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Originally Posted by RichieRich
Will this mean the customer can login and check their orders history on the new version with no problems once the upgrade has been applied?
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It depends on custom mods made to your store. In most cases it should work as you have described.
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Originally Posted by RichieRich
I am thinking it will be wise to upgrade store seperate from live store in case of problem, and then switch over?
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It is the only right way to upgrade your store. Never upgrade "live" stores!