diff --git a/roles/k3s_agent/tasks/main.yml b/roles/k3s_agent/tasks/main.yml
index 2dafa3ce..565ef258 100644
--- a/roles/k3s_agent/tasks/main.yml
+++ b/roles/k3s_agent/tasks/main.yml
@@ -35,6 +35,12 @@
         INSTALL_K3S_EXEC: "agent"
       changed_when: true
 
+- name: Delete any existing token from the environment if different from the new one
+  ansible.builtin.lineinfile:
+    state: absent
+    path: "{{ systemd_dir }}/k3s-agent.service.env"
+    regexp: "^K3S_TOKEN=\\s*(?!{{ token }}\\s*$)"
+
 - name: Add the token for joining the cluster to the environment
   no_log: true # avoid logging the server token
   ansible.builtin.lineinfile:
diff --git a/roles/k3s_server/tasks/main.yml b/roles/k3s_server/tasks/main.yml
index a61eb0b6..12131f2a 100644
--- a/roles/k3s_server/tasks/main.yml
+++ b/roles/k3s_server/tasks/main.yml
@@ -86,6 +86,12 @@
         line: "{{ item }}"
       with_items: "{{ extra_service_envs }}"
 
+    - name: Delete any existing token from the environment if different from the new one
+      ansible.builtin.lineinfile:
+        state: absent
+        path: "{{ systemd_dir }}/k3s.service.env"
+        regexp: "^K3S_TOKEN=\\s*(?!{{ token }}\\s*$)"
+
     # Add the token to the environment.
     - name: Add token as an environment variable
       no_log: true # avoid logging the server token
@@ -181,6 +187,12 @@
     - (groups[server_group] | length) > 1
     - inventory_hostname != groups[server_group][0]
   block:
+    - name: Delete any existing token from the environment if different from the new one
+      ansible.builtin.lineinfile:
+        state: absent
+        path: "{{ systemd_dir }}/k3s.service.env"
+        regexp: "^K3S_TOKEN=\\s*(?!{{ token }}\\s*$)"
+
     - name: Add the token for joining the cluster to the environment
       no_log: true # avoid logging the server token
       ansible.builtin.lineinfile: