This topic is quite old, but I want to join the question. Is there a solution for Jira Cloud to upload a lot of files to different issues at the same time? Without having to buy a plugin ...
JIRA Command Line Interface (CLI) is often used to automate such tasks using addAttachment perhaps combined with createIssue.
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Found my answer (not what I wanted to hear) at https://confluence.atlassian.com/display/JIRA/Modifying+Multiple+%28Bulk%29+Issues
The fields listed in this section have no operations for bulk editing. This is because there is an alternative method or it is not logical to perform bulk edit on them.
The following system fields are unavailable for bulk editing:
The following custom field types are unavailable for bulk editing:
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We have a use case for bulk update attachments. We use JIRA to approve financial documents at the end of the quarters. To do so we create multiple sub-tasks upon the creation of the task in the project. We need to be able to put the file on the sub-tasks after they are created.
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