improve errors for missing directories

Fixes juanfont#1761
Updates juanfont#1760

Signed-off-by: Kristoffer Dalby <kristoffer@tailscale.com>

hscontrol/app.go

@@ -11,6 +11,7 @@ import (
 	_ "net/http/pprof" //nolint
 	"os"
 	"os/signal"
+	"path/filepath"
 	"runtime"
 	"strings"
 	"sync"
@@ -70,6 +71,7 @@ const (
 	AuthPrefix         = "Bearer "
 	updateInterval     = 5000
 	privateKeyFileMode = 0o600
+	headscaleDirPerm   = 0o700
 
 	registerCacheExpiration = time.Minute * 15
 	registerCacheCleanup    = time.Minute * 20
@@ -556,6 +558,12 @@ func (h *Headscale) Serve() error {
 		return fmt.Errorf("unable to remove old socket file: %w", err)
 	}
 
+	socketDir := filepath.Dir(h.cfg.UnixSocket)
+	err = util.EnsureDir(socketDir)
+	if err != nil {
+		return fmt.Errorf("setting up unix socket: %w", err)
+	}
+
 	socketListener, err := net.Listen("unix", h.cfg.UnixSocket)
 	if err != nil {
 		return fmt.Errorf("failed to set up gRPC socket: %w", err)
@@ -923,6 +931,12 @@ func notFoundHandler(
 }
 
 func readOrCreatePrivateKey(path string) (*key.MachinePrivate, error) {
+	dir := filepath.Dir(path)
+	err := util.EnsureDir(dir)
+	if err != nil {
+		return nil, fmt.Errorf("ensuring private key directory: %w", err)
+	}
+
 	privateKey, err := os.ReadFile(path)
 	if errors.Is(err, os.ErrNotExist) {
 		log.Info().Str("path", path).Msg("No private key file at path, creating...")

hscontrol/db/db.go

@@ -6,6 +6,7 @@ import (
 	"errors"
 	"fmt"
 	"net/netip"
+	"path/filepath"
 	"strconv"
 	"strings"
 	"time"
@@ -344,6 +345,12 @@ func openDB(cfg types.DatabaseConfig) (*gorm.DB, error) {
 
 	switch cfg.Type {
 	case types.DatabaseSqlite:
+		dir := filepath.Dir(cfg.Sqlite.Path)
+		err := util.EnsureDir(dir)
+		if err != nil {
+			return nil, fmt.Errorf("creating directory for sqlite: %w", err)
+		}
+
 		db, err := gorm.Open(
 			sqlite.Open(cfg.Sqlite.Path+"?_synchronous=1&_journal_mode=WAL"),
 			&gorm.Config{

hscontrol/util/file.go

@@ -1,6 +1,8 @@
 package util
 
 import (
+	"errors"
+	"fmt"
 	"io/fs"
 	"os"
 	"path/filepath"
@@ -42,3 +44,21 @@ func GetFileMode(key string) fs.FileMode {
 
 	return fs.FileMode(mode)
 }
+
+func EnsureDir(dir string) error {
+	if _, err := os.Stat(dir); os.IsNotExist(err) {
+		err := os.MkdirAll(dir, PermissionFallback)
+		if err != nil {
+			if errors.Is(err, os.ErrPermission) {
+				return fmt.Errorf(
+					"creating directory %s, failed with permission error, is it located somewhere Headscale can write?",
+					dir,
+				)
+			}
+
+			return fmt.Errorf("creating directory %s: %w", dir, err)
+		}
+	}
+
+	return nil
+}