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For the features difference - check theSmart Checklist Cloud vs Server & Data Center Comparison for Smart Checklist
Jira Site Import
Check how to use Jira Site Import to migrate from server to cloud
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Go to Checklist Templates on Jira Server
 Get the checklist template from the source Jira Server instance as a raw markdown text
 Paste the checklist to any Jira issue in target Jira Cloud
 Save Template Proceed with rest of templates You may also use Full-Screen Editor for checklist adding/editing
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Can I Migrate my Smart Checklist for Jira Server License to Jira Cloud?
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