diff --git a/dstack/dstack-util/src/system_setup.rs b/dstack/dstack-util/src/system_setup.rs
index 6f258d34b..f55a3bcc5 100644
--- a/dstack/dstack-util/src/system_setup.rs
+++ b/dstack/dstack-util/src/system_setup.rs
@@ -2775,9 +2775,14 @@ impl Stage1<'_> {
         self.vmm
             .notify_q("boot.progress", "setting up dstack-gateway")
             .await;
-        GatewayContext::new(&self.shared, &self.keys)
+        if let Err(error) = GatewayContext::new(&self.shared, &self.keys)
             .setup(true)
-            .await?;
+            .await
+        {
+            warn!(
+                "dstack-gateway registration is unavailable during boot; continuing without a route: {error:#}"
+            );
+        }
         self.vmm
             .notify_q("boot.progress", "setting up docker")
             .await;
diff --git a/os/common/rootfs/wg-checker.sh b/os/common/rootfs/wg-checker.sh
index ba4149472..b81428187 100755
--- a/os/common/rootfs/wg-checker.sh
+++ b/os/common/rootfs/wg-checker.sh
@@ -6,6 +6,7 @@
 
 HANDSHAKE_TIMEOUT=180
 REFRESH_INTERVAL=180
+MISSING_CONFIG_RETRY_INTERVAL=30
 LAST_REFRESH=0
 STALE_SINCE=0
 DSTACK_WORK_DIR=${DSTACK_WORK_DIR:-/dstack}
@@ -80,6 +81,10 @@ while true; do
         check_and_refresh
     else
         STALE_SINCE=0
+        now=$(date +%s)
+        if [ "$LAST_REFRESH" -eq 0 ] || [ $((now - LAST_REFRESH)) -ge $MISSING_CONFIG_RETRY_INTERVAL ]; then
+            do_refresh "$now" "WireGuard configuration missing" 1
+        fi
     fi
     sleep 10
 done