So, as it happens someone we know submitted an email asking how to resolve the following error they were getting when attempting to send an invoice via email from QuickBooks Desktop.
This appears to be a ‘Webmail’ error, when using QuickBooks. There could be a couple of reasons for this.
Last year there were some errors and a work around was to change how users sent email in QuickBooks…. We wrote about it extensively. It maybe that you fixed it then, then a subsequent repair by QB altered your configuration such that ‘the fix’ was causing a problem. I can’t duplicate your problem.
One solution might be to make certain that the PDF function that is used in the emailing of Invoices is not corrupted, you can do this by downloading and installing the most recent version (1.5.0.0) of Intuit's QuickBooks Tool Hub, and then selecting and running the QuickBooks PDF & Print Repair Tool. In most cases this will resolve any issues associated with the PDF functionality that is required to generate the invoice for emailing.
You probably need to attempt to set your email preferences to what they should be, the configuration file maybe in error. Use the steps below depending on your actual email provider:
(1) Log in as the Admin to QuickBooks
(2) Select Preferences from the Edit menu
(3) Then select the ‘My Preferences’ tab
As I mentioned the error is typically associated with ‘Web Email’ (Gmail, Yahoo, Hotmail, Outlook.com, etc.)
You can select one of several options for sending email in QuickBooks including ‘Outlook’ if you use actual Outlook on your computer (not Outlook 365 in the Cloud).
(4) If you use Outlook then you need to:
or
(5) If you have emailing hosting service from Gmail or Yahoo or you have a mail account with them. You can link it for sending email from QuickBooks with easy steps. Which are almost similar but a bit different in terms of SSL Security, SMTP Server and Port Configuration that may differ as per the email service providers.
Hopefully these troubleshooting tips will resolve your problem. Otherwise I would contact Intuit QuickBooks Technical Support for assistance.