diff --git a/roles/wazuh/ansible-wazuh-agent/defaults/main.yml b/roles/wazuh/ansible-wazuh-agent/defaults/main.yml
index 4f587c86..d4684ab4 100644
--- a/roles/wazuh/ansible-wazuh-agent/defaults/main.yml
+++ b/roles/wazuh/ansible-wazuh-agent/defaults/main.yml
@@ -43,16 +43,6 @@ wazuh_profile_centos: 'centos, centos7, centos7.6'
 wazuh_profile_ubuntu: 'ubuntu, ubuntu18, ubuntu18.04'
 wazuh_auto_restart: 'yes'
 
-wazuh_agent_authd:
-  registration_address: 127.0.0.1
-  enable: false
-  port: 1515
-  agent_name: null
-  groups: []
-  ssl_agent_ca: null
-  ssl_agent_cert: null
-  ssl_agent_key: null
-  ssl_auto_negotiate: 'no'
 wazuh_notify_time: '10'
 wazuh_time_reconnect: '60'
 wazuh_crypto_method: 'aes'
@@ -74,26 +64,38 @@ wazuh_agent_repo:
   gpg: 'https://packages.wazuh.com/key/GPG-KEY-WAZUH'
   key_id: '0DCFCA5547B19D2A6099506096B3EE5F29111145'
 
+# This is deprecated, see: wazuh_agent_address
 wazuh_agent_nat: false
 
 ##########################################
 ### Wazuh
 ##########################################
 
+wazuh_agent_nolog_sensible: yes
 wazuh_agent_config_overlay: yes
 
-## Client
+# This is a middle ground between breaking existing uses of wazuh_agent_nat
+# and allow working with agents having several network interfaces
+wazuh_agent_address: '{{ "any" if wazuh_agent_nat else ansible_default_ipv4.address }}'
+
+# List of managers. The first one with register variable declared *and* set to true
+# is the one used to register the agent. Otherwise, the first one in the list will be used.
 wazuh_managers:
   - address: 127.0.0.1
     port: 1514
     protocol: tcp
     api_port: 55000
-    api_proto: 'http'
+    api_proto: https
     api_user: wazuh
     max_retries: 5
     retry_interval: 5
+    register: yes
+
+## Authentication Method: Enrollment section (4.x)
+
+# For more information see:
+# * https://documentation.wazuh.com/4.0/user-manual/reference/ossec-conf/client.html#enrollment
 
-## Enrollment
 wazuh_agent_enrollment:
   enabled: 'yes'
   manager_address: ''
@@ -110,6 +112,28 @@ wazuh_agent_enrollment:
   delay_after_enrollment: 20
   use_source_ip: 'no'
 
+## Authentication Method: invoking agent-auth
+
+# For more information see:
+# * https://documentation.wazuh.com/4.0/user-manual/registering/password-authorization-registration.html
+
+wazuh_agent_authd:
+  registration_address: 127.0.0.1
+  enable: false
+  port: 1515
+  agent_name: null
+  groups: []
+  ssl_agent_ca: null
+  ssl_agent_cert: null
+  ssl_agent_key: null
+  ssl_auto_negotiate: 'no'
+
+## Authentication Method: REST API
+
+# For more information see:
+# * https://documentation.wazuh.com/4.0/user-manual/registering/restful-api-registration.html
+wazuh_agent_api_validate: yes
+
 ## Client buffer
 wazuh_agent_client_buffer:
   disable: 'no'
diff --git a/roles/wazuh/ansible-wazuh-agent/tasks/Linux.yml b/roles/wazuh/ansible-wazuh-agent/tasks/Linux.yml
index 3279647a..8b8d9314 100644
--- a/roles/wazuh/ansible-wazuh-agent/tasks/Linux.yml
+++ b/roles/wazuh/ansible-wazuh-agent/tasks/Linux.yml
@@ -41,8 +41,7 @@
 - name: Linux | Check if client.keys exists
   stat:
     path: /var/ossec/etc/client.keys
-  register: check_keys
-  when: wazuh_agent_config.enrollment.enabled == 'no'
+  register: client_keys_file
   tags:
     - config
 
@@ -97,18 +96,18 @@
       vars:
         agent_name: "{% if single_agent_name is defined %}{{ single_agent_name }}{% else %}{{ ansible_hostname }}{% endif %}"
       when:
-        - not check_keys.stat.exists or check_keys.stat.size == 0
+        - not client_keys_file.stat.exists or client_keys_file.stat.size == 0
         - wazuh_agent_authd.registration_address is not none
 
     - name: Linux | Verify agent registration
       shell: echo {{ agent_auth_output }} | grep "Valid key received"
       when:
-        - not check_keys.stat.exists or check_keys.stat.size == 0
+        - not client_keys_file.stat.exists or client_keys_file.stat.size == 0
         - wazuh_agent_authd.registration_address is not none
 
   when:
-    - wazuh_agent_authd.enable
-    - not wazuh_agent_config.enrollment.enabled | length > 0 or wazuh_agent_config.enrollment.enabled == 'no'
+    - wazuh_agent_authd.enable | bool
+    - wazuh_agent_config.enrollment.enabled != 'yes'
   tags:
     - config
     - authd
@@ -116,69 +115,100 @@
 - name: Linux | Agent registration via rest-API
   block:
 
+    - name: Establish target Wazuh Manager for registration task
+      set_fact:
+        target_manager: '{{ manager_primary | length | ternary(manager_primary, manager_fallback) | first }}'
+      vars:
+        manager_primary: "{{ wazuh_managers | selectattr('register','true') | list }}"
+        manager_fallback: "{{ wazuh_managers | list }}"
+
+    - name: Linux | Obtain JWT Token
+      uri:
+        url: '{{ target_manager.api_proto }}://{{ target_manager.address }}:{{ target_manager.api_port }}/security/user/authenticate'
+        method: GET
+        url_username: '{{ target_manager.api_user }}'
+        url_password: '{{ api_pass }}'
+        status_code: 200
+        return_content: yes
+        force_basic_auth: yes
+        validate_certs: '{{ target_manager.validate_certs | default(false) }}'
+      no_log: '{{ wazuh_agent_nolog_sensible | bool }}'
+      delegate_to: '{{ ansible_host if wazuh_api_reachable_from_agent else "localhost"  }}'
+      changed_when: api_jwt_result.json.error == 0
+      register: api_jwt_result
+      become: no
+      tags:
+        - config
+        - api
+
     - name: Linux | Create the agent key via rest-API
       uri:
-        url: "{{ wazuh_managers.0.api_proto }}://{{ wazuh_agent_authd.registration_address }}:{{ wazuh_managers.0.api_port }}/agents/"
-        validate_certs: false
+        url: '{{ target_manager.api_proto }}://{{ target_manager.address }}:{{ target_manager.api_port }}/agents'
         method: POST
-        body: '{"name":"{{ agent_name }}"}'
         body_format: json
-        status_code: 200
+        body:
+          name: '{{ agent_name }}'
+          ip: '{{ wazuh_agent_address }}'
+          force_time: 1
         headers:
-          Content-Type: "application/json"
-        user: "{{ wazuh_managers.0.api_user }}"
-        password: "{{ api_pass }}"
-      register: newagent_api
-      delegate_to: "{{ 'localhost' if not wazuh_api_reachable_from_agent else inventory_hostname }}"
+          Authorization: 'Bearer {{ jwt_token }}'
+        status_code: 200
+        return_content: yes
+        validate_certs: '{{ target_manager.validate_certs | default(false) }}'
       become: no
-      changed_when: newagent_api.json.error == 0
-      when:
-        - not check_keys.stat.exists or check_keys.stat.size == 0
-        - wazuh_managers.0.address is not none
+      no_log: '{{ wazuh_agent_nolog_sensible | bool }}'
+      delegate_to: "{{ 'localhost' if not wazuh_api_reachable_from_agent else inventory_hostname }}"
+      changed_when: api_agent_post.json.error == 0
+      register: api_agent_post
+      vars:
+        agent_name: '{{ target_manager.agent_name | default(ansible_hostname) }}'
+        jwt_token: '{{ api_jwt_result.json.data.token }}'
       tags:
         - config
         - api
 
-    - name: Linux | Retrieve new agent data via rest-API
+    - name: Linux | Validate registered agent key matches manager record
       uri:
-        url: >-
-          "{{ wazuh_managers.0.api_proto }}://{{ wazuh_agent_authd.registration_address
-          }}:{{ wazuh_managers.0.api_port }}/agents/{{ newagent_api.json.data.id }}"
-        validate_certs: false
+        url: '{{ target_manager.api_proto }}://{{ target_manager.address }}:{{ target_manager.api_port }}/agents/{{ agent_id }}/key'
         method: GET
-        return_content: true
-        user: "{{ wazuh_managers.0.api_user }}"
-        password: "{{ api_pass }}"
-      when:
-        - not check_keys.stat.exists or check_keys.stat.size == 0
-        - wazuh_agent_authd.registration_address is not none
-        - newagent_api.json.error == 0
-      register: newagentdata_api
-      delegate_to: "{{ 'localhost' if not wazuh_api_reachable_from_agent else inventory_hostname }}"
+        headers:
+          Authorization: 'Bearer {{ jwt_token }}'
+        status_code: 200
+        return_content: yes
+        validate_certs: '{{ target_manager.validate_certs | default(false) }}'
       become: no
+      no_log: '{{ wazuh_agent_nolog_sensible | bool }}'
+      delegate_to: "{{ 'localhost' if not wazuh_api_reachable_from_agent else inventory_hostname }}"
+      register: api_agent_validation
+      vars:
+        agent_id: '{{ api_agent_post.json.data.id }}'
+        agent_key: '{{ api_agent_post.json.data.key }}'
+        jwt_token: '{{ api_jwt_result.json.data.token }}'
+      failed_when: api_agent_validation.json.data.affected_items[0].key != agent_key
+      when:
+      - wazuh_agent_api_validate | bool
+      - api_agent_post.json.error == 0
       tags:
         - config
         - api
 
-    - name: Linux | Register agent (via rest-API)
+    - name: Linux | Import Key (via rest-API)
       command: /var/ossec/bin/manage_agents
       environment:
         OSSEC_ACTION: i
-        OSSEC_AGENT_NAME: '{{ newagentdata_api.json.data.name }}'
-        OSSEC_AGENT_IP: '{% if wazuh_agent_nat %}any{% else %}{{ newagentdata_api.json.data.ip }}{% endif %}'
-        OSSEC_AGENT_ID: '{{ newagent_api.json.data.id }}'
-        OSSEC_AGENT_KEY: '{{ newagent_api.json.data.key }}'
+        OSSEC_AGENT_NAME: '{{ agent_name }}'
+        OSSEC_AGENT_IP: '{{ wazuh_agent_address }}'
+        OSSEC_AGENT_ID: '{{ api_agent_post.json.data.id }}'
+        OSSEC_AGENT_KEY: '{{ api_agent_post.json.data.key }}'
         OSSEC_ACTION_CONFIRMED: y
       register: manage_agents_output
-      when:
-        - not check_keys.stat.exists or check_keys.stat.size == 0
-        - wazuh_agent_authd.registration_address is not none
-        - newagent_api.json.error == 0
+      vars:
+        agent_name: '{{ target_manager.agent_name | default(ansible_hostname) }}'
       notify: restart wazuh-agent
-
   when:
-    - not wazuh_agent_authd.enable
-    - not wazuh_agent_config.enrollment.enabled | length > 0 or wazuh_agent_config.enrollment.enabled == 'no'
+    - not ( wazuh_agent_authd.enable | bool )
+    - wazuh_agent_config.enrollment.enabled != 'yes'
+    - not client_keys_file.stat.exists or client_keys_file.stat.size == 0
   tags:
     - config
     - api
diff --git a/roles/wazuh/ansible-wazuh-agent/templates/var-ossec-etc-ossec-agent.conf.j2 b/roles/wazuh/ansible-wazuh-agent/templates/var-ossec-etc-ossec-agent.conf.j2
index bb71ca45..22f94856 100644
--- a/roles/wazuh/ansible-wazuh-agent/templates/var-ossec-etc-ossec-agent.conf.j2
+++ b/roles/wazuh/ansible-wazuh-agent/templates/var-ossec-etc-ossec-agent.conf.j2
@@ -37,7 +37,7 @@
     <auto_restart>{{ wazuh_auto_restart }}</auto_restart>
     <crypto_method>{{ wazuh_crypto_method }}</crypto_method>
 
-  {% if wazuh_agent_config.enrollment.enabled | length > 0 %}
+  {% if wazuh_agent_config.enrollment.enabled == 'yes' %}
     <enrollment>
       <enabled>{{ wazuh_agent_config.enrollment.enabled }}</enabled>
       {% if wazuh_agent_config.enrollment.manager_address | length > 0 %}