Error message when sending e-mail

Almost everytime I send an e-mail from my server e-mail account, vs my gmail account, I get a message saying my outgoing mail.[server].com is not trusted and the e-mail isn't sent.
How do I make it trusted? I took about 7 tries just to get the iPhone to accept my e-mail account so I could receive them in the first place.
My host company has no special configure settings for the iPhone and it works fine with mail on my iMac.
Suggestions on how to fix it?

The SMTP server may require authentication so make sure that option is checked.

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