I just finished making a bulk emailer script with the mail() function. I would probably recommend doing a loop, sending one email at a time. Seems that way you're not putting too much pressure on it at one time (if that makes any sense). If you can find a decently-written smtp-class that uses the socket directly, that would be much better. Then, you're not limit to sending to one mail server, and there's greater flexibility in the code; room to edit/add code when needed, and you have the opportunity to log specific error messages if ya need to. The only problem is finding an SMTP class that'll work without too much editing, unless you have the socket knowledge to write your own. Whether or not the socket commands in PHP work well in Windows or not, I've not a clue. I know there are some Windows issues with the mail() command as well, and a few other PHP functions that just don't work under Windows. =)
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