Hi Brian,
I am not aware if JIRA allows to enable or disable history. Checklist should automatically write to the history.
https://marketplace-cdn.atlassian.com/files/images/3760673b-d7c1-406a-b048-e8842ef04103.png
If you see nothing, can you check into the JIRA logs to see if there are errors? Also, which version of JIRA and Checklist are you using?
Yves
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