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Hello, jk8.
Using a test file is one way to isolate this issue with Automatic Update option. Meaning, if it works in the test file, the issue lies within your company file.
The steps shared above were the basic solutions to fix the grayed out option for Quickbooks Desktop Automatic Update. Since you've tried the possible solutions above with no avail, it would be best to reach out to our QuickBooks Care Support. They have the tools to conduct a thorough investigation for a complete resolution.
Here are the steps to contact support:
- Click Help at the top menu and select QuickBooks Desktop Help.
- In the Have a Question? window, enter a topic.
- Click Contact us.
- Hit the Stat Messaging button.
Please take note our operating hours for chat support depends on the version of QuickBooks that you're using. Please see this article for more details: Support hours and types.
Keep me posted for additional questions or other concerns. I'd be more than happy to help. Wishing you the best of luck.