Cannot send out email

We can receive but cannot send out emails through outlook 2010, we are using yahoo bizmail accounts. Our Isa server 2004 is set to  allow unrestricted access. I have tried changing outlook smtp ports from 25, 587 and 465 Ssl to no avail. But configuring the same yahoo account via outlook outside of the office, sending email is fine. The strange thing is users with gmail accounts behind the Isa server in the same office network, using smtp ports 465 or 587, is also working fine.
Telnet smtp.bizmail.yahoo.com 587 does not work but telnet smtp.gmail.com 587 gives 220. But testing both in a different network (at home)  gives both 220 results.
What do you think is the problem? I read that it can be Dns issue? How do we check for that?
Siomao2Asked:
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Suliman Abu KharroubIT Consultant Commented:
What type of mail profile do you have , exchange or pop3/smtp ?

If pop3/SMTP, you have to get a smarthost IP  from your ISP and fill it as SMTP server ( make sure to not use authentication for SMTP out going mail address)
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footechCommented:
You can try the following inside your network to test for DNS resolution
nslookup smtp.bizmail.yahoo.com

If it didn't work outside of your network I would think that perhaps the Outlook settings were not right (i.e. didn't specify credentials for outgoing email).

However, since that is not the case, your best friend in this case is the Monitoring in ISA.  Open it up, then try to establish a connection with Outlook.  Look at the Monitoring results to see what traffic was denied (if any) and by which rule.  Then adjust firewall rules accordingly.

What firewall rules do you have in place to allow outbound email traffic?  Include To, From, Protocols, and Condition.
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Siomao2Author Commented:
Currently, we have allowed all protocols from internal, local host to external for all users. We have also changed firewall config for outlook from 1 to 0.  I will check the nslookup and monitoring status and revert.
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footechCommented:
I can't think of any reason to need a smarthost from your ISP unless they block all other SMTP traffic.  In which case you may be able to contact them and they could unblock you.

Have you seen the following (from yahoo regarding errors sending email)?
http://help.yahoo.com/l/us/yahoo/smallbusiness/bizmail/pop/pop-11.html
and
http://help.yahoo.com/l/us/yahoo/smallbusiness/bizmail/pop/pop-27.html
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Suliman Abu KharroubIT Consultant Commented:
@footech I have seen a lot of issues which cased by the ISP blocking SMTP traffic as a spam control process... and they provide a smart host to use SMTP
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footechCommented:
@Sulimanw - thanks for confirming my reasoning.  This wouldn't appear to be the case however if communication to Gmail SMTP servers is not being blocked.
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Siomao2Author Commented:
Footech,
Nslookup produced the ff results:

Server: file-svr.domain.loc
Address: 192.168.2.253
.
Non-authoritative answer:
Name: sg-smtp.bizmail.mail.fy4.b.yahoo.com
Address; 106.10.149.91
Aliases: smtp.bizmail.yahoo.com, smtp.bizmail.mail.fy4.b.yahoo.com

I have also attached  a screenshot of the monitoring log for your reference.

Sulimanw, we have a satellite office a few blocks from our main office using same settings, bizmail (pop3) with no problems with sending email. I have also checked with our ISP and they did not block our domain.

I suspect it is a configuration issue (isa?? active directory?) although it is driving me nuts to find it.
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Suliman Abu KharroubIT Consultant Commented:
try to telnet to 106.10.149.91 on port 25 ?

also can you post the ISA rule config ?
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Siomao2Author Commented:
telnet 106.10.149.91 25  (within office network)
result: connect failed.  same result for ports 587, 465

but telnet smtp.gmail.com 25 (within office network)
result: 220 mx.google.com. same results for ports 587, 465

and telnet smtp.bizmail.yahoo.com (outside of office network)
result: 220 also..
Log.jpg
Firewall-Policy.JPG
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Siomao2Author Commented:
Ok, i tried my personal Yahoo Plus mail account with outlook using plus.smtp.mail.yahoo.com with port 25. I was able to successfully send email within office network. Is it possible that my antivirus is blocking bizmail.yahoo.com?  

I don't think it's a port issue or an ISP issue. Could it be a antivirus issue? We are using symantec endpoint. What do you think? Help.
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Siomao2Author Commented:
I was able to send email at last. It was a combination of both of your suggestions that got it. I still do not understand why only smtp.bizmail.yahoo.com was blocked within this office, while in our other office (with same ISP), the old settings are and still working fine. I just want to thank both of you for the advice and leading me in the right direction. Thank you.
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footechCommented:
You might try a tracert to smtp.bizmail.yahoo.com or a ping to see the response if you wish to dig further.  The problem appears to be outside of ISA.

Glad you found a work-around.
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