diff --git a/core/tsnet.go b/core/tsnet.go
index ed2d18c..3e391b1 100644
--- a/core/tsnet.go
+++ b/core/tsnet.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	fmt2 "fmt"
 	"log/slog"
+	"time"
 
 	"tailscale.com/ipn"
 
@@ -40,7 +41,9 @@ func InitTsNet(ctx context.Context, cfg *Core, logger *slog.Logger, withDebugLog
 		return nil, err
 	}
 
-	status, err := srv.Up(ctx)
+	cnclCtx, cancel := context.WithTimeout(ctx, 30*time.Second)
+	defer cancel()
+	status, err := srv.Up(cnclCtx)
 	if err != nil {
 		logger.With(slog.String("error", err.Error())).Error("bring up tsnet server failed")
 		return nil, err
diff --git a/main.go b/main.go
index 9e38d7a..66e353e 100644
--- a/main.go
+++ b/main.go
@@ -2,6 +2,7 @@ package main
 
 import (
 	"context"
+	"errors"
 	"flag"
 	"log/slog"
 	"os"
@@ -21,9 +22,14 @@ func serviceLogic(configPath string, isTsnetDebug bool, logger *slog.Logger) boo
 	}
 
 	ctx, cancelAll := context.WithCancel(context.Background())
+	defer cancelAll()
 	logger.Info("initializing tsnet server")
 	srv, err := core.InitTsNet(ctx, &cfg.Core, logger, isTsnetDebug)
 	if err != nil {
+		if errors.Is(err, context.DeadlineExceeded) {
+			logger.Debug("tsnet initialization timed out, retrying")
+			return false
+		}
 		logger.With(
 			slog.String("error", err.Error())).Error("Error initializing tsnet")
 		os.Exit(1)