Big Tomato Tech Knowledge Base

Here's how to set up the WP Mail SMTP plugin for your Outlook email. We haven't been able to test this, since we use Google mail, so fingers crossed that it works. If not,  you'd likely have to pay for the Pro version of WP Mail SMTP to connect with Office 365, which is currently about $50/yearly.

1. In your backend admin panel go to WP Mail SMTP on the left menu (https://namiaffiliate.org/wp-admin/admin.php?page=wp-mail-smtp). (replace the domain namiaffiliate.org with your actual website domain).

2. On the Settings, General tab, scroll down until you see the icons for Mailers. Click Other SMTP (last icon) then scroll down and enter these settings:

Host: smtp-mail.outlook.com
Port: 587

Encryption: TLS
SMTP User Name: Your Outlook.com account email (e.g. john@outlook.com)
SMTP Password: Your Outlook.com account password

3. For the SMTP User Name and SMTP Password, this will be from whatever email account you choose to send website notification emails from. You could use officestaff@namiaffiliate.org or you could create a new email account called website@namiaffiliate.org or you could use your own email, although a generic one is generally better than using an individual's email. You might also need to change settings in your Microsoft Outlook Admin panel, to allow this, but try first to see if you can connect/authenticate. Enter the credentials then click Save.

4. Scroll back up and put the email you have chosen into the 'From Email' box, and check 'Force From Email', and then click Save.

6. If your account does authenticate correctly, then send a test email from the WP SMTP Mailer Tools menu (https://namiaffiliate.org/wp-admin/admin.php?page=wp-mail-smtp-tools&tab=test). You should also test a form submission that has a notification (e.g. Contact) to make sure that the Gravity Forms plugin is sending out emails from the email account you've entered in the SMTP plugin.  One note: whenever the SMTP password for the email account you use changes, it will likely break the SMTP Mailer's authentication, so you will need to remember to re-authenticate. This is why it might be best to set up a separate email account only for sending email from your website.

7. Finally, set up or have your IT people set up an SPF Record either in your GoDaddy DNS settings or in your MS Outlook Admin settings for your namiaffiliate.org domain. I think it depends on the kind of Microsoft server setup you have as to where you would do this. The SPF record is an important DNS record which indicates to all mail servers that interact with emails from your domain that your namipbc.org domain is allowed to send out emails from the server that your website is on, and having this will greatly reduce the likelihood of emails from your website, and from your office emails too, being flagged as spam and thus ending up in someone's junk mail. 

Add a new SPF record as follows, but double check with your email administrator for the correct value for the TEXT Value. You must contact support@namieasysite.com to get the IP address of the Big Tomato server your website is on.

Type: TXT
Host: check with us for the correct IP address
TEXT Value: v=spf1 ip4:[check with us for this] include:spfd.protection.outlook.com -all 

TTL: Choose the lowest value