diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index f315b1a75cc..529f78fdc96 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -21583,6 +21583,17 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                     else if (result = isRelatedTo(getTypeWithThisArgument(constraint, source), target, RecursionFlags.Source, reportErrors && constraint !== unknownType && !(targetFlags & sourceFlags & TypeFlags.TypeParameter), /*headMessage*/ undefined, intersectionState)) {
                         return result;
                     }
+                    if (sourceFlags & TypeFlags.IndexedAccess) {
+                        const indexType = (source as IndexedAccessType).indexType;
+                        if (indexType.flags & TypeFlags.Index) {
+                            const unresolvedIndexConstraint = getBaseConstraintOfType((indexType as IndexType).type);
+                            const indexConstraint = unresolvedIndexConstraint && unresolvedIndexConstraint !== noConstraintType ? getIndexType(unresolvedIndexConstraint) : keyofConstraintType;
+                            const constraint = getIndexedAccessType((source as IndexedAccessType).objectType, indexConstraint);
+                            if (result = isRelatedTo(constraint, target, RecursionFlags.Source, /*reportErrors*/ false, /*headMessage*/ undefined, intersectionState)) {
+                                return result;
+                            }
+                        }
+                    }
                     if (isMappedTypeGenericIndexedAccess(source)) {
                         // For an indexed access type { [P in K]: E}[X], above we have already explored an instantiation of E with X
                         // substituted for P. We also want to explore type { [P in K]: E }[C], where C is the constraint of X.
diff --git a/tests/baselines/reference/constraintWithIndexedAccess.errors.txt b/tests/baselines/reference/constraintWithIndexedAccess.errors.txt
new file mode 100644
index 00000000000..f8a8539b9b2
--- /dev/null
+++ b/tests/baselines/reference/constraintWithIndexedAccess.errors.txt
@@ -0,0 +1,60 @@
+tests/cases/compiler/constraintWithIndexedAccess.ts(28,102): error TS2344: Type 'DataFetchFns[T][T]' does not satisfy the constraint '(...args: any) => any'.
+  Type 'DataFetchFns[T]["Boat"] | DataFetchFns[T]["Plane"]' is not assignable to type '(...args: any) => any'.
+    Type 'DataFetchFns[T]["Boat"]' is not assignable to type '(...args: any) => any'.
+tests/cases/compiler/constraintWithIndexedAccess.ts(28,102): error TS2536: Type 'T' cannot be used to index type 'DataFetchFns[T]'.
+tests/cases/compiler/constraintWithIndexedAccess.ts(29,102): error TS2536: Type 'F' cannot be used to index type 'DataFetchFns'.
+tests/cases/compiler/constraintWithIndexedAccess.ts(29,102): error TS2344: Type 'DataFetchFns[F][F]' does not satisfy the constraint '(...args: any) => any'.
+  Type 'DataFetchFns[F][keyof DataFetchFns[T]]' is not assignable to type '(...args: any) => any'.
+    Type 'DataFetchFns[F][string] | DataFetchFns[F][number] | DataFetchFns[F][symbol]' is not assignable to type '(...args: any) => any'.
+      Type 'DataFetchFns[F][string]' is not assignable to type '(...args: any) => any'.
+        Type 'DataFetchFns[keyof DataFetchFns[T]][string]' is not assignable to type '(...args: any) => any'.
+tests/cases/compiler/constraintWithIndexedAccess.ts(29,102): error TS2536: Type 'F' cannot be used to index type 'DataFetchFns[F]'.
