"Invalid address" only when sending to multiple addresses

I can send an email to <username>@gmail.com and to <username>@mac.com, but if I try to send an email to both recipients at once, my mail server says "Invalid address" even though my colleague can send an email to those addresses without a problem.
Since my colleague can do it, it can't be the server; but I can't figure out the difference between my Mail configuration and his.
Any ideas?

I found my own answer. I didn't have password authentication on for the outgoing server. Weird. I was able to send mail to individuals without a password, but couldn't send to multiple people.
It's working now.

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