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Error in automation action 'Send Slack direct message'

Rosa Medellín_dj6229

Hello everyone.

I’m currently working on an automation that, if a work item has gone 3 days or more without comments and is in certain statuses, sends a Slack DM to the assignee requesting updates.

The problem arises in the “Send direct message on Slack” action. When the automation runs, it throws the error: “We couldn't send the Slack direct message because some users couldn't be found or aren't valid in Slack.” I checked the users assigned to the work items that meet the conditions, and they are all active on both platforms, and Jira and Slack are properly synchronized.

When I test it with my own user, everything works fine, so I assume the issue happens when multiple users are involved. Any idea how to fix this?

This is my automation:

Screenshot 2025-12-19 at 1.16.07 p.m..png

Accepted answers

Bill Sheboy

Hi @Rosa Medellín

Is your rule in a Jira Service Management (JSM) space / project and operating on an Incident work item type? I believe that action only works for that case:

https://support.atlassian.com/cloud-automation/docs/jira-automation-actions/#Send-direct-message-on-Slack

And, what do you mean by "multiple users" when you stated this?

When I test it with my own user, everything works fine, so I assume the issue happens when multiple users are involved. Any idea how to fix this?

Kind regards,
Bill

All comments

Bill Sheboy

Hi @Rosa Medellín

Is your rule in a Jira Service Management (JSM) space / project and operating on an Incident work item type? I believe that action only works for that case:

https://support.atlassian.com/cloud-automation/docs/jira-automation-actions/#Send-direct-message-on-Slack

And, what do you mean by "multiple users" when you stated this?

When I test it with my own user, everything works fine, so I assume the issue happens when multiple users are involved. Any idea how to fix this?

Kind regards,
Bill

Rosa Medellín_dj6229

Hi Bill, thank you for the answer.

In the automation actions there are two options to send direct messages via Slack: one when an incident occurs (which is the one you mention), and this other one, whose behavior—at least from what I’ve tested—is quite similar but intended for more general use. This is the one I’m using.

Screenshot 2025-12-19 at 2.57.00 p.m..png

Now, regarding multiple users: I’ve tested the automation with a manual trigger on a work item assigned to me, and I receive the message correctly. However, the current setup starts with a scheduled trigger that includes a JQL, and the goal is to send reminders to the users assigned to the work items returned by this JQL whose last comment was more than 3 days ago. This is where multiple users are involved and the error occurs, whereas doing it individually works fine.

Bill Sheboy

Hmm...interesting. Let's try a quick experiment with the Scheduled Trigger:

Please change the JQL for your Scheduled trigger to only return your single work item assigned to you [ e.g., key = ABC-123 ], and re-test
Now repeat that test, but change the JQL to return two work items, both assigned to you [ e.g., key IN ( ABC-123, ABC-456 ) ], and re-test
One more time...please change the JQL for your Scheduled trigger to only return a single work item NOT assigned to you [ e.g., key = ABC-789 ], and re-test

This might fault isolate if the problem is the users or the manner of looping from the scheduled trigger.

FYI -- Before that newer action was added to send direct Slack messages, the changes to the old Slack REST API prevented sending direct messages unless one stored the Slack user ID values somewhere in Jira (e.g., a user entity property). I believe only JSM has the correct mapping of users to Slack, which is why testing the above cases may help.

Rosa Medellín_dj6229

Scenarios 1 and 2 worked, but scenario 3 gave me the error again. Since all of them are Jira Software projects, I think the issue is due to the logic you mentioned at the end. Do you have any suggestions on how I should handle this?

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