First, you’ll need to open the Properties of the Default Virtual Server.The SMTP Service is administered by opening the Internet Information Services 6.0 Manager application in the Administrative Tools. Once the IIS SMTP service is installed, you’ll need to modify a few default settings. The SMTP Service is a Feature which can be added. You can install the SMTP Service on Windows 2008 by opening Server Manager. Once installed you’ll be able to configure all your applications, scanners, etc to use this server without authenticating. Mail to domains not hosted on Office 365 will be delivered directly from the IIS SMTP server to the final destination, it will not pass through the Office 365 SMTP servers. If you install a local IIS SMTP Relay Server, it will be able to route mail to Office 365 or other destinations, such as, , etc. STunnel acts as a bridge for applications that don’t support TLS and/or connecting on port 587. Use STunnel to allow a device or application which doesn’t support #1 and #2 in the requirements list above (Connect on Port 587 with TLS), to connect to an on-premise server over port 25.What we have found is that in most cases the existing applications don’t meet all those criteria or you need to send a higher volume of mail per day, so you then have to look at a couple of other options. In the shared account scenario you would just need to make sure the volume of mail per day does not exceed 1500 messages. That would then mean that you need to create an Office 365 account for each of those devices (if you wanted the From address on the message to be unique) or you could create a single account, with a generic name, which each application could then use to authenticate and send mail as. Let’s say all your applications/devices meet those requirements. So let’s walk through a couple of scenarios. So it’s pretty clear that Microsoft does not want you sending mass mailings using Office 365. The account you authenticate to the relay server with must be the same account as the from the address on the messages you send through the relay.Īnd if those requirements aren’t strict enough, an account is limited to sending 1500 messages per day.The sending application must authenticate with Office 365.The sending application must support TLS.The sending application must connect to the Office 365 servers on port 587.Requirements for SMTP Relay with Office 365 If the answer to the question above is No, your application or device needs to send mail to both people on the Internet and in your domain, then you need to relay mail. Granted it will look a little strange to Forefront that mail is coming from the Internet with a source address of but by adding the IP address(es) of the on premise devices sending mail to the safe senders’ list, you should be able to avoid those messages going to junk or getting quarantined. When the mail comes into Office 365 in this scenario, it will be accepted like other messages from the Internet. No authentication is necessary, no special ports are necessary. You can configure those applications/devices to send mail directly to your MX record in Office 365. If the answer is Yes, then you don’t need a relay server. The question you must ask yourself to determine if you really need a relay is: Do my applications, scanners, etc need to send ONLY to people in my domain? It seems there is some confusion about what actually constitutes a relay, so let’s start off with trying to determine if you actually need to relay with Office 365 and then we’ll get into the options. SMTP Relay with Office 365 is one of the more common questions we get at MessageOps.
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