diff --git a/src/fileshelter/main/main.cpp b/src/fileshelter/main/main.cpp
index 5e13f4e..6bc83bc 100644
--- a/src/fileshelter/main/main.cpp
+++ b/src/fileshelter/main/main.cpp
@@ -187,6 +187,7 @@ int main(int argc, char *argv[])
 		const std::string deployPath {Service<IConfig>::get()->getString("deploy-path", "/")};
 
 		Service<Share::IShareManager> shareManager {Share::createShareManager(Service<IConfig>::get()->getPath("working-dir") / "fileshelter.db", true /* enableCleaner */)};
+		shareManager->removeOrphanFiles(uploadedFilesPath);
 
 		ShareResource shareResource;
 		server.addResource(&shareResource, std::string {shareResource.getDeployPath()});
diff --git a/src/libs/share/impl/File.cpp b/src/libs/share/impl/File.cpp
index 6b9ca3f..db7c8df 100644
--- a/src/libs/share/impl/File.cpp
+++ b/src/libs/share/impl/File.cpp
@@ -36,7 +36,13 @@ namespace Share
 
 		session.flush();
 		return res;
+	}
 
+	File::pointer
+	File::getByPath(Wt::Dbo::Session& session, const std::filesystem::path& filePath)
+	{
+		return session.find<File>().where("path = ?").bind(filePath);
 	}
+
 }
 
diff --git a/src/libs/share/impl/File.hpp b/src/libs/share/impl/File.hpp
index cbf887f..1e5c379 100644
--- a/src/libs/share/impl/File.hpp
+++ b/src/libs/share/impl/File.hpp
@@ -39,6 +39,7 @@ namespace Share
 
 			// Helpers
 			static pointer	create(Wt::Dbo::Session& session, const FileCreateParameters& parameters, Wt::Dbo::ptr<Share> share);
+			static pointer	getByPath(Wt::Dbo::Session& session, const std::filesystem::path& path);
 
 			// Getters
 			const FileUUID&					getUUID() const { return _uuid; }
diff --git a/src/libs/share/impl/Share.cpp b/src/libs/share/impl/Share.cpp
index 0ca9d79..be4e00d 100644
--- a/src/libs/share/impl/Share.cpp
+++ b/src/libs/share/impl/Share.cpp
@@ -111,7 +111,13 @@ namespace Share
 				std::error_code ec;
 				std::filesystem::remove(file->getPath(), ec);
 				if (ec)
+				{
 					FS_LOG(SHARE, ERROR) << "Cannot remove file '" << file->getPath().string() << "' from share '" << share->getUUID().toString() << "': " << ec.message();
+					}
+				else
+				{
+					FS_LOG(SHARE, DEBUG) << "Removed file '" << file->getPath().string() << "' from share '" << share->getUUID().toString() << "'";
+				}
 			}
 		});
 
diff --git a/src/libs/share/impl/ShareCleaner.cpp b/src/libs/share/impl/ShareCleaner.cpp
index 89de018..3af0b14 100644
--- a/src/libs/share/impl/ShareCleaner.cpp
+++ b/src/libs/share/impl/ShareCleaner.cpp
@@ -24,6 +24,7 @@
 #include "utils/Logger.hpp"
 #include "utils/Service.hpp"
 #include "Db.hpp"
+#include "File.hpp"
 #include "Share.hpp"
 
 namespace Share
@@ -47,6 +48,44 @@ namespace Share
 		FS_LOG(SHARE, DEBUG) << "Stopped cleaner";
 	}
 
+	void
+	ShareCleaner::removeOrphanFiles(const std::filesystem::path& directory)
+	{
+		FS_LOG(SHARE, DEBUG) << "Removing orphan files in directory '" << directory.string() << "'";
+
+		for (const std::filesystem::path& directoryEntry: std::filesystem::directory_iterator {directory})
+		{
+			if (!std::filesystem::is_regular_file(directoryEntry))
+			{
+				FS_LOG(SHARE, DEBUG) << "Skipping '" << directoryEntry.string() << "': not regular";
+				continue;
+			}
+
+			if (isOrphanFile(directoryEntry))
+			{
+				std::error_code ec;
+				std::filesystem::remove(directoryEntry, ec);
+				if (ec)
+				{
+					FS_LOG(SHARE, ERROR) << "Cannot remove file '" << directoryEntry.string() << "'";
+				}
+				else
+				{
+					FS_LOG(SHARE, INFO) << "Removed orphan file '" << directoryEntry.string() << "'";
+				}
+			}
+		}
+	}
+
+	bool
+	ShareCleaner::isOrphanFile(const std::filesystem::path& filePath)
+	{
+		Wt::Dbo::Session& session {_db.getTLSSession()};
+		Wt::Dbo::Transaction transaction {session};
+
+		return !File::getByPath(session, filePath);
+	}
+
 	void
 	ShareCleaner::scheduleNextCheck()
 	{
@@ -58,6 +97,7 @@ namespace Share
 				return;
 
