diff --git a/update-instances.yml b/update-instances.yml
index 75d8870..9d02bab 100644
--- a/update-instances.yml
+++ b/update-instances.yml
@@ -3,10 +3,24 @@
   become: yes
 
   tasks:
-    - name: Apt Update
-      ansible.builtin.apt:
-        update_cache: true
-        
+    - name: Apt Update with Tailscale recovery
+      block:
+
+        - name: Apt Update
+          ansible.builtin.apt:
+            update_cache: true
+
+      rescue:
+
+        - name: Restart tailscaled if apt update failed
+          ansible.builtin.systemd:
+            name: tailscaled
+            state: restarted
+
+        - name: Retry Apt Update
+          ansible.builtin.apt:
+            update_cache: true
+
     - name: Apt Upgrade
       ansible.builtin.apt:
         upgrade: yes