We have a redesigned version of our website ready to go live. Is it possible to use Optimizer to A/B test the entire new site versus the entire old site?

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While it may be possible to accomplish a test like this, we do not recommend it. You would have to have your entire old/new site hosted (with unique URL's for each page) and it is likely that the data from the test would not be actionable. We recommend that you run tests that are smaller in size so that you can determine what elements of your site have the greatest influence on conversions.