MS-203 Microsoft 365 Messaging – Managing Connectors

1. Understanding Connectors

So what exactly are connectors in exchange Connectors are objects that we’re going to create in our Exchange organization that is going to decide what to do when email is flowing inside of Exchange or email needs to flow outside of Exchange. So this is going to have a direct impact on mail flow and what to do with mail that’s coming in or mail that’s going out. We are going to be dealing with our Exchange Connectors both with on premise Exchange servers as well as Exchange Online. Although you’re going to find that there are different types of Connectors that you’re going to be dealing with, whether if you are dealing with Exchange Server on premise or Exchange Online, but essentially they have the same job. All right? The job is to conduct mail flow, what to do with mail based upon certain conditions, certain criteria. If these certain conditions and certain criteria are met, then how is Exchange going to deal with that mail flow? And essentially that’s what your Connector is going to work with here. Okay? When I say conditions, this is not where you’re looking at mail transport.

You’re looking at, oh, is there sensitive information here or is somebody breaking rules or they emailing somebody outside the organization. It’s not like transport rules. This is more about just mail flow based on certain common criteria such as domain names of where mail is going, the IP address of certain servers. If the mail is flowing to what’s called a foreign host, which would be non SMTP, that’s what this is all about, making decisions based on some of the common criteria that you’re dealing with there. So let’s talk about some of the different kinds of Connectors that we’ve got here. Okay, so the first Connector type is going to either be called a Receive Connector or an Inbound Connector. All right? Now if you’re dealing with Exchange on premise, then Microsoft is going to use the terminology Receive Connector. If you’re dealing with Exchange online, microsoft is going to use the terminology inbound Connector. Essentially, both Connectors are going to perform the same job. They’re both dealing with incoming SMTP mail flow.

So when you have an SMTP based email server, a simple mail transfer protocol based email server trying to send email into your Exchange environment, well, a Received Connector or Inbound Connector is going to be the Connector that’s going to handle that. It’s going to be listening for those incoming connections. And then based on certain criteria that we define on the Connector, it decides what to do with that mail from there based on the settings that we’ve configured. Okay, so again, Receive Connector, Inbound Connector, both of these are handling incoming SMTP mail flow. Not form mail flow, but incoming.

Okay? The other type of Connector we have here is called a Sin Connector or an Outbound Connector. So a Sin Connector is the terminology that’s used for Exchange on premise. And the Outbound Connector terminology is going to be used with Exchange Online, okay? Same kind of deal here. Both of these types of connectors are all about managing mail flow, but in this case, going out, okay? This type of connector looks at basically mail flow upon the recipient. So who is the message recipient and how is the mail flow connector configured based upon the recipient? So in other words, if emails going out, who is this going to? Is it going to somebody within Exam Labpractice. com? Is it going to somebody@abccorp. com or Acme Corp. Or Traderesearch or Contoso. com, one of Microsoft’s favorite company names? And based on that criteria, this is going to decide what to do with that email based on this connector. Okay? All right, so then the next connector is called a foreign connector.

Now a foreign connector is all about controlling non SMTP based systems. So if Exchange is talking to a non SMTP based server, you’ve got some third party email servers out there, all that it’s dealing with non SMTP based email servers, then the way that mail flow is going to occur in that case is it’s going to essentially take that mail, that message, and it’s going to write it to a file.

And that file is going to be stored into a drop directory on the Exchange server that the foreign server would communicate with for having this mail delivered. So it’s going to use a drop directory to handle that. Okay? Now foreign connectors are only used with on premise Exchange. You will not have foreign connectors with Exchange Online. Now I will tell you though, that there’s an alternative to foreign connectors, which is a newer way of doing things, which is actually going to do going to be a better solution in a lot of cases and give you a better performance. This is called delivery agents and delivery agent. Connectors.

This is the final type of connector that we’re going to be dealing with and working with in Exchange. Okay? So this type of connector is also for dealing with outgoing mail flow. Not incoming, but outgoing, all right? And instead of writing the mail to a file, it actually uses a queue which is stored in memory, which is going to be a lot faster stored in Ram on the server.

So you’re going to get better performance. And of course, there’s also a few other little features you get with this that you don’t get with the foreign connector. Okay? This is also a connector type that you’re only going to see on an on premise Exchange server. It is not located in exchange online. Okay? So same kind of a rule as far as the foreign connector goes with this one.

