diff --git a/changelogs/fragments/debconf_bool_fix.yml b/changelogs/fragments/debconf_bool_fix.yml
new file mode 100644
index 00000000000..e8fb2ef44c1
--- /dev/null
+++ b/changelogs/fragments/debconf_bool_fix.yml
@@ -0,0 +1,2 @@
+bugfixes:
+    - Fix how debconf handles boolean questions to accurately compare
diff --git a/lib/ansible/modules/system/debconf.py b/lib/ansible/modules/system/debconf.py
index e241c61c56c..1edf6c1ac4b 100644
--- a/lib/ansible/modules/system/debconf.py
+++ b/lib/ansible/modules/system/debconf.py
@@ -87,6 +87,7 @@ EXAMPLES = r'''
     name: tzdata
 '''
 
+from ansible.module_utils._text import to_text
 from ansible.module_utils.basic import AnsibleModule
 
 
@@ -151,8 +152,17 @@ def main():
         if vtype is None or value is None:
             module.fail_json(msg="when supplying a question you must supply a valid vtype and value")
 
-        if question not in prev or prev[question] != value:
+        # if question doesn't exist, value cannot match
+        if question not in prev:
             changed = True
+        else:
+            # ensure we compare booleans supplied to the way debconf sees them (true/false strings)
+            if vtype == 'boolean':
+                value = to_text(value).lower()
+                existing = to_text(prev[question]).lower()
+
+            if value != existing:
+                changed = True
 
     if changed:
         if not module.check_mode: