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So What? Fixing Up Email Deliverability

So What? Marketing Analytics and Insights Live

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In this week’s episode of So What? we focus on setting up the right tools within Hubspot and Gmail for the best and most efficient email deliverability.

So What? Fixing Up Email Deliverability


In this episode you’ll learn: 

  • How to set up SPF, DKIM, and DMARC for your Hubspot instance
  • How to test your implementation with email tools
  • How to monitor your email deliverability with Gmail Postmaster Tools

Upcoming Episodes:

  • TBD


Have a question or topic you’d like to see us cover? Reach out here:

AI-Generated Transcript – Note that this is machine generated and may not be entirely accurate according to the recorded dialogue:

Katie Robbert 0:31
Well, hey everyone, Happy Thursday. Welcome to SWOT the marketing analytics and insights live show. I’m Katie joined by Chris and John. Hey, guys!

Christopher Penn 0:39

Katie Robbert 0:44
We’ve been talking a lot the past few weeks months about generative AI. And we also we wanted to sort of step back from that just this week. Because it’s not the only thing going on in digital marketing, if anything is overshadowing everything else. And so we wanted to acknowledge that there’s more to digital marketing and what’s going on in the industry than just generative AI. So this week, we’re talking about fixing up email deliverability. We’ll talk through how to set up your SPF D, K, AI, M, and D mark for your Hubspot instance. Got it? How to how to test your implementation with email tools and how to monitor your email deliverability with Gmail postmaster tools. So this came about as a question that Chris was working on with a community member. And it sort of struck us that Oh, right. You know, this sort of the digital marketing, different channels become second nature to us. But we also want to remind everybody that there’s other things going on in digital marketing. And so, Chris, you want to give a little more background to what’s going on with this email deliverability question. And where do we want to start today?

Christopher Penn 1:55
Absolutely. So for those who are Hubspot users, you got to notice in mid November, saying, hey, starting in February 2024, aka next month, Google and Yahoo are tightening restrictions on what you need to have in place to get your email delivered. Yahoo’s got a big announcement over on their website, Google’s got their announcement. But it basically boils down to three things. One, click unsubscribes authentication with protocols and then establishing a demark policy. So let’s, before we jump in, let’s do a quick recap. Spam has been a problem for a really long time with email is it’s one of the oldest challenges out there. And these protocols exist to essentially tell email companies like Gmail and Yahoo, hey, we are who we say we are, right? When you get an email from us, it really is from us. It’s not from some spammer pretending to be us. And to do the implementation, well, you’re going to need a few different ingredients, you’re going to need, obviously, your Hubspot instance, you will probably need, you probably need to talk to someone in it. If you have an IT team. If you don’t, that’s fine, you will need access to your DNS settings. So DNS domain name system is when you buy a domain name, you will typically get a control panel with your vendor. Or you can use third party service like Cloudflare that allows you to make changes that tell the servers around the internet, how to find you how to find your company’s website, your email, and so on and so forth. You will need a text editor also as well. And you will probably want some coffee with a caffeinated beverage of your choice.

Katie Robbert 3:36
I mean, seriously, you’re rattling off these things that I’m like, wow. I’m so glad I have a Chris Penn on my team to handle this stuff, because I’m already lost.

Christopher Penn 3:43
Yep. So SPF set stands for Sender Policy Framework, it is a text string that is in your DNS that says hey, here’s places we are sending email from. Right. So I’m gonna go over. So Trust Insights, we use a company called Cloudflare. There’s a free plan, we’re on the free plan that you, you sign up for it. And then you tell wherever it is, you bought your domain name, hey, I’m using Cloudflare. Now they have to have a sign up steps to migrate over to this system. I like this because I just like having everything in one place. But it doesn’t matter. Any place that you’ve bought domain name, you have the ability to make these changes. I just find Cloudforest first implementation easier. What these records are when you hear D SPF and DKIM and DMARC. They’re just text strings that gets attached to your domain name that say, Hey, here’s we are so I’m going to pull up just open up the edit box here for actually let’s go with our SPF record first. You can see it’s just a piece of text and this piece of text says here’s how here’s where we’re sending email from. So let’s start with your Hubspot instance itself. In Hubspot, they actually provide some very good Huh documentation on how uses demark policy how your SPF record and how you set up Deacon. Within your Hubspot instance. If you just go to the settings in your hub, you click your icon go to Settings, go down to website domains and URLs in here, you can start by connecting your domain so I’m gonna go ahead and click on connects domain and we want to do an email sending domain so this is not you know for your landing pages stuff this is for email sending. Now I will also caveat we are only on Hubspot sales. We do not use Hubspot marketing. I believe Hubspot marketing got you there’s more options. But either way you want email something it will ask you give us an example. email is an email address that you send email from. That’s all put in our Client Services email address. And it says your email comes from this right? That is correct. So it says it essentially goes through and does a connection and will show up here as a connected sending domains. This takes care of the domain key identification protocol D Kim. Right. That’s pretty straightforward for getting that connected. The next thing we have to do is we have to adjust the SPF record. Hubspot will give you a hint about how to do that. If you click on Advanced Options, bottom is SPF record. Just hit copy on that. And now pull up your text editor.