All right? So those are your four main types of connectors you’re going to be dealing with essentially whether you’re dealing with Exchange Online or Exchange On Premise. That should give you an idea, a nice little understanding of the different connectors. And of course, we’re going to do some hands on with the connectors and I’ll demonstrate help you get a better visualization of it all.

2. Creating Send and Receive Connectors with Exchange Server

Go to mail flow on the EAC. So we’ll click mail flow. All right. And over here to the right, you’ve got the Receive connectors and the Send connectors. Okay. Now you’re going to notice right out of the gate, you’ve already got some receive connectors that have been set up, all right? And these connectors here are built right into Exchange. When you install Exchange, you’ve already already got a connector that’s going to get you out to the Internet. You’ve already got a connector that’s going to let you talk to other Exchange servers in your organization. So a lot of that’s already been configured for us and we don’t have to go and reconfigure that. You will notice that some of the roles of these connectors will say front end and then some will say Hub Transport.

So Front end is a connector, a received connector that’s going to be interacting with a server or clients on the front end accepting connections to establish a session with those front end servers to relay email inbound. Okay, so Front end is going to interact with other servers to relay email inbound. This is going to communicate with the Internet.

This is going to communicate with your clients. And then you got Hub Transport. Now Hub Transport is going to be communicating with other Exchange servers, okay? So when you’re routing email within your Exchange organization, you’re going to be using Hub Transport to handle that. So the front end is dealing with interacting with clients for receiving email. It’s interacting with other servers like on the outside to receive email while the Hub Transport is within your Exchange organization and dealing with other Exchange servers.

I don’t actually have to create an inbound Internet connection for this Internet connector because I’ve already got one. If you want to edit, you can. If you wanted to create another one, I could click the plus sign here. It won’t let me create an exact duplicate of any of the ones that I’ve got, but I can go through here now and I could specify a connector, all right? And I can specify whether it’s going to be Hub Transport or front end. I can do a custom domain name for that connector. So to receive from a custom domain, I could specify if this is an internal server of some kind. So maybe if this was an intranet email server of some kind, I could do the Internet. I’ve already got one of those, a partner. So this would be to route mail with third party servers.

So in other words, nonexchange, but it’s a third party server. And then I could do clients if I’m interacting directly with clients. Now if you’re interacting with Outlook clients, you’ve already got connector for all. This is for non Outlook clients. So that’s going to be the difference between these different connectors. So I can choose whichever of these I want, I can click next, then it’s going to ask me to specify what the IP settings are for that connector. So if I’m interacting with computers, client computers, or server computers that are going to be sending email to me, I can specify what IP addresses I’m going to accept. I can specify what port I’m going to accept.

It’ll support. IPV four. It’ll also support IPV Six if you want to use IPV Six as well. Okay, so then I would click next. And then at this point it’s specifying remote network settings. If you wanted to specify like a specific subnet that you’re going to interact with, then you can do that right there. You can choose a range of specific IP addresses that you’re going to be accepting email from. And at that point you would click Finish. Okay, all right, let me jump over now and we’ll look at creating a send connector.

Now one thing interesting about send connectors, we don’t have any send connectors. You’ll notice that it’s blank here, there’s nothing there. Now I will tell you that if you’ve done an upgrade and you’ve got like Exchange 2013 in your environment, exchange 2016, and maybe this is Exchange 2019, then you will have some connectors that are relaying email to those other versions of Exchange. That’s if you did an upgrade. In this case, I’ve installed Exchange directly using Server 2019, and I don’t have any connectors, including, I don’t even have a connector that can relay email out to the Internet right now.

So if I tried to send an email out to the Internet, it’s not going to work. So what we’re going to do, we’re going to create a connector that’s going to let us send an email out to the Internet. So we’re going to click the plus sign here, all right?

And then at that point it’s going to ask me to give it a name. I’m going to call it Outgoing to Internet. That is going to be the name of my connector. And then at that point you have kind of the same thing you saw with their seed connector. I can do a custom, I can do internal, I can do Internet, or I can do partner. Now in my case, I’m wanting to relay out to the Internet. So I’m going to choose this option here and then I’m going to click Next. All right, then I’ve got to confirm how I want to send email on this connector. Do I want to use an MX record? All right, a mail Exchange record. This basically means that my email server is going to interact directly with DNS and try to locate the MX record of the server I’m talking to through the domain name.

And then at that point, it would locate the server based on DNS, and then it would be able to send email directly. In other words, my Exchange server is going to interact directly with another email server, whether it’s another Exchange server or whether it’s a different third party type of email server. I’m saying I want to handle it myself. Now there’s an alternative to that. You could use what’s called a smart host. A smart host is another email server on the outside that’s going to handle relaying the email if I want. I mean, I could push this to there are companies out there that will handle the relay of email for you, and they do spam filtering and all of that for you. Of course, Exchange Online can do that as well, but I’m not going to get into all that just yet.

But essentially that’s what a smart host is. A smart host is basically saying, hey, I’m just going to relay the email to the smart host, and I’m going to let the smart host take care of it from there. If it wants to go through spam filtering and malware filtering and making sure there’s not any extra sensitive information in the email, we can actually do that. There are companies you can pay to do that, or you could set your own smart host up, or you can even use cloud services to handle that. But I’m going to go with the MX record option, okay. And then I’m going to click Next, and then I’ve got to specify the address space. So what is going to be the address space for making the decision on how this is going to route to the Internet. So I’m going to click plus sign here.

At that point I’m using SMTP. All right, if I wanted to have a specific record for a specific domain name, I could, but in my case, I’m going to put the star there an asterisk. So that asterisk basically means, hey, everything. I’m going to send anything that’s going on the outside that’s not part of my Exchange organization except the domains. If it’s going on the outside, then this connector is going to basically handle that for me. Okay? All right, so now that I’ve done that, I’m going to click Save, and then I’m going to click Next, and then at this point, it’s going to make me specify which server is going to handle this. Now notice what it says up here.

A send connector sends mail from a list of servers with transport roles or edge servers. So if I’ve got an edge server, I can use that. In my case, I don’t in my little environment I’m in. So I’m actually going to use this server, which is the NYC Ex One server. So we’re going to go ahead and click the plus sign here, and then we’re going to specify the server here. Of course, I’ve also got Exchange server too as well, but I’m going to use Exchange Server One. He is going to be my server that’s going to be relaying email out to the Internet. So we’re going to add him. We’re going to click okay. And we’re going to click Finish. And we’ve now officially created our connector.

All right, so we’ve got an outgoing to the Internet connector. So all in all, hopefully you can see that creating the connectors, receive connectors, send connectors are pretty easy. There’s not too many configurations there you have to worry about. The main thing is with receive connectors, remember there’s already a lot of these built. I mean, if you wanted to delete them all and just build them yourself, you could.

But Exchange has already detected what we’ve got in our environment and it’s already built those connectors for us. And remember, we’ve got these different connectors for the different Exchange servers. So I’ve got to look to if I was dealing with Ex Two, I would also have to set connectors on that also. Okay? These are all just connectors that are for the NYC Ex One server. Okay? All right, so hopefully that gives you a nice little understanding now of working with receive and send connectors with Exchange on premise.

3. Creating Exchange Online Connectors

Let’s now take a look at working with Connectors on Exchange Online. Okay, so I’m on the portal Microsoft. com, also known as Admin Microsoft. com site. And I’m going to go and drop down the show all lips and we’re going to click on Exchange down here underneath Admin Center. So we’re going to click on Exchange and we are now officially in Exchange Online. Now just like with Exchange on premise, we are going to go down to Mail Flow and we’re going to click Connectors. All right. So Connectors, this is going to let us work with Connectors Exchange. And you’re already going to notice that it looks a little different, similar. You get your same way, but there’s a similar concept here. So you’re not seeing the receipt send and receive or any of that. You’re just seeing a little plus sign here. Okay. So I’m going to go ahead now and I’m going to click this little plus sign. All right.

And we’re going to drop down. The option on from is deciding where is the mail going to be from. And this is, as you can see, a different wizard than what we saw with our Exchange on Prem server. If you’ve worked with Exchange on Prem, this is a different looking option that we’ve got available here. Okay? All right. So what we’re going to do is if we’re saying we want to receive mail from our onpremise email server, we’re going to choose your organization’s email server and then we’re going to say to Office 365. So it’s going to tell us that we do need to set up a connector for this, right? All right. And so that’s what we’re going to do. We’re gonna, we’re going to now going to go ahead and select click Next. All right. And then we’re going to give this a name. Okay.

So this is, this is coming from our email server to us in Office 365 Exchange Online. So I’m going to say from on premise Exchange. All right. And it’s going to ask if I want to go ahead and turn it on and retain internal Exchange email headers. Yes, I’m going to leave all that on. I’m going to click Next and then it says, how should Office 365 identify the email server? So from there I’ve got by verifying that the subject name on the certificate that the sending server uses authenticates with Office 365. So basically it’s saying, hey, there’s got to be a name there. And if there’s a name there, then it needs to match, it needs to match a particular domain name. Or I could actually put in an IP address of a server that’s going to talk to it from onprem.

So I’m going to say no, it’s going to match a certificate. The certificate is going to be we’ll say examlabpractice. com. If it has that examlabpractice. com on it, then it is official. And even if you want, you can even do a star dot so that any certificate with an exam labpractice. com name on it is valid. Okay? So we’re going to click next to that and then we’re going to click Save and that is going to create our Connector that’s going to receive from our Exchange organization email server to our Office 365.

OK, now we’re not done, are we? We need to create another connector, right? We need to create a record that’s going to allow us to send email to our Exchange on premise server. Okay? So we’re going to click the plus sign, all right, click the plus sign. And then from this time we’re going to choose from Office 365 to now real quick, before I click on this one, your organization, I want to show you what happens if you click Internet. It tells you you don’t need a connector for that. Office 365 is already handling all that. It has no problem relaying stuff to the Internet. So you actually don’t have to have a connector from Office 365 to the Internet.

But I’m going to go from Office 365 to your Exchange email server, okay? And then we’re going to click Next and I’m going to say from Premise Exchange, that’s going to be the connector name. So we got the same options here down at the bottom. We’re going to leave that alone. We’re going to click Next and then it’s going to ask me, when do you want to use this connector? Only when I have transport rules set up that redirects messages to this connector. So that involves the transport rules for email addresses sent to all accepted domains in your organization.

So that involves your accepted domains and what you’ve done there, or only when email addresses are sent to these domains. So I could specify specific domains and then it would relay them into our Exchange organization based on the domain name. So if I had other domain names I wanted to use that aren’t part of accepted domains, I could do that. But my domain is part of the accepted domains. Examlabpractice. com has already been added as an accepted domain. So I’m going to go with that option and then I’m going to click Next.

And this is where I need to specify my Internet facing email server. So whatever that email server is that is connected to the Internet, or if you’re wanting to relay it to a smart host, if there’s a smart host out there that’s going to handle pushing your email into the environment, then you could specify the smart host. Okay? In my case, I’m going to hit the plus sign here and I’m going to put in Mail Examlabpractice. com because that was the domain name and all that stuff that we had set up with our on prem environment, okay? So that would resolve through DNS to our Internet facing email server that can relay our email in. This could be Edge or Smarthost or whatever. Okay? So I’m going to go ahead and click on save. All right. And then it’s confirmed. That’s the address I’m using.

I’m going to click next. And then here it says, how should Office 365 connect to your email server? Always use TLS. That’s transport layer security. That’s a step up from SSL. If you’re familiar with SSL, connect only if the recipient’s email server certificate matches this criteria. I could say any digital certificate, including self signed certificates, or I could say issued by a trusted CA. So the internet facing email server must of course have a trusted certificate authority. And I’m going to leave it a set to that. So I’m going to click Next and it says, okay, great. You’ve got your connector set up and I’m ready to now click Next. Okay, so the final step here is you’re just going to validate the connector. To validate the connector, it’s going to let you test this out. So you’re just going to click this little plus sign right here. You’re going to put in an email address. You’re going to click OK.

And at that point if it validates, okay, it goes through. You’ve now officially created your connectors. So as you can see, working with the Exchange connectors online, it’s not too different than Exchange. On Prem. You have the same concepts. The wizard is a little different, but ultimately you’re dealing with the same thing. You got to have connectors that are going to control the mail flow from something that’s going to be coming into your Exchange Online organization or going out of your Exchange Online organization.

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