Configure Outgoing E-Mail Settings for SharePoint 2010 / 2013 to using Office 365 or GMail Relay

Any SharePoint Client, User, or Developer need an SMTP server to send e-mails to Internal or External SharePoint site users from a Workflow, Alerts, Request Site Access, and/or Any custom Apps that use SharePoint Outgoing e-mail setting to send e-mails.

SharePoint cannot be configured to send e-mail over encrypted port to the e-mail service. And Office 365 and Gmail required an SMTP connection that supports TLS encryption .

Fortunately, Windows Server (2008-2012) supports an SMTP relay for Office 365 and Gmail by install a local SMTP Rely Server that supports an encrypted connection (over TCP Port 587) .

The Steps are easy and forward:

1. Install SMTP Role (Windows Server 2008 and 2012)
2. Configuring SMTP Service to Relying to Office365/Gmail SMTP
3. Testing the SMTP Service Connection
4. Configuring Outgoing E-Mail settings in SharePoint Servers
5. Test Sending an E-mail from SharePoint Site

The following is the detailed steps:

Install SMTP Role

Windows Server 2008

1. Open Server Manager and select Add Roles and Features.

2. On the Select Features screen, choose SMTP Server. You may be prompted to install additional components. If that’s the case, select Add Required Features and select Next.

3. Select Install

Windows Server 2012

1. Open Server Manager and select Add Roles and Features.

2. Select Server Selection and make sure that the server that will be running the SMTP server is selected and then select Features.

3. On the Select Features screen, choose SMTP Server. You may be prompted to install additional components. If that’s the case, select Add Required Features and select Next.

4. Select Install.

---

Configuring SMTP Service to Relying to Office365/Gmail SMTP

1. Open Administrative Tools > and Click on Internet Information Services (IIS) 6.0
2. Start SMTP Service by Expand the current server, Right-Click the [SMTP Virtual Server #1], and then select Start

   

3. Right-Click the [SMTP Virtual Server #1], and then select Properties
   

4. In Properties window, Click on Access tab
5. In Access tab, Do the Following
   • in Access Control, Click on Authentication button
     
   • Make sure Anonymous Access is checked, and click OK button
     
   • in Access tab again, Click on Connection button
     
   • Select which servers can connect to this virtual SMTP server, by default it is set to accept all. But we need to granting only localhost (127.0.0.1) access and all SharePoint Servers that will send emails using local SMTP server, this will limits only the server itself the ability to connect to the SMTP server. This is a requirement for security.
     

   • In Access tab again, Click on Relay button
     

   • Select which computer can relay through this SMTP, only allowing the localhost IP address (127.0.0.1) and all SharePoint Servers that will send emails using local SMTP server a relay permissions and it means that only the SMTP server itself can relay mail. This will prevents other computers on the internet to use your SMTP server and send spam emails which will lead your SMTP server to be BLACKLISTED
     

6. Now go to next tab, Messages tab, and change the limit message size to 10 MB. Then enter the email address where copies of non-delivery reports are sent to.
   

7. Go to next tab, Delivery tab, and do the following:

   1. Click on Outbound Security and enter the mail account credentials that will be used to send messages.
      

   2. Select Basic Authentication, and enter the Gmail/Office 365 account username and password, and make sure to select TLS Encryption checkbox. Click on OK.
      

   3. In Delivery tab again, click on Outbound Connections. We need to tell the server to use TCP port 587 when attempting to connect to Office 365/Gmail
      

   4. Enter the number 587 in TCP port textbox, then Click on OK
      

   5. In Delivery tab again, Click on Advanced button
      

   6. Here you will provide FQDN name of your domain and smart host, set the smart host to (smtp.office365.com) for using Office 365 SMTP, or (smtp.gmail.com) for using Gmail SMTP. Finally, clear the option to Attempt direct delivery before sending to smart host
      

Click on OK, and Apply changes. This completes our SMTP level configuration
 

---

Testing the SMTP Service Connection 

1. Create a Notepad file and enter the following
   

   To:username@outlook.com
   From:username@TempDomain.onmicrosoft.com
   Subject: Test E-Eail SMTP Rely
   
   
   
   
   This is a test email sent from my SMTP server (Office 365/Gmail)

2. Save the Notepad file as email.txt
3. Navigate to C:\inetpub\mailroot\Pickup
   
4. Copy the email.txt from the desktop and paste it into the Pickup folder. It should disappear and send the email.
   
5. Confirm the the Queue folder is empty (no stuck emails) after sending the message, and you have received the test email.
   
6. Office 365 rely email message
   
7. Gmail rely email message
   

---

Configuring Outgoing E-Mail settings in SharePoint Servers

1. Go to Central Administration –> System Settings –> Configure Outgoing Email Settings
2. Enter the FQDN of the local SMTP server (Mail.Dev.local)
3. Enter the From and Reply-to Address, and Select Character set, click OK to save settings.

   

4. Go to IIS manager on each SharePoint server, and select Server node from IIS, Right-Click on SMTP E-mail Icon, the Select Open Features
   

5. Make sure you enter and select the following:
   – Select Deliver e-mail to SMTP server
   – Enter FQDN of the mail server (Mail.Dev.Local)
   – Port number: 25
   – Authentication Settings: Not Required
   

6. Click on Apply, and Reset the IIS (CMD –> IISRESET)

---

Test Sending an E-mail from SharePoint Site

In SharePoint Team site, I enable E-Mail Notification when a task assigned to user in a Task List

So, I create a new task and assigned it to me, and waiting to receive the task notification email

I receive the Task notification email successfully and it is works great

I hope this is will be useful for you