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So I sent some TTM envelopes using the electronic machine and it told me it was $1.50 per envelope. However when I went up to the window they told me it was 62 cents extra because it was "rigid" (since I had put a piece of cardboard in it). Unfortunately I had put all the envelopes into the machine except for 1 so I don't know what will happen with those other ones.

My question is: Will the other envelopes get to where they are supposed to or will they come back? Especially since my SASEs only had the $1.50 I am hoping they will be sent to my address like they are supposed to and not get returned to the celeb. Anyone have any thoughts?

There's a good chance they'll still get there. I put 4 forever stamps on ones that are staying in the US and they get there. If I go up to the counter, they weigh it and charge me more. Both get there, and come back with the same 4 stamps.