diff --git a/tailscale/rootfs/etc/s6-overlay/s6-rc.d/post-tailscaled/run b/tailscale/rootfs/etc/s6-overlay/s6-rc.d/post-tailscaled/run
index db8ceb05..fe0594bc 100755
--- a/tailscale/rootfs/etc/s6-overlay/s6-rc.d/post-tailscaled/run
+++ b/tailscale/rootfs/etc/s6-overlay/s6-rc.d/post-tailscaled/run
@@ -10,6 +10,7 @@ declare -a routes=()
 declare ipinfo
 declare login_server
 declare tags
+declare keyexpiry
 
 function appendarray() {
   local -n array=${1}
@@ -105,4 +106,11 @@ do
   sleep 2
 done
 
+# Warn about key expiration
+if keyexpiry=$(/opt/tailscale status --self=true --peers=false --json | jq -rce '.Self.KeyExpiry'); then
+  bashio::log.warning "The connection's key will expire on: ${keyexpiry}"
+  bashio::log.warning "Consider disabling key expiry to avoid losing connection to your Home Assistant device."
+  bashio::log.warning "Please check your configuration based on the add-on's documentation under \"Configuration\""
+fi
+
 bashio::log.info "Tailscale is running"