Compare Automation smart value to list of options with a Regular Expression

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Summary

If we want an Automation to be able to compare based on the Labels field or other multi-select custom fields, we need to use a Regular Expression (also called RegEx) comparison.

For example, let's imagine we wish to case-insensitively match work items with a label that starts with either "assist-" or "help-".

Solution

Build a Regular Expression in the automation rule

In our automation rule, we use a contains regular expression condition in the "Advanced compare condition."

When we use the {{issue.labels}} Smart value, all of the labels on a work item will be returned, separated by commas. For a work item with three labels:

  • help-desktop

  • assist-email

  • customer-service

{{issue.labels}} will return:

  • help-desktop, assist-email, customer-service

So, our Advanced compare condition must account for the label at the start of the string, or right after a comma and a space. In RegEx, we can use the pipe character "|" as the "OR" operator.

Our regex should start with: (^|, )

Then we have the strings you'd like the label to begin with: "assist-" or "help-". Our RegEx should then be followed by "(assist-|help-)".

So, our complete RegEx in this case should be:

(^|, )(assist-|help-)

We compare this RegEx that with "{{issue.labels.toLowerCase()}}" to make sure that letter capitalization won't get in the way.

The complete Advanced compare Condition block would look like this:

  1. First value: {{issue.labels.toLowerCase()}}

  2. Condition: contains regular expression

  3. Regular expression: (^|, )(assist-|help-)

Updated on September 26, 2025

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