diff --git a/tailroute.go b/tailroute.go
index af83e5332d615ea1bd54846f0939eca8ea2c8a97..01e4d1695677207fc1c33e4eab9bfffeccaa7396 100644
--- a/tailroute.go
+++ b/tailroute.go
@@ -5,6 +5,7 @@ 	"context"
 	"crypto/tls"
 	"errors"
 	"fmt"
+	"log"
 	"net"
 	"net/http"
 	"os"
@@ -94,13 +95,17 @@ 	if err != nil {
 		return err
 	}
 
-	for {
-		upCtx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
-		defer cancel()
-		status, err := s.Up(upCtx)
-		if err == nil && status != nil {
-			break
+	// wait for tailscale to start before trying to fetch cert names
+	for i := 0; i < 60; i++ {
+		st, err := lc.Status(context.Background())
+		if err != nil {
+			log.Printf("error retrieving tailscale status; retrying: %v", err)
+		} else {
+			if st.BackendState == "Running" {
+				break
+			}
 		}
+		time.Sleep(time.Second)
 	}
 
 	ctx := context.Background()