diff --git a/core/os/os2/dir_windows.odin b/core/os/os2/dir_windows.odin
index 6c754a677..a4dadca75 100644
--- a/core/os/os2/dir_windows.odin
+++ b/core/os/os2/dir_windows.odin
@@ -18,7 +18,7 @@ find_data_to_file_info :: proc(base_path: string, d: ^win32.WIN32_FIND_DATAW, al
 	temp_allocator := TEMP_ALLOCATOR_GUARD({ allocator })
 	path := concatenate({base_path, `\`, win32_wstring_to_utf8(cstring16(raw_data(d.cFileName[:])), temp_allocator) or_else ""}, allocator) or_return
 
-	handle := win32.HANDLE(_open_internal(path, {.Read}, 0o666) or_else 0)
+	handle := win32.HANDLE(_open_internal(path, {.Read}, Permissions_Read_Write_All) or_else 0)
 	defer win32.CloseHandle(handle)
 
 	fi.fullpath = path
diff --git a/core/os/os2/file.odin b/core/os/os2/file.odin
index a9878a563..5375258ca 100644
--- a/core/os/os2/file.odin
+++ b/core/os/os2/file.odin
@@ -90,17 +90,56 @@ O_SPARSE  :: File_Flags{.Sparse}
 */
 O_INHERITABLE :: File_Flags{.Inheritable}
 
+Permissions :: distinct bit_set[Permission_Flag; u32]
+Permission_Flag :: enum u32 {
+	Execute_Other = 0,
+	Write_Other   = 1,
+	Read_Other    = 2,
+
+	Execute_Group = 3,
+	Write_Group   = 4,
+	Read_Group    = 5,
+
+	Execute_User  = 6,
+	Write_User    = 7,
+	Read_User     = 8,
+}
+
+Permissions_Execute_All :: Permissions{.Execute_User, .Execute_Group, .Execute_Other}
+Permissions_Write_All   :: Permissions{.Write_User,   .Write_Group,   .Write_Other}
+Permissions_Read_All    :: Permissions{.Read_User,    .Read_Group,    .Read_Other}
+
+Permissions_Read_Write_All :: Permissions_Read_All + Permissions_Write_All
+
+Permissions_All :: Permissions_Read_All + Permissions_Write_All + Permissions_Execute_All
+
+Permissions_Default_File      :: Permissions_Read_All + Permissions_Write_All
+Permissions_Default_Directory :: Permissions_Read_All + Permissions_Write_All + Permissions_Execute_All
+Permissions_Default           :: Permissions_Default_Directory
+
+perm :: proc{
+	perm_number,
+}
+
+@(require_results)
+perm_number :: proc "contextless" (perm: int) -> Permissions {
+	return transmute(Permissions)u32(perm & 0o777)
+}
+
+
+
+
 stdin:  ^File = nil // OS-Specific
 stdout: ^File = nil // OS-Specific
 stderr: ^File = nil // OS-Specific
 
 @(require_results)
 create :: proc(name: string) -> (^File, Error) {
-	return open(name, {.Read, .Write, .Create}, 0o777)
+	return open(name, {.Read, .Write, .Create}, Permissions_Default)
 }
 
 @(require_results)
-open :: proc(name: string, flags := File_Flags{.Read}, perm := 0o777) -> (^File, Error) {
+open :: proc(name: string, flags := File_Flags{.Read}, perm := Permissions_Default) -> (^File, Error) {
 	return _open(name, flags, perm)
 }
 
@@ -237,7 +276,7 @@ change_directory :: proc(name: string) -> Error {
 
 chmod :: change_mode
 
-change_mode :: proc(name: string, mode: int) -> Error {
+change_mode :: proc(name: string, mode: Permissions) -> Error {
 	return _chmod(name, mode)
 }
 
