Office 365 Smtp Server For Scan To Email – After migrating to Office 365 (Exchange Online), users complain that they stop receiving an email from a fax machine located in the organization’s Office.
You begin investigating this problem and recheck the fax machine settings. Everything looks fine and yet emails sent from the fax machine are not reaching their destination. Mmmm… what happened?
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The little thing we forgot is that until now Mailable DevicesApplication was configured to connect the local Exchange server.
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Before we can restore the ability of this email-enabled application to send email to organization recipients (located in the cloud), we need to overcome some “hurdles”. Fear not, there is a solution!
The current article is the third article in the series of articles dealing with the requirement to send mail through Office 365 mail services.
In the previous article, we described a scenario where we address Office 365 mail services using the MX record that represents “our mail server” in Office 365.
The downside of this method is that this configuration is configured as insecure and has built-in limitations such as not being able to email the external recipient or apply the “send on behalf” option.
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The “workaround” to this shortcoming and the preferred method of connecting the Office 365 email infrastructure is to use a secure communication channel based on the TLS protocol and the need for the email client to provide user credentials.
The main challenge we face is that in a scenario where the “email client” is a hardware device like a scanner or printer or a certain software, many times that “email client” does not support the mandatory need to establish a secure channel communication using the TLS protocol.
In this case, the solution is implemented using a broker or intermediary, which is described as a mail relay.
In the current article, we will look at how to use the built-in SMTP server present in Windows Server OS – IIS SMTP server.
Configure Office 365 Smtp Relay
In a scenario where LAN mail clients (devicesapplication) address an internal mail server, the basic assumption is that the LAN environment is considered “secure” (isolated from the external network).
For this reason, typical signs of communication between mail-enabled devices/applications and the local mail server are:
In an email flow scenario in a public network such as the cloud (Office 365 mail services), the communication channel characters are based on different assumptions – the communication channel – the communication channel between email-enabled devices/applications and Office mail 365 Services are created over a public network infrastructure (untrusted environment).
For this reason, the best practice from a security point of view is the need to create a security mechanism that allows emails to be sent through the Office 365 email infrastructure in a secure manner.
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The “translation” of “secure mode” is the implementation of an encrypted communication channel + the need for the Office 365 email infrastructure to recognize the “element” (mail-capable devicesapplications) connecting to it and requesting email services.
This scenario is email-enabled devices/applications that have the ability to address the Office 365 email infrastructure “directly” by addressing the Office 365 devices that represent the Exchange Online email services available to email clients.
In order to address the Office 365 email server – smtp.office365.com using a secure communication channel, email-enabled devices applications must be able to communicate with the TLS protocol + provide credentials for Office 365 users who have an Exchange Online mailbox.
The third scenario is a situation where we want to enable email enabled devices applications that address the Office 365 email infrastructure using a secure communication channel.
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Since email-enabled devicesapps don’t support the mandatory requirement to use TLS + authentication, we need to use an intermediary to act as a “logical link” between the email-enabled devicesapps organization and the Office registry 365 infrastructure (EOP server).
The IIS SMTP server can address the need for Exchange Online’s mandatory requirements for TLS and authentication. In the script, the IIS SMTP server will be configured with two “interfaces”:
In the following sections, we will go over all the settings and prerequisites that we need to implement in order to use IIS SMTP as a mail relay server.
The credentials that IIS SMTP uses to communicate with Exchange Online can be any validly licensed Office 365 user credentials (Exchange Online Mailbox license).
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You do not need to purchase a “discovered” license for this purpose. The only “problem” we have to look at with the recipient name (the Office 365 users we use to authenticate to the Exchange Online server) is that every message sent to the Exchange Online server defaults to that recipient name in the field from.
For example – if we configure the IIS SMTP server to use the credentials of an Office 365 user named John, each of the email addresses sent from a Mail-enabled DevicesApplications LAN to other Office 365 recipients will be accepted from the destination recipient as an email address sent by “John.”
Later we will look at the scenario where LAN Mail Applications enabled devices use different email addresses and how to enable IIS SMTP to send email “on behalf of” that host.
To allow the IIS SMTP server to establish a communication channel to Exchange Online, we need to create an outbound rule in the organization’s firewall that allows IIS SMTP to use TLS (Port 587 or Port 25).
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To find your Exchange Online server name information, use the instructions below
In the next section, we will demonstrate how to install the IIS SMTP server on a Windows 2008 server.
(There is no option to manage IIS SMTP using the “standard” IIS 7 management console). We can find IIS 6.0 Manager under Administrative Tools ->
In the next section, we will go through all the necessary settings to configure the IIS SMTP server as an “SMTP relay”.
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The first part relates to: the settings for the interface or “IIS Leg” serving the LAN hosts (mailable devicesapplications).
The “relay” settings used to configure the IP address of: Email-enabled devices/applications that will communicate (mail relay) to the IIS SMTP server.
The Help Desk application is installed on a workstation with IP address 10.100.102.2 and a fax machine using IP address: 10.100.102.3
To allow this host to send (forward) mail to the IIS SMTP server, we need to add this IP address to the “allow list”.
Smtp Relay In Office 365 Environment
In the Relay Restriction window, add the IP address of the mail-capable devices/applications that will communicate (relay mail) to the IIS SMTP server.
Note – Make sure you only enter the IP addresses of email enabled devices/apps you trust. This setting allows mail originating from these sources to be forwarded to any destination. In effect, this makes the local server running IIS an open relay.
Note – You can read additional information about relay settings in the next article – SMTP relay in Office 365 environment | Troubleshooting scripts | Part 4#4
In this section, we will create the necessary settings to allow the IIS SMTP server to forward email messages to the Exchange Online server.
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In the Outbound Security window, set the option: TLS encryption (to create a secure communication channel in Exchange Online).
(Make sure your organization’s firewall will have the outbound rule allowing the IIS SMTP server to use this port).
Note – if you need a reminder on how to find your Exchange Online server name, read section: 3. Exchange Online Host Name
The Fully Qualified Domain Name section is not a mandatory requirement. You can add the FQDN of the IIS SMTP server.
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After creating the necessary setup for IIS SMTP relay, we need to solve the additional problem which can be described as Enable IIS SMTP relay to send mail for another email address.
One host is a Helpdesk application using the email address: [email protected] and the other host is a fax machine using the email address: [email protected]
If this host tries to forward mail to the IIS SMTP server, this message will be rejected by the Exchange Online server because: by default, a recipient (in our example: [email protected]) cannot send messages “on behalf of” another recipient (in our example: [email protected] and [email protected]).
The good news is that we don’t need to create a user account and mailbox to “impersonate” these hosts, which will forward mail to the IIS SMTP server.
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To enable the IIS SMTP server to send mail for this host, we can choose one of the following solutions:
This solution relies on creating a distribution group for each of the hosts that need to forward email to the IIS SMTP server.
The next step is to: grant “Send as permission” for the recipient that the IIS SMTP server uses for authentication (in
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