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I'm here to provide additional steps so you can email invoices in QuickBooks, @bpike.
It's good to know that you've updated your QuickBooks to the latest release. Since you still experience the same thing, let's now run the verify/rebuild tool to isolate the error you received. Here's how:
- To verify data. Go to the File menu and select Utilities.
- Click Verify Data, then OK to close all windows. When the message “Your data has failed the integrity check” appears, rebuild your file. If none, it means that there are no problems within your file.
- To rebuild data. Go back to the File tab, then click Utilities.
- Tick Rebuild Data, then select OK to close all windows.
- Hit OK to create a backup of your company file.
- Once done, select OK.
Set-up and send email again. If the same result, make sure QuickBooks is running as administrator. Refer to these steps:
- Look for the QuickBooks icon then right-click. Select Properties.
- Click the Compatibility Tab.
- Deselect Run this program as Administrator. If the Run this program as Administrator option is grayed out, tick first "Show Settings for All Users".
- Hit Okay.
- Exit and restart QuickBooks.
However, if the issue persists, I recommend contacting our technical support team. This way, they can further investigate the root cause of the issue and provide additional steps to fix it for you. To connect with them, follow these steps:
- Head to the Contact support page at this link.
- Choose QuickBooks Desktop Mac.
- Click on Search for something else and enter Error: Unable to authenticate with the current session's credentials.
- Hit Search.
- Select Start a Message.
For your reference, you may visit this article: How to fix "Error: QuickBooks is unable to send your email to Outlook".
You might also want to visit this wonderful guide to browse topics that can help you with your QuickBooks tasks. To get started head to the QuickBooks for Mac user's guide.
Feel free to get back here if you have additional concerns about setting up and sending emails via QuickBooks. I'll be around to help. Have a good one.
