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Pre-condition

"Checklists" custom field (mandatory) and "Smart Checklist Progress" custom field (optional) must be added to your Jira Cloud instance and must keep checklists' values. 

When you migrate using XML backup - then Custom fields and Issue properties should be transferred too.

Check out this instruction from Atlassian: https://confluence.atlassian.com/adminjiraserver/migrating-from-jira-cloud-to-server-applications-938846963.html

Check instructions on adding Checklists and Smart Checklist Progress custom fields. 

Instructions

  1. Make sure the "Checklists" custom field is set up on your Cloud instance, is associated with all proper screens (Default Issue Screen and Edit Issue Screen in particular), and contains your checklists' data.
  2. Transfer Jira from Cloud to Server following all the needed steps from Atlassian Documentation.
  3. Make sure the "Checklists" custom field is created on your Server instance and is associated with all proper screens (Default Issue Screen and Edit Issue Screen in particular).
  4. Install Smart Checklist add-on on your Server instance.
  5. As soon as the add-on gets rendered on your issues, it will get all the values from the "Checklists" custom field.

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