@@ -255,7 +294,7 @@ fchange_directory :: proc(f: ^File) -> Error {
 
 fchmod :: fchange_mode
 
-fchange_mode :: proc(f: ^File, mode: int) -> Error {
+fchange_mode :: proc(f: ^File, mode: Permissions) -> Error {
 	return _fchmod(f, mode)
 }
 
@@ -331,7 +370,7 @@ _copy_file :: proc(dst_path, src_path: string) -> Error {
 		return .Invalid_File
 	}
 
-	dst := open(dst_path, {.Read, .Write, .Create, .Trunc}, info.mode & 0o777) or_return
+	dst := open(dst_path, {.Read, .Write, .Create, .Trunc}, info.mode & Permissions_All) or_return
 	defer close(dst)
 
 	_, err := io.copy(to_writer(dst), to_reader(src))
diff --git a/core/os/os2/file_linux.odin b/core/os/os2/file_linux.odin
index 85f639c8b..b2350d9b5 100644
--- a/core/os/os2/file_linux.odin
+++ b/core/os/os2/file_linux.odin
@@ -65,7 +65,7 @@ _standard_stream_init :: proc "contextless" () {
 	stderr = new_std(&files[2], 2, "/proc/self/fd/2")
 }
 
-_open :: proc(name: string, flags: File_Flags, perm: int) -> (f: ^File, err: Error) {
+_open :: proc(name: string, flags: File_Flags, perm: Permissions) -> (f: ^File, err: Error) {
 	temp_allocator := TEMP_ALLOCATOR_GUARD({})
 	name_cstr := clone_to_cstring(name, temp_allocator) or_return
 
@@ -88,7 +88,7 @@ _open :: proc(name: string, flags: File_Flags, perm: int) -> (f: ^File, err: Err
 	if .Trunc in flags         { sys_flags += {.TRUNC} }
 	if .Inheritable in flags   { sys_flags -= {.CLOEXEC} }
 
-	fd, errno := linux.open(name_cstr, sys_flags, transmute(linux.Mode)u32(perm))
+	fd, errno := linux.open(name_cstr, sys_flags, transmute(linux.Mode)transmute(u32)perm)
 	if errno != .NONE {
 		return nil, _get_platform_error(errno)
 	}
@@ -132,7 +132,7 @@ _clone :: proc(f: ^File) -> (clone: ^File, err: Error) {
 
 
 @(require_results)
-_open_buffered :: proc(name: string, buffer_size: uint, flags := File_Flags{.Read}, perm := 0o777) -> (f: ^File, err: Error) {
+_open_buffered :: proc(name: string, buffer_size: uint, flags := File_Flags{.Read}, perm: Permissions) -> (f: ^File, err: Error) {
 	assert(buffer_size > 0)
 	f, err = _open(name, flags, perm)
 	if f != nil && err == nil {
@@ -369,15 +369,15 @@ _fchdir :: proc(f: ^File) -> Error {
 	return _get_platform_error(linux.fchdir(impl.fd))
 }
 
-_chmod :: proc(name: string, mode: int) -> Error {
+_chmod :: proc(name: string, mode: Permissions) -> Error {
 	temp_allocator := TEMP_ALLOCATOR_GUARD({})
 	name_cstr := clone_to_cstring(name, temp_allocator) or_return
-	return _get_platform_error(linux.chmod(name_cstr, transmute(linux.Mode)(u32(mode))))
+	return _get_platform_error(linux.chmod(name_cstr, transmute(linux.Mode)transmute(u32)mode))
 }
 
-_fchmod :: proc(f: ^File, mode: int) -> Error {
+_fchmod :: proc(f: ^File, mode: Permissions) -> Error {
 	impl := (^File_Impl)(f.impl)
-	return _get_platform_error(linux.fchmod(impl.fd, transmute(linux.Mode)(u32(mode))))
+	return _get_platform_error(linux.fchmod(impl.fd, transmute(linux.Mode)transmute(u32)mode))
 }
 
