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Community Contributor *

Cannot reliably send invoices by email

QB Desktop 2019 for Mac. Send 17 invoices by email. All 17 email message go through but the last 8 have no invoices. Resend those 8 and the last 3 had no invoices. Sent the last 3 and they all go through correctly. I suspect there is some interface problem between QB and Mac Mail, which is the only permitted setup. Really embarrassing when customers receive emails stating "here is your invoice" and it's not there - more than once. To say nothing of getting extra emails.

QuickBooks Team

Re: Cannot reliably send invoices by email

Thanks for checking in with us, RichDoyle.

Let me lend a hand in sending invoices by email via QuickBooks Desktop for Mac.


To isolate this issue, as an initial step, you may want to check if your QuickBooks for Mac release version is up to date.


Here's how:


  1. Go to the QuickBooks Desktop menu and select Check for QuickBooks Updates.
  2. If a newer version of QuickBooks Desktop is available, click Install Update.
  3. When prompted, click Install and Relaunch. When the update is complete QuickBooks Desktop for Mac will automatically open.

You can get more information in this article:


After that, please make sure that you're connected to the internet and the email program is supported by QuickBooks before trying to send the invoices.  The time it takes for QuickBooks to send a document as a PDF depends on the size of the form, your computer’s speed, and your Internet connection speed.


I'm still here if you need more help with sending invoices via email in QuickBooks Desktop for Mac. Have a good one.

Community Contributor *

Re: Cannot reliably send invoices by email

I didn't have the absolutely most recent update, but have since done so. And yes, the email I use is supported (Mac Mail). I didn't use the "Send as PDF" option, just the straight "Email Forms". My problem now is how to test that this update fixes the problem. The nature of our organization is we send these emails out (roughly the same number) once every 6 months, and there are no more to send until October. It's sort of like testing dynamite, you know?


I tried changing a couple of settings in Mac Mail, like disabling spell checking. BTW, this function (direct mass mailings of invoices from QB) is the only use I make of Mac Mail, and only because QB offers me no other option. For my personal use I use Thunderbird and have had occasion to do mass mailings of multiple attached PDFs many times without incident.

QuickBooks Team

Re: Cannot reliably send invoices by email

Thank you for the quick response, RichDoyle.

I appreciate the details you've provided. Let's get this sending email issue sorted out.


In order to test if updating the release version of your QuickBooks for Mac can resolve the issue, you can try to send the invoices to your personal email to see if you're still getting the same issue.


Also, you may want to make sure that the QuickBooks draft in the Mail is correct.


Here's how:


  1. Go to Mail.
  2. Select Preferences and click Accounts.
  3. On the left will appear all the accounts you have configured.

Have you configured an account for the address you are using as the outbound address?  If so, check the Outgoing Mail server setting for that account and make sure it is correct.  Finally, click "Use only this server".


These articles are a good reference:


You know where to find me if you need more help with sending mass invoices in QuickBooks Desktop for Mac. I'll stick around to help.

Established Community Backer **

Re: Cannot reliably send invoices by email

QuickBooks supports several mechanisms for sending emails. The easiest is to use your default email application (in this case Apple Mail) and have QuickBooks communicate with it via AppleScript. 


Unfortunately AppleScript isn't always reliable on every person's Mac.  It sounds like this is the case for your machine - it is partially working but not completely.  Also unfortunately this is usually a problem with either Apple Mail or with the other things in your system that are interfering with AppleScript communication.  


For that reason we added an outbound email client into QuickBooks itself beginning with the 2016 version.  To use that go to QuickBooks->Preferences and click on the Email icon.  You'll have to enter your email configuration details like server address and password - these should be similar to the ones you have in Apple->System Preferences under Internet Accounts for Mail. 


Doing that will give you a much more reliable email experience as QuickBooks no longer has to talk to Apple Mail to make it happen.  

Community Contributor *

Re: Cannot reliably send invoices by email

Thanks, I'll give this a try.