Rolling rules is an optional toggle on Wheel Paycheck. It's off by default, and on by default if you deployed the Aggressive Growth version.
What it does
Normally, when a cash-secured put reaches expiration in the money, you get assigned the shares. That's a normal, expected part of the wheel — you bought a stock you approved at a price you chose.
With rolling rules on, the system gets one chance to do something else first. On the morning a put expires, at 9:40 AM Eastern, it checks whether it can buy that put back and sell a new one about 21 days out instead — collecting additional premium and pushing the decision further down the road.
When a roll actually happens
All three of these must be true. If any one fails, the put is left alone to expire and assign normally.
The new put is further out of the money. Its delta must be below 47. The system won't roll into a position that's even more likely to be assigned than the one you're in.
The roll brings in a net credit. The premium from the new put must exceed what it costs to buy back the expiring one. If rolling would cost you money, it isn't done.
This position hasn't been rolled before. Each position gets exactly one roll, ever. The system will not chase a losing trade out in time repeatedly.
Covered calls are never rolled
This setting applies to cash-secured puts only. If you're holding shares and a covered call is going in the money, it's allowed to be assigned and your shares are called away at the strike — which is the profitable end of the wheel, not something to avoid.
Why a roll didn't happen
Every reason is recorded in your execution history. The usual ones:
No qualifying contract at roughly 21 days out under 47 delta.
Not enough credit — the new put's bid didn't exceed the cost to close the current one.
Already rolled once.
Quotes were unavailable when the check ran.
In every one of these cases the outcome is the same and it's a safe one: nothing is done, and the put expires or assigns as it would have with the setting off.
Should you turn it on?
There's no wrong answer here, because assignment isn't a failure in this strategy.
Leave it off if you're comfortable owning the stocks in your approved list. Getting assigned means buying a name you already approved at a discount you already picked, and the system immediately starts selling covered calls against those shares.
Turn it on if you'd rather stay in cash and keep collecting premium where the numbers support it. You'll take assignment less often, and you'll collect an extra credit on the trades that qualify.
One thing to expect
During a roll there's a brief window where the buy-to-close order and the new put are both working, so your collateral for that symbol can look committed twice for a short time. This resolves as soon as the closing order fills.
If the new put fails to sell for any reason, the system cancels the close order and puts the original position back so it can settle normally. You're never left in a half-finished roll.
Changing the setting
Save whenever you like. It applies at the next expiration-day check. It doesn't affect a roll that has already happened, and turning it off won't unwind a position that was previously rolled.