Hello,

I am using cloudhare machine that has SharePoint 2010 Enterprise SP1. I have configured SMTP server to use gmail to send emails to users. I have test SMTP server to check if it sends emails by dropping an email file in "C:\inetpub\mailroot\Pickup" folder and the email is delivered successfully.

I have configured the SharePoint Outgoing emails as follows:
Outbound SMTP server: Fully qualified name of SharePoint Server
From address: gmail email account that is configured in SMTP

But the emails from SharePoint are not working. Below are the error details:
SharePoint Log Error:
#160002: Cannot connect to SMTP host 'sp2010.spdom.loc'. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.31 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation General 8kh7 High Cannot complete this action. Please try again. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.31 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation E-Mail 7946 Critical Cannot complete this action. Please try again. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.32 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation Runtime tkau Unexpected Microsoft.SharePoint.SPException: The user or users have been added successfully, but there was an error in sending the e-mail message. The server may not be set up correctly to send e-mail. To verify that e-mail is configured correctly, contact your server administrator. at Microsoft.SharePoint.ApplicationPages.AclInv.SendEmailInvitation(EntityEditor picker, String subject, String message)

Event Log Error
#160002: Cannot connect to SMTP host 'sp2010.spdom.loc'. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.31 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation General 8kh7 High Cannot complete this action. Please try again. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.31 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation E-Mail 7946 Critical Cannot complete this action. Please try again. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.32 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation Runtime tkau Unexpected Microsoft.SharePoint.SPException: The user or users have been added successfully, but there was an error in sending the e-mail message. The server may not be set up correctly to send e-mail. To verify that e-mail is configured correctly, contact your server administrator. at Microsoft.SharePoint.ApplicationPages.AclInv.SendEmailInvitation(EntityEditor picker, String subject, String message)

#160002: Cannot connect to SMTP host 'sp2010.spdom.loc'. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.31 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation General 8kh7 High Cannot complete this action. Please try again. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.31 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation E-Mail 7946 Critical Cannot complete this action. Please try again. 56cb14cc-7ec9-4200-8509-74f51586e68f
10/01/2015 01:31:27.32 w3wp.exe (0x0BB4) 0x22E0 SharePoint Foundation Runtime tkau Unexpected Microsoft.SharePoint.SPException: The user or users have been added successfully, but there was an error in sending the e-mail message. The server may not be set up correctly to send e-mail. To verify that e-mail is configured correctly, contact your server administrator. at Microsoft.SharePoint.ApplicationPages.AclInv.SendEmailInvitation(EntityEditor picker, String subject, String message)

If I try telnet command to check if smpt works then i get following results
telnet sp2010.spdom.loc 25
Connecting To sp2010.spdom.loc...Could not open connection to the host, on port
25: Connect failed

telnet sp2010.spdom.loc 587
220 SP2010.SPDOM.LOC Microsoft ESMTP MAIL Service, Version: 7.5.7601.17514 ready

So can anyone point what could be wrong with SharePoint not sending emails?

Thanks in advance.