I am trying to get SharePoint's email features to work with Google Apps (alerts, emails generated by workflows, etc).

Google Apps uses port 587 for smtp and I know that the default smtp port cannot be changed in SharePoint, so I have attempted to set up a new smtp virtual server as an smtp relay. In this, I've enabled TLS, and set the default TCP port to 587.

Under Central Admin -> Operations -> Outgoing Email Settings I already set up the correct configuration - I think:

To test this I'm using a program created by Rodney Viana. This reports "Email has been sent successfully via SharePoint", but I don't receive it.

  • Outbound SMTP server - IP address of my smtp server
  • From Address - administrator@foo.com
  • Reply-to Address - blank
  • Character Set - 65001 (Unicode UTF-8)

Any ideas?


This seems kinda "dirty" but it works.


Basically setting up a proxy for sending mail, pointing SharePoint to the proxy (standard port), and allowing the proxy to relay to the correct destination port.

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  • Yeah when I read this I was thinking a smtp proxy, it's the only real way. – Hugh Wood Nov 16 '12 at 11:21
  • This is the setup I have already tried (except that my SMTP server is running on a separate physical server). This may or may not be the problem, I can't tell. I will try installing an smtp server on the sharepoint server. – Black Knight Nov 16 '12 at 21:26
  • I also notice that the blogger in your linked article failed to get TLS working. Ideally I would like TLS to be enabled. Thanks for the link anyway - I'll try following it step by step. – Black Knight Nov 16 '12 at 21:26
  • The link is broken now. – bgmCoder Nov 30 '15 at 21:15

I tested and you are right with the TLS issue.

HOWEVER enter codeplex proxy solution

Does what it says "SMTP Proxy for GMail and Windows Live Mail/Hotmail"

Worked perfectly for my email alerts on my test server, while testing it.

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  • Looks nice. I'll try it. – Black Knight Nov 22 '12 at 14:06
  • I just CANNOT get this to work. I get "No connection could be made because the target machine actively refused it" where is my sharepoint server and where SMTPProxy is running. – Black Knight Jan 27 '13 at 20:41

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