+
+
+==== tests/cases/compiler/constraintWithIndexedAccess.ts (5 errors) ====
+    // #52399
+    type DataFetchFns = {
+        Boat: {
+            requiresLicense: (id: string) => boolean;
+            maxGroundSpeed: (id: string) => number;
+            description: (id: string) => string;
+            displacement: (id: string) => number;
+            name: (id: string) => string;
+        };
+        Plane: {
+            requiresLicense: (id: string) => boolean;
+            maxGroundSpeed: (id: string) => number;
+            maxTakeoffWeight: (id: string) => number;
+            maxCruisingAltitude: (id: string) => number;
+            name: (id: string) => string;
+        }
+    }
+    export type NoTypeParamBoatRequired<F extends keyof DataFetchFns['Boat']> = ReturnType<DataFetchFns['Boat'][F]>;
+    type TypeHardcodedAsParameterWithoutReturnType<T extends 'Boat', F extends keyof DataFetchFns[T]> = DataFetchFns[T][F];
+    export type allAreFunctionsAsExpected = TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>;
+    export type returnTypeOfFunctions = ReturnType<allAreFunctionsAsExpected>; //string | number | boolean as expected
+    export type SucceedingCombo = ReturnType<TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>>;
+    export type FailingCombo<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<TypeHardcodedAsParameterWithoutReturnType<T,F>>;
+    export type TypeHardcodedAsParameter<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+    type VehicleSelector<T extends keyof DataFetchFns> = DataFetchFns[T];
+    export type TypeHardcodedAsParameter2<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<VehicleSelector<T>[F]>;
+    export type TypeGeneric1<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+    export type TypeGeneric2<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][T]>; // error
+                                                                                                         ~~~~~~~~~~~~~~~~~~
+!!! error TS2344: Type 'DataFetchFns[T][T]' does not satisfy the constraint '(...args: any) => any'.
+!!! error TS2344:   Type 'DataFetchFns[T]["Boat"] | DataFetchFns[T]["Plane"]' is not assignable to type '(...args: any) => any'.
+!!! error TS2344:     Type 'DataFetchFns[T]["Boat"]' is not assignable to type '(...args: any) => any'.
+                                                                                                         ~~~~~~~~~~~~~~~~~~
+!!! error TS2536: Type 'T' cannot be used to index type 'DataFetchFns[T]'.
+    export type TypeGeneric3<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[F][F]>; // error
+                                                                                                         ~~~~~~~~~~~~~~~
+!!! error TS2536: Type 'F' cannot be used to index type 'DataFetchFns'.
+                                                                                                         ~~~~~~~~~~~~~~~~~~
+!!! error TS2344: Type 'DataFetchFns[F][F]' does not satisfy the constraint '(...args: any) => any'.
+!!! error TS2344:   Type 'DataFetchFns[F][keyof DataFetchFns[T]]' is not assignable to type '(...args: any) => any'.
+!!! error TS2344:     Type 'DataFetchFns[F][string] | DataFetchFns[F][number] | DataFetchFns[F][symbol]' is not assignable to type '(...args: any) => any'.
+!!! error TS2344:       Type 'DataFetchFns[F][string]' is not assignable to type '(...args: any) => any'.
+!!! error TS2344:         Type 'DataFetchFns[keyof DataFetchFns[T]][string]' is not assignable to type '(...args: any) => any'.
+                                                                                                         ~~~~~~~~~~~~~~~~~~
+!!! error TS2536: Type 'F' cannot be used to index type 'DataFetchFns[F]'.
