Should the cash flow planner pull in all of the transactions?

The Cash Flow Planner in QuickBooks Online (QBO) doesn't automatically pull in all transactions, Zirbel.
 
It primarily uses data from your connected bank and credit card accounts, as well as future-dated QuickBooks transactions such as invoices, bills, and expenses. 
 

Now, about the Money out displaying zero, this happens when there are no expenses or cash outflows expected or documented for a designated period. Since you have many accounts to be paid on June 27th, but it's showing $0, ensure that those bills are correctly set with due dates for the 27th of this month. 

If everything appears to be correct but still displays $0, clear your browser's cache to eliminate any excessive data build-up that may be affecting the platform's performance. You may also consider using other supported browsers if the issue persists.

Alternatively, you may follow the "Add an item" section of this article to manually input the money out transactions in the planner and correct your forecast accordingly: Cash flow planner in QuickBooks Online.

Once your cash flow concern is resolved, you can use this resource to guide you in generating reports to view both current and future finances: Track cash flow.

To further optimize your financial workflow and provide you with tips and advice, consider checking out our QuickBooks Live Expert Assisted team. 

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