diff --git a/CHANGELOG.md b/CHANGELOG.md
index 41298808..defecdee 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,7 +9,7 @@ All notable changes to this project will be documented in this file.
 
 ### Changed
 
-- None
+- Ensure boolean condition evaluations - from community PR #1897 ([#1916](https://github.com/wazuh/wazuh-ansible/pull/1916))
 
 ### Fixed
 
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/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]