diff --git a/Packaging/windows/CMakePresets.json b/Packaging/windows/CMakePresets.json
index 788b20272..c59a2c30c 100644
--- a/Packaging/windows/CMakePresets.json
+++ b/Packaging/windows/CMakePresets.json
@@ -74,15 +74,18 @@
 	"testPresets": [
 		{
 			"name": "ninja-vcpkg-debug",
-			"configurePreset": "ninja-vcpkg-debug"
+			"configurePreset": "ninja-vcpkg-debug",
+			"output": {"outputOnFailure": true}
 		},
 		{
 			"name": "ninja-vcpkg-relwithdebinfo",
-			"configurePreset": "ninja-vcpkg-relwithdebinfo"
+			"configurePreset": "ninja-vcpkg-relwithdebinfo",
+			"output": {"outputOnFailure": true}
 		},
 		{
 			"name": "ninja-vcpkg-discord-relwithdebinfo",
-			"configurePreset": "ninja-vcpkg-discord-relwithdebinfo"
+			"configurePreset": "ninja-vcpkg-discord-relwithdebinfo",
+			"output": {"outputOnFailure": true}
 		}
 	]
 }
diff --git a/Source/mpq/mpq_writer.cpp b/Source/mpq/mpq_writer.cpp
index fb448aaf0..56dc39e8f 100644
--- a/Source/mpq/mpq_writer.cpp
+++ b/Source/mpq/mpq_writer.cpp
@@ -88,15 +88,8 @@ bool IsUnallocatedBlock(const MpqBlockEntry *block)
 
 MpqWriter::MpqWriter(const char *path)
 {
-#ifdef DVL_HAS_FILESYSTEM
-	{
-		std::error_code error;
-		std::filesystem::create_directories(std::filesystem::path(path).parent_path(), error);
-		if (error) {
-			LogError("failed to create directory: {}", error.message());
-		}
-	}
-#endif
+	const std::string dir = std::string(Dirname(path));
+	RecursivelyCreateDir(dir.c_str());
 	LogVerbose("Opening {}", path);
 	std::string error;
 	bool exists = FileExists(path);
diff --git a/Source/options.cpp b/Source/options.cpp
index 02c34e617..0ece5640e 100644
--- a/Source/options.cpp
+++ b/Source/options.cpp
@@ -236,15 +236,7 @@ void SaveIni()
 {
 	if (!IniChanged)
 		return;
-#ifdef DVL_HAS_FILESYSTEM
-	{
-		std::error_code error;
-		std::filesystem::create_directories(paths::ConfigPath(), error);
-		if (error) {
-			LogError("failed to create directory: {}", error.message());
-		}
-	}
-#endif
+	RecursivelyCreateDir(paths::ConfigPath().c_str());
 	const std::string iniPath = GetIniPath();
 	FILE *file = OpenFile(iniPath.c_str(), "wb");
 	if (file != nullptr) {
diff --git a/Source/utils/file_util.cpp b/Source/utils/file_util.cpp
index e803bb3b2..114905adc 100644
--- a/Source/utils/file_util.cpp
+++ b/Source/utils/file_util.cpp
@@ -5,6 +5,7 @@
 
 #include <algorithm>
 #include <string>
+#include <vector>
 
 #include <SDL.h>
 
@@ -38,6 +39,13 @@
 #include <copyfile.h>
 #endif
 
+// We include sys/stat.h for mkdir where available.
+#if !defined(DVL_HAS_FILESYSTEM) && defined(__has_include) && !defined(_WIN32)
+#if __has_include(<sys/stat.h>)
+#include <sys/stat.h>
+#endif
+#endif
+
 namespace devilution {
 
 #if (defined(_WIN64) || defined(_WIN32)) && !defined(NXDK)
@@ -55,6 +63,18 @@ std::unique_ptr<wchar_t[]> ToWideChar(string_view path)
 }
 #endif
 
+string_view Dirname(string_view path)
+{
+	while (path.size() > 1 && path.back() == DirectorySeparator)
+		path.remove_suffix(1);
+	if (path.size() == 1 && path.back() == DirectorySeparator)
+		return DIRECTORY_SEPARATOR_STR;
+	const size_t sep = path.find_last_of(DIRECTORY_SEPARATOR_STR);
+	if (sep == string_view::npos)
+		return ".";
+	return string_view { path.data(), sep };
+}
+
 bool FileExists(const char *path)
 {
 #if defined(_WIN64) || defined(_WIN32)
@@ -95,9 +115,10 @@ bool FileExists(const char *path)
 #endif
 }
 
