Well, the title really says it all.
In a snarkathon at the organizer of my 5-year brewfest/high school reunion, one of my friends brought up that the form the organizer wrote stated that Cash or Check can be mailed to her for payment into the event. We’re not sure if this is illegal, or just something that the USPS frowns against since cash is a little obvious in an envelope and doesn’t have any of the security features of tracking or cancelling that a check or money order has.
According to USPS’s website,
“Money orders are a safe alternative to sending cash through the mail. A lost or stolen money order can be replaced. You can buy money orders at all Post Offices in amounts up to $1,000 each. Most money orders cost $0.90-$1.25.”
This implies that it isn’t illegal, but isn’t recommended, either.
Ditto DMM 601, entitled “Mailability”
http://pe.usps.com/text/dmm300/601.htm (no mention of money or currency).
And see, DMM 609 4.2(c) (maximum indemnity for lost currency is $15).
USPS doesn’t really care but they don’t want unhappy customers, either. Theft of cash sent through the mail does occur. Even non-cash negotiable instruments aren’t wise to send. I was surprised at the link that shows that they have any liability whatsoever.
My mother once sent me a gift card from a consumer electronics store for my birthday, inside a birthday card, sent US mail. I received a sealed envelope with the birthday card mentioning the gift card, but no gift card. An investigation, including video from the store when the card was used, led to the arrest of a postal employee who opened the envelope, took out the gift card and resealed the envelope sending it along its merry way.
I’ve sent large quantities of cash (thirty bucks or so) in a padded envelope and had no problems. Most people don’t expect to find cash in a padded envelope, especially if it contains a CD case (the money was inside the case) so it doesn’t feel like a packet of money. Maybe suggest doing that to people hell-bent on sending cash? I probably wouldn’t do the same thing today though, now that I have checks.
You can also fold it up in a few sheets of paper so it looks like a letter. If the paper is old junk mail with lots of printing on it, so much the better.
Postal Employee checking in…
Sending cash is entirely up to you. Do you want to risk a small chance of your $50 being stolen, or do you want to play safe and spend $52 (or whatever it is) on a money order?
Personally I’d post the fifty bucks cash, but i’d be sensible about it, probably sending it in a greeting card.
As mentioned by CookingWithGas, theft happens. Postal workers can and do steal stuff. Yet it is rare. Take my facility for example - I am under constand video surveillance by multiple cameras. There are also sting operations put in place if they suspect you (or even if they don’t). I have found articles which have come open through poor wrapping and with valuables or cash inside. The first thing I do is stop any machinery I may be using, hold the article up to the nearest camera as theatrically as possible, and then summon a manager over, making it his problem, and I go back to work. I have seen two or three employees busted, but that’s over hundreds of staff over fifteen years’ service.
Some points to consider:
You’re never going to get rich stealing from the mail. You can do it once or twice, and possibly get away with it. You might be in front a few bucks. Then customer complaints start coming in, and these will be handed over to the Corporate Security Group, who will then conduct an investigation so quick and simple it would be every policeman’s dream - they just work out the common link in the different missing items’ path, what time of day it would have been through the suspected area, who was rostered, and then they set up a sting, and get the video rolling. Theft is rare because of this.
Working at speed, it is difficult to even tell what articles may contain cash, especially in greeting cards. I sort manually at about an article every second and a half, which is just time to pick it out of my hand and glance at the bottom line of the address as I flick it into a pigeon hole and pick up the next one. You develop a cadence, and tend not to stop for cash.
For the sorting machines which do 38 000 articles per hour, it is a matter for the operator of picking up large bundles of mail and dropping them onto a belt. He/or she would only have direct physical and visual contact with the letters on the end of the bundle - two out of possibly hundreds. The only articles that give themselves away are those that contain coins.
Everyone’s talking about theft of mail, but don’t forget that mail does tend to get lost from time to time. Lost cash is gone cash. A lost money order, with the receipt and a lot of patience, can eventually be reimbursed.
Of course, if your package is suspicious and if they open it up and find $10,000 or more, don’t expect to get it back. 
I’ve heard of unscrupulous postal employees looking in greeting card envelopes for cash from the grandparents, so wouldn’t this be a bad way of hiding the money?
Another thing to keep in mind is that if your friend receives an envelope with no cash or check, they will only have the sender’s word that cash was enclosed. It will be sender’s word vs. receivers. You’re not in high school anymore, so hopefully everyone will be onboard with checking accounts by now.
Umm… depends. I certainly wouldn’t address it as going to a child. You’d need to use a bit of imagination if you really wanted to be safe; maybe an envelope with “In Sympathy” on it or something, or one that looks like an invitation. The thing to remember is that the sheer volume of mail dictates that there are zillions of greeting cards in the system. The odds are on your side. A standard business envelope is a little less rigid, and might be easier to spot. Once again though, the massive volumes of mail are your friend.
The padded bag or disk mailer idea is good, but the extra postage might defeat the purpose of not getting a money order in the first place.
To be perfectly honest, if you took ten standard business envelopes, put a $1 bill inside each, and mailed them to your friends, I’d have the odds on all ten arriving. Mail a hundred of them, and you might lose one. Maybe.
Those employees who do steal from the mail often suffer the arrogance of criminals in thinking they won’t get caught, and they do tend to look out for obvious or not-so-obvious signs of cash. These people are rare. Any extra precaution you take above just throwing the bill into a normal envelope is only going to be protection against those people. For the rest of us, it’s wasted effort. you could place money in a clear envelope and send it and it would more likely arrive at its destination than not. In fact some people have done just that: Postal Experiments
Another risk for those of us with rural delivery mailboxes (or anything other than a locked box or a slot in the door) is that some random passerby can take things out. One summer we had a problem with checks not being received by their intended recipients. I thought it was the post office, until one day our letter carrier brought us a whole bunch of stuff that I had mailed out, which he had found dumped in a gutter elsewhere in our neighborhood. These particular items were rather thick envelopes that I was sending out as part of a program for a group I belonged to. Somebody was apparently going around the neighborhood raiding mailboxes. My stuff contained no cash, but the thief must have thought they looked as if it might.
This is certainly true. And most mailboxes are unlocked and wide open to any thief. Probably much more likely to be stolen from the mailbox on the front of your house than while in USPO hands.
This used to be a common problem back in the days before electronic funds transfers and direct deposit. Things like Social Security checks, Welfare checks, Food Stamps, etc. all came at a specific time of the month, and generally in a very identifiable envelope. It was common for thieves to steal these from mailboxes, forge an endorsement, and cash them. That’s one of the advantages for the government of direct deposit – it eliminates this mailbox theft, and the problems that caused for both the recipient and the check issuer.
There’s always going to be a special case where you have to send cash. (In my case, someone was in the hospital AND it was too far to visit easily AND I’m guessing a Postal Money Order would be difficult to negotiate in a hospital.)
Anyway, I asked the post office clerk if I could insure money if I mailed it. He said no but since this was a special case, he suggested the best course of action was just to send the money first class mail - nothing special. So, I already had an envelope ready with a short letter and I wrapped a $20 in the letter and sent it. The clerk could easily see what I was doing and I just gave him the envelope and he stamped it. The letter arrived the next day at the hospital with letter envelope and money intact. Happy ending. (CookingWithGas - too bad your experience was not as fortunate as mine).
TheLoadedDog - So, you are a Postal Employee? Here at the SDMB I’ve got a reputation for complaining about a LOT of things. The Post Office is NOT one of them.