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Send an email with a list of work items that contain attachments with long filename

Pavol Sočuvka
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September 29, 2025

Hi all, 

I would like to get a list of work items that contain an attachment that has a filename longer than 50 chars. Then, I'd like to send this list as an email. 

What I tried is:

Smart value comparison:

  • Run a scheduled rule with a JQL search (attachments is not empty)
  • Compare smart value {{attachment.filename.length}} greater than 50
  • Then send an email.

  • Caveat: Sends multiple emails because of the 'Scheduled' trigger. Works OK with logging to audit log 

Conditional expression

  • Run a scheduled rule (or manual for testing)
  • Lookup work items (attachments is not empty)
  • Send an email with a conditional smart value expression 

  • Caveat: Doesn't work. I have tried
({{#if(issue.attachment.filename.length.gt(50))}} {{lookupIssues}} {{/}} 

or

{{#lookupIssues}}
* {{#if(attachment.filename.length.gt(50))}} {{key}} {{/}}
{{/}}

 I can't seem to be able to get the syntax right.

What does everyone think? I'm tempted to tag the automation goat @Bill Sheboy , I think you might like this.

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