-bool FileExistsAndIsWriteable(const char *path)
-{
 #if defined(_WIN64) || defined(_WIN32)
+namespace {
+DWORD WindowsGetFileAttributes(const char *path)
+{
 #if defined(NXDK)
 	const DWORD attr = ::GetFileAttributesA(path);
 #else
@@ -108,8 +129,7 @@ bool FileExistsAndIsWriteable(const char *path)
 	}
 	const DWORD attr = ::GetFileAttributesW(&pathUtf16[0]);
 #endif
-	const bool exists = attr != INVALID_FILE_ATTRIBUTES;
-	if (!exists) {
+	if (attr == INVALID_FILE_ATTRIBUTES) {
 		if (::GetLastError() == ERROR_FILE_NOT_FOUND || ::GetLastError() == ERROR_PATH_NOT_FOUND) {
 			::SetLastError(ERROR_SUCCESS);
 		} else {
@@ -120,7 +140,31 @@ bool FileExistsAndIsWriteable(const char *path)
 #endif
 		}
 	}
-	return exists && (attr & FILE_ATTRIBUTE_READONLY) == 0;
+	return attr;
+}
+} // namespace
+
+#endif
+
+bool DirectoryExists(const char *path)
+{
+#if defined(_WIN64) || defined(_WIN32)
+	const DWORD attr = WindowsGetFileAttributes(path);
+	return attr != INVALID_FILE_ATTRIBUTES && (attr & FILE_ATTRIBUTE_DIRECTORY) != 0;
+#elif defined(DVL_HAS_FILESYSTEM)
+	std::error_code error;
+	return std::filesystem::is_directory(path, error);
+#elif (_POSIX_C_SOURCE >= 200112L || defined(_BSD_SOURCE) || defined(__APPLE__)) && !defined(__ANDROID__)
+	struct ::stat statResult;
+	return ::stat(path, &statResult) == 0 && S_ISDIR(statResult.st_mode);
+#endif
+}
+
+bool FileExistsAndIsWriteable(const char *path)
+{
+#if defined(_WIN64) || defined(_WIN32)
+	const DWORD attr = WindowsGetFileAttributes(path);
+	return attr != INVALID_FILE_ATTRIBUTES && (attr & FILE_ATTRIBUTE_READONLY) == 0;
 #elif (_POSIX_C_SOURCE >= 200112L || defined(_BSD_SOURCE) || defined(__APPLE__)) && !defined(__ANDROID__)
 	return ::access(path, W_OK) == 0;
 #else
@@ -164,6 +208,74 @@ bool GetFileSize(const char *path, std::uintmax_t *size)
 #endif
 }
 
+bool CreateDir(const char *path)
+{
+#ifdef DVL_HAS_FILESYSTEM
+	std::error_code error;
+	std::filesystem::create_directory(path, error);
+	if (error) {
+		LogError("failed to create directory {}: {}", path, error.message());
+		return false;
+	}
+	return true;
+#elif defined(_WIN64) || defined(_WIN32)
+#ifdef NXDK
+	if (::CreateDirectoryA(path, /*lpSecurityAttributes=*/nullptr) != 0)
+		return true;
+	if (::GetLastError() == ERROR_ALREADY_EXISTS)
+		return true;
+	LogError("failed to create directory {}", path);
+	return false;
+#else
+	const auto pathUtf16 = ToWideChar(path);
+	if (pathUtf16 == nullptr) {
+		LogError("UTF-8 -> UTF-16 conversion error code {}", ::GetLastError());
+		return false;
+	}
+	if (::CreateDirectoryW(&pathUtf16[0], /*lpSecurityAttributes=*/nullptr) != 0)
+		return true;
+	if (::GetLastError() == ERROR_ALREADY_EXISTS)
+		return true;
+	LogError("failed to create directory {}", path);
+	return false;
+#endif
+#else
+	const int result = ::mkdir(path, 0777);
+	if (result != 0 && result != EEXIST) {
+		LogError("failed to create directory {}", path);
+		return false;
+	}
+	return true;
+#endif
+}
+
+void RecursivelyCreateDir(const char *path)
+{
+#ifdef DVL_HAS_FILESYSTEM
+	std::error_code error;
+	std::filesystem::create_directories(path, error);
+	if (error) {
+		LogError("failed to create directory {}: {}", path, error.message());
+	}
+#else
+	if (DirectoryExists(path))
+		return;
+	std::vector<std::string> paths;
+	std::string cur { path };
+	do {
+		paths.push_back(cur);
+		string_view parent = Dirname(cur);
+		if (parent == cur)
+			break;
+		cur.assign(parent.data(), parent.size());
+	} while (!DirectoryExists(cur.c_str()));
+	for (auto it = std::rbegin(paths); it != std::rend(paths); ++it) {
+		if (!CreateDir(it->c_str()))
+			return;
+	}
+#endif
+}
+
 bool ResizeFile(const char *path, std::uintmax_t size)
 {
 #if defined(_WIN64) || defined(_WIN32)
diff --git a/Source/utils/file_util.h b/Source/utils/file_util.h
index 9de80cae4..6485775e1 100644
--- a/Source/utils/file_util.h
+++ b/Source/utils/file_util.h
@@ -9,6 +9,14 @@
 
