diff --git a/Siv3D/include/Siv3D/DragDrop.hpp b/Siv3D/include/Siv3D/DragDrop.hpp
index 4ae40a9c1..7a408fa48 100644
--- a/Siv3D/include/Siv3D/DragDrop.hpp
+++ b/Siv3D/include/Siv3D/DragDrop.hpp
@@ -70,6 +70,10 @@ namespace s3d
 		/// @brief 指定したファイルのドラッグを開始します。
 		/// @param path ファイルパス
 		void MakeDragDrop(FilePathView path);
+
+		/// @brief 指定したファイルのドラッグを開始します。
+		/// @param paths ファイルパスの配列
+		void MakeDragDrop(const Array<FilePath>& paths);
 	}
 
 # endif
diff --git a/Siv3D/src/Siv3D-Platform/Linux/Siv3D/DragDrop/CDragDrop.cpp b/Siv3D/src/Siv3D-Platform/Linux/Siv3D/DragDrop/CDragDrop.cpp
index 6a482bdfb..9b33a64da 100644
--- a/Siv3D/src/Siv3D-Platform/Linux/Siv3D/DragDrop/CDragDrop.cpp
+++ b/Siv3D/src/Siv3D-Platform/Linux/Siv3D/DragDrop/CDragDrop.cpp
@@ -155,7 +155,7 @@ namespace s3d
 		return dropped;
 	}
 
-	void CDragDrop::makeDragDrop(const FilePathView)
+	void CDragDrop::makeDragDrop(const Array<FilePath>&)
 	{
 		// [Siv3D ToDo]
 	}
diff --git a/Siv3D/src/Siv3D-Platform/Linux/Siv3D/DragDrop/CDragDrop.hpp b/Siv3D/src/Siv3D-Platform/Linux/Siv3D/DragDrop/CDragDrop.hpp
index d7276194a..1d36dd3c9 100644
--- a/Siv3D/src/Siv3D-Platform/Linux/Siv3D/DragDrop/CDragDrop.hpp
+++ b/Siv3D/src/Siv3D-Platform/Linux/Siv3D/DragDrop/CDragDrop.hpp
@@ -42,7 +42,7 @@ namespace s3d
 
 		Array<DroppedText> getDroppedText() override;
 
-		void makeDragDrop(FilePathView path) override;
+		void makeDragDrop(const Array<FilePath>& paths) override;
 
 		//
 		//	Linux
diff --git a/Siv3D/src/Siv3D-Platform/Web/Siv3D/DragDrop/CDragDrop.cpp b/Siv3D/src/Siv3D-Platform/Web/Siv3D/DragDrop/CDragDrop.cpp
index afdc75e8c..708a7e4f5 100644
--- a/Siv3D/src/Siv3D-Platform/Web/Siv3D/DragDrop/CDragDrop.cpp
+++ b/Siv3D/src/Siv3D-Platform/Web/Siv3D/DragDrop/CDragDrop.cpp
@@ -165,7 +165,7 @@ namespace s3d
 		return dropped;
 	}
 
-	void CDragDrop::makeDragDrop(const FilePathView path)
+	void CDragDrop::makeDragDrop(const Array<FilePath>&)
 	{
 		// [Siv3D ToDo]
 	}
diff --git a/Siv3D/src/Siv3D-Platform/Web/Siv3D/DragDrop/CDragDrop.hpp b/Siv3D/src/Siv3D-Platform/Web/Siv3D/DragDrop/CDragDrop.hpp
index d7276194a..1d36dd3c9 100644
--- a/Siv3D/src/Siv3D-Platform/Web/Siv3D/DragDrop/CDragDrop.hpp
+++ b/Siv3D/src/Siv3D-Platform/Web/Siv3D/DragDrop/CDragDrop.hpp
@@ -42,7 +42,7 @@ namespace s3d
 
 		Array<DroppedText> getDroppedText() override;
 
-		void makeDragDrop(FilePathView path) override;
+		void makeDragDrop(const Array<FilePath>& paths) override;
 
