Mastering deliverability with Alyssa Dulin


In this episode, Alyssa provides valuable insights into various deliverability challenges faced by email senders and offers practical strategies to ensure successful email campaigns and maintain a positive sending reputation.

Key timestamps:

00:18 – Who is Alyssa Dulin?

01:38 – How to prevent email deliverability issues after a long break from sending newsletters.

04:23 – Tips for warming up your email list gradually to maintain a good sending reputation.

08:02 – Understanding the promotions tab in Gmail and dealing with emails going to spam.

10:40 – Steps to take if an ESP gets blocklisted.

18:49 – Intermission questions

20:58 – Challenges with business email addresses bouncing.

26:38 – Understanding email spoofing.

26:55 – is recommended as a resource for information and guidance on setting up DMARC records.

31:16 – Addressing automatic opens and clicks.

35:33 – Handling open rate drops and spam issues after switching ESPs.

43:05 – Kickbox, a helpful email validation tool for checking email health


Lesley (00:00) – If you’re a news or media publication running on WordPress, check out Newsletter Glue. It cuts your newsletter publishing time in half and enables you to manage your entire newsletter ops in WordPress. Go to to learn more..

Lesley (00:18) – Welcome to Sticky, the podcast that helps you build a must-subscribe, must-read newsletter through actionable case studies and playbooks. Today’s guest is Alyssa Doolin. I’m so excited to have Alyssa on the show. She’s now the head of creative growth at ConvertKit, but before that, she used to head up Deliverability. She also is the co-host of the Deliverability Defined podcast. Prior to ConvertKit, she also worked on Deliverability at Campaign Monitor, and is clearly an industry expert on the subject. Today’s episode is a little different.

Rather than interviewing her about deliverability, which I worried would be a little bit too dry, I put together a series of common deliverability issues that people often run into, and got her to walk us through what’s happening, how to solve it, and how to prevent it for the future. This episode is chock full of really specific troubleshooting tips, and takes you behind the scenes of what’s really going on when your emails go to spam. I loved it and got so much out of it personally, so I can’t wait to share it with you. Let’s get to it! Welcome, Alyssa!

Alyssa (01:21) – Thank you so much! I’m excited to be here. 

Lesley (01:24) – I’ve identified a large handful of common deliverability scenarios and I’d like to talk through them and see how we can solve them and prevent them in the first place. 

Alyssa (01:34) – Sounds great. I’m excited to get into it. 

Lesley (01:38) – So the first one is, I haven’t sent a newsletter in a year and I just sent a new one and a lot of my emails are now getting marked as spam. What do I do? How do I recover from this?

Alyssa (01:53) – I’ve seen this one happen before. So first I’ll just have a quick bit on how you prevent this. So the way to prevent this from happening in the first place is to kind of what I was mentioning just a second ago, slowly warm up your email list. If you’ve taken a year off, the reason why I try to explain that a sending domain reputation is sort of like a credit score and you have to be sending pretty regularly to keep up that score, with all of the mailbox providers. So if you take a year off, the mailbox providers no longer have a reputation for you. So it’s sort of like when someone doesn’t have a credit score and it’s just a big question mark. We’re like, I don’t know, can I trust you? Can I not? So since you don’t have a reputation at the moment, if you just go and send to your full list out of nowhere, it usually is seen as very risky by mailbox providers. So they’re gonna place a lot of your messages in the spam folder.

So the best way to prevent that is to not send a huge amount all at once. It’s to start with whoever you can think of as your most engaged subscribers when you were sending, um, sending to them first and then slowly adding in more and more people. So that’s how to prevent it, but let’s say it happened. So now you need to clean up from it. Um, I would, if you can do it, I would take two weeks off of sending completely just to like give your reputation a little break.

I would then go and ramp up your sending so that you’re starting with your most engaged people if you know who they are. But you’re starting with a much smaller list. And so it’s not so risky to the mailbox providers. They don’t see a huge burst of volume from you all at once. They’re going to see these little bits and they can kind of be like, okay, I feel a little more secure about them, a little more secure. And then eventually they’re going to see once your subscribers are engaging with your messages in a positive way, they’re going to feel more confident and send your messages to the inbox. So another tip to add on to that when you are warming up your list in this process, recommend or really advocate that your subscribers reply to your messages. That’s very helpful. So the more replies you can get as you’re ramping up your list, the bigger boost that’s going to be for your reputation. 

Lesley (04:10) – Can you give in a ballpark of how many you should be sending. So for example, if I have a really small list of a hundred people, then I probably don’t have to be doing this. At what size do I have to start worrying about it? How do I break those down into chunks of subscribers to send to? 

Alyssa (04:23) – Yeah, that’s a great question. It kind of depends on how long you haven’t been sending and all the variables, but in general, I would say like, don’t even think about this.

If you’re sending, gonna send less than 10,000 emails. Once you get above 10,000, I think it depends on how long it’s been. If it’s only been a month that you haven’t been sending, I probably wouldn’t worry about warming up your list unless you have over like 50,000 subscribers. If it’s been that year that we’re talking about, I think even at 10,000, it would be helpful to start with like 500 at first. And depending on how the results go, you can ramp up a little faster. I have a kind of this template that I share with customers who come over to ConvertKit. And I basically, I should just put this up on my website or something. I basically take their overall goal, you know, at the end, how much volume they want to send. And I, the simple way would be like divided by four, you know, and do it in chunks of four. The template I use does more of a like, you know, it starts really small and then it gets a little bigger and then it gets a lot bigger. I don’t know if this is making sense verbally. 

Lesley (05:33) – It does. 

Alyssa (05:34) – Okay, great. 

