Email Experts Series: Free Email Infrastructure Tips

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The best things in life are free, and thus we asked a couple of our most savvy email experts to list and explain some of the best free email development features in this edition of our Email Experts Series.

From unsubscribe headers making subscribers’ lives a little easier (helping you reduce your number of spam complaints) to branded links and images to keep your sender reputation completely in your wheelhouse, these are the deliverability tips you need to know today.

(We’ve found key timestamps and transcribed this video below.)


Total Run Time: 15 minutes

00:40 – Overview of the two types of list-unsubscribes, mailbox provider support, examples and benefits of both
03:10 – Differences between a spam complaint and an unsubscribe
04:07 – Encrypting your email in transit with Transport Layer Security (TLS) and its impact on user experience
05:47 – Gmail feedback-ID header for Google Postmaster Tools (GPT)
07:34 – Benefits in security, trust, and reporting in implementing domain-based message authentication, reporting & conformance (DMARC)
10:27 – Unique benefits of brand indicators for message identification (BIMI) as both an authentication incentive and marketing benefit
12:14 – Branding your email’s links and images to reflect your own authenticated domain and control your reputation

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Anthony Chiulli
Hi, everyone. Thanks for joining. My name is Anthony Chiulli, and we’ve got a great topic for you today. We’re going to be sharing some hidden tricks and tips about some free infrastructure items that you may or may not be aware of that can actually help optimize your email program. Joining me today are my colleagues Luke Martinez and Alex Heinz. And we’re going to be breaking down a series of authentication standards and some really cool infrastructure items that can certainly help an email marketer optimize their performance. So why don’t we kick things off and talk about our first topic here. Heinz, why don’t you share a little bit about the List-Unsubscribe header.

Alex Heinz
Yeah, of course. So one of the great things that any marketer can really implement right now is a List-Unsubscribe header. It’s a great way for you to be able to give your subscribers another option of kind of unsubscribing to your email, bowing out without clicking that spam button, having to find your opt-out, all of that sort of stuff. So the nice thing is that you can add it directly to your headers. It shows up in many mailbox providers right at the kind of top of the email there. We’ll see that there’s a couple of different versions that are available right now. First is the mailto version. It’s just essentially you give an email address, somewhere that’s a monitored mailbox that you can have available to process that unsubscribe, or you can have a link. It could be kind of that one-clicky sort of link, or it could be something that goes to your subscriber page or your profiles, like that. So there’s a few different ways to look at it. So as we kind of progress here and look at the different mailbox provider support, you can see that there’s many different providers that do have an option for it. iOS Mail does have mailto. It does not include the HTTP yet or the one-click. But Gmail includes them all. Outlook has pretty limited, just like an iOS. And Verizon Media Group has that one-click unsubscribe, and it has the mailto unsubscribe. So there’s a couple of different options there, but really to cover your bases on a lot of these things, you should probably add in either the mailto or the mailto and an HTTP URL.

So if we progress forward, we can take a look at a couple of these examples and see how that actually manifests when you have it in your inbox, right? So you can see in a couple of our examples, we have the iOS Mail, we have Gmail, Outlook, and Yahoo Mail. And it shows up in pretty similar spots when you’re looking at it. iOS Mail, obviously, has a little bit of a header. Gmail has it kind of to the right of your sending domain. Outlook gives you a little bit of a different option where you can unsubscribe and also manage your subscriptions in that way. And then Yahoo Mail definitely has a little bit more of an interesting view of that. But there’s a multitude of different ways that it shows up in your mailbox, but when it shows up, it’s a really valuable asset for you have and certainly a free thing to add into your system that gives you a lot of value there. So something to note, as we kind of touched on before, obviously mailto has most support out of all of the different options that you can have with List-Unsubscribe. And most postmasters find that the mailto is probably the option to go with more than anything else. It’s the more preferred method.

You can actually have both included in your header as well. But agreed, I think the mailto version is usually the most widely adopted and supported version of List-Unsubscribe. And List-Unsubscribe is one of those things where a mailbox provider is providing a way for customers– for ease of use of removing yourself from your mail. So in fact, it’s a huge benefit for senders because the alternative is complaining about your mail, which is very common and misunderstood tactic of removing yourself from one’s email. Clearly, that one has more of a negative impact on a sender than naturally unsubscribing.

Luke Martinez
When I’ve spoken about this subject with a lot of senders, trying to get them to implement it, and it wasn’t uncommon to get the pushback, “Why would I want to make it easier for people to unsubscribe?” And it’s kind of counterintuitive, but 100 unsubscribes is better for you than a single spam complaint. Spam complaints are the killer. Give people the frictionless way to get off your mailing list, and List-Unsubscribe helps you do that.

