There's a few "gotchas" when it comes to Character Encoding. But the key thing in you case is understanding the character encoding being used by the receiving system. This should be something specified in the specification of the receiving system, but many times it's not.
If I had to guess, it's most likely that the receiving system is using UTF-8 simply because latin1/ISO-8859-1 encodes the pound symbol as hex "A3" whereas UTF-8 encodes to "C2 A3". As there's no solitary "A3" in UTF-8, there's nothing to print, which is why you get the ? instead. I'm sure there's other character sets where this can happen, but I would start there.
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