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Tips and Tricks HQ Support Portal › Forums › WP eStore Forum › Different emails for purchase and subscription.
Your earlier test was flawed a little. What you are doing is buying the SAME subscription product using the same email address (meaning same customer) again and again. The plugin will correctly figure out that this is a repeat purchase and it won’t send the email. Which is what happened in your earlier test.
Go to the manage customers menu of the plugin and do a search with the “rmac79@me.com” email address. You will see that you have purchased the same subscription product more than once. Because you are testing, you can delete your older purchases for that product to create a real world scenario so you can see how the plugin will work in that condition.