Best practices to avoid workflow issues during Jira Server to Cloud migration?

[FunnelsFlex]

I’m planning a Jira Server to Cloud migration and wanted to get advice from others who’ve gone through this recently.

At Funnelsflex, we’re reviewing an existing Jira Server setup with multiple custom workflows, automations, and integrations. Before moving to Cloud, I want to make sure we avoid common issues around workflow behavior, permissions, and post-migration cleanup.

Specifically, I’m looking for guidance on:

• Which workflow or automation elements tend to cause the most friction after migration?

• Are there cases where simplifying workflows before migration is strongly recommended?

• How do you validate that workflows and automations behave the same way in Cloud after the move?

I’m not asking about tooling selection, just practical lessons and best practices from real migrations.

[Artem Taranenko]

Hi @FunnelsFlex 

I've written a couple of pieces on this topic, I hope you may find them helpful:

https://community.atlassian.com/forums/Jira-Cloud-Admins-articles/Third-Party-Automation-The-Ticking-Time-Bomb-in-Jira-Data-Center/ba-p/3174232 (I'm publishing second part of this next week)

https://community.atlassian.com/forums/Jira-articles/Lift-and-Shift-Is-Not-Lift-the-Mess-in-Your-Jira-Data-Center-to/ba-p/3159978