It’s likely that the Automatically Send Emails feature was turned off, Eric, which can explain why the invoices were not sent on 5/30/25.
In your case, you can check whether the option is enabled. Here's how:
- Click the Gear icon on the top right.
- Select Recurring transactions.
- Find the transaction in question and click Edit under the Action column.
- Go to Manage Gear and select Scheduling.
- Under More options, enable Send later.
- Click Edit beside the Recurring invoice section.
- Check if you have enabled Automatically send emails under Template options.
If the option is turned off, you can enable it and click Save template. This will ensure the invoice is sent automatically during the next scheduled invoice. In the meantime, you can manually create transactions from the template.

However, if the Automatically Send Emails feature is turned on, I suggest contacting our QuickBooks Live Support team. They can assist with reviewing your settings and provide guidance to correct any issues.
To enhance your QuickBooks experience or get help with bookkeeping tasks and navigation, reach out to our QuickBooks Live Expert Assisted team. These professionals are ready to provide support tailored to your business needs.
I’ve included an article with additional insights on recurring payments and FAQs, including guidance on how to cancel a recurring payment: Recurring Payments Overview.
We’ll stay in touch if you need further assistance with your recurring invoices or any QuickBooks concerns.