Tax question: Best way to pay large sum to IRS?

Thanks for the replies everybody - I definitely have some research to do this weekend.

Regarding:



The various problems with ATM and debit card fraud I've read about in the last few years has made me keep only enough in checking to cover monthly expenses. Everything else I keep in other accounts. That way, even if my debit card does get compromised, my loss or hassle in dealing with the situation is minimized. Yeah, I might be able to get a larger sum back if it was compromised and taken somehow, but I suspect the hassle dealing the various financial institutions would be a nightmare.

I just prefer to keep larger sums in accounts that aren't linked in any way to cards (like debit or credit cards) that I use at merchants for general purchases. Yeah, it might be overly paranoid, but I just prefer to do it that way.
One way around this is to wire the money to your bank, then as soon as the wire clears go to the bank and get the check certified, or buy a cashiers check from the bank. In the case of a certified check the bank takes the amount of the check and sets it aside so the check is known good. A cashiers check means the money transfers to the bank when the check is purchased. Note that cashiers checks also fall under FDIC insurance.
 
If your bank is anything like mine, you don't have to leave large sums sitting in your checking account. You can just write the check and when it comes in, the bank will transfer to checking to cover the overdrawn amount. My credit union does not charge a fee to do so.
 
But when a crook steals a check, don't the 'wash' it, and replace the payee with their own name or some account they have access to? The check would only have LoneAspen's info on it, nothing to indicate it was made out to the Govt.

-ERD50

That can happen but it's pretty rare. Think about who and how they are gaining physical possession of the check in the first place. They stole it out of a mail box or from the post office stream (which is fairly automated by now). That type of person is not a pro, not sophisticated, and probably doesn't know that just using a pencil eraser is going to raise eyebrows with a 2nd week bank teller.

All that said yes, there are events where someone in a more organized group is there solely to get the checks and pass them on to more capable individuals. But I'd wager the odds on that are akin to winning the lottery.

Of course winning the lottery is better.:LOL:
 
I used to send six and seven figure checks for estimated taxes by certified mail (at the last minute of course) and never had a problem. Now that I'm FIRE'd, I have more control over my taxable income and such lunacy is not necessary.

Seven figures to the left of the decimal point? No leading zeros?

Would you like to adopt a son? :)
 
RE: 'washing' the check and replacing the payee name...
That can happen but it's pretty rare. Think about who and how they are gaining physical possession of the check in the first place. They stole it out of a mail box or from the post office stream (which is fairly automated by now). That type of person is not a pro, not sophisticated, and probably doesn't know that just using a pencil eraser is going to raise eyebrows with a 2nd week bank teller.

All that said yes, there are events where someone in a more organized group is there solely to get the checks and pass them on to more capable individuals. But I'd wager the odds on that are akin to winning the lottery.

Of course winning the lottery is better.:LOL:

OK, but then I guess I'm confused as to what they do then. I thought 'washing' the check (acetone, benzine, tri-chlor, or some other ink dissolving chemical) was pretty low tech. Erase the payee, write in your own name, and cash it.

I think I also read they sometimes create a new account with a fake ID and then do a bunch so it can't be tracked back so easily, not sure that is so easy anymore.

If the check was still made out to the Treasury Dept, what do dumb crooks do?

My MIL had a check stolen out of her mailbox years ago, and the thieves 'washed' it, filled out what they wanted (signature wasn't even close). She was on the ball enough to catch it on the monthly statement and dispute it, and the charge was reversed.

-ERD50
 
RE: 'washing' the check and replacing the payee name...


OK, but then I guess I'm confused as to what they do then. I thought 'washing' the check (acetone, benzine, tri-chlor, or some other ink dissolving chemical) was pretty low tech. Erase the payee, write in your own name, and cash it.

I think I also read they sometimes create a new account with a fake ID and then do a bunch so it can't be tracked back so easily, not sure that is so easy anymore.

If the check was still made out to the Treasury Dept, what do dumb crooks do?

My MIL had a check stolen out of her mailbox years ago, and the thieves 'washed' it, filled out what they wanted (signature wasn't even close). She was on the ball enough to catch it on the monthly statement and dispute it, and the charge was reversed.