Luke, talk to me about this next topic here around a really cool trick and something to be aware of about encrypting your mail and the benefits.

Yeah, yeah. So TLS is a pretty standard thing these days, Transport Layer Security. And it’s really all about protecting your messages, making it so people can’t read your messages. They can’t intercept them in transmission and figure out what’s in them. From a security standpoint, TLS is just– it makes the world a better place because any communication that’s more secure and harder for the bad guys to read in or listen in on, I think that’s a good thing. But from a deliverability perspective, there’s some small bumps that you get. And what we see on the screen here is the red padlock. So if your message is not encrypted, you actually get– if someone chooses to hit this little drop-down, they can tell. They’ll see the red padlock with the line through it and tell it’s not secure. It’s really not a great look for you as a brand to be sending this kind of stuff, especially when a big provider like Gmail is going to surface it like this. If you do it right, you get no red alert. It makes people more comfortable that their messages aren’t being read by someone who shouldn’t be there. One important thing to note about TLS is that if you’re using a commercial email service provider, this is likely something they’re doing for you on your behalf. So it’s not like a switch that you have to flip. You don’t have to ask for it. I think most of them do it right out of the box. If you’re managing your own infrastructure, there could be a little bit more homework and reading to do to get this implemented. But I’d say if you’re like the vast majority of senders using a commercial ESP, you’re probably covered and likely no additional steps required, but it’s certainly a conversation worth having.

As we’re looking at the example here on Gmail, there’s another sort of free-ish infrastructure hack, if you will, that we wanted to talk about. It involves Google Postmaster Tools interface. Google Postmaster Tools, if you’re familiar, is a dashboard where you can go and review your IP and domain reputation, delivery errors, all kinds of different things. What they also have is this Feedback Loop portion that works off of a Feedback-ID header. So as a sender, you can add this Feedback-ID header to your messages. It allows, if you can see it – it’s kind of small on the screen maybe – but you can see it’s a colon-separated string of characters. And each of those values separated by the colons are different identifiers. So you can use it to track your spam complaint rate, your amount of spam complaints you’re getting, not just as a whole for your IP address, but even down to campaign IDs. So it can really give you powerful insight into what’s otherwise a black box with Gmail. You don’t get complaint data from them in the traditional way. Using this header allows you to actually get that mysterious complaint data from the biggest mailbox provider out there and hopefully turn it into something actionable. And again, it’s free to do. Just put the header in there, label your campaigns and your different mail streams accordingly, log into Postmaster Tools, and you should be getting a lot more valuable data for literally nothing.

Yeah. GPT is one of those free third-party tools that marketers can register domains for. A lot of ESPs will help support that. And I’ve found that there’s a lot of information in GPT that marketers tend to gravitate to. And the Feedback Loop complaint data is something that without that ID, it’s– if you have data populating, it’s very hard to tie that back to and focus on what campaign or campaigns did that originate from. Well, let’s shift gears and talk about DMARC, which is an authentication standard that’s been around for quite a long time but, again, another free tip that can certainly add benefit for a sender.

Yeah, absolutely. DMARC, like you said, it’s something that’s been around for a long time. The adoption rate on that is certainly increasing as time goes on, and it’s something that a lot of senders are really putting a lot of value towards. They understand that this is going to give them quite a bit. And really, all it takes is going into your DNS, adding a TXT record in there, and it’s very straightforward. It just has your policy. You tell it kind of what level that you want to have it at. DMARC has three different levels you can start with. You have a monitoring policy, which basically just allows for you to get an understanding of what you’re sending infrastructure really looks like. You can see what kind of mail that you’re sending, how often you’re failing authentication, and who potentially might be using your domains in a way that you really didn’t intend it.

Once you kind of get through that monitoring process and you really have an understanding of your entire ecosystem, you can start to progress that record up to a quarantine record, which just gives you the ability to say, “Hey, if this mail doesn’t pass my DMARC policy, that will all just go right to the spam box.” So essentially, it’s a little aggressive, but not too much, and still gives you time to really work through your data to make sure you’ve got everything locked down before you hit the full reject policy. Reject really puts it in the place where if mail is not coming from you, or if it’s not coming from the standard in which you set within your DMARC policy, it gets outright rejected. So it makes it harder for bad actors to start using your domains in a way that you really didn’t intend, or other people within your organization to use the sending domains that you really care about in a way that you really didn’t predict coming up.