 namespace devilution {
 
+#ifdef _WIN32
+constexpr char DirectorySeparator = '\\';
+#define DIRECTORY_SEPARATOR_STR "\\"
+#else
+constexpr char DirectorySeparator = '/';
+#define DIRECTORY_SEPARATOR_STR "/"
+#endif
+
 bool FileExists(const char *path);
 
 inline bool FileExists(const std::string &str)
@@ -16,8 +24,19 @@ inline bool FileExists(const std::string &str)
 	return FileExists(str.c_str());
 }
 
+bool DirectoryExists(const char *path);
+string_view Dirname(string_view path);
 bool FileExistsAndIsWriteable(const char *path);
 bool GetFileSize(const char *path, std::uintmax_t *size);
+
+/**
+ * @brief Creates a single directory (non-recursively).
+ *
+ * @return True if the directory already existed or has been created sucessfully.
+ */
+bool CreateDir(const char *path);
+
+void RecursivelyCreateDir(const char *path);
 bool ResizeFile(const char *path, std::uintmax_t size);
 void RenameFile(const char *from, const char *to);
 void CopyFileOverwrite(const char *from, const char *to);
diff --git a/Source/utils/paths.h b/Source/utils/paths.h
index 406104f5e..639059a74 100644
--- a/Source/utils/paths.h
+++ b/Source/utils/paths.h
@@ -6,14 +6,6 @@
 
 namespace devilution {
 
-#ifdef _WIN32
-constexpr char DirectorySeparator = '\\';
-#define DIRECTORY_SEPARATOR_STR "\\"
-#else
-constexpr char DirectorySeparator = '/';
-#define DIRECTORY_SEPARATOR_STR "/"
-#endif
-
 namespace paths {
 
 const std::string &BasePath();
diff --git a/test/file_util_test.cpp b/test/file_util_test.cpp
index 44143263f..edfe5899f 100644
--- a/test/file_util_test.cpp
+++ b/test/file_util_test.cpp
@@ -61,4 +61,25 @@ TEST(FileUtil, ResizeFile)
 	EXPECT_EQ(size, 30);
 }
 
+TEST(FileUtil, Dirname)
+{
+	EXPECT_EQ(Dirname(""), ".");
+	EXPECT_EQ(Dirname("abc"), ".");
+	EXPECT_EQ(Dirname(DIRECTORY_SEPARATOR_STR), DIRECTORY_SEPARATOR_STR);
+	EXPECT_EQ(Dirname(DIRECTORY_SEPARATOR_STR DIRECTORY_SEPARATOR_STR), DIRECTORY_SEPARATOR_STR);
+	EXPECT_EQ(Dirname("a" DIRECTORY_SEPARATOR_STR "b"), "a");
+	EXPECT_EQ(Dirname("a" DIRECTORY_SEPARATOR_STR "b" DIRECTORY_SEPARATOR_STR "c"),
+	    "a" DIRECTORY_SEPARATOR_STR "b");
+	EXPECT_EQ(Dirname("a" DIRECTORY_SEPARATOR_STR "b" DIRECTORY_SEPARATOR_STR "c"),
+	    "a" DIRECTORY_SEPARATOR_STR "b");
+}
+
+TEST(FileUtil, RecursivelyCreateDir)
+{
+	const std::string path = GetTmpPathName(/*suffix=*/"") + DIRECTORY_SEPARATOR_STR
+	    + "a" + DIRECTORY_SEPARATOR_STR + "b" + DIRECTORY_SEPARATOR_STR + "c";
+	RecursivelyCreateDir(path.c_str());
+	EXPECT_TRUE(DirectoryExists(path.c_str()));
+}
+
 } // namespace