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/constraintWithIndexedAccess.js b/tests/baselines/reference/constraintWithIndexedAccess.js
new file mode 100644
index 00000000000..9a60445571e
--- /dev/null
+++ b/tests/baselines/reference/constraintWithIndexedAccess.js
@@ -0,0 +1,35 @@
+//// [constraintWithIndexedAccess.ts]
+// #52399
+type DataFetchFns = {
+    Boat: {
+        requiresLicense: (id: string) => boolean;
+        maxGroundSpeed: (id: string) => number;
+        description: (id: string) => string;
+        displacement: (id: string) => number;
+        name: (id: string) => string;
+    };
+    Plane: {
+        requiresLicense: (id: string) => boolean;
+        maxGroundSpeed: (id: string) => number;
+        maxTakeoffWeight: (id: string) => number;
+        maxCruisingAltitude: (id: string) => number;
+        name: (id: string) => string;
+    }
+}
+export type NoTypeParamBoatRequired<F extends keyof DataFetchFns['Boat']> = ReturnType<DataFetchFns['Boat'][F]>;
+type TypeHardcodedAsParameterWithoutReturnType<T extends 'Boat', F extends keyof DataFetchFns[T]> = DataFetchFns[T][F];
+export type allAreFunctionsAsExpected = TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>;
+export type returnTypeOfFunctions = ReturnType<allAreFunctionsAsExpected>; //string | number | boolean as expected
+export type SucceedingCombo = ReturnType<TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>>;
+export type FailingCombo<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<TypeHardcodedAsParameterWithoutReturnType<T,F>>;
+export type TypeHardcodedAsParameter<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+type VehicleSelector<T extends keyof DataFetchFns> = DataFetchFns[T];
+export type TypeHardcodedAsParameter2<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<VehicleSelector<T>[F]>;
+export type TypeGeneric1<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+export type TypeGeneric2<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][T]>; // error
+export type TypeGeneric3<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[F][F]>; // error
+
+
+//// [constraintWithIndexedAccess.js]
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
diff --git a/tests/baselines/reference/constraintWithIndexedAccess.symbols b/tests/baselines/reference/constraintWithIndexedAccess.symbols
new file mode 100644
index 00000000000..60802dd4688
--- /dev/null
+++ b/tests/baselines/reference/constraintWithIndexedAccess.symbols
@@ -0,0 +1,163 @@
+=== tests/cases/compiler/constraintWithIndexedAccess.ts ===
+// #52399
+type DataFetchFns = {
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+
+    Boat: {
+>Boat : Symbol(Boat, Decl(constraintWithIndexedAccess.ts, 1, 21))
+
+        requiresLicense: (id: string) => boolean;
+>requiresLicense : Symbol(requiresLicense, Decl(constraintWithIndexedAccess.ts, 2, 11))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 3, 26))
+
+        maxGroundSpeed: (id: string) => number;
+>maxGroundSpeed : Symbol(maxGroundSpeed, Decl(constraintWithIndexedAccess.ts, 3, 49))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 4, 25))
+
+        description: (id: string) => string;
+>description : Symbol(description, Decl(constraintWithIndexedAccess.ts, 4, 47))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 5, 22))
+
+        displacement: (id: string) => number;
+>displacement : Symbol(displacement, Decl(constraintWithIndexedAccess.ts, 5, 44))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 6, 23))
+
+        name: (id: string) => string;
+>name : Symbol(name, Decl(constraintWithIndexedAccess.ts, 6, 45))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 7, 15))
+
+    };
+    Plane: {
+>Plane : Symbol(Plane, Decl(constraintWithIndexedAccess.ts, 8, 6))
+
+        requiresLicense: (id: string) => boolean;
+>requiresLicense : Symbol(requiresLicense, Decl(constraintWithIndexedAccess.ts, 9, 12))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 10, 26))
+
+        maxGroundSpeed: (id: string) => number;
+>maxGroundSpeed : Symbol(maxGroundSpeed, Decl(constraintWithIndexedAccess.ts, 10, 49))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 11, 25))
+
+        maxTakeoffWeight: (id: string) => number;
