I had a problem with sending over WiFi with an HTC Eris with my own domain email provider, and found this thread. It helped me remember a solution from the past, and this worked for my Eris.
Some ISP's block email from any other than their own accounts - like, you can send email with your Cox account when logged in through Cox, but not while on the internet by any other means. They do that to block spammers. Of course, you're not a spammer, and every spammer knows these tricks anyway. But I digress.
The way around it is to use a port for outgoing mail other than the default of 25.
When I had a paid yahoo account, I could send using the Yahoo server through Cox on port 587. Right now I'm using port 3535 with a GoDaddy hosted email account. Another possibility I know of is port 80.
Right now I have AT&T DSL, and I'm using port 3535 with my GoDaddy hosted email. I don't think just any random port will work, but try those.
In Outlook 2003, go to
tools > options > email accounts > View or change existing email accounts
keep picking stuff until you get to the screen with a bunch of pop3 settings, fill those in, and then click the More Settings button (in the bottom right of the window in Outlook 2003)
In the window that opens, click on the Advanced tab
There you'll see "Outgoing Server (SMTP):"
in the box to the right of that, type in your alternate port number.
Try 80, 3535, maybe 587
Below are detailed instructions I got from Yahoo which give some command prompt methods of testing that are a lot faster than changing Outlook settings every time.
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1. Select the Start menu button, then click Run.
2. Type "cmd" or "command" without the quotation marks and press Enter.
3. Type "telnet pop.mail.yahoo.com 110" and press Enter. If you are successful, you should now see "+OK hello from popgate" against a black screen. If you do not see this, close the window and start over or check your internet or network connection.
4. From this screen, type "user xxx" (where xxx is your Yahoo! ID) and press Enter. You should be prompted with "+OK password required."
5. Type "pass yyy" (where yyy is your case-sensitive password) and press Enter. If this is successful, you should receive a prompt with "+OK maildrop ready," followed by mailbox details. If this was not successful, you will receive "-ERR Error logging in. Please visit http://mail.yahoo.com/".
6. Type "quit" and press Enter to sign off the POP server.
7. Type "exit" and press Enter to return to Windows.
If you were not able to achieve POP authentication during the first try, wait a few minutes and try again. After several tries, you should be able to tell if your ID and password will allow you to achieve POP authentication.
Next, please perform the following test to confirm if you are able to communicate with the Yahoo! Mail Plus SMTP server:
Select the Start menu, click Run, then type the following command:
telnet://smtp.mail.yahoo.com:25 (of course, put your applicable email server in there in place of the yahoo one)
Alternatively, you may also return to the command prompt using the POP telnet test instructions earlier (above), but instead type the command syntax "telnet smtp.mail.yahoo.com 25", then press Enter.
If the port is not blocked, you should receive a response similar to "220 smtpxxx.mail.yahoo.com ESMTP" (where "xxx" is the server number you connected to). If you do not receive this specific response or if you receive a different response, your ISP, networking equipment, or security software may be blocking or scanning outgoing mail servers.
NOTE: Please also try port 587 in place of 25. It is pertinent that you try the alternate port, as some ISPs will block port 25 by default.