Reply all to about 50 addresses

I can hit reply all if I only have three or four addresses, but my school alumni association has about 50 members. Every time I try to do a reply all to them, I get an error that my email won't go through. It says "the server response was: unrouteable address"
It's very frustrating because if I send them individually, they seem to go through but this is neither productive nor expedient.
I can't find any limitations on sending, but I know it must be something...
Any ideas?

That may be the case, but why are other people able to do a reply all and have it work, out of the box so to speak, without any issues, but I can't?
Also, I think I have tried sending 3 or 4 of these at a time and they worked ... or sending to everyone using the same addresses, but as a new email. I can't do a forward of the same mail though. I get the same errors.

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