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I have a free subscription for Google Apps (grandfathered in), and my user count is increasing beyond 10. On the google help page, it says that I can create 10 free users with my account, but on my admin billing page, it says I have 50 licenses. What exactly is the difference between users and licenses? Can I create 50 emails and assign each to one license?

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According to the G Suite Pricing page (bottom left): a user is defined as one personalized email address (you@yourcompany). Group email aliases such as sales@yourcompany and support@yourcompany are included in pricing and don't count as additional users.

A user needs a license to use a Google service, and a single user can have several licenses for diferent tools.

More info about licenses: https://support.google.com/a/answer/6309862?hl=en

Hope this helps :)