Katie Robbert 6:28
I noticed on that Chris, it actually said setting up an SPF record is optional. It sounds like based on what I’m hearing you say is it’s really not optional to have really good email deliverability and hygiene. Correct.

Christopher Penn 6:43
And with SPF in particular. So demark is is a newest protocol, it’s nine years old SPF, I want to say like 15 years old. I mean, these things have been around for a while. The reason why marketers don’t know about them is because it’s largely the provenance of it right? Not to cast aspersions on our marketing brethren. But most marketers should not be monkeying around in their DNS. Because you can do very bad things like remove your site from the intranet.

Katie Robbert 7:11
You know, it’s funny you say that I’ll tell a quick anecdote while you’re getting set up. When I worked at when I was the product manager at a company. Our developers gave us instructions to edit our DNS files on our computers in order to switch the different environments that they were developing on so that we could see things on staging and on production, you know, one versus the other. And they were basically just loosely giving out these instructions, saying like, Oh, you just do this, and you change your local host file and you do this, that and the other. And it was so dangerous looking back because given into the hands of people who had no idea what they were doing, and it did cause a lot of chaos, they spent more time fixing people’s DNS files than they did actually developing. So just as you know, Chris is making a good point like just Don’t monkey around with your files if you don’t know what you’re doing,

Christopher Penn 8:05
Or as as the kids say F around there, find out the poor policy. Okay, so SPF records. The easiest way to build them is with one of the many many many many free wizards that are available on the internet. I happen to like MX toolbox, but you can google SPF Wizard and find the tool of your choice depending on on what is easier for you

John Wall 8:37
Need to veto that Chris recommends MX toolbox use MX toolbox. You know, there are many Russian sites that would love to mess with your record. So go with what Chris has proven.

Christopher Penn 8:51
So SPF West wizard asks things like do you send email from your web server? Write it nowhere. Yes, you specify this? Do you send email from the same server in your MX records? So this question means whatever it is system that you use to send email, your MX records do you send email from that same service? In this case? For us we do we use Google Suite for businesses. So that is the domain that we send email from any any other server hosting or domain that delivers email from your domain. So if you use Marketo or Pardot, or whatever, Hubspot, etc, you would put that in there for now we don’t want to do we don’t want to leave Phil edit because we copied this directly from Hubspot. So we’re going to, we’re going to leave that here and says Enter your domains, IP address range, and your ipv6 address range. So wherever your domain is sending email from if it’s a dedicated server, the other than Google, Google suite or Microsoft Outlook, you know, office 365, whatever this is it It’s something that if there’s a physical box that you administer that would information would go here. And then you would have third party systems like Google, etc. And then for the, for the strictness, start with neutral. What it has done is that it unfortunately, it’s already pulled our existing record. So this is not what the average person is going to say. Let me show you how would format this. So initially, you had the V SPF one. And then there’s our Hubspot record. Right. You’re also if you go to your email service providers, documentation for for Google Suite, for example, you have Google’s which is, which is this one here for for G Suite. And you basically start gluing together your SPF statement, any other services that you send from so for example, with us, we do send email from Amazon, right, we sent email from Amazon Simple email service, we use the modoch marketing automation system, and Amazon has our back end. So this is another really important point. You probably, if you have an IT department, if you have an ID, it thing you absolutely positively should be talking to them about like, hey, what systems do we use? And or talks about, hey, what about? Oh, I don’t know. Can you help with this? Because there are some teams incorporated to you like you were not, you know, you’re gonna you’re not gonna touch this.

