diff --git a/src/commands/connect-container.yml b/src/commands/connect-container.yml
index ca01dc4..4406f85 100644
--- a/src/commands/connect-container.yml
+++ b/src/commands/connect-container.yml
@@ -40,7 +40,15 @@ steps:
       name: "Tailscale Up"
       command: |
         HOSTNAME="circleci-$(cat /etc/hostname)"
-        tailscale --socket=/tmp/tailscaled.sock up --authkey ${<< parameters.auth-key >>} --hostname=${HOSTNAME} --accept-routes --timeout=10s
+        for run in {1..3}; do
+          echo "Tailscale connection attempt #${run}"
+          tailscale --socket=/tmp/tailscaled.sock up --authkey ${<< parameters.auth-key >>} --hostname=${HOSTNAME} --accept-routes --timeout=10s
+          if [ $? = 0 ]; then
+            exit 0
+          fi
+        done
+        echo "Error: could not connect to tailscale"
+        exit 1
   - when:
       condition: << parameters.export-proxies >>
       steps: