Server to Cloud, looking for real-world feedback
We’re currently looking into moving from Jira and Confluence Server to Atlassian Cloud and I’d really appreciate insights from people who’ve actually done it at scale.
Context: around 2000 internal users and a similar number for external/customer users, with a fairly mature setup (lots of projects/spaces, apps, integrations, custom workflows).
Server EOL + security + maintenance overhead are pushing us in this direction, but the jump in cost obviously makes the decision non-trivial.
For those who’ve gone through it: was it actually worth it?
How did you justify the ROI and get leadership buy-in, especially moving from a relatively low-cost on-prem setup to SaaS? What ended up being the real value drivers in practice?
On the ground, what changed for users? What did they genuinely gain from Cloud, and what did they lose or end up missing?
From an admin/ops perspective, how much did Cloud really reduce the burden vs what Atlassian markets? Any new constraints or surprises?
And on the migration itself, what hurt the most? Apps, integrations, permissions, data structure, anything you underestimated early on?
Finally, looking back now, what do you wish you had asked Atlassian before starting, what hidden costs or trade-offs caught you off guard, and would you still make the same decision today?
Would really value honest experiences, especially from larger orgs where this wasn’t a simple lift-and-shift.