Attach 400+ unique documents to 400+ different tickets?

[Bryan Howard]

Hi all, I looked around but didn't find quite what I'm looking for.

We're digitizing some documents, and I need to attach about 400+ unique documents to that same 400+ unique tickets. I can do this individually, but I'm nothing if not a man in pursuit of automation.

I have all the documents named the same name as the tickets (ie SR-12345). Is there a way to mass upload those documents (ideally with a comment) to their respective tickets?

Thanks for any help!

[Matt Doar _Adaptavist_]

My approach would be to use Jira Python and the underlying REST API to upload each document to the intended issue. And add a comment to the issue. I'd start with 

https://confluence.atlassian.com/jirakb/how-to-add-an-attachment-to-a-jira-issue-using-rest-api-699957734.html

and then follow on from there