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Cannot send mail via SMTP (but can receive)

I have an SBS2003 server using bizmail.yahoo.com as the mail server.  It stopped sending mail last Friday (although it still receives).  My end-users use Outlook with only the exchange server account set up.  Pop3 settings are managed using the POP3 connector manager.

 When I called their ISP for support, they only seem to be familiar with setting up POP mail on workstations, not servers, but they were able to confirm that they had made both a port change (from 25 for outgoing mail to 465) and that they were now requiring a secure connection (SSL).  I opened my SMTP virtual server properties box, and can see where to change the outbound connection from port 25 to 465, but I am unsure where exactly to set the secure connection.  Under outbound authentication I can set basic authentication (I would assume this would use the core email account username and password), integrated windows authentication, or TSL encryption.  TSL encryption looks like the safest bet, but SBC-Ameritech could not confirm for me whether this is the same as their required 'secure connection (SSL)' setting.  

Any thoughts?  Am I in the right area?

Thanks,
Scott
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corptech
Asked:
corptech
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2 Solutions
 
jordibartrinaCommented:
First: try to connect with telnet from command line:

telnet bizmail.yahoo.com 25 or telnet bizmail.yahoo.com 465

Any response of server?

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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
Actually it's a bit confusing because you need to set the port in the Outbound Connections on the Default SMTP Virtual Server, but then you must set the other options on the SmallBusiness SMTP Connector.

On the General Tab, select "Forward all mail through this connector to the following smart hosts" and enter the ISP's SMTP server name.

Then on the Advanced Tab > Outbound Security, select Basic Authentication and tick the TLS encryption.

Jeff
TechSoEasy
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corptechAuthor Commented:
jordibartrina,
I tried telnetting to the smtp.bizmail.yahoo.com server... on port 25 i received:
     220 smtp107.biz.mail.mud.yahoo.com  ESMTP       (this is a 'good' response, correct?)
on port 465 I didn't receive any response at all.

I would assume that this means level one support at yahoo was incorrect in telling me that I need to be using port 465.

Next I will try Jeff's recommendations to set up encryption.

Thanks to both of you.. I will post the results in a bit.

Scott
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jordibartrinaCommented:
Hello corptech,

Yes all you say it's true. Port 465 seems to be cutted.
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
I don't think Yahoo was incorrect in telling you to use port 465... however you can also try using port 587 according to their documentation:  http://help.yahoo.com/help/us/bizmail/pop/pop-32.html

Jeff
TechSoEasy
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corptechAuthor Commented:
Thanks to both of you for your help.  I ended up resolving the problem (temporarily) by leaving the SMTP connector on 25 (authenticated) but removing the smarthost entry altogether.  I am now worried that the client could eventually be blacklisted by spamfilters (if i understand things correctly, because the client has a domain called Guelzowlaw.com but their email is routing through bizmail.yahoo.com, a reverse DNS lookup will notice the discrepancy and could flag them as spammers).  It makes sense to add smtp.bizmail.yahoo.com as the smarthost, but we seemed to be having problems with this entry earlier.  The client is feeling a little frustrated, so I don't want to experiment until I am sure of the solution.  Yahoo  support isn't being all that helpful, as their script that they read from mainly deals with Outlook client setup, not Exchange server setup, but I am researching.  
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
The proper way to use a smarthost in those situations is to use their Internet Access Provider's SMTP server for outbound.  (ie, Verizon, Comcast, etc.)

Jeff
TechSoEasy
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