The tool will never automatically withdraw funds from a 529 account. You must either set up manual one-time disbursements or annual disbursements per account. The basic steps are below:

Step 1: Go to My Plan > Expenses

Step 2: Open the Disbursements section

Step 3: Press "Add a Disbursement +"

Step 4: Indicate the amount and whether or not it is recurring (for this exercise, it will be a one-time disbursement)

Step 5: Select that it will be coming from your 529

Step 6: Enter the age the primary planner will be when you expect the disbursement to occur. If a recurring disbursement, set a start and end age

Step 7: Decide if this disbursement is qualified (tax-deductible) or not

Step 8: Don't forget to press "Save" when complete

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