How do I leave a letter to be picked up by the mailman?

Question

Pardon the silly question... do I leave it on top of the mailbox, or inside it? The USPS website says leave it IN, does the mailman/woman actually go over all existing items in the mailbox and compares the addresses to mine to know if anything is outgoing mail?
I live in a Chicago townhouse.

As said, it's a townhouse, so no flag, just a big pull-out box for all 3 apartments.
We don't pick the mail every day, so some mornings there's still lots of junkmail in... but I get that if there are single items inside, they're gonna look at them...

I put it in the mailbox, for two days, and they didn't pick it up...

Answer 1

When I leave mail in the box to be picked up, I open the top and clip it to the inside with a clothes pin. This will keep your mail inside, but keep the top open a bit, clueing the mailman that there's mail to go out.

Answer 2

Good question. First of all never leave anything on top of the mailbox that you don't want to have blown away or stolen. If you have the standard outdoor apartment box, known in the trade by the acronym NDCBU, then what you want to do is put your envelope as far in your mailbox as you can (with the uncanceled stamp showing) because the Letter Carrier probably loads the box from the rear. If you have one of the new boxes (its 6 feet tall and looks like it has French doors) there should be an outgoing mail slot built into it between the doors for apartments M and N.

Answer 3

Leave it inside the mailbox, and put the red flag up. The red flag is the signal to tell the mailperson that there's something new inside the mailbox.
It's also normal to take all of the old mail out before you put new mail in, so the only thing in the mailbox when the red flag is up should be outgoing mail.

Answer 4

leave it in the mail box, or mail it at a box on the street corner. yes they know if its not your mail.