diff --git a/src/api/environment.cc b/src/api/environment.cc
index bd9de560d08120..2b9eab2bc0b236 100644
--- a/src/api/environment.cc
+++ b/src/api/environment.cc
@@ -20,8 +20,11 @@ using v8::Function;
 using v8::FunctionCallbackInfo;
 using v8::HandleScope;
 using v8::Isolate;
+using v8::Just;
 using v8::Local;
+using v8::Maybe;
 using v8::MaybeLocal;
+using v8::Nothing;
 using v8::Null;
 using v8::Object;
 using v8::ObjectTemplate;
@@ -501,7 +504,7 @@ MaybeLocal<Object> GetPerContextExports(Local<Context> context) {
 
   Local<Object> exports = Object::New(isolate);
   if (context->Global()->SetPrivate(context, key, exports).IsNothing() ||
-      !InitializePrimordials(context))
+      InitializePrimordials(context).IsNothing())
     return MaybeLocal<Object>();
   return handle_scope.Escape(exports);
 }
@@ -514,7 +517,7 @@ Local<Context> NewContext(Isolate* isolate,
   auto context = Context::New(isolate, nullptr, object_template);
   if (context.IsEmpty()) return context;
 
-  if (!InitializeContext(context)) {
+  if (InitializeContext(context).IsNothing()) {
     return Local<Context>();
   }
 
@@ -581,16 +584,17 @@ void InitializeContextRuntime(Local<Context> context) {
   }
 }
 
-bool InitializeContextForSnapshot(Local<Context> context) {
+Maybe<bool> InitializeContextForSnapshot(Local<Context> context) {
   Isolate* isolate = context->GetIsolate();
   HandleScope handle_scope(isolate);
 
   context->SetEmbedderData(ContextEmbedderIndex::kAllowWasmCodeGeneration,
                            True(isolate));
+
   return InitializePrimordials(context);
 }
 
-bool InitializePrimordials(Local<Context> context) {
+Maybe<bool> InitializePrimordials(Local<Context> context) {
   // Run per-context JS files.
   Isolate* isolate = context->GetIsolate();
   Context::Scope context_scope(context);
@@ -603,10 +607,10 @@ bool InitializePrimordials(Local<Context> context) {
 
   // Create primordials first and make it available to per-context scripts.
   Local<Object> primordials = Object::New(isolate);
-  if (!primordials->SetPrototype(context, Null(isolate)).FromJust() ||
+  if (primordials->SetPrototype(context, Null(isolate)).IsNothing() ||
       !GetPerContextExports(context).ToLocal(&exports) ||
-      !exports->Set(context, primordials_string, primordials).FromJust()) {
-    return false;
+      exports->Set(context, primordials_string, primordials).IsNothing()) {
+    return Nothing<bool>();
   }
 
   static const char* context_files[] = {"internal/per_context/primordials",
@@ -623,27 +627,27 @@ bool InitializePrimordials(Local<Context> context) {
             context, *module, &parameters, nullptr);
     Local<Function> fn;
     if (!maybe_fn.ToLocal(&fn)) {
-      return false;
+      return Nothing<bool>();
     }
     MaybeLocal<Value> result =
         fn->Call(context, Undefined(isolate), arraysize(arguments), arguments);
     // Execution failed during context creation.
-    // TODO(joyeecheung): deprecate this signature and return a MaybeLocal.
     if (result.IsEmpty()) {
-      return false;
+      return Nothing<bool>();
     }
   }
 
-  return true;
+  return Just(true);
 }
 
-bool InitializeContext(Local<Context> context) {
-  if (!InitializeContextForSnapshot(context)) {
-    return false;
+Maybe<bool> InitializeContext(Local<Context> context) {
+  if (InitializeContextForSnapshot(context).IsNothing()) {
+    return Nothing<bool>();
   }
 
   InitializeContextRuntime(context);
-  return true;
+
+  return Just(true);
 }
 
 uv_loop_t* GetCurrentEventLoop(Isolate* isolate) {
diff --git a/src/node.h b/src/node.h
index 066c0eadfb6b05..1628a2147ea203 100644
--- a/src/node.h
+++ b/src/node.h
@@ -367,7 +367,7 @@ NODE_EXTERN v8::Local<v8::Context> NewContext(
 
 // Runs Node.js-specific tweaks on an already constructed context
 // Return value indicates success of operation
-NODE_EXTERN bool InitializeContext(v8::Local<v8::Context> context);
+NODE_EXTERN v8::Maybe<bool> InitializeContext(v8::Local<v8::Context> context);
 
 // If `platform` is passed, it will be used to register new Worker instances.
 // It can be `nullptr`, in which case creating new Workers inside of
diff --git a/src/node_internals.h b/src/node_internals.h
index 8f7929994f3243..06b2bdefb74a6e 100644
--- a/src/node_internals.h
+++ b/src/node_internals.h
@@ -92,8 +92,9 @@ void SignalExit(int signal, siginfo_t* info, void* ucontext);
 std::string GetProcessTitle(const char* default_title);
 std::string GetHumanReadableProcessName();
 
-void InitializeContextRuntime(v8::Local<v8::Context>);
-bool InitializePrimordials(v8::Local<v8::Context> context);
+// TODO(RaisinTen): return a v8::Maybe<bool>.
+void InitializeContextRuntime(v8::Local<v8::Context> context);
+v8::Maybe<bool> InitializePrimordials(v8::Local<v8::Context> context);
 
 class NodeArrayBufferAllocator : public ArrayBufferAllocator {
  public: