diff --git a/CHANGELOG.md b/CHANGELOG.md
index ef566eec..1c7547af 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,6 +1,25 @@
 # Change Log
 All notable changes to this project will be documented in this file.
 
+## [4.14.4]
+
+### Added
+
+- None
+
+### Changed
+
+- Remove meta yamls that prevent indexer and agent role installation from PR #1806 ([#1921](https://github.com/wazuh/wazuh-ansible/pull/1921))
+- Ensure boolean condition evaluations - from community PR #1897 ([#1916](https://github.com/wazuh/wazuh-ansible/pull/1916))
+
+### Fixed
+
+- None
+
+### Deleted
+
+- None
+
 ## [4.14.3]
 
 ### Added
diff --git a/VERSION.json b/VERSION.json
index 07c404b3..04478604 100644
--- a/VERSION.json
+++ b/VERSION.json
@@ -1,4 +1,4 @@
 {
-    "version": "4.14.3",
-    "stage": "rc2"
+    "version": "4.14.4",
+    "stage": "rc1"
 }
diff --git a/roles/wazuh/ansible-wazuh-agent/meta/main.yml b/meta/main.yml
similarity index 83%
rename from roles/wazuh/ansible-wazuh-agent/meta/main.yml
rename to meta/main.yml
index 7cd460c4..4b059bf0 100644
--- a/roles/wazuh/ansible-wazuh-agent/meta/main.yml
+++ b/meta/main.yml
@@ -1,7 +1,7 @@
 ---
 galaxy_info:
   author: Wazuh
-  description: Installing, deploying and configuring Wazuh Agent.
+  description: Installing, deploying and configuring Wazuh using Ansible.
   company: wazuh.com
   license: license (GPLv3)
   min_ansible_version: 2.0
diff --git a/roles/elastic-stack/ansible-kibana/defaults/main.yml b/roles/elastic-stack/ansible-kibana/defaults/main.yml
index 9036a5de..ead0f6ba 100644
--- a/roles/elastic-stack/ansible-kibana/defaults/main.yml
+++ b/roles/elastic-stack/ansible-kibana/defaults/main.yml
@@ -7,7 +7,7 @@ kibana_server_host: "0.0.0.0"
 kibana_server_port: "5601"
 kibana_conf_path: /etc/kibana
 elastic_stack_version: 7.10.2
-wazuh_version: 4.14.3
+wazuh_version: 4.14.4
 wazuh_app_url: https://packages.wazuh.com/4.x/ui/kibana/wazuh_kibana
 
 elasticrepo:
diff --git a/roles/wazuh/ansible-filebeat-oss/defaults/main.yml b/roles/wazuh/ansible-filebeat-oss/defaults/main.yml
index 4e1a035d..9db7cd96 100644
--- a/roles/wazuh/ansible-filebeat-oss/defaults/main.yml
+++ b/roles/wazuh/ansible-filebeat-oss/defaults/main.yml
@@ -1,7 +1,7 @@
 ---
 filebeat_version: 7.10.2
 
-wazuh_template_branch: v4.14.3
+wazuh_template_branch: v4.14.4
 
 filebeat_node_name: node-1
 
diff --git a/roles/wazuh/ansible-filebeat-oss/meta/main.yml b/roles/wazuh/ansible-filebeat-oss/meta/main.yml
deleted file mode 100644
index 4fd7e900..00000000
--- a/roles/wazuh/ansible-filebeat-oss/meta/main.yml
+++ /dev/null
@@ -1,29 +0,0 @@
----
-dependencies: []
-
-galaxy_info:
-  author: Wazuh
-  description: Installing and maintaining Filebeat-oss.
-  company: wazuh.com
-  license: license (GPLv3)
-  min_ansible_version: 2.0
-  platforms:
-    - name: EL
-      versions:
-        - 6
-        - 7
-    - name: Fedora
-      versions:
-        - all
-    - name: Debian
-      versions:
-        - jessie
-    - name: Ubuntu
-      versions:
-        - precise
-        - trusty
-        - xenial
-  galaxy_tags:
-    - web
-    - system
-    - monitoring
diff --git a/roles/wazuh/ansible-wazuh-agent/defaults/main.yml b/roles/wazuh/ansible-wazuh-agent/defaults/main.yml
index 304ba8d3..9868cc27 100644
--- a/roles/wazuh/ansible-wazuh-agent/defaults/main.yml
+++ b/roles/wazuh/ansible-wazuh-agent/defaults/main.yml
@@ -1,5 +1,5 @@
 ---
-wazuh_agent_version: 4.14.3
+wazuh_agent_version: 4.14.4
 
 # Custom packages installation
 
diff --git a/roles/wazuh/ansible-wazuh-manager/defaults/main.yml b/roles/wazuh/ansible-wazuh-manager/defaults/main.yml
index 5b6a8be0..06d1a67b 100644
--- a/roles/wazuh/ansible-wazuh-manager/defaults/main.yml
+++ b/roles/wazuh/ansible-wazuh-manager/defaults/main.yml
@@ -1,5 +1,5 @@
 ---
-wazuh_manager_version: 4.14.3
+wazuh_manager_version: 4.14.4
 
 wazuh_manager_fqdn: "wazuh-server"
 wazuh_manager_package_state: present
diff --git a/roles/wazuh/ansible-wazuh-manager/meta/main.yml b/roles/wazuh/ansible-wazuh-manager/meta/main.yml
deleted file mode 100644
index 1275d232..00000000
--- a/roles/wazuh/ansible-wazuh-manager/meta/main.yml
+++ /dev/null
@@ -1,23 +0,0 @@
----
-galaxy_info:
-  author: Wazuh
-  description: Installing, deploying and configuring Wazuh Manager.
-  company: wazuh.com
-  license: license (GPLv3)
-  min_ansible_version: 2.0
-  platforms:
-    - name: EL
-      versions:
-        - all
-    - name: Ubuntu
-      versions:
-        - all
-    - name: Debian
-      versions:
-        - all
-    - name: Fedora
-      versions:
-        - all
-  galaxy_tags:
-    - monitoring
-dependencies: []
diff --git a/roles/wazuh/ansible-wazuh-manager/tasks/main.yml b/roles/wazuh/ansible-wazuh-manager/tasks/main.yml
index 1614ed84..6bbd5b33 100644
--- a/roles/wazuh/ansible-wazuh-manager/tasks/main.yml
+++ b/roles/wazuh/ansible-wazuh-manager/tasks/main.yml
@@ -10,7 +10,7 @@
           - tar
         state: present
       register: package_status
-      until: "package_status is not failed"  
+      until: "package_status is not failed"
       retries: 10
       delay: 10
 
@@ -20,7 +20,7 @@
         state: present
       when: ansible_distribution != "Amazon" and ansible_distribution_version != "2023"
       register: package_status
-      until: "package_status is not failed"  
+      until: "package_status is not failed"
       retries: 10
       delay: 10
 
@@ -30,7 +30,7 @@
         state: present
       when: ansible_distribution == "Amazon" and ansible_distribution_version == "2023"
       register: package_status
-      until: "package_status is not failed"  
+      until: "package_status is not failed"
       retries: 10
       delay: 10
 
@@ -73,7 +73,7 @@
   tags:
     - init
     - config
-  
+
 - name: Install expect
   package:
     name: expect
@@ -242,7 +242,7 @@
   notify: restart wazuh-manager
   when:
     - csyslog_enabled.stdout == '0' or "skipped" in csyslog_enabled.stdout
-    - syslog_output is defined and syslog_output
+    - syslog_output is defined and (syslog_output | bool)
   tags:
     - config
 
diff --git a/roles/wazuh/check-packages/defaults/main.yml b/roles/wazuh/check-packages/defaults/main.yml
index 5c780343..57d8f5e3 100644
--- a/roles/wazuh/check-packages/defaults/main.yml
+++ b/roles/wazuh/check-packages/defaults/main.yml
@@ -1,2 +1,2 @@
 ---
-wazuh_version: 4.14.3
+wazuh_version: 4.14.4
diff --git a/roles/wazuh/wazuh-dashboard/defaults/main.yml b/roles/wazuh/wazuh-dashboard/defaults/main.yml
index 5a50ecae..b4e19f1d 100644
--- a/roles/wazuh/wazuh-dashboard/defaults/main.yml
+++ b/roles/wazuh/wazuh-dashboard/defaults/main.yml
@@ -8,12 +8,12 @@ dashboard_node_name: node-1
 dashboard_server_host: "0.0.0.0"
 dashboard_server_port: "443"
 dashboard_server_name: "dashboard"
-wazuh_version: 4.14.3
+wazuh_version: 4.14.4
 indexer_cluster_nodes:
   - 127.0.0.1
 
 # The Wazuh dashboard package repository
-dashboard_version: "4.14.3"
+dashboard_version: "4.14.4"
 
 # API credentials
 wazuh_api_credentials:
diff --git a/roles/wazuh/wazuh-dashboard/vars/debian.yml b/roles/wazuh/wazuh-dashboard/vars/debian.yml
index a3b66e60..c403caea 100644
--- a/roles/wazuh/wazuh-dashboard/vars/debian.yml
+++ b/roles/wazuh/wazuh-dashboard/vars/debian.yml
@@ -1,2 +1,2 @@
 ---
-dashboard_version: 4.14.3
+dashboard_version: 4.14.4
diff --git a/roles/wazuh/wazuh-indexer/defaults/main.yml b/roles/wazuh/wazuh-indexer/defaults/main.yml
index 3cfe27de..3752d8c4 100644
--- a/roles/wazuh/wazuh-indexer/defaults/main.yml
+++ b/roles/wazuh/wazuh-indexer/defaults/main.yml
@@ -1,6 +1,6 @@
 ---
 # Cluster Settings
-indexer_version: 4.14.3
+indexer_version: 4.14.4
 
 single_node: false
 indexer_node_name: node-1
diff --git a/roles/wazuh/wazuh-indexer/meta/main.yml b/roles/wazuh/wazuh-indexer/meta/main.yml
deleted file mode 100644
index 1b9648a6..00000000
--- a/roles/wazuh/wazuh-indexer/meta/main.yml
+++ /dev/null
@@ -1,24 +0,0 @@
----
-galaxy_info:
-  author: Wazuh
-  description: Installing and maintaining Wazuh indexer.
-  company: wazuh.com
-  license: license (GPLv3)
-  min_ansible_version: 2.0
-  platforms:
-    - name: EL
-      versions:
-        - all
-    - name: Ubuntu
-      versions:
-        - all
-    - name: Debian
-      versions:
-        - all
-    - name: Fedora
-      versions:
-        - all
-  galaxy_tags:
-    - web
-    - system
-    - monitoring
diff --git a/roles/wazuh/wazuh-indexer/tasks/main.yml b/roles/wazuh/wazuh-indexer/tasks/main.yml
index 48034ae6..24a2291f 100644
--- a/roles/wazuh/wazuh-indexer/tasks/main.yml
+++ b/roles/wazuh/wazuh-indexer/tasks/main.yml
@@ -108,7 +108,8 @@
       delay: 5
       tags: debug
       when:
-        - hostvars[inventory_hostname]['private_ip'] is not defined or not hostvars[inventory_hostname]['private_ip']
+        - hostvars[inventory_hostname]['private_ip'] is not defined or
+          (hostvars[inventory_hostname]['private_ip'] | length) == 0
 
     - name: Wait for Wazuh indexer API (Private IP)
       uri:
@@ -127,7 +128,8 @@
       delay: 5
       tags: debug
       when:
-        - hostvars[inventory_hostname]['private_ip'] is defined and hostvars[inventory_hostname]['private_ip']
+        - hostvars[inventory_hostname]['private_ip'] is defined and
+          (hostvars[inventory_hostname]['private_ip'] | length) > 0
 
     - import_tasks: "RMRedHat.yml"
       when: ansible_os_family == "RedHat"
diff --git a/roles/wazuh/wazuh-indexer/tasks/security_actions.yml b/roles/wazuh/wazuh-indexer/tasks/security_actions.yml
index 6df4de92..f29a9b16 100644
--- a/roles/wazuh/wazuh-indexer/tasks/security_actions.yml
+++ b/roles/wazuh/wazuh-indexer/tasks/security_actions.yml
@@ -114,5 +114,5 @@
   register: result
   until: result.status in [200,201,401]
   when:
-    - indexer_custom_user is defined and indexer_custom_user
+    - indexer_custom_user | default('') | trim | length > 0
     - inventory_hostname == ansible_play_hosts[0]