 // NOTE: will throw error without super user priviledges
diff --git a/core/os/os2/file_posix.odin b/core/os/os2/file_posix.odin
index a251a3ae7..fd409b9d4 100644
--- a/core/os/os2/file_posix.odin
+++ b/core/os/os2/file_posix.odin
@@ -46,7 +46,7 @@ init_std_files :: proc "contextless" () {
 	stderr = new_std(&files[2], posix.STDERR_FILENO, "/dev/stderr")
 }
 
-_open :: proc(name: string, flags: File_Flags, perm: int) -> (f: ^File, err: Error) {
+_open :: proc(name: string, flags: File_Flags, perm: Permissions) -> (f: ^File, err: Error) {
 	if name == "" {
 		err = .Invalid_Path
 		return
@@ -72,7 +72,7 @@ _open :: proc(name: string, flags: File_Flags, perm: int) -> (f: ^File, err: Err
 	temp_allocator := TEMP_ALLOCATOR_GUARD({})
 	cname := clone_to_cstring(name, temp_allocator) or_return
 
-	fd := posix.open(cname, sys_flags, transmute(posix.mode_t)posix._mode_t(perm))
+	fd := posix.open(cname, sys_flags, transmute(posix.mode_t)posix._mode_t(transmute(u32)perm))
 	if fd < 0 {
 		err = _get_platform_error()
 		return
@@ -284,17 +284,17 @@ _fchdir :: proc(f: ^File) -> Error {
 	return nil
 }
 
-_fchmod :: proc(f: ^File, mode: int) -> Error {
-	if posix.fchmod(__fd(f), transmute(posix.mode_t)posix._mode_t(mode)) != .OK {
+_fchmod :: proc(f: ^File, mode: Permissions) -> Error {
+	if posix.fchmod(__fd(f), transmute(posix.mode_t)posix._mode_t(transmute(u32)mode)) != .OK {
 		return _get_platform_error()
 	}
 	return nil
 }
 
-_chmod :: proc(name: string, mode: int) -> (err: Error) {
+_chmod :: proc(name: string, mode: Permissions) -> (err: Error) {
 	temp_allocator := TEMP_ALLOCATOR_GUARD({})
 	cname := clone_to_cstring(name, temp_allocator) or_return
-	if posix.chmod(cname, transmute(posix.mode_t)posix._mode_t(mode)) != .OK {
+	if posix.chmod(cname, transmute(posix.mode_t)posix._mode_t(transmute(u32)mode)) != .OK {
 		return _get_platform_error()
 	}
 	return nil
diff --git a/core/os/os2/file_posix_other.odin b/core/os/os2/file_posix_other.odin
index d2946098b..8871a0062 100644
--- a/core/os/os2/file_posix_other.odin
+++ b/core/os/os2/file_posix_other.odin
@@ -8,7 +8,7 @@ import "core:sys/posix"
 
 _posix_absolute_path :: proc(fd: posix.FD, name: string, allocator: runtime.Allocator) -> (path: cstring, err: Error) {
 	temp_allocator := TEMP_ALLOCATOR_GUARD({ allocator })
-	cname := clone_to_cstring(name, temp_allocator)
+	cname := clone_to_cstring(name, temp_allocator) or_return
 
 	buf: [posix.PATH_MAX]byte
 	path = posix.realpath(cname, raw_data(buf[:]))
diff --git a/core/os/os2/file_util.odin b/core/os/os2/file_util.odin
index 5934f02f5..be2f1f8c7 100644
--- a/core/os/os2/file_util.odin
+++ b/core/os/os2/file_util.odin
@@ -161,7 +161,7 @@ read_entire_file_from_file :: proc(f: ^File, allocator: runtime.Allocator, loc :
 }
 
