Pfsense Office 365 Smtp
  1. Pfsense Office 365 Smtp Setup
  2. Pfsense Office 365 Smtp Outlook
  3. Pfsense Office 365 Smtp Configuration
  4. Pfsense Office 365 Smtp Settings
This really does eliminate so much of the hassle with using an Office 365 SMTP account to send email. I really think that the app password is kind of hack, it's just another password that can be cracked! We are using Mailjet. Office365 SMTP: smtp.office365.com; port 587 TLS or port 25 without authentication. If you have any other email provider, simply go ahead and google “NameOfYourEmailProvider smtp settings” and you will very likely find it with the first result. So let’s get started with it right away. Setting up pfSense Email Notifications.

Prerequisites:

1- Office 365 Licensed User.

2- Windows Server 2016 OS.

3- Public Static IP (To add to the SPF policy to avoid getting emails flagged as spam)

4- Allow outbound port 587 on your Firewall.



Regardless of Windows Operating system you’re going to install the SMTP Role the steps are the same. You’re going to install the SMTP Server feature from the Server Manager as following:


First Launch Server Manager (Windows 2016) and click on ManageAdd Roles and Features


Next

Click next to choose the installation type, Make sure you choose the Role-based or Feature type of installation

Pfsense Office 365 Smtp Setup

Next select the server where you want to install the SMTP Feature

Click next to head to the next step, The SMTP feature is normally located in the Features page not the role so proceed further by clicking Next

Pfsense

Scroll down in the Feature page until you get to SMTP Server

Pfsense Office 365 Smtp Outlook

Click on the checkbox next to SMTP Server and add the features which will automatically pop up

Click Next

Click Next again, Leave unchanged here

Click Install and you will get your SMTP Server ready


Open IIS 6.0 Manager to Manage your Relay

To setup SMTP server for relay through Office 365 follow those steps:


Set up SMTP

Open Server Manager, select Tools, and then select Internet Information Services (IIS) 6.0.

  1. – Expand the current server, right-click the SMTP Virtual Server, and then select Properties.
  2. – In the IP Address box, specify the address of the server that’s hosting the SMTP server.
  3. – On the Access tab, do the following:


On the Access tab, do the following:

  1. Select Authentication and make sure that Anonymous Access is selected.

Select Connection > Only the List Below, and then specify the IP addresses of the devices that will be connecting to the SMTP server, such as printers.

Select Relay > Only the List Below, and then specify the IP address of the devices relaying through this SMTP server

  1. On the Delivery tab, select Outbound Security, and then do the following:
    1. Enter the credentials of the Office 365 user who you want to use to relay SMTP mail.
    2. Select Outbound Connections, and in the TCP Port box, enter 587 and select OK.
    3. Select Advanced and specify SMTP.office365.com as the Smart Host.

Pfsense Office 365 Smtp Configuration


https://technet.microsoft.com/en-us/library/dn592151v=exchg.150).aspx>


Let’s make a test by creating a notepad file with the following Test

Ref:

Pfsense Office 365 Smtp Settings

https://technet.microsoft.com/en-us/library/dn592151(v=exchg.150).aspx