diff --git a/Core/FileLoaders/DiskCachingFileLoader.cpp b/Core/FileLoaders/DiskCachingFileLoader.cpp
index 27379a9bc9..7935e0f021 100644
--- a/Core/FileLoaders/DiskCachingFileLoader.cpp
+++ b/Core/FileLoaders/DiskCachingFileLoader.cpp
@@ -54,6 +54,11 @@ DiskCachingFileLoader::~DiskCachingFileLoader() {
 }
 
 bool DiskCachingFileLoader::Exists() {
+	if (cache_->HasData()) {
+		// It may require a slow operation to check - if we have data, let's say yes.
+		// This helps initial load, since we check each recent file for existence.
+		return true;
+	}
 	return backend_->Exists();
 }
 
@@ -718,6 +723,19 @@ void DiskCachingFileLoaderCache::CloseFileHandle() {
 	fd_ = 0;
 }
 
+bool DiskCachingFileLoaderCache::HasData() const {
+	if (!f_) {
+		return false;
+	}
+
+	for (size_t i = 0; i < blockIndexLookup_.size(); ++i) {
+		if (blockIndexLookup_[i] != INVALID_INDEX) {
+			return true;
+		}
+	}
+	return false;
+}
+
 u64 DiskCachingFileLoaderCache::FreeDiskSpace() {
 	std::string dir = cacheDir_;
 	if (dir.empty()) {
diff --git a/Core/FileLoaders/DiskCachingFileLoader.h b/Core/FileLoaders/DiskCachingFileLoader.h
index ac944ce08d..511507d240 100644
--- a/Core/FileLoaders/DiskCachingFileLoader.h
+++ b/Core/FileLoaders/DiskCachingFileLoader.h
@@ -89,6 +89,8 @@ public:
 	// Guaranteed to read at least one block into the cache.
 	size_t SaveIntoCache(FileLoader *backend, s64 pos, size_t bytes, void *data);
 
+	bool HasData() const;
+
 private:
 	void InitCache(const std::string &path);
 	void ShutdownCache();
diff --git a/Core/Loaders.cpp b/Core/Loaders.cpp
index db28d4d315..4632c58714 100644
--- a/Core/Loaders.cpp
+++ b/Core/Loaders.cpp
@@ -194,16 +194,41 @@ IdentifiedFileType Identify_File(FileLoader *fileLoader) {
 
 FileLoader *ResolveFileLoaderTarget(FileLoader *fileLoader) {
 	IdentifiedFileType type = Identify_File(fileLoader);
-	if (type == FILETYPE_PSP_PBP_DIRECTORY && !endsWith(fileLoader->Path(), "/EBOOT.PBP")) {
-		std::string ebootFilename = fileLoader->Path() + "/EBOOT.PBP";
-
-		// Switch fileLoader to the actual EBOOT.
-		delete fileLoader;
-		fileLoader = ConstructFileLoader(ebootFilename);
+	if (type == FILETYPE_PSP_PBP_DIRECTORY) {
+		const std::string ebootFilename = ResolvePBPFile(fileLoader->Path());
+		if (ebootFilename != fileLoader->Path()) {
+			// Switch fileLoader to the actual EBOOT.
+			delete fileLoader;
+			fileLoader = ConstructFileLoader(ebootFilename);
+		}
 	}
 	return fileLoader;
 }
 
+std::string ResolvePBPDirectory(const std::string &filename) {
+	bool hasPBP = endsWith(filename, "/EBOOT.PBP");
+#ifdef _WIN32
+	hasPBP = hasPBP || endsWith(filename, "\\EBOOT.PBP");
+#endif
+
+	if (hasPBP) {
+		return filename.substr(0, filename.length() - strlen("/EBOOT.PBP"));
+	}
+	return filename;
+}
+
+std::string ResolvePBPFile(const std::string &filename) {
+	bool hasPBP = endsWith(filename, "/EBOOT.PBP");
+#ifdef _WIN32
+	hasPBP = hasPBP || endsWith(filename, "\\EBOOT.PBP");
+#endif
+
+	if (!hasPBP) {
+		return filename + "/EBOOT.PBP";
+	}
+	return filename;
+}
+
 bool LoadFile(FileLoader **fileLoaderPtr, std::string *error_string) {
 	FileLoader *&fileLoader = *fileLoaderPtr;
 	// Note that this can modify filename!
@@ -227,9 +252,7 @@ bool LoadFile(FileLoader **fileLoaderPtr, std::string *error_string) {
 				std::string path = fileLoader->Path();
 				size_t pos = path.find("/PSP/GAME/");
 				if (pos != std::string::npos) {
-					if (path.rfind("/EBOOT.PBP") != std::string::npos) {
-						path = path.substr(0, path.length() - strlen("/EBOOT.PBP"));
-					}
+					path = ResolvePBPDirectory(path);
 					pspFileSystem.SetStartingDirectory("ms0:" + path.substr(pos));
 				}
 				return Load_PSP_ELF_PBP(fileLoader, error_string);
diff --git a/Core/Loaders.h b/Core/Loaders.h
index f7d297923f..4fbe126a5a 100644
--- a/Core/Loaders.h
+++ b/Core/Loaders.h
@@ -82,8 +82,9 @@ FileLoader *ConstructFileLoader(const std::string &filename);
 // Resolve to the target binary, ISO, or other file (e.g. from a directory.)
 FileLoader *ResolveFileLoaderTarget(FileLoader *fileLoader);
 