+>maxTakeoffWeight : Symbol(maxTakeoffWeight, Decl(constraintWithIndexedAccess.ts, 11, 47))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 12, 27))
+
+        maxCruisingAltitude: (id: string) => number;
+>maxCruisingAltitude : Symbol(maxCruisingAltitude, Decl(constraintWithIndexedAccess.ts, 12, 49))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 13, 30))
+
+        name: (id: string) => string;
+>name : Symbol(name, Decl(constraintWithIndexedAccess.ts, 13, 52))
+>id : Symbol(id, Decl(constraintWithIndexedAccess.ts, 14, 15))
+    }
+}
+export type NoTypeParamBoatRequired<F extends keyof DataFetchFns['Boat']> = ReturnType<DataFetchFns['Boat'][F]>;
+>NoTypeParamBoatRequired : Symbol(NoTypeParamBoatRequired, Decl(constraintWithIndexedAccess.ts, 16, 1))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 17, 36))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 17, 36))
+
+type TypeHardcodedAsParameterWithoutReturnType<T extends 'Boat', F extends keyof DataFetchFns[T]> = DataFetchFns[T][F];
+>TypeHardcodedAsParameterWithoutReturnType : Symbol(TypeHardcodedAsParameterWithoutReturnType, Decl(constraintWithIndexedAccess.ts, 17, 112))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 18, 47))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 18, 64))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 18, 47))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 18, 47))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 18, 64))
+
+export type allAreFunctionsAsExpected = TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>;
+>allAreFunctionsAsExpected : Symbol(allAreFunctionsAsExpected, Decl(constraintWithIndexedAccess.ts, 18, 119))
+>TypeHardcodedAsParameterWithoutReturnType : Symbol(TypeHardcodedAsParameterWithoutReturnType, Decl(constraintWithIndexedAccess.ts, 17, 112))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+
+export type returnTypeOfFunctions = ReturnType<allAreFunctionsAsExpected>; //string | number | boolean as expected
+>returnTypeOfFunctions : Symbol(returnTypeOfFunctions, Decl(constraintWithIndexedAccess.ts, 19, 118))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>allAreFunctionsAsExpected : Symbol(allAreFunctionsAsExpected, Decl(constraintWithIndexedAccess.ts, 18, 119))
+
+export type SucceedingCombo = ReturnType<TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>>;
+>SucceedingCombo : Symbol(SucceedingCombo, Decl(constraintWithIndexedAccess.ts, 20, 74))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>TypeHardcodedAsParameterWithoutReturnType : Symbol(TypeHardcodedAsParameterWithoutReturnType, Decl(constraintWithIndexedAccess.ts, 17, 112))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+
+export type FailingCombo<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<TypeHardcodedAsParameterWithoutReturnType<T,F>>;
+>FailingCombo : Symbol(FailingCombo, Decl(constraintWithIndexedAccess.ts, 21, 120))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 22, 25))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 22, 42))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 22, 25))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>TypeHardcodedAsParameterWithoutReturnType : Symbol(TypeHardcodedAsParameterWithoutReturnType, Decl(constraintWithIndexedAccess.ts, 17, 112))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 22, 25))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 22, 42))
+
+export type TypeHardcodedAsParameter<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+>TypeHardcodedAsParameter : Symbol(TypeHardcodedAsParameter, Decl(constraintWithIndexedAccess.ts, 22, 137))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 23, 37))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 23, 54))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 23, 37))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 23, 37))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 23, 54))
+
+type VehicleSelector<T extends keyof DataFetchFns> = DataFetchFns[T];
+>VehicleSelector : Symbol(VehicleSelector, Decl(constraintWithIndexedAccess.ts, 23, 121))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 24, 21))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 24, 21))
+
+export type TypeHardcodedAsParameter2<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<VehicleSelector<T>[F]>;
