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If you enabled the Reuse anonymous account, it will try to find the first account matching the email and assign the order to that account. It's unpredictable which account gets the order if you already have duplicate accounts with the same email address.  You could enable the Requires unique email feature and clean up all duplicate accounts in the system if you absolutely want it to be very clean.  Please contact us for a quote if you need our assistance to clean up duplicate accounts for you.

There shouldn't be any issue with non-anonymous accounts checking out with the same email address. However, if you enabled Requires unique email, the user may not be able to register a new account because that email address has already been used anonymously on your site. In this case, the user will be prompted that the email address is already registered and can simply request the forgotten password.

Single use coupons (configured with max usage per user) is limited per user account and not by their email. If you want it to be restricted per email, then enabling the Requires unique email feature would satisfy that requirement.

I want to point out the recent Storefront 7.5.1 has a fix for the Reuse anonymous account feature so make sure you're always running the latest version when testing out this feature.