 			checkExpiredShares();
+			scheduleNextCheck();
 		});
 	}
 
@@ -80,6 +120,10 @@ namespace Share
 				FS_LOG(SHARE, INFO) << "Removing expired share '" << share->getUUID().toString() << "'";
 				Share::destroy(share);
 			}
+			else
+			{
+				FS_LOG(SHARE, DEBUG) << "Share '" << share->getUUID().toString() << "' not due to removal";
+			}
 		});
 	}
 } // namespace Share
diff --git a/src/libs/share/impl/ShareCleaner.hpp b/src/libs/share/impl/ShareCleaner.hpp
index 7d9a1a8..7862181 100644
--- a/src/libs/share/impl/ShareCleaner.hpp
+++ b/src/libs/share/impl/ShareCleaner.hpp
@@ -20,12 +20,14 @@
 #pragma once
 
 #include <chrono>
+#include <filesystem>
 #include <boost/asio/steady_timer.hpp>
 #include <Wt/WIOService.h>
 
 namespace Share
 {
 	class Db;
+	class Share;
 	class ShareCleaner
 	{
 		public:
@@ -37,7 +39,10 @@ namespace Share
 			ShareCleaner& operator=(const ShareCleaner&) = delete;
 			ShareCleaner& operator=(ShareCleaner&&) = delete;
 
+			void removeOrphanFiles(const std::filesystem::path& directory);
+
 		private:
+			bool	isOrphanFile(const std::filesystem::path& file);
 			void	scheduleNextCheck();
 			void	checkExpiredShares();
 
diff --git a/src/libs/share/impl/ShareManager.cpp b/src/libs/share/impl/ShareManager.cpp
index 08ee78f..6500487 100644
--- a/src/libs/share/impl/ShareManager.cpp
+++ b/src/libs/share/impl/ShareManager.cpp
@@ -273,6 +273,13 @@ namespace Share
 		share.modify()->incReadCount();
 	}
 
+	void
+	ShareManager::removeOrphanFiles(const std::filesystem::path& directory)
+	{
+		if (_shareCleaner)
+			_shareCleaner->removeOrphanFiles(directory);
+	}
+
 	void
 	ShareManager::validateShareSizes(const std::vector<FileCreateParameters>& files, const std::vector<FileSize>& fileSizes)
 	{
diff --git a/src/libs/share/impl/ShareManager.hpp b/src/libs/share/impl/ShareManager.hpp
index 8ee8e3b..47601f4 100644
--- a/src/libs/share/impl/ShareManager.hpp
+++ b/src/libs/share/impl/ShareManager.hpp
@@ -53,6 +53,7 @@ namespace Share
 			ShareDesc		getShareDesc(const ShareEditUUID& shareUUID) override;
 			void			visitShares(std::function<void(const ShareDesc&)>) override;
 			void			incrementReadCount(const ShareUUID& shareUUID) override;
+			void			removeOrphanFiles(const std::filesystem::path& directory) override;
 
 			void			validateShareSizes(const std::vector<FileCreateParameters>& files, const std::vector<FileSize>& fileSizes);
 
diff --git a/src/libs/share/include/share/IShareManager.hpp b/src/libs/share/include/share/IShareManager.hpp
index 17c5ce4..8cc2752 100644
--- a/src/libs/share/include/share/IShareManager.hpp
+++ b/src/libs/share/include/share/IShareManager.hpp
@@ -56,6 +56,7 @@ namespace Share
 			virtual	void					visitShares(std::function<void(const ShareDesc&)>) = 0;
 
 			virtual void					incrementReadCount(const ShareUUID& shareUUID) = 0;
+			virtual void					removeOrphanFiles(const std::filesystem::path& directory) = 0;
 	};
 
 	std::unique_ptr<IShareManager> createShareManager(const std::filesystem::path& dbFile, bool enableCleaner);