+>TypeHardcodedAsParameter2 : Symbol(TypeHardcodedAsParameter2, Decl(constraintWithIndexedAccess.ts, 24, 69))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 25, 38))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 25, 55))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 25, 38))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>VehicleSelector : Symbol(VehicleSelector, Decl(constraintWithIndexedAccess.ts, 23, 121))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 25, 38))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 25, 55))
+
+export type TypeGeneric1<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+>TypeGeneric1 : Symbol(TypeGeneric1, Decl(constraintWithIndexedAccess.ts, 25, 125))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 26, 25))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 26, 54))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 26, 25))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 26, 25))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 26, 54))
+
+export type TypeGeneric2<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][T]>; // error
+>TypeGeneric2 : Symbol(TypeGeneric2, Decl(constraintWithIndexedAccess.ts, 26, 121))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 27, 25))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 27, 54))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 27, 25))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 27, 25))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 27, 25))
+
+export type TypeGeneric3<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[F][F]>; // error
+>TypeGeneric3 : Symbol(TypeGeneric3, Decl(constraintWithIndexedAccess.ts, 27, 121))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 28, 25))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 28, 54))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>T : Symbol(T, Decl(constraintWithIndexedAccess.ts, 28, 25))
+>ReturnType : Symbol(ReturnType, Decl(lib.es5.d.ts, --, --))
+>DataFetchFns : Symbol(DataFetchFns, Decl(constraintWithIndexedAccess.ts, 0, 0))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 28, 54))
+>F : Symbol(F, Decl(constraintWithIndexedAccess.ts, 28, 54))
+
diff --git a/tests/baselines/reference/constraintWithIndexedAccess.types b/tests/baselines/reference/constraintWithIndexedAccess.types
new file mode 100644
index 00000000000..0c236abe404
--- /dev/null
+++ b/tests/baselines/reference/constraintWithIndexedAccess.types
@@ -0,0 +1,89 @@
+=== tests/cases/compiler/constraintWithIndexedAccess.ts ===
+// #52399
+type DataFetchFns = {
+>DataFetchFns : { Boat: { requiresLicense: (id: string) => boolean; maxGroundSpeed: (id: string) => number; description: (id: string) => string; displacement: (id: string) => number; name: (id: string) => string; }; Plane: { requiresLicense: (id: string) => boolean; maxGroundSpeed: (id: string) => number; maxTakeoffWeight: (id: string) => number; maxCruisingAltitude: (id: string) => number; name: (id: string) => string; }; }
+
+    Boat: {
+>Boat : { requiresLicense: (id: string) => boolean; maxGroundSpeed: (id: string) => number; description: (id: string) => string; displacement: (id: string) => number; name: (id: string) => string; }
+
+        requiresLicense: (id: string) => boolean;
+>requiresLicense : (id: string) => boolean
+>id : string
+
+        maxGroundSpeed: (id: string) => number;
+>maxGroundSpeed : (id: string) => number
+>id : string
+
+        description: (id: string) => string;
+>description : (id: string) => string
+>id : string
+
+        displacement: (id: string) => number;
+>displacement : (id: string) => number
+>id : string
+
+        name: (id: string) => string;
+>name : (id: string) => string
+>id : string
+
+    };
+    Plane: {
+>Plane : { requiresLicense: (id: string) => boolean; maxGroundSpeed: (id: string) => number; maxTakeoffWeight: (id: string) => number; maxCruisingAltitude: (id: string) => number; name: (id: string) => string; }
+
+        requiresLicense: (id: string) => boolean;
+>requiresLicense : (id: string) => boolean
+>id : string
+
+        maxGroundSpeed: (id: string) => number;
+>maxGroundSpeed : (id: string) => number
+>id : string
+
+        maxTakeoffWeight: (id: string) => number;
+>maxTakeoffWeight : (id: string) => number
+>id : string
+
