Prerequisites

"Save checklist data to Jira custom fields" option must be enabled in Issue Checklist Global Settings. 

Guide

1. Go to Automation listing page (it is either Project settings > Project automation or Jira Settings > System > Automation rules) and press Create rule button:
   
   
   
   
2. On the New trigger page select Issue created trigger:
   
   
   
   
3. On the Issue created page click Save:
   
   
   
   
4. One the New component select New condition option:
   
   
   
   
5. On the New condition page select Issue fields condition option:
   
   
   
   
6. On the Issue fields condition page select the desired field and the value required to add checklist:
   
   
   
   
7. On the New component select New action option: 
   
   
   
   
8. On the New action page select Edit issue option:
   
   
   
   
9. On the Edit issue page:
   
   
   1. select Checklist Text custom field in the dropdown:
      
      
      
      
   2. type or paste your checklist into Checklist Text custom field:
      
      
      
      and press Save button
      
      
10. On the Add component page, add a name to the Automation rule and press Turn it on button:
    
    
    
    
11. Test your setup, i.e. create issue with the custom field value that meets the configured condition and spot your checklist applied:
    
    
    
    Hint: page refresh might be required to see the checklist.