diff --git a/src/xenia/cpu/xex_module.cc b/src/xenia/cpu/xex_module.cc
index 1e4b56f26..2ecd3581b 100644
--- a/src/xenia/cpu/xex_module.cc
+++ b/src/xenia/cpu/xex_module.cc
@@ -24,6 +24,7 @@
 #include "xenia/cpu/processor.h"
 #include "xenia/emulator.h"
 #include "xenia/kernel/kernel_state.h"
+#include "xenia/kernel/user_module.h"
 #include "xenia/kernel/xmodule.h"
 
 #include "third_party/crypto/TinySHA1.hpp"
@@ -1062,6 +1063,15 @@ bool XexModule::LoadContinue() {
                   opt_import_libraries->string_table.count);
       assert_not_null(string_table[library_name_index]);
       auto library_name = std::string(string_table[library_name_index]);
+
+      if (!kernel_state_->IsModuleLoaded(library_name)) {
+        if (auto module = kernel_state_->LoadUserModule(library_name)) {
+          if (kernel_state_->FinishLoadingUserModule(module, false)) {
+            library_name = module->path();
+          }
+        }
+      }
+
       SetupLibraryImports(library_name, library);
       library_offset += library->size;
     }
diff --git a/src/xenia/kernel/kernel_state.cc b/src/xenia/kernel/kernel_state.cc
index f0d0c439e..861c7cc33 100644
--- a/src/xenia/kernel/kernel_state.cc
+++ b/src/xenia/kernel/kernel_state.cc
@@ -217,6 +217,28 @@ bool KernelState::IsKernelModule(const std::string_view name) {
   return false;
 }
 
+bool KernelState::IsModuleLoaded(const std::string_view name) {
+  if (name.empty()) {
+    return true;
+  }
+
+  for (auto kernel_module : kernel_modules_) {
+    if (kernel_module->Matches(name)) {
+      return true;
+    }
+  }
+
+  auto global_lock = global_critical_region_.Acquire();
+
+  for (auto user_module : user_modules_) {
+    if (user_module->Matches(name)) {
+      return true;
+    }
+  }
+
+  return false;
+}
+
 object_ref<KernelModule> KernelState::GetKernelModule(
     const std::string_view name) {
   assert_true(IsKernelModule(name));
@@ -431,9 +453,14 @@ object_ref<UserModule> KernelState::LoadUserModule(
   auto name = xe::utf8::find_name_from_guest_path(raw_name);
   std::string path(raw_name);
   if (name == raw_name) {
-    assert_not_null(executable_module_);
-    path = xe::utf8::join_guest_paths(
-        xe::utf8::find_base_guest_path(executable_module_->path()), name);
+    if (!executable_module_) {
+      path = xe::utf8::join_guest_paths(
+          xe::utf8::find_base_guest_path((*user_modules_.cbegin())->path()),
+          name);
+    } else {
+      path = xe::utf8::join_guest_paths(
+          xe::utf8::find_base_guest_path(executable_module_->path()), name);
+    }
   }
 
   object_ref<UserModule> module;
@@ -521,6 +548,9 @@ X_RESULT KernelState::FinishLoadingUserModule(
         1,  // DLL_PROCESS_ATTACH
         0,  // 0 because always dynamic
     };
+
+    module->is_attached_ = true;
+
     auto thread_state = XThread::GetCurrentThread()->thread_state();
     processor()->Execute(thread_state, module->entry_point(), args,
                          xe::countof(args));
@@ -808,9 +838,16 @@ void KernelState::OnThreadExecute(XThread* thread) {
     if (user_module->is_dll_module() && user_module->entry_point()) {
       uint64_t args[] = {
           user_module->handle(),
-          2,  // DLL_THREAD_ATTACH
-          0,  // 0 because always dynamic
+          user_module->is_attached_
+              ? static_cast<uint64_t>(2)   // DLL_THREAD_ATTACH - Used to call
+                                           // DLL for each thread created.
+              : static_cast<uint64_t>(1),  // DLL_PROCESS_ATTACH - Used only
+                                           // once for initialization.
+          0,                               // 0 because always dynamic
       };
+
+      user_module->is_attached_ = true;
+
       processor()->Execute(thread_state, user_module->entry_point(), args,
                            xe::countof(args));
     }
diff --git a/src/xenia/kernel/kernel_state.h b/src/xenia/kernel/kernel_state.h
index 26ccad48e..60d5ac07c 100644
--- a/src/xenia/kernel/kernel_state.h
+++ b/src/xenia/kernel/kernel_state.h
@@ -226,6 +226,7 @@ class KernelState {
   bool RegisterUserModule(object_ref<UserModule> module);
   void UnregisterUserModule(UserModule* module);
   bool IsKernelModule(const std::string_view name);
+  bool IsModuleLoaded(const std::string_view name);
   object_ref<XModule> GetModule(const std::string_view name,
                                 bool user_only = false);
 
diff --git a/src/xenia/kernel/user_module.h b/src/xenia/kernel/user_module.h
index 02dbc3e7d..49c812233 100644
--- a/src/xenia/kernel/user_module.h
+++ b/src/xenia/kernel/user_module.h
@@ -108,6 +108,11 @@ class UserModule : public XModule {
                                         ByteStream* stream,
                                         const std::string_view path);
 
+  // TODO(Gliniak): This shouldn't be required. It is used for initial DLL
+  // initialization. Which should happen on main thread before main execution
+  // which isn't really possible right now.
+  bool is_attached_ = false;
+
  private:
   void CalculateHash();