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We have an old and unsupported Jira Server instance version 7.4, and want to migrate to cloud. We already bought the cloud licence, but apparently, it is not recommended to migrate Jira version between 7.0.0 and 7.6.0.
Has anyone tried do the migration from non-recommended versions? What were the implications? Maybe we can workaround this issue by putting the trial licence, upgrading to v7.13, and then migrating to Cloud?
We recommend doing exactly as you suggested - using a server evaluation license to upgrade to v7.6 or above, and then migrating from there. You can find more information in our related documentation: Migrate to cloud with an expired server license
I'd recommend upgrading to at least 7.8 before attempting the Cloud move. Generally, the higher the version of your Server, the fewer problems you will encounter with it.
7.x versions have quite a smooth upgrade path - going from 7.4 to 7.13 is barely any different from going from 7.4 to 7.6 and a lot smoother than upgrading even 6.2 to 6.3.
In your case, I'd strongly recommend an upgrade to 7.13 as you suggest.
Cloud migrations from below 7.8 often turn out to be a nightmare (since 7.0 came out, we've done, or been heavily involved in hundreds). Officially it's 7.6 minimum, but from our experience, we've only seen it work properly with 7.8 and above.
The implications of using range from "please reset my now utterly broken Cloud system so I can try again" through to minor data losses. It might work ok, but I'd plan for an upgrade.