Katie Robbert 11:43
So if I understand at a high level, what this SPF string, this text is meant to say. It’s basically saying, verify that it’s Trust Insights, when you get the at trust e mail, and it comes from one of these various domains from this range of IP addresses.

Christopher Penn 12:10
That’s correct. So if an email comes from this Hubspot domain, this Google domain, this Amazon domain, or these IP addresses, these IP addresses are from our website, we host on WP Engine. So we have their domain ranges. SPF is saying yes, you’re legit, I will let this email through because it meant when the email comes in, it matches these records. That’s That’s what SPF does. It is important to have any place that is sending email on your behalf. Right. So I saw last week, I was looking at the website for an upcoming conference. And they’re like, Oh, you need to whitelist our domain because for some reason, our emails are not getting through to people, I look at them, like you don’t have your mail service in your SPF records. So everything you send is being interpreted as spam. Like that’s you’re telling everyone you are you are the biggest spammer.

Katie Robbert 13:09
Well, and it’s just sort of go back to the instruction from Hubspot. And it’s saying that this setting up your SPF record is optional. My sense is that this is probably the root of a lot of companies deliverability issues. And this is the step that’s often either skipped or not known that they need to do because of instructions like this is optional.

John Wall 13:34
Exactly. Yeah. Another way to I’ve seen this botch now is people are at this point here, and they’re only concerned about their own department. So you set this up, and you don’t realize that oh, customer service, those tickets actually come from Zendesk. And so if you set this up, and you haven’t talked to other departments about what services they’re mailing email from, you could inadvertently send all the customer service requests into spam and totally kill that. And so one workaround for that is that’s why you’ll see a lot of companies have like, customer service at at, you know, customer service dot Acme, or whatever, have different domains so that if other departments are messing with this, they’re not telling their stuff.

Christopher Penn 14:11
Yep, exactly. And that really raises a good point. If you have a male is a male subdomain, it will probably have its own SPF records, which should because one of the one of the problems, what things it’s best practice for larger corporations is your marketing emails should come from separate subdomain and then your customer service emails because of marketing misbehaves and gets, you know, crap listed. At least your customer service and transactional emails will still get through. Okay, so we’ve got our, I’m gonna go ahead and copy in our record here. So this is this is our current record. I’m just going to expand on this a bit. We’re at She’s going to make a change to our record. You’ll notice it says include Hubspot Hubspot gave us this very specific include, and we’re going to replace that in ours. And the reason for that is, you don’t want other people with Hubspot instances pretending to be you. So we’re going to swap this one in, it’s going to take this whole string. Now in your domain name system. If this record, were not here, I would say we’re going to add a new record, the type of record is a TXT record. Right. And then from there, from there, you’re going to choose your domain name as your as the name of it. So trust And then the content is that SPF record, I’m gonna hit cancel here, because we already have this, you don’t want to double up records. But I am going to replace our current content with that change to the Hubspot one. I have the time to live set to two minutes, which means that every two minutes, it’s going to go through the worldwide DNS servers, we’ll take a look at and say, Hey, has that changed. So if you had the set to say, five hours, for example, if you make a change, this record will take five hours for that to propagate around the internet, but set to two minutes it will do its thing. If you’re using a service like CloudFlare, there’s a good chance you can just use auto I just chose two minutes because I want things to be updated sooner rather than later.

John Wall 16:28
Yeah, right. Remember that? That’s not how fast do you feel it should propagate? It’s when it hits the fan, how fast you need to be able to clean up. If you’ve screwed up and set that to a day and you screw something up, now you have to wait a day for it to fix but by keeping it down at two minutes, hopefully you’re gonna get a life raft faster.

Katie Robbert 16:49
Chris, we have a question regarding what you’ve been talking about. So when I am setting up my domain for emailing and Hubspot, it is asking me to update my DNS records. Is that going to mess up? Me getting my email through Gmail?

