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GP 2013 Troubleshooting emailing invoicing

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I have set up GP 2013 to send emails from sales invoices. We are using Exchange and I have set it to use PDF's. The customer has valid email address. When I go to Transactions->Sales->Print Sales Documents and choose invoices and email and select the invoice for this customer and click Print, no emails are received. We receive no error message. How do I troubleshoot this? How to a determine where in the process it is breaking down? I have gone to Tools->Sales->eMail Settings and set the Message ID's and well as set this computer to get emailed Sales invoices.


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