diff --git a/CHANGES/6643.bugfix b/CHANGES/6643.bugfix
new file mode 100644
index 000000000..bbf65a415
--- /dev/null
+++ b/CHANGES/6643.bugfix
@@ -0,0 +1 @@
+Fixed the pulpcore/plugin compatibility check accidentally enforcing on upgrades when plugins have their upgrade variable specified, and the latest version of the plugin actually is compatible.
diff --git a/roles/pulp/tasks/install.yml b/roles/pulp/tasks/install.yml
index 1a289e81b..3dea39bec 100644
--- a/roles/pulp/tasks/install.yml
+++ b/roles/pulp/tasks/install.yml
@@ -197,7 +197,10 @@
           changed_when: false
 
         - name: Run pip-compile to check pulpcore/plugin compatibility
-          command: '{{ pulp_install_dir }}/bin/pip-compile'
+          command: '{{ pulp_install_dir }}/bin/pip-compile
+{% for plugin, value in pulp_install_plugins.items() %}
+{% if value["upgrade"]|default(false, true) %} -P {{ plugin }} {% endif %}
+{% endfor %}'
           args:
             chdir: '{{ pulp_install_dir }}'
           register: compatibility