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The Site selection prompt will only show up for users that are members of multiple sites. If you have a user or group of users that only belong to one site, not only will they not see the dialog upon logging in but also they will not even know that other sites exist.
For any user that has access to multiple sites, he or she will see the prompt but again will only see the sites to which they have been granted access. They will also be unaware of other sites existing on the Tableau Server.
Hope this helps,
Thanks - that helps for one set of cases (where people only have one site) but I also have people that belong to multiple site and they would like to avoid the extra click since they'll normally just be going to one site. Is there a way to make a site default for someone? Ideally, this would be done at the back end so users won't be too disrupted when the change is made.