I found that when sending mail decorated with older stamps, there was a strong tendency for the stamps to make it through the system uncancelled. I know this because a few get returned for bad addresses.
Now, I got this rubber stamp,
POSTAL WORKERS: YOU WANT TO GET PAID AND STAMP COLLECTORS WANT NON-PEN CANCELS. PLEASE DON'T LEAVE SKIPPED STAMPS.
and it seems to be working. I put elastic bands around bundles of letters and this message facing out on the backsides of letters on both ends. I got returned mail with hand-stamped cancels from the PD & C in my area. An index card with that message would probably work if there's one on each end of the bundle.
I also recently obtained rubber stamps saying
TO SAVE MONEY, THIS ITEM BEARS DISCOUNT POSTAGE WHICH SELLS BELOW FACE VALUE.
A charity is more likely to be happy getting discount postage donations if they also have this rubber stamp. This rubber stamp will educate a lot of persons about the folly of "investing" in new issues. Getting older stamps in the mail will ignite philatelic interest in a few. Demand for discount postage will also increase with public awareness.
You can get a mailer's permit and canceling device and cancel your own mail. That would also eliminate skipped stamps. The USPS doesn't care if some stamps do not get canceled - only collectors.
Charities can file for the non-profit discount and mail items for much less than 47 cents. There's not much incentive to use time-consuming "discount postage" for the larger charities. Have you actually convinced any local charities to use discount postage like the local fraternal order of police?
One of the reasons your mail is not getting canceled is because you are using older stamps. They may not be tagged, and the canceling equipment can not read that there is a stamp there.
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