When you move all mailboxes to the office365 (“cloud”), the next thing in your task is to migrate the SMTP Relay Service. If you plan to keep your existing on premise exchange server then it can be used / utilized as a SMTP Relay server. Else, if you plan to decommission the exchange server for good, in that case you can utilize Office365 as a SMTP Relay server to relay the emails.

June 19, 2018 Stefan 0 Comments office365, smtp, test mail 1 min read Today I will show you how to test Office 365 SMTP server using PowerShell. It is very easy to check if your SMTP Server is working correctly by simply utilizing PowerShell.

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. After done about 60+ Office 365 migrations, I’ve noticed that almost all customers have Applications, Multi function printers or other devices that send some kind of email to end-users or suppliers/Customers. These devices normally use the SMTP-Protocol. Anyone else using Office 365 for their (Exchange) email and have it configured for SMTP notifications from pfSense? I have tried the settings to authenticate, and I can't seem to get it to work. Any assistance would be greatly appreciated! That said, there is a 'Postfix forwarder' package available for pfSense that may do what you need. I haven't used it (due to the above reasons), so I can't vouch for its functionality or utility. But really, don't do this. Keep running postfix on an internal server. It's trivial to maintain an internal SMTP server for these purposes.

There are three methods which you can use to configure / utilize Office 365 SMTP Relay Service. Any of the given methods can be used to configure the SMTP Relay. However, each one is having a different set of configuration and requirements. I will show you how to configure it using all the three methods. Depending upon your requirement, select the best option and configure it for your Devices like Printers/scanners/Application Servers/Powershell or any other Scripts or Tools which you are using in your environment.

Configuration Options

SMTP Authenticated Submission

Pfsense Office 365 Smtp Settings

Requirements / Important Points:

• Easiest to setup, No extra configuration or steps required in Office365.
• A Licensed Office365 User Mailbox is required (This will be the from address which will be used to send the emails).
• Use this option if you want to send the emails within your organization as well as outside your organization.
• Send the Email from any location or IP.
• SMTP Auth must be Enabled on Organisation or Mailbox Level.
• Device must support TLS 1.2 or above (Please check the vendor documentation to confirm this).
• SMTP Authenticated Submission cannot be used to send bulk email or newsletters.
• Firewall must allow Port 587 or Port 25.

Once you confirm that you are meeting the above mentioned requirements, Go ahead and configure the device to send the emails using below information.

Direct Send Method

How to get a quickbooks validation code. Requirements / Important Points:

• Static Public IP Address of your Device or Server or the Application.
• Firewall must allow Port 25 from Client to Office365.
• MX Endpoint of your domain.
• No Office365 Mailbox is required.

Once you meet all the above requirements and noted down the points. You can start configuration of Direct Send SMTP Relay.

1. You can find the MX Endpoint of your domain from office365 portal by clicking on Setup -> Domains and Click on the your company domain. This will open below page, you can copy the Point to address or value for MX record Type

2. Add Static IP Address of your Device or Server or the Application to SPF Record [Optional]

Let’s take an example: Your Office Public IP Address is 1.2.3.4 and your server or application or printer /scanner is in the office so it will use the Public IP address 1.2.3.4 to go out and communicate with office365. Therefore, include the IP Address 1.2.3.4 in your SPF Record so that your emails are not marked as SPAM.

Note: Well, this is optional but recommended step to perform, and if your emails are landing in the SPAM folder you can configure this.

v=spf1 ip4:1.2.3.4 include:spf.protection.outlook,com -all

3. If your emails are still going into the SPAM folder. Please create a SPAM Bypass rule on office365 for the email ID which you have used to send the email from. Login to Exchange online management portal ->click mail flow -> Rule -> Create a Rule.

Create a connector on Office365

Requirements / Important Points:

• Static Public IP Address of your Device or Server or the Application.
• Firewall must allow Port 25 from Client to Office365.
• MX Endpoint of your domain.
• No Office365 Mailbox is required.
• A Connector will need to be created on office365 for accepting the email from the Static Public IP noted before.

Once A connector is configured then use below settings on the device to configure for SMTP Service.

Well, Mostly its a direct Send Method + A Connector on Office365 which will be required so that you can send the email to external users. Please follow below instructions to create a connector:

• Logon to Microsoft Office365 Exchange Online Portal with admin rights.
• Click on mail flow and then connectors tab.
• Click on + Sign to create a New Connector
• Select From: Your Organization’s email Server and To: Office365
• Provide appropriate name to this connector e.g <companyname> SMTP Relay
• Select the Option “By verifying that the IP address of the sending server matches one of these IP addresses that belong to your organization“
• Add the Static Public IP noted earlier.
• Click Save to Save this connector.
• Its [Optional] but recommended to add this Static Public IP Address to your SPF Record.
• If your emails are still going into the SPAM folder. Please create a SPAM Bypass rule on office365 for the email ID which you have used to send the email from. Go to mail flow -> Rule -> Create a Rule.

Pfsense Office 365 Smtp Configuration

References:

Check SMTP Auth at organization level

Check SMTP Auth at Mailbox level

In my case you can see its blank, That means this setting is controlled by the corresponding SmtpClientAuthenticationDisabled parameter on the Set-TransportConfig cmdlet for the whole organization.

External Links: Pdf xchange editor v6 serial key.

Pfsense Office 365 Smtp Setup