diff --git a/home/.chezmoitemplates/secrets/TAILSCALE_AUTH_KEY b/home/.chezmoitemplates/secrets/TAILSCALE_AUTH_KEY
index 0ebb58e9..e18fd7fc 100644
--- a/home/.chezmoitemplates/secrets/TAILSCALE_AUTH_KEY
+++ b/home/.chezmoitemplates/secrets/TAILSCALE_AUTH_KEY
@@ -1,8 +1,8 @@
 -----BEGIN AGE ENCRYPTED FILE-----
-YWdlLWVuY3J5cHRpb24ub3JnL3YxCi0+IFgyNTUxOSB4eUNoMlc0VXNQS21zaURI
-aFVtVGpsOGRWQTI0ZFc5ZmpEVUNZRSs5VTMwCmswKzcwOExpbVNZTHpXTE9hK1RW
-N0dkRVRjZXNIYzhXT2tGcmZVMm1XbkkKLS0tIDFCeWJZR1hPN3BISi8wVUo1TmFa
-QmVMNnhDUEtGbHNLL0kvcDRpN2FYK2sKjKuAZ9XM2UmZOj9ieANMi6i40MeHCWQV
-aT+tQqnolBmenn0J+VVMSalhnc8/GsIx0kyUV2yM6WvfMWwnlzMUlLk4ULFJy2nl
-vkooM7iZIf8DNXjAZ17uEJs=
+YWdlLWVuY3J5cHRpb24ub3JnL3YxCi0+IFgyNTUxOSBsaGJ1ZG9VWVduVDA4VFA1
+empCeDNERmtWeGhVWTQ5QlpSRXpybjZ2MUFNCkV3UzhXQ3BmRjdwc09LaU5XclNq
+VnMyUjdBUXYrWERYVmdPSG4wZWk3TWMKLS0tIE0xQXVBWExnSkl0bndtTjg0cC93
+TjVadlVqU3U3aEFCcTB2WFN6UnZxSHcKQszLGd6LHfPXSqkIiF4BzCERqF34QOXJ
+1vPj7h70g1ay2kjSZ73bw38eLtvne2nzUzEPu0J+XLq30S7j5Tcj9DC3JaetPnnx
+25BHfHuTSD++Cj6aq/HA0fsQR9AcWw==
 -----END AGE ENCRYPTED FILE-----
\ No newline at end of file
diff --git a/home/dot_local/bin/post-installx/executable_post-tailscale.sh b/home/dot_local/bin/post-installx/executable_post-tailscale.sh
index 4cd8b348..1ea9ef32 100644
--- a/home/dot_local/bin/post-installx/executable_post-tailscale.sh
+++ b/home/dot_local/bin/post-installx/executable_post-tailscale.sh
@@ -15,15 +15,34 @@ if [ -d /Applications ] && [ -d System ]; then
   else
     logg info 'tailscaled does not appear to be installed'
   fi
+
+  ### Open Tailscale.app
+  if [ -d /Applications/Tailscale.app ]; then
+    logg info 'Opening Tailscale.app menu bar widget' && open -a Tailscale
+  else
+    logg info '/Applications/Tailscale.app is missing from the system'
+  fi
 fi
 
 ### Connect to Tailscale network
-if command -v tailscale > /dev/null && [ "$TAILSCALE_AUTH_KEY" != "" ]; then
-  logg info 'Connecting to Tailscale with user-defined authentication key'
-  timeout 14 tailscale up --authkey="$TAILSCALE_AUTH_KEY" --accept-routes || EXIT_CODE=$?
-  if [ -n "$EXIT_CODE" ]; then
-    logg warn 'tailscale up timed out'
+if [ -n "$TAILSCALE_AUTH_KEY" ] && [ "$TAILSCALE_AUTH_KEY" != "" ]; then
+  if [ -f /Applications/Tailscale.app/Contents/MacOS/Tailscale ]; then
+    logg info 'Connecting to Tailscale with user-defined authentication key (TAILSCALE_AUTH_KEY)'
+    timeout 30 /Applications/Tailscale.app/Contents/MacOS/Tailscale up --authkey="$TAILSCALE_AUTH_KEY" --accept-routes || EXIT_CODE=$?
+    if [ -n "$EXIT_CODE" ]; then
+      logg warn '/Applications/Tailscale.app/Contents/MacOS/Tailscale timed out'
+    fi
+  elif command -v tailscale > /dev/null && [ "$TAILSCALE_AUTH_KEY" != "" ]; then
+    logg info 'Connecting to Tailscale with user-defined authentication key (TAILSCALE_AUTH_KEY)'
+    timeout 30 tailscale up --authkey="$TAILSCALE_AUTH_KEY" --accept-routes || EXIT_CODE=$?
+    if [ -n "$EXIT_CODE" ]; then
+      logg warn 'tailscale up timed out'
+    else
+      logg success 'Connected to Tailscale network'
+    fi
   else
-    logg success 'Connected to Tailscale network'
+    logg info 'tailscale does not appear to be installed'
   fi
-fi
\ No newline at end of file
+else
+  logg info 'TAILSCALE_AUTH_KEY is not defined so not logging into Tailscale network'
+fi