diff --git a/changelogs/fragments/fix-allow-duplicates.yml b/changelogs/fragments/fix-allow-duplicates.yml
new file mode 100644
index 00000000000000..fb0c8171fc1f9b
--- /dev/null
+++ b/changelogs/fragments/fix-allow-duplicates.yml
@@ -0,0 +1,2 @@
+bugfixes:
+  - allow_duplicates - fix evaluating if the current role allows duplicates instead of using the initial value from the duplicate's cached role.
diff --git a/lib/ansible/playbook/role/__init__.py b/lib/ansible/playbook/role/__init__.py
index 9bf28cd26b849d..1c82e5335c4d84 100644
--- a/lib/ansible/playbook/role/__init__.py
+++ b/lib/ansible/playbook/role/__init__.py
@@ -584,7 +584,7 @@ def has_run(self, host):
         at least one task was run
         '''
 
-        return host.name in self._completed and not self._metadata.allow_duplicates
+        return host.name in self._completed
 
     def compile(self, play, dep_chain=None):
         '''
diff --git a/lib/ansible/plugins/strategy/free.py b/lib/ansible/plugins/strategy/free.py
index fda3a0dd633137..6f33a68920b486 100644
--- a/lib/ansible/plugins/strategy/free.py
+++ b/lib/ansible/plugins/strategy/free.py
@@ -175,7 +175,7 @@ def run(self, iterator, play_context):
                         # role which has already run (and whether that role allows duplicate execution)
                         if not isinstance(task, Handler) and task._role:
                             role_obj = self._get_cached_role(task, iterator._play)
-                            if role_obj.has_run(host) and role_obj._metadata.allow_duplicates is False:
+                            if role_obj.has_run(host) and task._role._metadata.allow_duplicates is False:
                                 display.debug("'%s' skipped because role has already run" % task, host=host_name)
                                 del self._blocked_hosts[host_name]
                                 continue
diff --git a/lib/ansible/plugins/strategy/linear.py b/lib/ansible/plugins/strategy/linear.py
index 71d6380211f014..29f94c4699bbeb 100644
--- a/lib/ansible/plugins/strategy/linear.py
+++ b/lib/ansible/plugins/strategy/linear.py
@@ -170,7 +170,7 @@ def run(self, iterator, play_context):
                     # role which has already run (and whether that role allows duplicate execution)
                     if not isinstance(task, Handler) and task._role:
                         role_obj = self._get_cached_role(task, iterator._play)
-                        if role_obj.has_run(host) and role_obj._metadata.allow_duplicates is False:
+                        if role_obj.has_run(host) and task._role._metadata.allow_duplicates is False:
                             display.debug("'%s' skipped because role has already run" % task)
                             continue
 
diff --git a/test/integration/targets/include_import/runme.sh b/test/integration/targets/include_import/runme.sh
index 98bc8c31612550..12ee15b1476ca6 100755
--- a/test/integration/targets/include_import/runme.sh
+++ b/test/integration/targets/include_import/runme.sh
@@ -121,6 +121,10 @@ ansible-playbook valid_include_keywords/playbook.yml "$@"
 ansible-playbook tasks/test_allow_single_role_dup.yml 2>&1 | tee test_allow_single_role_dup.out
 test "$(grep -c 'ok=3' test_allow_single_role_dup.out)" = 1
 
+# Test allow_duplicate with include_role and import_role
+test "$(ansible-playbook tasks/test_dynamic_allow_dup.yml --tags include | grep -c 'Tasks file inside role')" = 2
+test "$(ansible-playbook tasks/test_dynamic_allow_dup.yml --tags import | grep -c 'Tasks file inside role')" = 2
+
 # test templating public, allow_duplicates, and rolespec_validate
 ansible-playbook tasks/test_templating_IncludeRole_FA.yml 2>&1 | tee IncludeRole_FA_template.out
 test "$(grep -c 'ok=6' IncludeRole_FA_template.out)" = 1
diff --git a/test/integration/targets/include_import/tasks/test_dynamic_allow_dup.yml b/test/integration/targets/include_import/tasks/test_dynamic_allow_dup.yml
new file mode 100644
index 00000000000000..82e08b339a2d49
--- /dev/null
+++ b/test/integration/targets/include_import/tasks/test_dynamic_allow_dup.yml
@@ -0,0 +1,30 @@
+---
+- name: test for allow_duplicates with include_role
+  hosts: localhost
+  gather_facts: false
+  tags:
+    - include
+  tasks:
+    - include_role:
+        name: dup_allowed_role
+        allow_duplicates: false
+    - include_role:
+        name: dup_allowed_role
+    - include_role:
+        name: dup_allowed_role
+        allow_duplicates: false
+
+- name: test for allow_duplicates with import_role
+  hosts: localhost
+  gather_facts: false
+  tags:
+    - import
+  tasks:
+    - import_role:
+        name: dup_allowed_role
+        allow_duplicates: false
+    - import_role:
+        name: dup_allowed_role
+    - import_role:
+        name: dup_allowed_role
+        allow_duplicates: false