diff --git a/roles/kolibri/tasks/install.yml b/roles/kolibri/tasks/install.yml
index c34b1ce87..81e879b41 100644
--- a/roles/kolibri/tasks/install.yml
+++ b/roles/kolibri/tasks/install.yml
@@ -66,6 +66,18 @@
   when: kolibri_version_pip is defined
 
 - block:
+  # handles going from pip to deb installs during --reinstall
+  - name: Test for {{ kolibri_exec_path }}
+    ansible.builtin.stat:
+      path: "{{ kolibri_exec_path }}"
+    register: sym
+
+  - name: Remove if {{ kolibri_exec_path }} is a symlink
+    file:
+      state: absent
+      path: "{{ kolibri_exec_path }}"
+    when: sym.stat.islnk is defined and sym.stat.islnk
+  # end test
 # https://kolibri.readthedocs.io/en/latest/install/ubuntu-debian.html claims:
 # "When you use the PPA installation method, upgrades to newer versions
 # will be automatic, provided there is internet access available."