ts, 96, 20))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 96, 35))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 96, 18))
+>If : Symbol(If, Decl(mappedTypeAsClauses.ts, 90, 104))
+>Equal : Symbol(Equal, Decl(mappedTypeAsClauses.ts, 86, 35))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 96, 18))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 96, 35))
+>V : Symbol(V, Decl(mappedTypeAsClauses.ts, 96, 20))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 96, 35))
+
+type GetObjWithIf<S, V> = { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any };
+>GetObjWithIf : Symbol(GetObjWithIf, Decl(mappedTypeAsClauses.ts, 96, 91))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 98, 18))
+>V : Symbol(V, Decl(mappedTypeAsClauses.ts, 98, 20))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 98, 29))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 98, 18))
+>If : Symbol(If, Decl(mappedTypeAsClauses.ts, 90, 104))
+>Equal : Symbol(Equal, Decl(mappedTypeAsClauses.ts, 86, 35))
+>S : Symbol(S, Decl(mappedTypeAsClauses.ts, 98, 18))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 98, 29))
+>V : Symbol(V, Decl(mappedTypeAsClauses.ts, 98, 20))
+>TP : Symbol(TP, Decl(mappedTypeAsClauses.ts, 98, 29))
+
+type Task = {
+>Task : Symbol(Task, Decl(mappedTypeAsClauses.ts, 98, 85))
+
+  isDone: boolean;
+>isDone : Symbol(isDone, Decl(mappedTypeAsClauses.ts, 100, 13))
+
+};
+
+type Schema = {
+>Schema : Symbol(Schema, Decl(mappedTypeAsClauses.ts, 102, 2))
+
+  root: {
+>root : Symbol(root, Decl(mappedTypeAsClauses.ts, 104, 15))
+
+    title: string;
+>title : Symbol(title, Decl(mappedTypeAsClauses.ts, 105, 9))
+
+    task: Task;
+>task : Symbol(task, Decl(mappedTypeAsClauses.ts, 106, 18))
+>Task : Symbol(Task, Decl(mappedTypeAsClauses.ts, 98, 85))
+  }
+  Task: Task;
+>Task : Symbol(Task, Decl(mappedTypeAsClauses.ts, 108, 3))
+>Task : Symbol(Task, Decl(mappedTypeAsClauses.ts, 98, 85))
+
+};
+
+type Res1 = GetKey<Schema, Schema['root']['task']>;  // "Task"
+>Res1 : Symbol(Res1, Decl(mappedTypeAsClauses.ts, 110, 2))
+>GetKey : Symbol(GetKey, Decl(mappedTypeAsClauses.ts, 92, 76))
+>Schema : Symbol(Schema, Decl(mappedTypeAsClauses.ts, 102, 2))
+>Schema : Symbol(Schema, Decl(mappedTypeAsClauses.ts, 102, 2))
+
+type Res2 = GetKeyWithIf<Schema, Schema['root']['task']>;  // "Task"
+>Res2 : Symbol(Res2, Decl(mappedTypeAsClauses.ts, 112, 51))
+>GetKeyWithIf : Symbol(GetKeyWithIf, Decl(mappedTypeAsClauses.ts, 94, 96))
+>Schema : Symbol(Schema, Decl(mappedTypeAsClauses.ts, 102, 2))
+>Schema : Symbol(Schema, Decl(mappedTypeAsClauses.ts, 102, 2))
+
+type Res3 = keyof GetObjWithIf<Schema, Schema['root']['task']>;  // "Task"
+>Res3 : Symbol(Res3, Decl(mappedTypeAsClauses.ts, 113, 57))
+>GetObjWithIf : Symbol(GetObjWithIf, Decl(mappedTypeAsClauses.ts, 96, 91))
+>Schema : Symbol(Schema, Decl(mappedTypeAsClauses.ts, 102, 2))
+>Schema : Symbol(Schema, Decl(mappedTypeAsClauses.ts, 102, 2))
+
diff --git a/tests/baselines/reference/mappedTypeAsClauses.types b/tests/baselines/reference/mappedTypeAsClauses.types
