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You didn't mention what you are using for documents creation. Pandoc has support for Jira Wiki markup, and supports a lot of different input formats.

• utkarsh_apoorva 6y ago
  Usually Google Docs. Lately Notion. Jira Wiki markup seems like a viable solution, even if it has a bit of learning curve.
  • lwrm 6y ago
    You could use Google Docs, save it as ODT or some other format, and then convert it to Jira markup, (hopefully) preserving formatting. It sounds manual, but I am sure there are ways to automate it.
    • utkarsh_apoorva 6y ago
      Interesting idea. Will try to do this. If I can automate it, probably that's it.