[samandlily]

A friend and I both use MS Entourage on iMacs that are about five years old. She uses Comcast, I use a wireless high speed ISP. Whenever I send her an email from Entourage, I get back a "Failed mail after 20 attempts SMTP connection failed". If I send her something via my ISP web mail site, she receives it. This only happens to me on Comcast. What kind of setting do I, or her, need to change to fix this problem? Thanks.

[JKT]

It could be the port that you are trying to send the mail over is blocked. Look at your settings and see what port is being used to send mail via SMTP (typically it is port 25, which is often blocked by ISPs).

[samandlily]

It is port 25, so what do I do to remedy the situation, just leave it blank?

[Cold Warrior]

I think comcast uses SMTP authentication. In Entourage's Accounts setup, open the comcast account and ensure you're using smtp.comcast.net. Let me know if it's something else.

Click 'click here for advanced sending options'. Select 'smtp server requires authentication' and, below that, 'use same settings as incoming mail server'. Also check 'override default smtp port' and enter 587.

I've summarized the instructions from here.

[samandlily]

When I did what you said on MY Entourage (I do NOT use Comcast), it would not send the email. Do I need to do what you said on my friend's computer (Entourage also), and/or on both computers (she DOES use Comcast)? Thanks for the help

[Cold Warrior]

ok, I read your post wrong. I read it quickly and thought your friend was having issues sending.

Can you send email to others using Entourage?

Like JKT said, it could be issues with port 25. Take a look at your ISP's help documentation to see if you can find a setting for SMTP authentication.

[samandlily]

I can send email to EVERYONE except this friend at Comcast. I am suspecting that she needs to change one of her settings in Entouage to get email from me. Strangly enough, if I use my ISPs webmail, I can send to her AND she can reply to me through my Entourage. I have asked my ISP for help, as you suggested. I will post again here in a few days when I hear from them. Thanks for your help!

[samandlily]

I believe that the problem has been solved. As suggested by my ISP, I replaced my outgoing Entourage mail setting "smtp.xxxx.." with "mail.xxxx...", and that seems to do it. Apparantly, Comcast blocks the smtp setting, and I am not sure why.