 @(require_results)
-write_entire_file :: proc(name: string, data: []byte, perm: int = 0o644, truncate := true) -> Error {
+write_entire_file :: proc(name: string, data: []byte, perm := Permissions_Read_All + {.Write_User}, truncate := true) -> Error {
 	flags := O_WRONLY|O_CREATE
 	if truncate {
 		flags |= O_TRUNC
diff --git a/core/os/os2/file_wasi.odin b/core/os/os2/file_wasi.odin
index 1d417ffb1..ec464fc52 100644
--- a/core/os/os2/file_wasi.odin
+++ b/core/os/os2/file_wasi.odin
@@ -51,8 +51,8 @@ init_std_files :: proc "contextless" () {
 }
 
 @(init)
-init_preopens :: proc() {
-	strip_prefixes :: proc(path: string) -> string {
+init_preopens :: proc "contextless" () {
+	strip_prefixes :: proc "contextless" (path: string) -> string {
 		path := path
 		loop: for len(path) > 0 {
 			switch {
@@ -69,6 +69,8 @@ init_preopens :: proc() {
 		return path
 	}
 
+	context = runtime.default_context()
+
 	n: int
 	n_loop: for fd := wasi.fd_t(3); ; fd += 1 {
 		_, err := wasi.fd_prestat_get(fd)
@@ -171,7 +173,7 @@ match_preopen :: proc(path: string) -> (wasi.fd_t, string, bool) {
 	return match.fd, relative, true
 }
 
-_open :: proc(name: string, flags: File_Flags, perm: int) -> (f: ^File, err: Error) {
+_open :: proc(name: string, flags: File_Flags, perm: Permissions) -> (f: ^File, err: Error) {
 	dir_fd, relative, ok := match_preopen(name)
 	if !ok {
 		return nil, .Invalid_Path
@@ -373,11 +375,11 @@ _fchdir :: proc(f: ^File) -> Error {
 	return .Unsupported
 }
 
-_fchmod :: proc(f: ^File, mode: int) -> Error {
+_fchmod :: proc(f: ^File, mode: Permissions) -> Error {
 	return .Unsupported
 }
 
-_chmod :: proc(name: string, mode: int) -> Error {
+_chmod :: proc(name: string, mode: Permissions) -> Error {
 	return .Unsupported
 }
 
diff --git a/core/os/os2/file_windows.odin b/core/os/os2/file_windows.odin
index b39e65fe2..be5aeb8ab 100644
--- a/core/os/os2/file_windows.odin
+++ b/core/os/os2/file_windows.odin
@@ -12,7 +12,6 @@ import win32 "core:sys/windows"
 
 INVALID_HANDLE :: ~uintptr(0)
 
-S_IWRITE :: 0o200
 _ERROR_BAD_NETPATH :: 53
 MAX_RW :: 1<<30
 
@@ -81,7 +80,7 @@ _handle :: proc "contextless" (f: ^File) -> win32.HANDLE {
 	return win32.HANDLE(_fd(f))
 }
 
-_open_internal :: proc(name: string, flags: File_Flags, perm: int) -> (handle: uintptr, err: Error) {
+_open_internal :: proc(name: string, flags: File_Flags, perm: Permissions) -> (handle: uintptr, err: Error) {
 	if len(name) == 0 {
 		err = .Not_Exist
 		return
@@ -122,7 +121,7 @@ _open_internal :: proc(name: string, flags: File_Flags, perm: int) -> (handle: u
 	}
 
 	attrs: u32 = win32.FILE_ATTRIBUTE_NORMAL|win32.FILE_FLAG_BACKUP_SEMANTICS
-	if perm & S_IWRITE == 0 {
+	if .Write_User not_in perm {
 		attrs = win32.FILE_ATTRIBUTE_READONLY
 		if create_mode == win32.CREATE_ALWAYS {
 			// NOTE(bill): Open has just asked to create a file in read-only mode.
@@ -150,7 +149,7 @@ _open_internal :: proc(name: string, flags: File_Flags, perm: int) -> (handle: u
 }
 