Christopher Penn 17:04
So that’s a good question. receiving email is different than sending email. So for sending email, the SPF record update, which is what we’re doing now is the primary mechanism that you are going to work on, you will also notice the in or should note in your DNS, there are things called MX records. This is the mail exchange records. These are the receive email. So again, we use Google Suite. So you can see that we have five different MX records here that say, Hey, when email comes into the trust domain, where should that email be routed to? And we have essentially Google’s five different servers they told they tell you to when you’re setting up Google’s Google work workspace. So when you update your SPF record, as long as you don’t touch your MX records, there’ll be no change from how you get email today. Okay, so that’s SPF. And if you do it right, then it’s loaded. Just one line of text goes in your in your record. So we’ve done DKM from inside Hubspot itself. We’ve done SPF, now we need to go and do our demark record. The demark record is a third protocol. So demark is, again, it’s another authentication mechanism that says, hey, when email comes in, verify it’s from us. Again, do your do Google search for the demark wizard of your choice. I like to use the D Marcian. D Marcian is a company that provides demark services. I don’t use their services, I just use the wizard because it’s a pretty easy wizard. So the wizard, pretty straightforward. What email Do you want to create a record for? Let’s do trust Before you do a demark record, you must must must have SPF and decam done. It is reliant on those two protocols. So you cannot do this first. Alright, what kind of policy? Do you demark policy record you want? So one of the things that demark does is it specifies where questionable email should be sent. Right. So there’s three settings is permissive quarantine and reject. In general, people should start with collects data. However, one of the things that was discussed in in both the Yahoo and the Google statements was they may be looking for less permissive demark implementations. They want to see demark implantation period. So you’ll start with collect data. Eventually, you’ll probably move to quarantine. We actually ran into issues with this with QuickBooks. So at one point Katie was sending out an invoice from QuickBooks and it didn’t match our demark records. And so those invoices just went to double black holes. And we fix that by adding QuickBooks to that. Yeah, record centers.

Katie Robbert 19:58
Right. So you definitely don’t want that to happen. You Want your invoices to go out on time? To the recycle?

Christopher Penn 20:03
Exactly. Which again, is one of those things where having your administrative email separate from your marketing emails? It could be a good thing. Okay, where do you want your aggregate reports sent. So you need a working email address to put in here that will receive emails from ISPs that will say like, Hey, this, this is what we see. Again, this has to be a working email address. And I strongly recommend if you have, if you have the time to do so set up a separate inbox, because the amount of email you get is gargantuan. So we use the Trust Insights, we have a newsletter mailbox for this. And just to give you a sense, real quick here, let me close my sidebar here. That’s where you get hundreds of notifications per day, in this inbox, and what’s in these emails, is essentially log files. So these log files are coming in from the different services like Google and Yahoo, and everybody else saying, Hey, we got this email. Here’s says your domain has a demark record setup. Here’s the return address. So you should probably read this and make sure everything is good to go. I do recommend once in a blue moon checking that make sure it is back to you know, no one spamming audio half but at the same time, you probably want do not want this in your main inbox, or you’ll never see the rest of your inbox again.

Katie Robbert 21:39
I have a question. Excuse me, I remember when I worked at that same company that allowed us to edit our own DNS records, which was in our local host files. Once a week from it, we would get a request to log into a portal that basically had all of we had to manually whitelist and blacklist emails that were coming in through our system. And so basically, you know, because the name of my company, at the time, had two x’s in the name, it often got marked as spam. But then that meant also emails coming into our system. Were getting flagged and quarantine. So we would log into this quarantine system. Excuse me, is that something that do you think companies still do that? Is that very old school? Like, has it evolved? Has email deliverability evolved to where you don’t you shouldn’t be going through a system weekly, to unquote quarantine things?

Christopher Penn 22:37
Oh, no. The companies still do that. Even Google workspace still does that fact, Google workspace, I as a system administrator get messages saying, hey, this thing has this email has been quarantined. I even get notifications about outgoing email saying, Hey, this looks suspicious. John has sent a couple of suspicious looking emails, at least according to Google. And I always have to go into the system say release this, it’s fine. Job. John’s just asking you to hire Trust Insights.

Katie Robbert 23:03
I always mark John is supersystem.

Christopher Penn 23:08
Okay, so let’s put in I’ll go ahead and put in newsletter. Trust as our aggregate report mailbox, do you want to receive individual failure reports? The answer here is no. Unless you are running into deliverability problems where you want to see individual reports. You will still get aggregate reports and they’re big, but the individual reports will give you a report on every single email address that bounces. If you want to make sure that someone in your company never gets email again. This too, yes.

