@krcroteau

Your Check on the 28th is an Error.

Here is how this works: On the 22nd, because of the Paycheck, the Gross Wage expense for the employee is not fully paid to the employee. The Employee's share of taxes, and IRA, are held back. That makes this amount Not paid out of Checking, seen as a Liability (to be paid out later, instead of being part of takehome).

As a result of the setup, the Employer Share of taxes and the Employer's share of IRA is also computed. It is posted for the 22nd as Expense, and since it was not immediately paid out, it is also seen in Liability for the 22nd.

Later, these are NEVER banking checks as CHK. They are all Special. They are Liability Checks, because they are part of Payroll activities. They are never Expense; the Expense was posted as part of the computation on the 22nd. The 28th simply is the Banking, that the Liability Payment happened.

It doesn't matter that Vanguard "pulls" the funds. You need to do the Bookkeeping of the Liability Payment, and for Check #, you can put EFT or ACH, to show you did not issue this as a paper check. You want to show how much Vanguard took this time, as a Payroll Liability check activity.

Hope that helps.