 
-_open :: proc(name: string, flags: File_Flags, perm: int) -> (f: ^File, err: Error) {
+_open :: proc(name: string, flags: File_Flags, perm: Permissions) -> (f: ^File, err: Error) {
 	flags := flags if flags != nil else {.Read}
 	handle := _open_internal(name, flags, perm) or_return
 	return _new_file(handle, name, file_allocator())
@@ -193,7 +192,7 @@ _new_file :: proc(handle: uintptr, name: string, allocator: runtime.Allocator) -
 
 
 @(require_results)
-_open_buffered :: proc(name: string, buffer_size: uint, flags := File_Flags{.Read}, perm := 0o777) -> (f: ^File, err: Error) {
+_open_buffered :: proc(name: string, buffer_size: uint, flags := File_Flags{.Read}, perm: Permissions) -> (f: ^File, err: Error) {
 	assert(buffer_size > 0)
 	flags := flags if flags != nil else {.Read}
 	handle := _open_internal(name, flags, perm) or_return
@@ -744,7 +743,7 @@ _fchdir :: proc(f: ^File) -> Error {
 	return nil
 }
 
-_fchmod :: proc(f: ^File, mode: int) -> Error {
+_fchmod :: proc(f: ^File, mode: Permissions) -> Error {
 	if f == nil || f.impl == nil {
 		return nil
 	}
@@ -753,7 +752,7 @@ _fchmod :: proc(f: ^File, mode: int) -> Error {
 		return _get_platform_error()
 	}
 	attrs := d.dwFileAttributes
-	if mode & S_IWRITE != 0 {
+	if .Write_User in mode {
 		attrs &~= win32.FILE_ATTRIBUTE_READONLY
 	} else {
 		attrs |= win32.FILE_ATTRIBUTE_READONLY
@@ -780,7 +779,7 @@ _chdir :: proc(name: string) -> Error {
 	return nil
 }
 
-_chmod :: proc(name: string, mode: int) -> Error {
+_chmod :: proc(name: string, mode: Permissions) -> Error {
 	f := open(name, {.Write}) or_return
 	defer close(f)
 	return _fchmod(f, mode)
diff --git a/core/os/os2/path_wasi.odin b/core/os/os2/path_wasi.odin
index b8240e188..f26e16158 100644
--- a/core/os/os2/path_wasi.odin
+++ b/core/os/os2/path_wasi.odin
@@ -34,7 +34,7 @@ _mkdir_all :: proc(path: string, perm: int) -> Error {
 		return .Exist
 	}
 
-	clean_path := clean_path(path, temp_allocator)
+	clean_path := clean_path(path, temp_allocator) or_return
 	return internal_mkdir_all(clean_path)
 
 	internal_mkdir_all :: proc(path: string) -> Error {
@@ -114,3 +114,7 @@ _get_executable_path :: proc(allocator: runtime.Allocator) -> (path: string, err
 
 	return concatenate({"/", arg}, allocator)
 }
+
+_get_absolute_path :: proc(path: string, allocator: runtime.Allocator) -> (absolute_path: string, err: Error) {
+	return "", .Unsupported
+}
diff --git a/core/os/os2/stat.odin b/core/os/os2/stat.odin
index d6b524684..338bdffca 100644
--- a/core/os/os2/stat.odin
+++ b/core/os/os2/stat.odin
@@ -12,7 +12,7 @@ File_Info :: struct {
 
 	inode:             u128, // might be zero if cannot be determined
 	size:              i64 `fmt:"M"`,
-	mode:              int `fmt:"o"`,
+	mode:              Permissions,
 	type:              File_Type,
 
 	creation_time:     time.Time,
diff --git a/core/os/os2/stat_linux.odin b/core/os/os2/stat_linux.odin
index 373765be5..6185252cf 100644
--- a/core/os/os2/stat_linux.odin
+++ b/core/os/os2/stat_linux.odin
@@ -26,7 +26,7 @@ _fstat_internal :: proc(fd: linux.Fd, allocator: runtime.Allocator) -> (fi: File
 	case linux.S_IFREG:  type = .Regular
 	case linux.S_IFSOCK: type = .Socket
 	}
-	mode := int(0o7777 & transmute(u32)s.mode)
+	mode := transmute(Permissions)(0o7777 & transmute(u32)s.mode)
 