+        maxCruisingAltitude: (id: string) => number;
+>maxCruisingAltitude : (id: string) => number
+>id : string
+
+        name: (id: string) => string;
+>name : (id: string) => string
+>id : string
+    }
+}
+export type NoTypeParamBoatRequired<F extends keyof DataFetchFns['Boat']> = ReturnType<DataFetchFns['Boat'][F]>;
+>NoTypeParamBoatRequired : NoTypeParamBoatRequired<F>
+
+type TypeHardcodedAsParameterWithoutReturnType<T extends 'Boat', F extends keyof DataFetchFns[T]> = DataFetchFns[T][F];
+>TypeHardcodedAsParameterWithoutReturnType : TypeHardcodedAsParameterWithoutReturnType<T, F>
+
+export type allAreFunctionsAsExpected = TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>;
+>allAreFunctionsAsExpected : ((id: string) => boolean) | ((id: string) => number) | ((id: string) => string) | ((id: string) => number) | ((id: string) => string)
+
+export type returnTypeOfFunctions = ReturnType<allAreFunctionsAsExpected>; //string | number | boolean as expected
+>returnTypeOfFunctions : string | number | boolean
+
+export type SucceedingCombo = ReturnType<TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>>;
+>SucceedingCombo : string | number | boolean
+
+export type FailingCombo<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<TypeHardcodedAsParameterWithoutReturnType<T,F>>;
+>FailingCombo : FailingCombo<T, F>
+
+export type TypeHardcodedAsParameter<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+>TypeHardcodedAsParameter : TypeHardcodedAsParameter<T, F>
+
+type VehicleSelector<T extends keyof DataFetchFns> = DataFetchFns[T];
+>VehicleSelector : VehicleSelector<T>
+
+export type TypeHardcodedAsParameter2<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<VehicleSelector<T>[F]>;
+>TypeHardcodedAsParameter2 : TypeHardcodedAsParameter2<T, F>
+
+export type TypeGeneric1<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+>TypeGeneric1 : TypeGeneric1<T, F>
+
+export type TypeGeneric2<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][T]>; // error
+>TypeGeneric2 : TypeGeneric2<T, F>
+
+export type TypeGeneric3<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[F][F]>; // error
+>TypeGeneric3 : TypeGeneric3<T, F>
+
diff --git a/tests/cases/compiler/constraintWithIndexedAccess.ts b/tests/cases/compiler/constraintWithIndexedAccess.ts
new file mode 100644
index 00000000000..4b40399820c
--- /dev/null
+++ b/tests/cases/compiler/constraintWithIndexedAccess.ts
@@ -0,0 +1,29 @@
+// #52399
+type DataFetchFns = {
+    Boat: {
+        requiresLicense: (id: string) => boolean;
+        maxGroundSpeed: (id: string) => number;
+        description: (id: string) => string;
+        displacement: (id: string) => number;
+        name: (id: string) => string;
+    };
+    Plane: {
+        requiresLicense: (id: string) => boolean;
+        maxGroundSpeed: (id: string) => number;
+        maxTakeoffWeight: (id: string) => number;
+        maxCruisingAltitude: (id: string) => number;
+        name: (id: string) => string;
+    }
+}
+export type NoTypeParamBoatRequired<F extends keyof DataFetchFns['Boat']> = ReturnType<DataFetchFns['Boat'][F]>;
+type TypeHardcodedAsParameterWithoutReturnType<T extends 'Boat', F extends keyof DataFetchFns[T]> = DataFetchFns[T][F];
+export type allAreFunctionsAsExpected = TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>;
+export type returnTypeOfFunctions = ReturnType<allAreFunctionsAsExpected>; //string | number | boolean as expected
+export type SucceedingCombo = ReturnType<TypeHardcodedAsParameterWithoutReturnType<'Boat', keyof DataFetchFns['Boat']>>;
+export type FailingCombo<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<TypeHardcodedAsParameterWithoutReturnType<T,F>>;
+export type TypeHardcodedAsParameter<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+type VehicleSelector<T extends keyof DataFetchFns> = DataFetchFns[T];
+export type TypeHardcodedAsParameter2<T extends 'Boat', F extends keyof DataFetchFns[T]> = ReturnType<VehicleSelector<T>[F]>;
+export type TypeGeneric1<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][F]>;
+export type TypeGeneric2<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[T][T]>; // error
+export type TypeGeneric3<T extends keyof DataFetchFns, F extends keyof DataFetchFns[T]> = ReturnType<DataFetchFns[F][F]>; // error