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i don't think it'll automatically mean hand-cancelling, no. i used dark brown envelopes for my STDs and had to pay more postage, but they didn't hand cancel them. i did find out though that they put that ugly white sticker on it. =( i think you have to specifically ask for hand cancelling, but i heard that it may still go through machines (depending on how many post offices the letter has to go through to get to its destination).
One of the bees paid for hand-cancelling on her red envelopes, and they later ended up going through the machine anyway as the red ink of the hand-cancelling stamp didn't show up well enough on the envelope. I think its just the chance you take with dark colored envelopes. Your alternative is to get a lighter color for the outer envelope. 
It is easy to find 7-inch square cream envelopes, if you wanted to put your nice chocolate envelopes inside something else.
nope, you have to specifically ask for hand canceling and the dark envelops may be a problem since the stamp won't show up well. I would take it to your post master to ask about it.
Maybe you make your own white sticker to put in the corner with enough room for a stamp and the hand cancel mark so you can see it.
Our response card envelopes are red, and some have come back with a white barcode sticker on them, and some have not. Based on that, I think that there is some chance that at least some of your invites will end up with the white barcode sticker.
Bride.jpg (66.1 KB, 115 downloads) 2 years old
Maybe you could try mailing one of the envelopes to yourself so you can see how it will look. Then you can make adjustments if you are unhappy with the results. My FI and I did this with our STD postcards and it was very helpful.
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Hi ladies,
I am still months from mailing out invites, but am already thinking about the postal process. My envelopes are 6.5" squares in a dark chocolate tone, and with that size/shape I know I will be paying extra postage.... however does that automatically mean that they will be hand canceled? Plus, does anyone know how they go about canceling dark colored envelopes? I'm shuddering at the thought of some hideous white sticker with a bar code slapped on the bottom of my invites!