-// This can modify the string, for example for stripping off the "/EBOOT.PBP"
-// for a FILETYPE_PSP_PBP_DIRECTORY.
+std::string ResolvePBPDirectory(const std::string &filename);
+std::string ResolvePBPFile(const std::string &filename);
+
 IdentifiedFileType Identify_File(FileLoader *fileLoader);
 
 // Can modify the string filename, as it calls IdentifyFile above.
diff --git a/UI/GameInfoCache.cpp b/UI/GameInfoCache.cpp
index c82fe9fdcd..f47d9e372e 100644
--- a/UI/GameInfoCache.cpp
+++ b/UI/GameInfoCache.cpp
@@ -72,8 +72,8 @@ bool GameInfo::Delete() {
 	case FILETYPE_PSP_SAVEDATA_DIRECTORY:
 		{
 			// TODO: This could be handled by Core/Util/GameManager too somehow.
-			const char *directoryToRemove = filePath_.c_str();
-			INFO_LOG(HLE, "Deleting %s", directoryToRemove);
+			std::string directoryToRemove = ResolvePBPDirectory(filePath_);
+			INFO_LOG(HLE, "Deleting %s", directoryToRemove.c_str());
 			if (!File::DeleteDirRecursively(directoryToRemove)) {
 				ERROR_LOG(HLE, "Failed to delete file");
 				return false;
@@ -109,7 +109,7 @@ bool GameInfo::Delete() {
 	}
 }
 
-static int64_t GetDirectoryRecursiveSize(std::string path) {
+static int64_t GetDirectoryRecursiveSize(const std::string &path) {
 	std::vector<FileInfo> fileInfo;
 	getFilesInDir(path.c_str(), &fileInfo);
 	int64_t sizeSum = 0;
@@ -129,9 +129,8 @@ u64 GameInfo::GetGameSizeInBytes() {
 	switch (fileType) {
 	case FILETYPE_PSP_PBP_DIRECTORY:
 	case FILETYPE_PSP_SAVEDATA_DIRECTORY:
-	{
-		return GetDirectoryRecursiveSize(filePath_);
-	}
+		return GetDirectoryRecursiveSize(ResolvePBPDirectory(filePath_));
+
 	default:
 		return GetFileLoader()->FileSize();
 	}
@@ -358,11 +357,14 @@ public:
 		: gamePath_(gamePath), info_(info) {
 	}
 
+	~GameInfoWorkItem() override {
+		info_->DisposeFileLoader();
+	}
+
 	virtual void run() {
 		if (!info_->LoadFromPath(gamePath_))
 			return;
 
-		std::string filename = gamePath_;
 		{
 			lock_guard lock(info_->lock);
 			info_->working = true;
@@ -376,8 +378,11 @@ public:
 				FileLoader *pbpLoader = info_->GetFileLoader();
 				std::unique_ptr<FileLoader> altLoader;
 				if (info_->fileType == FILETYPE_PSP_PBP_DIRECTORY) {
-					pbpLoader = ConstructFileLoader(pbpLoader->Path() + "/EBOOT.PBP");
-					altLoader.reset(pbpLoader);
+					std::string ebootPath = ResolvePBPFile(gamePath_);
+					if (ebootPath != gamePath_) {
+						pbpLoader = ConstructFileLoader(ebootPath);
+						altLoader.reset(pbpLoader);
+					}
 				}
 
 				PBPReader pbp(pbpLoader);
@@ -593,8 +598,6 @@ handleELF:
 			info_->installDataSize = info_->GetInstallDataSizeInBytes();
 		}
 
-		info_->DisposeFileLoader();
-
 		lock_guard lock(info_->lock);
 		info_->pending = false;
 		info_->working = false;
diff --git a/Windows/MainWindow.cpp b/Windows/MainWindow.cpp
index 317bf72fbc..b8e17d378a 100644
--- a/Windows/MainWindow.cpp
+++ b/Windows/MainWindow.cpp
@@ -829,11 +829,11 @@ namespace MainWindow
 				else
 				{
 					TCHAR filename[512];
-					DragQueryFile(hdrop,0,filename,512);
-					TCHAR *type = filename+_tcslen(filename)-3;
-					
-					NativeMessageReceived("boot", ConvertWStringToUTF8(filename).c_str());
-					Core_EnableStepping(false);
+					if (DragQueryFile(hdrop, 0, filename, 512) != 0) {
+						const std::string utf8_filename = ReplaceAll(ConvertWStringToUTF8(filename), "\\", "/");
+						NativeMessageReceived("boot", utf8_filename.c_str());
+						Core_EnableStepping(false);
+					}
 				}
 			}
 			break;