So we've just not dealt with this for ~3 years, and so we are well out of date on our crucible versioning, and was hoping someone could help, how can I migrate with as little risk as possible from? Can I go direct, or is this a multihop process? If it helps or hinders I am running postgres, and win2k3?
Please take a look at https://confluence.atlassian.com/display/CRUCIBLE/Crucible+upgrade+guide, there you'll find detailed steps for that. I suggest you set up a test instance and perform the upgrade there first before you do that in production, and if anything fails during your steps, please open a support ticket with us on https://support.atlassian.com
It's a single step process. FishEye and Crucible will perform all the necessary upgrade processes required to bring the instance up to date from its current version. Nevertheless, as Felipe indicates you should take a full backup before commencing the upgrade and use a test instance to be sure the upgrade goes ahead without issues. It will also give you some indication of the total upgrade time that will be required so you can plan a production upgrade.
You should also check out the supported platform information here https://confluence.atlassian.com/display/CRUCIBLE/Supported+platformsas the required platform components may have changed from your current instance. In particular, since you are using Windows, please note the changes to supported versions of Internet Explorer.
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