Our policies and procedures stipulate that all cash advances have to be run through the account (cash deposit / Cash withdrawal) so we have record of when they are done, and it allows Accounting know where to draw the funds if the transaction is disputed later as fraud...So for us we would file.
When we have non customers conduct cash advances we have a "dummy" account that they do the transaction on, and we limit the amount to 1,000 to avoid possible CTR transactions and loss...
If you do not have this type of system in place then as I see it you have 2 different transactions for amounts less than CTR reporting and you would not file... Plus they just happen to come in at the same time... If they would have come in at different times and withdrawn the funds from the account separately you still would not be required to file if your system is advanced enough to know the conductor of the transactions as not a single person left with over 10k.
I'm interested to see how others would handle this?
Always Learning