random_number.yaml

- name: Generate a random number
  ansible.builtin.set_fact:
    num: "{{ pick_from | random(start=1) }}"

- name: Set the condition flag
  ansible.builtin.set_fact:
    condition_met: "{{ num|int == number_to_match }}"

- name: Get out quick when condition is met
  ansible.builtin.fail:
  when: condition_met

site.yaml

- hosts: localhost
  gather_facts: False
  vars:
    condition_met: False
    max_iterations: 10
    number_to_match: 5
    pick_from: 20
    
  tasks:
  - block:
    - ansible.builtin.include_tasks:
        file: random_number.yaml
      loop: "{{ range(0, max_iterations, 1) }}"
    - name: Fail if the condition isn't met
      ansible.builtin.fail:
        msg: "max iterations completed"
      when: not condition_met
    rescue:
    - debug:
        msg: "Sorry, after {{ max_iterations }} attempts, num was {{ num }}"
      when: not condition_met
      failed_when: not condition_met
   
    
  - debug:
      msg: "We survived, num was {{ num }}"