 	// TODO: As of Linux 4.11, the new statx syscall can retrieve creation_time
 	fi = File_Info {
diff --git a/core/os/os2/stat_posix.odin b/core/os/os2/stat_posix.odin
index 6ffbdf1da..4ed96b389 100644
--- a/core/os/os2/stat_posix.odin
+++ b/core/os/os2/stat_posix.odin
@@ -14,7 +14,7 @@ internal_stat :: proc(stat: posix.stat_t, fullpath: string) -> (fi: File_Info) {
 	fi.inode = u128(stat.st_ino)
 	fi.size = i64(stat.st_size)
 
-	fi.mode = int(transmute(posix._mode_t)(stat.st_mode - posix.S_IFMT))
+	fi.mode = transmute(Permissions)u32(transmute(posix._mode_t)(stat.st_mode - posix.S_IFMT))
 
 	fi.type = .Undetermined
 	switch {
diff --git a/core/os/os2/stat_windows.odin b/core/os/os2/stat_windows.odin
index 3dee42be6..20a708145 100644
--- a/core/os/os2/stat_windows.odin
+++ b/core/os/os2/stat_windows.odin
@@ -211,11 +211,11 @@ _file_type_from_create_file :: proc(wname: win32.wstring, create_file_attributes
 	return file_type(h)
 }
 
-_file_type_mode_from_file_attributes :: proc(file_attributes: win32.DWORD, h: win32.HANDLE, ReparseTag: win32.DWORD) -> (type: File_Type, mode: int) {
+_file_type_mode_from_file_attributes :: proc(file_attributes: win32.DWORD, h: win32.HANDLE, ReparseTag: win32.DWORD) -> (type: File_Type, mode: Permissions) {
 	if file_attributes & win32.FILE_ATTRIBUTE_READONLY != 0 {
-		mode |= 0o444
+		mode += Permissions_Write_All
 	} else {
-		mode |= 0o666
+		mode += Permissions_Read_Write_All
 	}
 
 	is_sym := false
@@ -229,7 +229,7 @@ _file_type_mode_from_file_attributes :: proc(file_attributes: win32.DWORD, h: wi
 		type = .Symlink
 	} else if file_attributes & win32.FILE_ATTRIBUTE_DIRECTORY != 0 {
 		type = .Directory
-		mode |= 0o111
+		mode += Permissions_Execute_All
 	} else if h != nil {
 		type = file_type(h)
 	}
diff --git a/core/os/os2/temp_file.odin b/core/os/os2/temp_file.odin
index e3e74bd11..6e7a37788 100644
--- a/core/os/os2/temp_file.odin
+++ b/core/os/os2/temp_file.odin
@@ -7,7 +7,7 @@ MAX_ATTEMPTS :: 1<<13 // Should be enough for everyone, right?
 
 // Creates a new temperatory file in the directory `dir`.
 //
-// Opens the file for reading and writing, with 0o666 permissions, and returns the new `^File`.
+// Opens the file for reading and writing, with `Permissions_Read_Write_All` permissions, and returns the new `^File`.
 // The filename is generated by taking a pattern, and adding a randomized string to the end.
 // If the pattern includes an "*", the random string replaces the last "*".
 // If `dir` is an empty string, `temp_directory()` will be used.
@@ -26,7 +26,7 @@ create_temp_file :: proc(dir, pattern: string) -> (f: ^File, err: Error) {
 	attempts := 0
 	for {
 		name := concatenate_strings_from_buffer(name_buf[:], prefix, random_string(rand_buf[:]), suffix)
-		f, err = open(name, {.Read, .Write, .Create, .Excl}, 0o666)
+		f, err = open(name, {.Read, .Write, .Create, .Excl}, Permissions_Read_Write_All)
 		if err == .Exist {
 			close(f)
 			attempts += 1