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

[nagata shumpei]

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

[Aron Gombas _Midori_ · Accepted solution]

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.  

[Liam Do - DevSamurai · Accepted solution]

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

[Laura Marin - Millarum]

Full disclosure: I’m part of the team behind the tool mentioned below.

Unfortunately, Jira native bulk-upload feature for attachments during CSV imports require some heavy organization before even trying the bulk operation.

While our app doesn’t offer a one-click bulk upload tool either, it can drastically cut down your manual drag-and-drop workload.

Instead of opening, loading, and closing dozens of tickets one by one to drop your PDFs, you can use our File Explorer for Jira. It lets you navigate your entire issue hierarchy and ticket details in a single, continuous view. You can click down your list of issues and drag files directly into them without ever leaving the central screen—plus, you get an instant document preview right there to double-check your work on the fly.

It’s not a 100% automated bulk fix, but it eliminates about 80% of the opening-and-closing clicks that make the job so tedious.

If you want to see if it speeds up your workflow, feel free to check it out here: Millarum File Explorer