 		//
 		//	Linux
diff --git a/Siv3D/src/Siv3D-Platform/WindowsDesktop/Siv3D/DragDrop/CDragDrop.cpp b/Siv3D/src/Siv3D-Platform/WindowsDesktop/Siv3D/DragDrop/CDragDrop.cpp
index e213dd78c..1c3d9c0e6 100644
--- a/Siv3D/src/Siv3D-Platform/WindowsDesktop/Siv3D/DragDrop/CDragDrop.cpp
+++ b/Siv3D/src/Siv3D-Platform/WindowsDesktop/Siv3D/DragDrop/CDragDrop.cpp
@@ -670,12 +670,21 @@ namespace s3d
 			}
 		};
 
-		static void BeginDrop(IDataObject** lpDataObejct, IDropSource** lpDropSource, const FilePath& path)
+		static void BeginDrop(IDataObject** lpDataObejct, IDropSource** lpDropSource, const Array<FilePath>& paths)
 		{
-			std::wstring pathW = (FileSystem::FullPath(path)).toWstr();
-			pathW.push_back(L'\0');
-			pathW.push_back(L'\0');
-			const size_t path_size_bytes = (sizeof(wchar_t) * pathW.size());
+			// must be double null terminated
+			std::wstring data;
+			{
+				for (const auto& path : paths)
+				{
+					data += (FileSystem::FullPath(path)).toWstr();
+					data.push_back(L'\0');
+				}
+
+				data.push_back(L'\0');
+			}
+
+			const size_t data_size_bytes = (sizeof(wchar_t) * data.size());
 
 			FORMATETC formatetc;
 			formatetc.cfFormat = CF_HDROP;
@@ -687,14 +696,14 @@ namespace s3d
 			STGMEDIUM medium
 			{
 				.tymed		= TYMED_HGLOBAL,
-				.hGlobal	= ::GlobalAlloc(GMEM_MOVEABLE, sizeof(DROPFILES) + path_size_bytes)
+				.hGlobal	= ::GlobalAlloc(GMEM_MOVEABLE, sizeof(DROPFILES) + data_size_bytes)
 			};
 			
 			if (void* p = ::GlobalLock(medium.hGlobal))
 			{
 				((DROPFILES*)p)->pFiles = sizeof(DROPFILES);
 				((DROPFILES*)p)->fWide = true;
-				std::memcpy((char*)p + sizeof(DROPFILES), pathW.data(), path_size_bytes);
+				std::memcpy((char*)p + sizeof(DROPFILES), data.data(), data_size_bytes);
 				::GlobalUnlock(medium.hGlobal);
 			}
 
@@ -818,27 +827,27 @@ namespace s3d
 		return dropped;
 	}
 
-	void CDragDrop::makeDragDrop(const FilePathView path)
+	void CDragDrop::makeDragDrop(const Array<FilePath>& paths)
 	{
 		std::lock_guard lock{ m_mutex };
 
-		m_newDragPath = path;
+		m_newDragPaths = paths;
 	}
 
 	void CDragDrop::process()
 	{
-		FilePath path;
+		Array<FilePath> paths;
 
 		{
 			std::lock_guard lock{ m_mutex };
 
-			if (m_newDragPath)
+			if (m_newDragPaths)
 			{
-				path.swap(m_newDragPath);
+				paths.swap(m_newDragPaths);
 			}
 		}
 
-		if (not path)
+		if (not paths)
 		{
 			return;
 		}
@@ -847,7 +856,7 @@ namespace s3d
 			ComPtr<IDataObject> dataObject;
 			ComPtr<IDropSource> dropSource;
 
-			detail::BeginDrop(&dataObject, &dropSource, path);
+			detail::BeginDrop(&dataObject, &dropSource, paths);
 
 			DWORD dropEffect;
 			HRESULT hr = ::DoDragDrop(dataObject.Get(), dropSource.Get(), DROPEFFECT_MOVE | DROPEFFECT_COPY, &dropEffect);
diff --git a/Siv3D/src/Siv3D-Platform/WindowsDesktop/Siv3D/DragDrop/CDragDrop.hpp b/Siv3D/src/Siv3D-Platform/WindowsDesktop/Siv3D/DragDrop/CDragDrop.hpp
index 1c8e43d2e..a4f493de6 100644
--- a/Siv3D/src/Siv3D-Platform/WindowsDesktop/Siv3D/DragDrop/CDragDrop.hpp
+++ b/Siv3D/src/Siv3D-Platform/WindowsDesktop/Siv3D/DragDrop/CDragDrop.hpp
@@ -49,7 +49,7 @@ namespace s3d
 
