One more Q for the pros...
Let's say I go to Disney and come home on the 18th of the month. My credit cycle goes through the 12th. So, do I need to wait until the 12th for those rewards to officially post to pay myself back and keep the rewards, or can I pay myself back prior to the credit cycle ending? I usually pay my credit card off the day I return home from a vacation so I know it's all done and paid for, I don't wait for the billing cycle to end. However, if I choose to do the PYB my reason would be to earn the points on those purchases, so I don't want to NOT bc I paid them early.
In essence it doesn't matter when you use PYB as the points for your purchases that you made on your trip before you return home have been earned it's just that they won't be available to spend until the 12th. So if you have enough Rewards Dollars in your bank currently you can wipe them out on the 18th and then on the 12th the points you earned from your trip would be added to your Rewards Dollars balance. What really matters is if you have enough to wipe out a complete charge because you can only apply rewards dollars once to a transaction so if you apply $0.01 to a transaction as
@trenty and I have done or the whole amount it disappears as a transaction that you can apply your Rewards dollars to.
Assume you have a current Statement balance of $0 but your Rewards Dollar Balance is $200 on 2/13/26.
You go down to Disney on 2/14-2/17 and have a VDAY Date night at Narcoossee's for $175, Grab some Merch at the Emporium for $75 on 2/15 and had some drinks at Trader Sam's for $50 on 2/16. All told you have 3 transactions that qualify for PYB and a total of $300.
Assuming that only those 3 purchases were made for the entire statement balance and that you have the premier card ($49 AF) on 3/12 you will have $6 added to your Rewards Balance whether you redeem the points before 3/12 or not and your Statement Balance on 3/12 would be $300 that you would owe to Chase.
If you come back on the 18th you can go in and wipe out the $175 Narcoossee's charge which leaves you with $25 in your bank. This also leaves you with 2 qualify transactions that you can later apply rewards dollars towards (5/16/26 would be the cutoff for $75 Emporium and 5/17/26 would be the cutoff for the $50 at Trader Sam's)
On 3/12 your Statement would show that you owe Chase a total of $125 after making 3 purchases and redeeming 1 Statement Credit from PYB.
Rewards Dollar Balance would show a starting balance of $200 with a $175 Redemption and $6 in Earnings giving you a total of $31 left in your Rewards Dollars Balance.
If you decide not to utilize PYB until the statement closes then on 3/12:
Your statement would read that you owe Chase $300 with 3 charges showing.
Your Rewards Dollar Balance would show Starting Balance of $200 + $6 in Earnings with your new Balance of $206.
You can then go in and wipe out the $175 purchase which means you would then need to pay Chase $125 to pay off the statement balance which would be the same as if redeeming the rewards dollars before the statement close date.
Your Rewards balance will now go from $206 - $175 = $31 which is the same as redeeming them before.
Let's now say on 3/12 you will just wipe out your $31 and apply it towards the $50 Trader Sam's purchase.
On 3/15 you found out that SAK's was having a going out of business sale and you spend $1,900.
At 1% back for general purchases that means $19 would be added to your Rewards Bank on 4/12.
On 4/13 you go to apply that $19 but you discover the Trader Sam's is no longer there since you had cashed in $31 towards it previously.
The good news for you is if you want to you still have 1 eligible purchase that you could redeem towards which would be the $75 Emporium purchase.
Knowing that I will earn more rewards dollars on my 5/12 statement and that I have until 5/16 to redeem Rewards dollars to that purchase I would wait until that 5/12 statement and apply the maximum rewards dollars at that time.
Of course you could just keep banking the rewards dollars in anticipation of your next trip.
When doing PYB I always look at which charge is going to drop off first since you only have 90 days to redeem them and which charge is the least amount so that I can completely wipe it off or use a good chunk of rewards to knowing that I only get one shot at wiping it off.