Why deposit them into your checking account in the first place? Mailing the MO as payments directly to the credit card companies eliminates a lot of the sketchiness involved. Usually your cc statement even says 'Mail check or Money Order to...'.

Definitely not sketchy. Banks love getting tons of MO's in the mail for CC payments, ideally multiple MO's in small denominations.

Using them to pay bills seems more legit than depositing a bunch into your own checking accounts filled out with the same person as sender and recipient. The unbanked and people who are paranoid about giving out their account information use money orders to pay bills. But hey, I'm sure banks think there's a legitimate reason for continually writing out money orders to yourself and depositing them.

.....

https://www.fincen.gov/statutes_regs...ck_casher.html

"
Thus, if a financial institution cashes a check with a face value of over $10,000 by providing the customer with $9,000 in cash and the remainder in monetary instruments (because, for example, a customer would like to pay bills with money orders), the financial institution would not be required to file a CTR, because the physical transfer of currency to the customer was under $10,000.
"

Indeed, it is true that banks need not file CTR if the cash (not MO or such like) amount of transaction is below 10K. Therefore, it appears that none of you who ever deposited over 10K in MO triggered CTR. However, SAR is still a possibility.

My supermarket chain apparently makes no difference between using cash and debit for purchasing MO, and, as shown in the example above, if I structure while using debit for payment, I will still be trying to avoid SAR.

If it is few thousand dollars a month you want to spend, this might not be a bad idea and will work.

On cards where you have to cycle your CL few times or do lot of volume, I don't know logistically how it's going to work out.

Let's say you collect few MOs for 5-10 days before you would mail them out, by the time they reach the CC company and posted to your account it will be easily a week from the time you mailed them. This can certainly be one of the pillars of MS game. The other issue is mailing them safely.Not all banks send you a secure envelops. I would prefer this to loading to serve, go bank, other avenues ..which is always a nightmare.

In your example, just because the financial institution 30 seconds later exchanged $10xx+ for some money orders, does not change the fact that the initial transaction was cashing a check for more than $10,000.

Pretty good necroscare either way. :)

Got a call from my banks financial crimes division on Friday. I also happen to be employed in corporate IT at said bank, so I have "special" employee checking and savings accounts.

I went whole hog in November and December, clearing a total of $140,000 in money orders through my bank.

The guy asked me how I was doing it and what they were for. I explained my methods of MS, and he said "oh its for rewards points? that's actually really common. Ok, thanks!"

I asked him if I could keep doing it and he said "yeah, you may get called from us every now and then to make sure everything is ok, but you are good to go, we won't terminate your account because of this."

Sweet.

Good outcome for you. However, I'm not sure that I would mess with a bank that I work for...

How am I messing with my bank? I am doing nothing illegal, and its a checking account.

Money comes in, money goes out. You can't explain that.

It get's lost from time to time in these MO topics but doing 5-10k a month and doing 40K a month are different scenarios altogether. If you're doing 40K a month BB wasn't much help to you either even before the shutdown unless you had more than a couple BB's.

Which bank do you use, if I may ask?

There are two problems with this statement: 1) you cannot structure while using debit as a method of payment, and 2) 31 U.S.C. 5324 does not prohibit structuring to avoid a SAR. Section 5324 prohibits structuring to evade the requirements of either 5313 (CTR) or 5325 (ID required for currency purchase of monetary instruments), while SARs are governed by 5318(g).

CAVEAT: This is not intended as legal advice.

The difference is in the key phrase "the physical transfer of currency" which is the definition (at least in the federal pattern jury instructions) of a "currency transaction." Here are two scenarios; according to the FinCen link, the first would require a CTR, while the second would not:
1) Customer surrenders $10,000 check, receives $10,000 in currency. Then hands $1,000 back to cashier to purchase MO.
2) Customer surrenders $10,000 check, receives $9,000 in currency and $1,000 MO.