diff --git a/spire/entrypoint.agent.sh b/spire/entrypoint.agent.sh
index 4f6d443..99623ec 100755
--- a/spire/entrypoint.agent.sh
+++ b/spire/entrypoint.agent.sh
@@ -18,7 +18,7 @@ fi
 # Check if this agent is enrolling for the first time
 if [ ! -f /opt/spire/data/agent/svid.key ] && [ ! -f /opt/spire/data/agent/agent_svids.json ]; then
   echo "[SPIRE Agent] Initial enrollment detected. Waiting for bootstrap join token..."
-  for i in $(seq 1 30); do
+  for i in $(seq 1 60); do
     if [ -f /opt/spire/data/bootstrap_token ]; then
       break
     fi
@@ -28,10 +28,9 @@ if [ ! -f /opt/spire/data/agent/svid.key ] && [ ! -f /opt/spire/data/agent/agent
   if [ -f /opt/spire/data/bootstrap_token ]; then
     JOIN_TOKEN=$(cat /opt/spire/data/bootstrap_token | tr -d ' \r\n')
     echo "[SPIRE Agent] Joining SPIRE cluster with token..."
-    rm -f /opt/spire/data/bootstrap_token
     exec /usr/local/bin/spire-agent "$@" -joinToken "$JOIN_TOKEN"
   else
-    echo "[SPIRE Agent] Warning: No bootstrap_token found after 30s. Attempting standard startup..."
+    echo "[SPIRE Agent] Warning: No bootstrap_token found after 60s. Attempting standard startup..."
   fi
 fi
 
diff --git a/spire/entrypoint.server.sh b/spire/entrypoint.server.sh
index f7cdf35..146f695 100755
--- a/spire/entrypoint.server.sh
+++ b/spire/entrypoint.server.sh
@@ -13,26 +13,29 @@ fi
 /usr/local/bin/spire-server "$@" &
 SERVER_PID=$!
 
-# Helper: Auto-generate bootstrap join token for local agent on initial enrollment
+# Helper: Maintain auto-bootstrap join token until local agent has successfully enrolled
 (
   SOCKET="/opt/spire/data/server/api.sock"
-  for i in $(seq 1 30); do
-    if [ -S "$SOCKET" ]; then
-      break
-    fi
+  while [ ! -S "$SOCKET" ]; do
     sleep 1
   done
 
-  if [ -S "$SOCKET" ] && [ ! -f /opt/spire/data/agent/svid.key ]; then
-    echo "[SPIRE Server] Generating auto-bootstrap join token for local agent..."
-    TOKEN_OUTPUT=$(/usr/local/bin/spire-server token generate -spiffeID spiffe://system.local/agent -socketPath "$SOCKET" 2>/dev/null || true)
-    TOKEN=$(echo "$TOKEN_OUTPUT" | grep -i "token:" | awk '{print $2}')
-    if [ -n "$TOKEN" ]; then
-      echo "$TOKEN" > /opt/spire/data/bootstrap_token
-      chmod 600 /opt/spire/data/bootstrap_token
-      echo "[SPIRE Server] Auto-bootstrap token ready."
+  while [ ! -f /opt/spire/data/agent/svid.key ] && [ ! -f /opt/spire/data/agent/agent_svids.json ]; do
+    if [ ! -f /opt/spire/data/bootstrap_token ]; then
+      echo "[SPIRE Server] Generating auto-bootstrap join token for local agent..."
+      TOKEN_OUTPUT=$(/usr/local/bin/spire-server token generate -spiffeID spiffe://system.local/agent -socketPath "$SOCKET" -ttl 3600 2>/dev/null || true)
+      TOKEN=$(echo "$TOKEN_OUTPUT" | grep -i "token:" | awk '{print $2}')
+      if [ -n "$TOKEN" ]; then
+        echo "$TOKEN" > /opt/spire/data/bootstrap_token
+        chmod 600 /opt/spire/data/bootstrap_token
+        echo "[SPIRE Server] Auto-bootstrap token ready."
+      fi
     fi
-  fi
+    sleep 5
+  done
+
+  echo "[SPIRE Server] Agent enrollment verified. Cleaning up bootstrap tokens."
+  rm -f /opt/spire/data/bootstrap_token
 ) &
 
 wait "$SERVER_PID"