I have a spreadsheet with a whole bunch of images in it. Is there a way I can bulk upload these into JIRA and attach them to issues?
Have you tried automating it using the JIRACLI?
https://bobswift.atlassian.net/wiki/display/JCLI/3.6.0+-+Examples
jira --action addAttachment --issue "ZJIRACLI-3" --file "src/itest/resources/binary.bin"
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