Internal Server Error encountered when attempting to upload an attachment

[mbaig]

We have a proprietary tool that allows users to create bugs and adds a bunch of information about the state of their client at the time the bug was encountered.  It also allows them to attach screenshots/videos.  One user has reported intermittent failures uploading videos, I can very intermittently repro the error in question.

Got error while saving attachment: Got exception while saving attachment in attachment store. Exception: com.atlassian.jira.issue.attachment.store.media.MediaApiStreamAttachmentStore$FailureMediaApiResponseException: [AttachmentUploadFailure] Could not upload attachment
Failure: Failure{cause=org.apache.http.client.ClientProtocolException, reason=TRANSPORT_ERROR, retryAfter=null, message='null', httpStatusCode=null} caused by: [AttachmentUploadFailure] Could not upload attachment

The file isn't too large as it can be manually drag/dropped onto a bug and uploads successfully.  Furthermore retrying an upload from our tool can sometimes happen to work so it doesn't appear to be a case of our http request being malformed.

Is there any mechanism for getting more useful information about the server error we're encountering?  I can't seem to find any information about the FailureMediaApiResponseException in the API docs.

[Shawn Doyle - ReleaseTEAM]

Hi @mbaig 

Check what you have set as the maximum file size for attachments. 

[mbaig]

File size was indeed our first guess, 1GB is our maximum file size and the files that fail are well below that.  We've had users report failure with videos as small as 60MB.  And as I mentioned earlier we are able to "work around" this by manually attaching the file through the web interface.

[Shawn Doyle - ReleaseTEAM]

Ah I missed the first few words of your question. "We have a proprietary tool"

If it works directly in Jira, then all signs point to your proprietary tool. How much insight do you have into it?

[mbaig]

I didn't write it but have full source access, it's a C++ tool and the attachment is loaded in as a byte array and we're sending the http request as a multipart form data.

[mbaig]

Did find this: https://jira.atlassian.com/browse/JRACLOUD-66689

Seems tied to something resolved years back but we're getting this error intermittently in 2025, it's by no means reliable/consistent.