My e-mail won't send on one account. How do I fix it?
September 3, 2009 5:31 PM   Subscribe

I'm having trouble with my Apple Mail program. I have a number of e-mail accounts (some with Optimum online, a g-mail, yahoo, etc.) Apple Mail has no problem at all reading and downloading any mail from any of the services. My problem is with Optimum Mail ( Mail refuses to send anything through that set-up.

I've been on the phone for hours with Optimum and the settings are all correct. I've tried connecting directly to the cable modem and mail gets sent. This would make me believe that it is the Apple Airport Extreme router that is at fault. I've tried restarting it, re-initializing it and setting it up again and the problem continues. All my Optimum mail is picked up and can be read but it will not send anything through Optimum. It asks if I want to send it through another server (like g-mail or yahoo) and if I pick yes the mail sends. It happens on all my computers a G-3 and pre Intel iMac G-5 on Tiger and my Macbook on Leopard. Anyone else hear of this problem? Both Apple support and Optimum online say they have never heard of it. Talking for hours with their tech departments have found no solutions. Any thoughts would be apprectiated.
posted by hdh to Computers & Internet (3 answers total)
I use Optimum Online, and I have a Mac.

Have you tried using I found it accidentally, and it might work a bit better than just would.

Please feel free to MeMail me. I'm poking at this a bit; I use Thunderbird myself, but this is an interesting question.
posted by mephron at 6:59 PM on September 3, 2009

OK, just as a follow-up, I did some more testing. Use, and uncheck "Use Authentication". It zipped on through the setup. That may help you.
posted by mephron at 7:08 PM on September 3, 2009

OOL blocks port 25 outgoing. You'll either need to use a different port (I have my mail server set to listen on 25 and 26, some people use port 587) or use OOL's mail server for outgoing mail, as mephron indicates.

This is a standard anti-spam ISP practice, read more here: and if you want me to explain more, I will.
posted by Brian Puccio at 7:23 PM on September 3, 2009

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