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When we attach something in Service Desk, sometimes the customer receives it as an attachment, but sometimes they have to log into Atlassian which confuses them (we don't use the portal) - so then we have to send the attachment via Outlook.
Jira Service Desk doesn’t email attachments automatically. The customers should have to log into the portal to view them.
There are a couple of open feature requests for this:
These feature requests are for the Cloud based version, but we have corresponding requests for Server too. Please take a moment to vote for the issues, to show your support. If you’re interested in finding out more about feature requests - check out our New Features Policy
Your case sounds a little unusual, can you check out the following: