How To Send Email Using Iis Smtp – After migrating to Office 365 (Exchange Online), users complain that they stop receiving mail from the fax machine located in the organization’s office.
You begin to investigate the problem and recheck the settings on the fax machine. Everything looks good, but the e-mail messages sent from the fax machine do not reach their destination. Ummm…. what happened?
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The little thing we forgot is that, until now, the mail-enabled DevicesApplication was configured to connect to the on-premises Exchange server.
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Before we can restore the ability of this mail-enabled device/app to send mail to the organization’s recipients (which reside in the cloud), we need to overcome some bottlenecks. Fear not, there is a solution!
This article is the third article in a series of articles dealing with the need to send mail through Office 365 mail services.
In a previous article, we described a scenario where we address Office 365 mail services using an MX record that represents “our mail server” in Office 365.
The disadvantage of this method is that this configuration is configured as insecure and has inherent limitations such as the inability to send mail to external recipients or execute the “send on behalf” option.
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The “workaround” for this flaw and the preferred method of connecting to the Office 365 mail infrastructure is to use a secure communication channel based on the TLS protocol and require the mail client to provide user credentials.
The primary challenge we face is that whether the “mail client” is a hardware device such as a scanner or printer or specific software, many times this “mail client” does not support the mandatory requirement of the TLS protocol to become secure. communication channels using
In this case, the solution is implemented with the help of a broker or intermediary, described as a mail relay.
In this article, we will look at how to use the built-in SMTP server that is present in Windows Server OS – IIS SMTP Server.
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In a scenario where LAN mail clients (devicesapplications) address an internal mail server, the basic assumption is that the LAN environment is considered “secure” (separated from the external network).
For this reason, the communication between mail-enabled DevicesApplications and the on-premises mail server has typical signs:
In the scenario of mail flow in a public network such as the cloud (Office 365 mail services), communication channel characters are based on various assumptions – Communication channel – Communication channel between mail-enabled devices application and mail services Office 365 Public network structure (untrusted environment).
For this reason, best practices from a security perspective require setting up a security mechanism that will allow mail to be sent through the Office 365 mail infrastructure in a secure manner.
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“Translation” in “secure mode” implements encrypted communication channels + requires the Office 365 mail infrastructure to identify the “element” (mail-enabled deviceapplication) it is connecting to and for mail services it requires.
The charter of this scenario is mail-enabled devices/applications that have the ability to “directly” address the Office 365 mail infrastructure, addressing the Office 365 entities that represent the Exchange Online mail services available to the mail client.
To be able to address the Office 365 mail server – smtp.office365.com using a secure communication channel, mail-enabled devices applications need to be able to communicate using the TLS protocol + user of Office 365 users Provide credentials that have an Exchange Online mailbox.
The third scenario is a situation where we want to enable mail-enabled devicesapplications in the Office 365 mail infrastructure using a secure communication channel.
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Since the mail-enabled deviceapp does not support the mandatory requirement to use the TLS + authentication protocol, we need to use an intermediary element that acts as a “logical connector” between the organization’s mail-enabled deviceapp and Office 365 Mail. work as Infrastructure (EOP server).
The IIS SMTP server can address the need for mandatory TLS and Exchange Online authentication requirements. In the scenario, the IIS SMTP server will be configured with two “interfaces”:
In the next section, 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 used by IIS SMTP to communicate with Exchange Online can be any Office 365 user credentials that have a valid license (Exchange Online mailboxes license).
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There is no need to purchase a “tracked” license for this purpose. The only “problem” we need to consider regarding the recipient name (the Office 365 user we use to authenticate to the Exchange Online server) is that by default, any message transmitted by the Exchange Online servers will include the name to this receiver from the field.
For example – If we configure the IIS SMTP server to use the credentials of an Office 365 user named John, then any email address sent from LAN DevicesApplications enabled mail to other Office 365 recipients will be accepted. to the destination recipient as an email sent by “John”.
Later, we will look at the scenario where LAN mail enabled devices/applications use different mail addresses and how to enable IIS SMTP to send email on behalf of this host.
To enable the IIS SMTP server to create a communication channel on Exchange Online, we need to create, in the firewall in the organization, an outbound rule that allows IIS SMTP to use TLS (port 587 or port 25).
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If you want to get Exchange Online server name information, use the following command
In the next section, we will show how to install an 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 over all the settings required to configure the IIS SMTP server as an “SMTP Relay”.
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The first part deals with: Settings for the interface or “IIS leg” serving LAN hosts (mail-enabled devices/applications).
The “relay” settings are used to configure the IP address: mail-enabled devices/applications that will communicate (relay mail) with the IIS SMTP server.
Help Desk application installed on workstation with IP address 10.100.102.2 and fax machine using IP address: 10.100.102.3
To enable this host to send (relay) mail to the IIS SMTP server, we need to add this IP address to the “allowed list”.
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In the Relay Restrictions window, add the IP address of the Mail Enabled DevicesApplications that will communicate (relay mail) with the IIS SMTP server.
Note – Make sure you only enter the IP addresses of Mail-Enabled DevicesApplications that you trust. This setting allows incoming mail from these sources to be forwarded to any destination. In effect, this makes the on-premises server running IIS an open relay.
Note – You can read more information about relay settings in the following article – SMTP relay in the Office 365 environment | Troubleshooting Scenarios | Part 4 #4
In this section, we will make the necessary settings that enable the IIS SMTP server to transmit mail messages to the Exchange Online server.
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Select the option in the Outbound Security window: TLS Encryption (to create a secure communication channel for Exchange Online).
(Please confirm that the organization’s firewall will have the necessary egress rule to allow the IIS SMTP server to use this port).
Note – If you need a reminder on how to find the Exchange Online server name, read the section: 3. Exchange Online Server Host Name
The fully qualified part of a domain name is not a mandatory requirement. You can add the FQDN of the IIS SMTP server.
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After making the necessary settings for the IIS SMTP relay, we will need to address an additional issue that may describe the IIS SMTP relay as being unable to send mail on behalf of 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]
In the event that this host tries to deliver mail to the IIS SMTP server, that mail will be rejected by the Exchange Online server because: By default, the recipient (in our example: [email protected]) cannot “to” email. send to the 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, passing mail to the IIS SMTP server.
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To enable the IIS SMTP server to send email for this host, we can choose one of the following solutions:
This solution is based on creating a distribution group for each host that needs to forward email to the IIS SMTP server.
The next step is: Specifying “allow send as” for the recipient that the IIS SMTP server uses for authentication (in ours)
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