diff --git a/meta/main.yml b/meta/main.yml
index bec6a61..4cb9be5 100644
--- a/meta/main.yml
+++ b/meta/main.yml
@@ -29,6 +29,7 @@ galaxy_info:
     - pyenv
     - pipx
     - precommit
+    - tox
     - workstation
 
 dependencies:
diff --git a/tasks/custom_facts.yml b/tasks/custom_facts.yml
new file mode 100644
index 0000000..dd52727
--- /dev/null
+++ b/tasks/custom_facts.yml
@@ -0,0 +1,4 @@
+---
+- name: Set command path based on distribution
+  ansible.builtin.set_fact:
+    pipx_path: "{{ '/usr/bin' if ansible_distribution_release == 'bookworm' else ansible_env.HOME + '/.local/bin' }}"
diff --git a/tasks/main.yml b/tasks/main.yml
index 5a0da0e..0b374e7 100644
--- a/tasks/main.yml
+++ b/tasks/main.yml
@@ -1,4 +1,7 @@
 ---
+- name: Load custom facts
+  ansible.builtin.import_tasks: custom_facts.yml
+
 - name: Install pyenv
   ansible.builtin.import_role:
     name: staticdev.pyenv
@@ -17,16 +20,21 @@
     - python3-venv # needed for nox
 
 - name: Check if pipx is installed
-  ansible.builtin.command: "{{ ansible_env.HOME }}/.local/bin/pipx --version"
+  ansible.builtin.command: "{{ pipx_path }}/pipx --version"
   register: pipx_version_cmd
   changed_when: false
   ignore_errors: true
 
-- name: Install pipx
+- name: Install pipx on Debian Bookworm
+  ansible.builtin.package:
+    name: pipx
+  when: pipx_version_cmd is failed and ansible_distribution_release == 'bookworm'
+
+- name: Install pipx on non-Bookworm OS
   ansible.builtin.pip:
     name: pipx
     extra_args: --user
-  when: pipx_version_cmd is failed
+  when: pipx_version_cmd is failed and ansible_distribution_release != 'bookworm'
 
 - name: Check if pre-commit is installed
   ansible.builtin.command: "{{ ansible_env.HOME }}/.local/bin/pre-commit --version"
@@ -35,7 +43,7 @@
   ignore_errors: true
 
 - name: Install pre-commit
-  ansible.builtin.command: "{{ ansible_env.HOME }}/.local/bin/pipx install pre-commit"
+  ansible.builtin.command: "{{ pipx_path }}/pipx install pre-commit"
   register: output
   changed_when: "output.rc == 0"
   when: pre_commit_check is failed
@@ -44,9 +52,10 @@
   ansible.builtin.stat:
     path: "{{ ansible_env.HOME }}/.local/pipx/venvs/cookiecutter"
   register: cookiecutter_folder_check
+  ignore_errors: true
 
 - name: Install cookiecutter
-  ansible.builtin.command: "{{ ansible_env.HOME }}/.local/bin/pipx install cookiecutter"
+  ansible.builtin.command: "{{ pipx_path }}/pipx install cookiecutter"
   register: output
   changed_when: "output.rc == 0"
   when: cookiecutter_folder_check is failed
@@ -79,13 +88,13 @@
   ignore_errors: true
 
 - name: Install nox
-  ansible.builtin.command: "{{ ansible_env.HOME }}/.local/bin/pipx install nox"
+  ansible.builtin.command: "{{ pipx_path }}/pipx install nox"
   register: output
   changed_when: "output.rc == 0"
   when: nox_version_cmd is failed
 
 - name: Install nox-poetry
-  ansible.builtin.command: "{{ ansible_env.HOME }}/.local/bin/pipx inject nox nox-poetry"
+  ansible.builtin.command: "{{ pipx_path }}/pipx inject nox nox-poetry"
   register: output
   changed_when: "output.rc == 0"
   when: nox_version_cmd is failed
@@ -97,7 +106,7 @@
   ignore_errors: true
 
 - name: Install tox
-  ansible.builtin.command: "{{ ansible_env.HOME }}/.local/bin/pipx install tox"
+  ansible.builtin.command: "{{ pipx_path }}/pipx install tox"
   register: output
   changed_when: "output.rc == 0"
   when: tox_version_cmd is failed