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We would like to move our chatter free users to the new community that we have set up. We are looking to retain their chatter data and part of this change would include giving them access to visual force tabs and custom objects.

We can map them to a new user and assign chatter data but this doesn't seem to be clean solution as only about 90% of the chatter data can be copied over. For a start, private messages and @mentions would be a problem.

Can someone please advise of a cleaner approach?

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Since Chatter Free users don't have access to visualforce or custom objects, you'll need to upgrade to a different user license.

The most cost effective solution is probably to upgrade from Chatter Free to Chatter Plus (you can keep the same users, just with a different user license).

With Chatter Plus, you can add these users to a community and give them access to custom objects and visualforce pages.

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