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My organization currently uses JIRA, Confluence, and Crowd. We are considering adding Bitbucket as well, but we have questions about users. Currently we have a license for 2000 users with Crowd, JIRA, and Confluence, but we don't need anywhere near that for Bitbucket. In order to integrate Bitbucket with these other products does it require 2000 users as well, or can we get a license for 250 users instead? That's a difference of roughly $40,000.
No, you can get separate licences.
You can tell different systems about different numbers of users - for example, if you have groups Jira, Conf and Bb, and tell the three systems to use their "can log in" group as those, then yes, you could do 2000 Jira, 2000 Confluence and 250 Bitbucket.
It can be a bit more simple - if, for example, you always know Jira and Confluence systems are always going to have the same set of login users, you could do something like create group "jac-login", and use that in both for the login group. Adding a user to that one group then lets them into both systems.
I prefer to keep them simple, clear and separate myself.
No, each product does not have to have the same amount of licenses, in my environment we have half the licenses for Bitbucket compared to Jira/Confluence.