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I found this from jrr:
Can't speak for Fidelity, but it's easy to set up a T-bill ladder at TD. When you set up a purchase, tell it to repeat the purchase on a schedule. Tell it that the source of of funds for subsequent purchases is the "Zero-Percent C-of-I". Then set the T-bills to pay out into the 0%CofI. The money will be in the 0% account for a day or two, and then will be rolled over into the next T-bill.

I had seen this before and called Fidelity to get their take on it. Basically in a taxable account you can order the new T-bill and the old and the new will settle on the same day so your money will stay invested.

In a retirement account the problem would be entering the new order and not having the funds available. The guy at Fidelity assured me that the order could be entered through a representative. When I pointed out that that would involve a commission he assured me that they would be willing to wave the commission (I am a preferred customer at Fidelity so I don't know if this option would be available for all). This also would keep you money working.

The other option at Fidelity would be to let the cash from the old bill set in the cash reserve account for a week at the current yield of 4.66%. Of course your ladder would slip a week.

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