Bulk attaching PDF files to existing issues or CSV imported issues in Jira Cloud

Question

Is there a way to bulk attach PDF files to existing Jira issues, or to issues newly created via CSV import in Jira Cloud?

Currently, we manually drag and drop PDF files into each issue one by one. However, since the number of files is quite large, the operational workload has become very heavy.

We also considered using SharePoint links instead of file attachments, but the generated URLs exceed 255 characters, which makes that approach difficult to manage in our operation.

Therefore, we would like to attach the PDF files themselves directly to Jira issues in bulk.

If there are any recommended approaches or commonly used operational methods, we would greatly appreciate your advice.

Environment:

* Jira cloud
* Attachment type : PDF only

Liam Do - DevSamurai · Accepted Answer

Hi @nagata shumpei ,

Jira Cloud's CSV import does support importing attachments. You can attach files to issues created (or updated) via CSV import by following this document:

Import data from a CSV file (under Importing attachments)

The files need to be hosted somewhere your Jira Cloud site can reach via URL (e.g., a web server, cloud storage with public/shared links, or SharePoint). Local file paths won't work.

You can also use the Jira REST API to programmatically attach local PDF files to issues.

With a simple script (Python, PowerShell, etc.), you can loop through a list of issue keys and their corresponding PDF files to attach them in bulk. Here's the document:

Add Attachments

Hope it helps 🙌
Liam

Aron Gombas _Midori_ · Accepted Answer

I would use Rovo or Claude to build a script that migrates the files using the REST API end-point suggested by @Liam Do - DevSamurai. It sounds like a routine task.