So as we’re looking at the DMARC policy on this screen here, it’s pretty straightforward. It’s got a couple of different values in here that just give you some option to mail your record to you, how much of it you want to apply to it. You can get really deep into it. But if we progress forward here, we can see that there’s a couple of different alignment options for when you’re using DMARC. So DMARC really benefits from giving you the option of saying, “I want to make sure that my SPF record and my DKIM record both have the same policy– have the same organizational domain.” Or you can say that, “I want them to have the exact same domain across the board.” So email.test.com has to be your SPF, your DKIM, and then also in your DMARC policy. So there’s a couple of different ways to go about doing it, and you can set it as a fully aligned. You can keep it as DKIM only, SPF only. But then you can also have your alignment full-on fail. And there’s a couple of different options for it. But keeping everything fully aligned gives you a lot of power and really makes it so that you have a really good, robust understanding of your infrastructure, your network, and really who’s sending mail on your behalf.

So if we go one further here, there’s a newer protocol that’s out that’s gotten a lot of adoption through a lot of the big providers, so through Verizon Media Group, which is Yahoo, AOL, and Verizon, and then Gmail– is BIMI. And what BIMI does is it gives any sender that is using DMARC to a policy of quarantine or reject, and it’s not 100% on quarantine or further through reject. It gives you the ability to brand your emails in a really interesting way that gives your customers a nice little kind of additive when they’re looking through their email lists, and they see something like your sending domain but also gives you your company logo. It has your brand there. It gives a lot of recognition on that. And then, also, it’s just a very simple, straightforward TXT record to add into your DNS, and you’re good to go.

Yeah. It’s a really cool new standard. And what I want to reiterate with BIMI is BIMI and DMARC are related, and you have to have a DMARC policy at enforcement in order to take advantage of BIMI. And so I think for marketers that maybe have not paid attention to this–

A little weary.

–this security type of authentication protocol and really weary, I think BIMI– one of the benefits is it is a carrot. It’s an incentive for marketers and brands to authenticate their mail, fully aligned, and then take advantage of this new powerful marketing impression opportunity in BIMI.

One thing I’ll add with BIMI, too, is you can have multiple BIMI images too. So if you happen to send with two different domains, like you have a transactional domain–

Like a couple mail streams?


Pretty cool.

Yeah, exactly. So you can have your, I don’t know, a security padlock for your password resets, and you can have your standard marketing logo for your newsletter and, yeah, do different kind of tangentially related brands. You can have different logos if you want. So there’s some powerful impression and marketing opportunities if you do BIMI right.

Luke, let’s talk about this last item that we have here in our deck. And that’s branded links and images and why that’s important.

Sure, yeah. So again, this usually costs nothing. It’s something that you can do either in your ESP settings and your MTA settings or however you’re deploying your messages. But the idea behind branded links and images is that you want to control all the domains that are found in your email. If you host your images on a CDN or something, oftentimes those links to those images will point to a CDN. That content network is also used by hundreds or thousands of other people. So you’re kind of indirectly sharing a reputation with anyone else hosting images in that location. If you use link branding or image branding, those become wrapped with your domain. So you can save your images, host them wherever you want, but wrap them as you send them out so that the only domains that appear in your message are your own.

The same thing with all the URLs that are in there. You don’t want your ESP’s domain showing up, and they do that frequently to track clicks. That’s a totally normal thing to do. They need to track how many clicks you get and which things get clicked. But you want that to be your own domain. And it’s mostly about reputation sharing purposes. You don’t want to be– you don’t want your messages to contain the same links that every potential spammer– people abuse ESP systems all the time. Those networks are crowded with mostly good people but some really bad people too. But yeah, branded links are about taking ownership of all the content in your messages. The last quick thing I’ll say, if you have links to third-party websites – like maybe in your newsletter, you’re sharing links to other partners or other websites – if you wrap the links, you’re not beholden to the reputation of those websites that you might be pointing people to because they’re wrapped with your domain. It’s all you. So if you have third-party links, I think this branding thing becomes even more important. If you’re pointing to websites other than your own, wrap them, and then you’re safe.

Well said. There’s many more topics out there that are these free kind of tools and tricks of the trade to help not only alignment, but security as well as deliverability and reputation. And so we encourage you guys to check those out. I wanted to thank both of your for joining me today and revealing some of these tips and tricks. And thanks, everyone, for tuning in and watching. Certainly, if some of these topics are new, I hope that you found it helpful. And if not, then– I don’t know.

It’s a good refresher.

It is a good refresher. Thanks, everybody.





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