diff --git a/changelogs/fragments/75642-free-strat-fix-executing-includes.yml b/changelogs/fragments/75642-free-strat-fix-executing-includes.yml
new file mode 100644
index 00000000000..6c11758cb97
--- /dev/null
+++ b/changelogs/fragments/75642-free-strat-fix-executing-includes.yml
@@ -0,0 +1,2 @@
+bugfixes:
+  - Fix executing includes in the always section in the free strategy (https://github.com/ansible/ansible/issues/75642)
diff --git a/lib/ansible/plugins/strategy/free.py b/lib/ansible/plugins/strategy/free.py
index 7e0406984d8..326c347ad3e 100644
--- a/lib/ansible/plugins/strategy/free.py
+++ b/lib/ansible/plugins/strategy/free.py
@@ -120,17 +120,19 @@ class StrategyModule(StrategyBase):
                 (state, task) = iterator.get_next_task_for_host(host, peek=True)
                 display.debug("free host state: %s" % state, host=host_name)
                 display.debug("free host task: %s" % task, host=host_name)
-                if host_name not in self._tqm._unreachable_hosts and task:
 
+                # check if there is work to do, either there is a task or the host is still blocked which could
+                # mean that it is processing an include task and after its result is processed there might be
+                # more tasks to run
+                if (task or self._blocked_hosts.get(host_name, False)) and not self._tqm._unreachable_hosts.get(host_name, False):
+                    display.debug("this host has work to do", host=host_name)
                     # set the flag so the outer loop knows we've still found
                     # some work which needs to be done
                     work_to_do = True
 
-                    display.debug("this host has work to do", host=host_name)
-
+                if not self._tqm._unreachable_hosts.get(host_name, False) and task:
                     # check to see if this host is blocked (still executing a previous task)
-                    if (host_name not in self._blocked_hosts or not self._blocked_hosts[host_name]):
-
+                    if not self._blocked_hosts.get(host_name, False):
                         display.debug("getting variables", host=host_name)
                         task_vars = self._variable_manager.get_vars(play=iterator._play, host=host, task=task,
                                                                     _hosts=self._hosts_cache,
diff --git a/test/integration/targets/strategy_free/aliases b/test/integration/targets/strategy_free/aliases
new file mode 100644
index 00000000000..b59832142f2
--- /dev/null
+++ b/test/integration/targets/strategy_free/aliases
@@ -0,0 +1 @@
+shippable/posix/group3
diff --git a/test/integration/targets/strategy_free/inventory b/test/integration/targets/strategy_free/inventory
new file mode 100644
index 00000000000..39034f1435e
--- /dev/null
+++ b/test/integration/targets/strategy_free/inventory
@@ -0,0 +1,2 @@
+[local]
+testhost ansible_connection=local ansible_python_interpreter="{{ ansible_playbook_python }}"
diff --git a/test/integration/targets/strategy_free/last_include_tasks.yml b/test/integration/targets/strategy_free/last_include_tasks.yml
new file mode 100644
index 00000000000..6c87242ccb0
--- /dev/null
+++ b/test/integration/targets/strategy_free/last_include_tasks.yml
@@ -0,0 +1,2 @@
+- debug:
+    msg: "INCLUDED TASK EXECUTED"
diff --git a/test/integration/targets/strategy_free/runme.sh b/test/integration/targets/strategy_free/runme.sh
new file mode 100755
index 00000000000..f5b912c6da7
--- /dev/null
+++ b/test/integration/targets/strategy_free/runme.sh
@@ -0,0 +1,10 @@
+#!/usr/bin/env bash
+
+set -eux
+
+export ANSIBLE_STRATEGY=free
+
+set +e
+result="$(ansible-playbook test_last_include_in_always.yml -i inventory "$@" 2>&1)"
+set -e
+grep -q "INCLUDED TASK EXECUTED" <<< "$result"
diff --git a/test/integration/targets/strategy_free/test_last_include_in_always.yml b/test/integration/targets/strategy_free/test_last_include_in_always.yml
new file mode 100644
index 00000000000..205f3231277
--- /dev/null
+++ b/test/integration/targets/strategy_free/test_last_include_in_always.yml
@@ -0,0 +1,9 @@
+- hosts: testhost
+  gather_facts: false
+  strategy: free
+  tasks:
+    - block:
+        - name: EXPECTED FAILURE
+          fail:
+      always:
+        - include_tasks: last_include_tasks.yml