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It is possible to create several checklist items and groups (headers) at once - simply paste multi-line text into item creation field and then press Enter.

Multiline paste and creating several items at once is useful for: 

  • copy-paste bullet point list of items from external list (issue Comment or Description, Trello, web page, MS Word, etc.),
  • pasting checklist copied from another issue

Paste multi-line text (e.g., bullet list copied from the web page or Word):

and get the following checklist:

List characters support

New item field accepts items with list characters like dash -, star * and empty square brackets [] as well as completed square brackets [x]:

Checklist items status support

New item field accepts items with status defined:

Markdown support

New item field accepts Markdown and other formatting elements: