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I'd like to setup sites from within the Master Trial Org to be used by each of the 30 Day Trail Orgs generated from this Master Trial Org. My question, is this technically feasible or do they need to be setup separately in each of the 30 Day Trail Org created from the Master Trial Org?

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    Good question. Sites cannot be deployed but when a sandbox is created a site that existed in production is created in the sandbox. So I would summarize that it can be done but could find no documentation on it. Best way to find out it to create a template with a site, submit for approval, and create a trial and check the results.
    – Eric
    Commented Aug 31, 2016 at 19:14

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Trial orgs are not eligible to use Sites anyway. And you want to be able to allow your converted Trials to set their own force.com subdomain. So for those reasons, you should absolutely not create Sites in a trial source org.

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