 		Array<DroppedText> getDroppedText() override;
 
-		void makeDragDrop(FilePathView path) override;
+		void makeDragDrop(const Array<FilePath>& paths) override;
 
 		void process();
 
@@ -73,7 +73,7 @@ namespace s3d
 		//
 		std::mutex m_mutex;
 
-		FilePath m_newDragPath;
+		Array<FilePath> m_newDragPaths;
 		//
 		//////////
 	};
diff --git a/Siv3D/src/Siv3D-Platform/macOS/Siv3D/DragDrop/CDragDrop.cpp b/Siv3D/src/Siv3D-Platform/macOS/Siv3D/DragDrop/CDragDrop.cpp
index 8334e6e66..ce03cb178 100644
--- a/Siv3D/src/Siv3D-Platform/macOS/Siv3D/DragDrop/CDragDrop.cpp
+++ b/Siv3D/src/Siv3D-Platform/macOS/Siv3D/DragDrop/CDragDrop.cpp
@@ -170,7 +170,7 @@ namespace s3d
 		return dropped;
 	}
 
-	void CDragDrop::makeDragDrop(const FilePathView)
+	void CDragDrop::makeDragDrop(const Array<FilePath>&)
 	{
 		// [Siv3D ToDo]
 	}
diff --git a/Siv3D/src/Siv3D-Platform/macOS/Siv3D/DragDrop/CDragDrop.hpp b/Siv3D/src/Siv3D-Platform/macOS/Siv3D/DragDrop/CDragDrop.hpp
index a143ed767..300762783 100644
--- a/Siv3D/src/Siv3D-Platform/macOS/Siv3D/DragDrop/CDragDrop.hpp
+++ b/Siv3D/src/Siv3D-Platform/macOS/Siv3D/DragDrop/CDragDrop.hpp
@@ -42,7 +42,7 @@ namespace s3d
 
 		Array<DroppedText> getDroppedText() override;
 
-		void makeDragDrop(FilePathView path) override;
+		void makeDragDrop(const Array<FilePath>& paths) override;
 		
 		//
 		//	macOS
diff --git a/Siv3D/src/Siv3D/DragDrop/IDragDrop.hpp b/Siv3D/src/Siv3D/DragDrop/IDragDrop.hpp
index 9ce3c731c..3dd7e641f 100644
--- a/Siv3D/src/Siv3D/DragDrop/IDragDrop.hpp
+++ b/Siv3D/src/Siv3D/DragDrop/IDragDrop.hpp
@@ -43,6 +43,6 @@ namespace s3d
 
 		virtual Array<DroppedText> getDroppedText() = 0;
 
-		virtual void makeDragDrop(FilePathView path) = 0;
+		virtual void makeDragDrop(const Array<FilePath>& paths) = 0;
 	};
 }
diff --git a/Siv3D/src/Siv3D/DragDrop/SivDragDrop.cpp b/Siv3D/src/Siv3D/DragDrop/SivDragDrop.cpp
index 65db46959..153361dbb 100644
--- a/Siv3D/src/Siv3D/DragDrop/SivDragDrop.cpp
+++ b/Siv3D/src/Siv3D/DragDrop/SivDragDrop.cpp
@@ -64,7 +64,14 @@ namespace s3d
 	{
 		void MakeDragDrop(const FilePathView path)
 		{
-			SIV3D_ENGINE(DragDrop)->makeDragDrop(path);
+			const Array<FilePath> paths = { FilePath{ path } };
+
+			SIV3D_ENGINE(DragDrop)->makeDragDrop(paths);
+		}
+
+		void MakeDragDrop(const Array<FilePath>& paths)
+		{
+			SIV3D_ENGINE(DragDrop)->makeDragDrop(paths);
 		}
 	}