There’s no needs to have “Checklists” and “Smart Checklist Progress” custom fields to be set on Cloud instance. Data would be pulled from Jira Issue Properties
Prepare Backup on Jira Cloud. Go to System → “Import and Export” section → Backup manager → Backup for the server
Restore Jira data from Backup on Jira Server. Go to System → “Import and Export” section → Restore System → Restore Jira from backup
Then install "Smart Checklist for Jira" on the server, go to addon "Settings" -> "Global Settings" and Start Migration Note: Make sure you have Smart Checklist older than 5.3+ and above version installed.
Once migration is completed - Smart checklist values would be successfully migrated from an Issue Property to a new Data Storage (Database) and custom fields would be synced as well!
Check if the migration was successful in Issue Search view by adding “Smart Checklist” custom field