I’m here to help so you can continue to send invoices from QuickBooks using your Gmail account, @dlw66.
You’ve mentioned that your preferences have already been modified. Did you set up enhanced security in Gmail?
Last May 30, 2022, Google will no longer support using only your username and password. This affects how you send transactions with Gmail in QuickBooks. If you have Gmail without Enhanced Security checked, you’ll need to switch to Enhanced Security. See this guide for complete instructions: Set up enhanced security in Gmail for QuickBooks Desktop.
On the other hand, if you’ve done this and it's still unable to send invoices, you can run Quick Fix my Program from the QuickBooks tools. Before that, you’ll want to download and install the QuickBooks Tool Hub.
Here’s how:
- Close your QuickBooks account.
- Download the most recent version of the QuickBooks Tool Hub, then save the file somewhere you can easily spot it.
- Open the file you downloaded (QuickBooksToolHub.exe).
- Pay heed to the onscreen prompts to install, then agree to the terms and conditions.
- When the installation completes, click the icon on the Windows desktop to open the tool hub.
Then, performs the steps below to repair your QuickBooks.
- In the QuickBooks Tools Hub, select Program Problems.
- Click Quick Fix my Program.
- Try to send a transaction.

In case you’d like to upgrade to a newer version of QuickBooks Desktop in the future, you can refer to this article for more details: Upgrade QuickBooks Desktop Pro Plus, Premier Plus, or Enterprise.
Please know that I appreciate you for being part of the QuickBooks family for a long time. If you have any other questions or concerns besides sending transactions through Gmail, don’t hesitate to tap the Reply button below. Assistance is just one click away.