What is weird is that “Send Test Email” on “Emails->Email Settings” page works perfectly fine. It’s just the actual Purchase receipts and Sales notifications that are not being dispatched…
Are the purchase records marked as Complete in Downloads > Payment History?
Yes. All of them are complete. I tried doing an actual transaction a couple of times myself (even for different emails) and everything works fine EXCEPT for the purchase emails and sales confirmation emails.
When I complete a purchase I am correctly being redirected back to the Purchase Complete page. However, neither do I receive a sales confirmation message from the Plugin nor do I receive a Purchase Receipt with the download.
Please see this FAQ about email issues: http://docs.easydigitaldownloads.com/article/189-email-receipts-are-not-being-sent
In that doc are several links to SMTP plugin (Mandrill and SendGrid). I would recommend you use one of those to resolve the issue.
I think it started working when I installed the WP SMTP Plugin and configured the SMTP setting manually (confirmed when I received an actual live Purchase Confirmation).
Although I still think it is a plugin bug as mails were being sent previously – manually by send test purchase confirmation (from the plugin) and the Check Mail plugin also worked fine.
Emails in WordPress are notoriously finicky, especially with shared and lower-end hosting accounts.