-ERD50
If you are sending the check certified mail and give it to the clerk at the post office then it travels in a more restricted stream than regular mail. It goes to a bank lock box service that does the transfer (the addresses for estimated taxes are bank lock box service just like other bills.) This is why for example the address to send a tax return with a refund is different than with a payment, the payment goes to the lock box service and the remainder is then forwared to the IRS.
Certified mail means the movements of the letter are tracked, and unless its an inside job at the post office it is delivered to the lock box and cashed.
 
If it is that big a deal, why not deliver the check in person? Airfare and rental car could be a tax-prep fee.
 
You'd think so, but a former co-worker of mine embezzled over a million dollars from the City of Seattle by using a method not too different. He opened a joint account for himself and "City of SEA" and was then able to deposit checks made out to the City into this account for his own use.
Must have either been pre patriot act or a bank failure, you have to show ID as city of SEA, to open the account now, did he have inside help?
Well, he could show ID because he was a city employee at the time but I am still amazed that he got away with it for so long, and at such a major bank. My mom put me as joint account holder on some of her accounts after my father died, one of which was at B of A, and we had to go through all sorts of rigmarole—come to the branch in person, both show ID, sign the papers in the banker's presence and so forth. I've always wondered whether Joe didn't have either some sort of forged document OKing the account, or if someone at the bank was in cahoots with him, but if so I've heard nothing about it. You would think also that someone at the B of A would have said, "wait a minute, the City does all their banking with Wells Fargo—what's going on here"? But apparently that didn't happen either.
 
Well, he could show ID because he was a city employee at the time but I am still amazed that he got away with it for so long, and at such a major bank. My mom put me as joint account holder on some of her accounts after my father died, one of which was at B of A, and we had to go through all sorts of rigmarole—come to the branch in person, both show ID, sign the papers in the banker's presence and so forth. I've always wondered whether Joe didn't have either some sort of forged document OKing the account, or if someone at the bank was in cahoots with him, but if so I've heard nothing about it. You would think also that someone at the B of A would have said, "wait a minute, the City does all their banking with Wells Fargo—what's going on here"? But apparently that didn't happen either.

This is what you get for bank employees who get paid minimum wage.
 
I used to hate worrying about checks to the IRS getting lost in the mail, so I'd do the certified return receipt thing which was such a hassle. I was so relieved to switch to EFTPS - never looked back.
 
I used to hate worrying about checks to the IRS getting lost in the mail, so I'd do the certified return receipt thing which was such a hassle. I was so relieved to switch to EFTPS - never looked back.

I think the post office has standing orders not to lose mail sent to the IRS. In 15 years of sending in estimated tax payments "first class", they have always received my payment.

Now mail to my house? Seems like we get other peoples mail and have ours lost at least once per month.
 
RE: 'washing' the check and replacing the payee name...


OK, but then I guess I'm confused as to what they do then. I thought 'washing' the check (acetone, benzine, tri-chlor, or some other ink dissolving chemical) was pretty low tech. Erase the payee, write in your own name, and cash it.

I think I also read they sometimes create a new account with a fake ID and then do a bunch so it can't be tracked back so easily, not sure that is so easy anymore.
-ERD50

Then the washed check is handled no differently than a stolen blank check. That happens (or used to anyway) a lot. I was always surprised at how many people left their checkbooks in their cars. And then don't read, let alone balance, their statements. Stolen checks were a lot easier to spot when you got the canceled checks back with the statement.

A separate issue from a mere stolen check is identity theft in which the thief opens an account in your name and then proceeds to bounce checks all over. Or gets credit cards in your name or takes out a mortgage on your house. That can be a royal PITA to straighten out.

I've been out of fraud investigation for over ten years now so I'm not sure if or how much the Patriot Act regulations changed anything.
 
I think the post office has standing orders not to lose mail sent to the IRS. In 15 years of sending in estimated tax payments "first class", they have always received my payment.

Now mail to my house? Seems like we get other peoples mail and have ours lost at least once per month.

I suspect that's true, but having no recourse unless the check cleared bugged me. I just always hated having to use mail as the intermediary including the visit to the post office, and love being able to do everything electronically now.
 
It should be noted that diamonds are often shipped by registered mail. and that classified material up to the classification of secret can be shipped registered mail. It costs $11.05 compared to the 3.30 of certified mail, but is more secure.
 
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