index 5ada8893a6f..55bb1c780d0 100644
--- a/tests/baselines/reference/mappedTypeAsClauses.types
+++ b/tests/baselines/reference/mappedTypeAsClauses.types
@@ -170,3 +170,58 @@ type KeysOfPrimitives<T> = keyof OnlyPrimitives<T>;
 let carKeys: KeysOfPrimitives<Car>;  // "name" | "seats"
 >carKeys : "name" | "seats"
 
+// Repro from #41453
+
+type Equal<A, B> = (<T>() => T extends A ? 1 : 2) extends (<T>() => T extends B ? 1 : 2) ? true : false;
+>Equal : Equal<A, B>
+>true : true
+>false : false
+
+type If<Cond extends boolean, Then, Else> = Cond extends true ? Then : Else;
+>If : If<Cond, Then, Else>
+>true : true
+
+type GetKey<S, V> = keyof { [TP in keyof S as Equal<S[TP], V> extends true ? TP : never]: any };
+>GetKey : keyof { [TP in keyof S as Equal<S[TP], V> extends true ? TP : never]: any; }
+>true : true
+
+type GetKeyWithIf<S, V> = keyof { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any };
+>GetKeyWithIf : keyof { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any; }
+
+type GetObjWithIf<S, V> = { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any };
+>GetObjWithIf : GetObjWithIf<S, V>
+
+type Task = {
+>Task : Task
+
+  isDone: boolean;
+>isDone : boolean
+
+};
+
+type Schema = {
+>Schema : Schema
+
+  root: {
+>root : { title: string; task: Task; }
+
+    title: string;
+>title : string
+
+    task: Task;
+>task : Task
+  }
+  Task: Task;
+>Task : Task
+
+};
+
+type Res1 = GetKey<Schema, Schema['root']['task']>;  // "Task"
+>Res1 : "Task"
+
+type Res2 = GetKeyWithIf<Schema, Schema['root']['task']>;  // "Task"
+>Res2 : "Task"
+
+type Res3 = keyof GetObjWithIf<Schema, Schema['root']['task']>;  // "Task"
+>Res3 : "Task"
+
diff --git a/tests/cases/conformance/types/mapped/mappedTypeAsClauses.ts b/tests/cases/conformance/types/mapped/mappedTypeAsClauses.ts
index 747307f3652..6c13786d81d 100644
--- a/tests/cases/conformance/types/mapped/mappedTypeAsClauses.ts
+++ b/tests/cases/conformance/types/mapped/mappedTypeAsClauses.ts
@@ -88,3 +88,31 @@ let keys: keyof OnlyPrimitives<Car>;  //  "name" | "seats"
 type KeysOfPrimitives<T> = keyof OnlyPrimitives<T>;
 
 let carKeys: KeysOfPrimitives<Car>;  // "name" | "seats"
+
+// Repro from #41453
+
+type Equal<A, B> = (<T>() => T extends A ? 1 : 2) extends (<T>() => T extends B ? 1 : 2) ? true : false;
+
+type If<Cond extends boolean, Then, Else> = Cond extends true ? Then : Else;
+
+type GetKey<S, V> = keyof { [TP in keyof S as Equal<S[TP], V> extends true ? TP : never]: any };
+
+type GetKeyWithIf<S, V> = keyof { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any };
+
+type GetObjWithIf<S, V> = { [TP in keyof S as If<Equal<S[TP], V>, TP, never>]: any };
+
+type Task = {
+  isDone: boolean;
+};
+
+type Schema = {
+  root: {
+    title: string;
+    task: Task;
+  }
+  Task: Task;
+};
+
+type Res1 = GetKey<Schema, Schema['root']['task']>;  // "Task"
+type Res2 = GetKeyWithIf<Schema, Schema['root']['task']>;  // "Task"
+type Res3 = keyof GetObjWithIf<Schema, Schema['root']['task']>;  // "Task"