We are using the JETI plugin for Jira to let our users send issues via email. Jira is used as a support desk and will for some issues replace the to-and-fro via Outlook since we are encouraging the users to use Jira to receive (Jira checks emails and adds comments) and send email. There could be many attachments per issue.
One feature missing to make this user-friendly is the ability of JETI to link to the attached documents. When you send an email from Jira using JETI you can select attachments to include. JETI then puts the email (subject, adressees, attachments) in the issue comments which is great. If the attachments listed could be links (using [^] markup, see Jira wiki syntax) that would be even better!
Does that make sense?
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