Katie Robbert 23:47
Can I volunteer? I guess the answer is no.

Christopher Penn 23:53
I mean, you’re the boss so or it’s awkward. So do you want relaxed restrict again, start off with relaxed you can upgrade to strict later. What this means is it looks for pass and fails on D Kim and SPF and if it fails either one, then the emails just don’t go through. Do you want a different policy for subdomains? Again, if you’re a bigger company of mail dot trust or accounting dot AI remarketing dot trust You would use separate domains and have different policies for each of the domains to keep them subdomains keep them separate. And what percentage of email Do you want supply to apply to if you’re starting from report only set it to 100% if you’re starting at four, quarantine or reject, start at like 10% to see it just to make sure that nothing has gone wrong. From a governance perspective, if you’re going to make changes like that probably tell people first like hey, this Sunday we’re changing things so if you stop getting email, please let it know.

Katie Robbert 25:00
It seems you know, it’s interesting because like that kind of advice feel so like, oh, no, of course, we’re going to do this 10 times out of 10, that communication never happens. And people come in Monday freaking out that, like, their inbox hasn’t updated for six hours.

John Wall 25:15
Yeah, and they’re doing it on Cyber Monday too always.

Katie Robbert 25:19
it’s never convenient.

Christopher Penn 25:22
Exactly. So here’s our demark record, we’re gonna go back into Cloudflare. And again, as we did before, you can see here we have a single TXT record, the record name is underscore D Mark, here’s our content, which is this, the demark string that comes out, right, so it has, here’s the, here’s the return address. The RS is slightly different than what came out of the wizard, because Cloudflare also allows you to do demark management with them. So I’ll show you that in just a second. But this is demark. The the strictest right now is set to to moderate only. And you can see our our return address, therefore the reports go, so I’m gonna hit cancel because nothing’s different there. So that would be the third protocol to set up. Now. If you’re using any other DNS provider, you know, GoDaddy or whoever, at this point, you’re done, you’ve got your record set. If you’re using CloudFlare, you go to the email, and there’s a demark management panel. This is a this tool is in beta, you can give it a test. And it will tell you hey, here’s an email starts to come in. I just turned this on, like 10 minutes ago. So it there’s nothing here. But as email starts to come in, it will read some of those reports for you, which is super nice. And then summarize and tell you like, Hey, this is what I see happening.

Katie Robbert 26:45
That is really handy. So prior to that, how would you get that information?

Christopher Penn 26:53
You would suffer?

Katie Robbert 26:55
Well, I guess I’m asked, I’m asking the question, because not everyone’s using Cloudflare. And maybe not everyone has the option to turn on features. They don’t have permissions.

Christopher Penn 27:06
I will show you, you get log files every day. And in those log files, you have to go through and parse and read each of the log files and judge the conditions of the log files. They’re all in XML format. So they’re open formats. But they it’s not pretty. Yeah, that does not look like fun. No, it’s not fun. That’s why they’re like there actually are companies that will just do this for you. They were paid services in the past. Now, obviously Cloudflare is offering it as part of their free package, which is which is really, really nice. Okay, so you’ve now gone through and you’ve done SPF, DKIM, and demark. And you’ve set them up for your Hubspot instance, while not blowing up all of your other existing email infrastructure, which again, I I can’t say that enough, you got to work together with with other other teams if you have them. The last thing you want to do is you want to make sure that you have access. And again, you may have to work with it if you work at a large organization to Google’s postmaster tools, Hostmaster tools, and we’ve done the last few on the in the past on this, but it’s probably worth revisiting is a free service from Google go to postmaster that You will have to authenticate your domain, you’ll have to verify that you are an authorized administrator of your domain. It’s a relatively simple process. And then you get access to love the control panel that tells you these are the seven things you for authentication, authentication, this is one thing where Google is a little weird. And there are multiple warnings about this from Hubspot from Mailgun from all these companies, whatever reason Google always shows SPF as a soft fail, and we don’t know why. But it is. So if your SPF in postmenstrual shows a zero don’t panic, as long as the record is there. And again, you can use use MX toolbox to validate the record is okay. That you don’t need to worry about Google’s thing if you see the thing to pay attention to for Google is the demark success rate if demark success is below 100%. You know there’s a problem. So this will tell you that Google is seeing things a okay. Yahoo doesn’t have this. I don’t know why they just they provide no feedback. That’s one key part. Another key part of this is let’s go to our spam rate. Google has said I believe Yahoo said this as well. They’re holding people now to a 0.3% Spam rate which means that on your list you are on an on it. They didn’t say what aggregate number but I’m presuming it’s probably either weekly or monthly. You must be at a 0.3 percents you know report as spam market spam rate or lower. So you’ll see for example, here, we we brushed with that on December 11. Have 0.2 But we’ve, for the last 60 days, we are consistently stay below that number. So we our list is healthy. Our email services are healthy. We are. We are not annoying people.

