I know this sounds stupid

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sprinkle0420

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I know this sounds stupid, but when they say an application must be "postmarked by such and such date" that is the day it must be received by the post office and not the school correct? Also, do you have to request to have the date postmarked on the envelope or do they automatically do it?
 
Yes, the postmark is automatically done by the post office and postmarked by means the last possible date it can be sent by the post office. I would play it safe though and bring it atleast a few days early.
 
Yes - its automatically done by machine at the central post office where it is processed (not necessarily where you mailed it).

Remember...you're now into a big mail time (holiday cards). Huge amounts of mail go thru these machines & some go thru together, in which case, the back envelope never gets cancelled & there is no mark indicating when it was mailed.

I'd advise....take it to the post office, wait in line, mail it & ask for a certificate of mailing - it adds 0.90 to a domestic letter & provides you with your own evidence it was mailed on a particular day, no matter what cancellation date appeared on the envelope (or if your envelope got lost after it got to its destination).