Katie Robbert 30:15
I probably asked this question on the past episode one, we covered Google postmaster tools. And if you want past episodes, you can go to trust and search for the episode there under our so what playlist? Are there other tools besides Google postmaster tools that you can use to do this kind of analysis?

Christopher Penn 30:37
Um, MX toolbox will let you know, for like old school, blacklists, if you’re, if your domain or your service are on anyone’s blacklist. So it will say like, Hey, we found you on this list. We we are not on any blacklists right now, which is nice. But it will say like, Hey, you know, you were flagged by by one or more of these places?

Katie Robbert 31:03
Because you’d like to talk about regulations. I know, the FTC has the can spam Act, which they launched in 2003. Where does this apply? And is it still something that’s relevant to email marketers? In present day, 21 years later.

Christopher Penn 31:26
Spam was appropriately named because it basically it was Congress’s attempt at legislation that was so miserably backwards, that basically tell people exactly how they can spam you. And and so is as legislation goes completely ineffective. The the legislation that is the most strict in the world right now is Canada’s so Canadian anti spam law Castle, is the most stringent. And essentially, it is very much what we’re implementing now. So one, click on subscriber easy unsubscribe, fast response. You cannot send unsolicited commercial email, right? So you can’t just go cold emailing people. And there are decent fines for for doing that the EU has some similar spam laws. But Canada’s are the toughest right now.

Katie Robbert 32:14
Gotcha. No, that’s helpful. Because I remember when I was first starting, and this was back around 2005. So the law was only two years old. There was a lot of talk about how we don’t violate the can spam because I believe it was something ridiculous, like a fine of $16,000 per spammy email, you know, that they catch you on and it was just ridiculous money. And we everybody was terrified. Yeah.

Christopher Penn 32:40
Yeah, the can spam law is largely ineffective. David asked a question in, in chat about setting up Bimi. So Bimi is a protocol that is built on top of demark. What it does is it is essentially branding for your emails. And that requires you to set up some DNS records. But then you have to go and pay a bunch of money on a regular basis. John, you you looked at this, most recently, you want to talk about it?

John Wall 33:06
Yeah, I’ve done this a couple times. So it is uncertain male clients, it’s cool, because you’ll see this where you see an icon for all the messages, but you’ll actually see a company logo for like, Bank of America or some airlines or some of these huge brands. And of course, that makes sense because these brands are getting spammed so many times like you get these all these things in your inbox about how you know, your Bank of America account needs you to log in, and I’m like, I don’t even have a bank account of America account. How can this be happening. And so Bimi is basically kind of the cream of the crop, but unfortunately, it is priced accordingly. I think it’s something like last time I looked at about a year and a half ago or so around there. It was like $5,000 a year for that certification. And then there’s some other fees too, that go into it. I think like for each brand you want to have in there, that there’s more cash on top of that. So that’s pretty much you know, if you have a 20 person marketing department, you’re not going to notice it. But for mid to mid sized or smaller businesses, it’s probably way out of your budget, there’s better things you can do with the money.

Christopher Penn 34:08
Exactly. So the big thing to remember here for postmaster tools is you do want to keep an eye on your authentication rates and make sure that they’re not. They’re not like going downwards. And again, remember, the SPF does not work for whatever reason it within Google. And then you want to look at your market spam rate, how many people are marking to spam, and you want to keep that 2.3% or lower, so three 1,007% or lower, because that’s what the new threshold is. So if you do all these steps, so SPF D Kim D mark, and then monitor and postmasters rules, and you have the your email service provider provides the one click unsubscribe mechanism. You will be okay. I will warn you right now. Be B2B email provide B2B marketers are going to experience a lot of hardship with with these changes, because one click unsubscribe is something that can be very problematic. The reason for it is a lot of corporate firewalls will get an email and click on every single link automatically to detect malware. If you have a true one click unsubscribe mechanism, that the corporate firewall just unsubscribe the entire list for that company. And there’s really no good workaround for that. The the better implementations of that are you go to one click, it takes you to an unsubscribe page, and someone confirms that they want to unsubscribe. And that has been that weight remains to be seen whether or not that’s the implication Google is looking for. Google also says looking for the list unsubscribe header, which is programmatically sent behind the scenes. And if in Gmail there, if a company has set that up properly, there’ll be an unsubscribe from this list button inside the Gmail interface that will send the appropriate data to the sender. Hubspot says they’re going to be implementing it soon. I know you will have to check with your vendor of choice as to as to how that works. But most marketing automation software that is reputable should support that.

Katie Robbert 36:24
So if I can sort of summarize where we’re at a little bit, am I understanding correctly that to do your deliverability hygiene and set up correctly, it doesn’t all happen through one single system. So if I set up my CRM, then I look in my settings, the settings aren’t advanced enough to be able to confidently send emails through that system, and know that they’re going to get through to my customers.

Christopher Penn 36:55
Correct. If you have multiple vendors or tools that are sending email, you have to has we did kind of Frankenstein stuff together so that you account for all the sources of email in your organization in one single SPF and, and decom setup. If you don’t do that, then yes, it’s going to get not pretty.

Katie Robbert 37:15
And it sounds like even if you have a very simple tech stack. So let’s say you’re just using Google Suite and you’re just using Hubspot, for example. Those are two different domains that you could be sending emails from. And so you still want to go through this process, even for a very simplistic tech stack.

Christopher Penn 37:38
Yeah, I mean, we use Hubspot. We use Mautic. With through Amazon, and we use Google workspace. And you saw in our SPF statement, we had to account for those systems plus our website. So our website itself, which is hosted on WP Engine has its own IP range. And we had to make sure that the IP addresses of our web server are also there. Because when you fill out a form on the Trust Insights website, that we use a tool called Gravity Forms as part of WordPress that is sending email from the physical web server itself. So it’s not us is not connected to Hubspot directly. So it’s not sending the email through Hubspot. It’s not sending an email through Mautic. It is sending it from WordPress itself. So that needs to be in there too. If you skip that step, then what you may find is that people will fill out a contact form on your website and it goes to send a confirmation email to the customer and they never get it.

John Wall 38:31
Don’t forget our friends at QuickBooks,

Katie Robbert 38:33
and QuickBooks Yes.

Christopher Penn 38:35
Accounting systems, sales systems. Where, again, this comes back to good IT governance. Where does email come from any organization? Yeah.

Katie Robbert 38:46
Always got to start with the your requirements and what systems are you using? Alright, so let’s say we set all of this up. How do we know it’s working? How do we test this?

Christopher Penn 38:56
So testing it is matter. So there’s a couple different ways. One straightforward way is to set up a a consumer mailbox on most systems, a Hotmail address, a Gmail address, Yahoo address, and check them right so subscribing to your lists, and then see like hey, did you Did Did our test accounts get those emails? So for example, you know, we have we all have personal Gmail addresses, I’m subscribed all of our stuff on our things and I make sure we get our emails every week when we send them. I often use my personal Gmail account to fill out forms on the Trust Insights website to again just to make sure that the email gets through. There are companies litmus validity, return path or voter passport validity now that I’ve essentially paid versions of this so what they do is they have 10s of 1000s of of dummy accounts set up around the around the world. And when you know, they they basically monitor those for your sins and then the services are As you would expect reassuringly expensive, but they do work really well.

Katie Robbert 40:03
Oh, and depending on the nature of what’s gonna say, depending on the nature of your business that might be worth it.

John Wall 40:10
Yeah, absolutely, because I’ve used some of those services in the past, it’s great, you can go to a screen, and it will have, you know, a grid of 65 things that’s like, Okay, here’s your email on like, every single major phone, every single major tablet, every single major browser, and to be able to just see on 65 Different platforms in one shot, what’s working? Yeah, if you’re that size, those totals are a huge benefit, huge value. Yep.

Christopher Penn 40:35
And with postmaster tools, it should be someone’s job in your company or on your team to check this console. And spam written authentication once, once a quarter, once a month, depends on how important email marketing is to your company. Right? So email marketing is a critical part of your business, then you should check this this console accordingly. I check it once a month, I just go in and look at and go, Huh, that’s weird. But thankfully, for you know, Trust Insights, because we don’t do bad stuff with our, our data. We don’t have a complaints problem.

Katie Robbert 41:07
Is there a way in this system to set up alerts that could, I know, ironic, email you, or notify you somehow, to say, like, you’ve gone over your threshold or something. So basically, you wouldn’t have to go into the tool, you could basically just say, like, you know, if my spam goes above this number, you know, basically set off the alarm bells and bring me into the system. Because I hear what you’re saying about like, for us, we don’t send a lot of email, you know, outside of our normal client communications, that kind of thing. You know, so checking it once a month is fine for us. But for companies that are doing big, heavy email marketing programs, enterprise sized companies, even businesses that are just starting, they have to check it a little bit more frequently.

Christopher Penn 41:58
Not for this tool, in particular, but again, when you pay a company like validity, they handle all the monitoring and reporting for you. And I remember last time, I worked with a turn path, which is a while ago now is something like 10 or $15,000 a month.

Katie Robbert 42:14
No, so you know, nice and affordable.

Christopher Penn 42:18
You know, if you’re Amazon, that’s like pocket change. So you like you will find that the couch cushions?

Katie Robbert 42:24
Know that? Excuse me, that makes sense. We have another question. And I think this is a good place for us to start to wrap up. If you are a solopreneur or freelancer and don’t have an IT team, which a lot of you know, companies don’t, or individuals don’t? Is there a company you’d recommend who can help set these things up for us or keep us in compliance?

John Wall 42:46

Katie Robbert 42:47
I’m gonna go ahead and say, Trust You know, I, Chris, literally, and I don’t mean like Chris Linux, Chris literally wrote a book on email marketing. It is. Aside from generative AI, one of his favorite things about digital marketing. He spent a lot of time working in email marketing, he obviously knows the ins and outs of tech. And things that go into it and hygiene. You know, I personally don’t know anyone better suited to do email deliverability. And that is completely biased. Because, you know, obviously, it serves us, but I say that in, you know, Chris has been able to debunk pretty much any other vendor that we’ve ever looked at and say, well, they’re not doing these six things. So I would say definitely give us a shout first. And if we’re not the right fit, we can certainly connect you with someone else. I forgot actually wrote two books on he literally wrote the two books on email.

Christopher Penn 43:56
which isnt available anymore.

Katie Robbert 44:01
would you add anything to that, Chris?

Christopher Penn 44:04
No, I mean, again, it’s one of those things that ideally, as long as you don’t change your Mar tech stack, once it’s done, that’s just a question of monitoring, to make sure that things are working. But it’s it these are systems that you should not be messing with on a regular frequent basis. So you’ll get it done. And then then really set it and forget it.

Katie Robbert 44:26
John, final thoughts.

John Wall 44:28
I do have more bad news, you know, the, there is reputation scoring in there too. So like, even if you have all this technical stuff straight, you can still behave badly and get treated poorly because of that. So there is another level of stuff up there. But yeah, this is a great place to start. Like you’ve got to if you want to have any chance of getting your email through you’ve got to do all this stuff. So run through all this and get that going and at least you’re you know making the best effort and after that don’t be a jerk. I guess that’s the my parting shot.

Christopher Penn 44:58
Yeah, I mean, don’t don’t some crappy email. Oh yeah, people don’t want that that 10 sale an awful lot. All right, so that’s gonna do it for this week on email deliverability. Thanks for tuning in, and we’ll talk to you next time. Thanks for watching today. Be sure to subscribe to our show wherever you’re watching it. For more resources and to learn more, check out the Trust Insights podcast at trust AI podcast, and a weekly email newsletter at trust Got questions about what you saw on today’s episode? Join our free analytics for markers slack group at trust for marketers, see you next time.

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