Lesley (05:34) – So it’s like, start with 500 and then have it scale up to a thousand and then you can quickly scale up to five thousand and then like ten thousand. 

Alyssa (05:43) –  Yes, exactly. The most important thing is just that each step of the way you’re adjusting. So if you send to that five thousand and you’re like, oh no, messages are going to spam again, don’t ramp up to twenty thousand, you know, maybe stick with the five thousand or even go backwards if you need to. It doesn’t happen very often, but that’s just one note or, you know, in the opposite direction, if you’re going really slow and your open rates are amazing and everything is going great, then you can ramp it up some. 

Lesley (06:12) – Right. You can probably be a bit more aggressive. One thing I wanted to talk about, which you mentioned briefly was getting subscribers to reply to you. I just wanted to highlight like there’s lots of great ways to do that naturally. So a common way is to ask subscribers for feedback. So you could say something like, “Hey, I’m starting to send my newsletters out again. I’d really love to hear what you want me to write about. So reply to this email and just share what you love most about – whatever it is that you are into.” I think that’s kind of a great way to casually get lots of replies and indicate to mailbox providers that you’re not dodgy. 

Alyssa (06:52) – Yes, I love that. That’s so good. In one of my recent newsletters, I said, what’s your biggest challenge with email deliverability right now? And that was really helpful because it helps me have more content to write. I’m like, what should I be writing about? But also it brought in a lot of replies and I think subscribers were excited to share like what they’re struggling with so that I can try and help. So I love that advice. 

Lesley (07:08) – Nice. Kill two birds with one stone, right? Yeah, exactly. 

Key Takeaway: To summarize, if your list is smaller than 10,000 and you’ve really only not sent emails for a month or two, then you really don’t have to worry about this too much. If your list is over 10,000 and you’re seeing emails go to spam, you really want to rest your list for two weeks to let your reputation recover. And then after that, you want to do some list warming where you’re sending your emails to a small batch of most engaged users to begin with. And then of course, engagement really counts. So coming up with creative ways to get your subscribers to reply to you really helps your reputation as well. 

Lesley (07:49) – Okay, let’s move on to the next one. Our subject line – Last chance to get 50% off fire emoji is causing our emails to go to spam and promotions during black Friday and we are freaking out. 

Alyssa (08:02) – This is a good one. It’s very loaded. Like there’s so many layers, but I’m excited to get into them. Maybe the first thing I’ll touch on is promotions. Um, so the promotions tab is actually the inbox and I know a lot of people don’t want to be in the promotions tab. It’s not a fun place to be. I know we all want to be in that primary tab, but especially, you know, like you mentioned that Black Friday email, it was a sale email that technically does belong in the promotions tab. So I would not worry about that. Um, because it’s just Gmail’s algorithms working the way they’re supposed to in trying to fight it. Just doesn’t work. I did try once. I was just very curious, ran a lot of tests about the promotions tab and it’s crazy how it all, I mean, it doesn’t work the way you would think it would at all. I have an episode about that on Deliverability Defined if anyone’s curious. It’s something about the promotions tab test that I ran and what I learned from it, but it doesn’t work the way you think it would. And it’s just going to drive anyone crazy to try and figure it out and try to always get their messages to go to primary. So I would not worry about the promotions tab. It’s the inbox. And especially if you’re sending emails about a sale on Black Friday, like that’s just sort of where they’re going to land. But spam is a different story. So we definitely don’t want emails going to spam. I would be curious why the sender thinks that the subject line is causing the problem. Like how do they know that? I don’t know if they knew that through testing or whatever it may be. I find it very rare for a subject line to be what’s causing a message to go to spam. So I would probably want to dig in deeper and see what else could be going on. If you know, somebody truly thinks it’s the subject line. They could try resending to unopens and changing up the subject line and seeing if that one has better results. But if not, I would wonder if it’s more domain reputation based. How many emails have you been sending on this Black Friday? Have you just been like blasting your list for the last, you know, couple days with sales? And if they’re not engaging with those messages, that could be what caused your message to go to the spam folder. So hopefully that’s not too layered. But that would be my take on the situation at first.

Lesley (10:20) – That’s awesome. Yeah. Makes a lot of sense. I like how you kind of unpacked everything. 

Alyssa (10:25) – Oh, good. Thank you. 

Lesley (10:27) – Okay. Next question. It seems like our ESP got blacklisted and I reached out to them, but they’re not giving me good answers, but I’m kind of panicked because I have to send out my newsletter in the next hour. 

Alyssa (10:40) – Oof. This is a good one. It’s, it’s a scary scenario that, um, I think is not as uncommon as people think depending on the ESP. Um, so I’m trying, I will first go into what to do if that happens to you. And then maybe I can talk about some preventative things, but if you are in that situation, I think maybe the first step would be to push a little bit harder on the support team if possible. So you said they weren’t giving you good answers. Um, hopefully at any reputable ESP, there is at least one deliverability expert in the house. Sometimes it’s hard to get a hold of them. That’s one thing I’ve been really passionate about at ConvertKit is to make sure that it’s easy to talk to someone who knows about deliverability because I know how stressful it can be if you don’t have that access. So hopefully if you can respond to that support ticket and say like, I really need to talk to someone on the deliverability team. You know, you could even go to their website, maybe try to find who that person is who is on their deliverability team, go to LinkedIn. And if you can name them, then maybe the support team will be like, Oh, they know so-and-so, let me transfer them over and then explain the situation. Maybe before I keep going on this tangent, one note I’ll say is it’s very common for the IP address of an ESP you’re using to be on a block list, just very generally. And that doesn’t mean that there’s a problem. So that’s another thing that I do see happen often. There are thousands of block lists out there and only a handful of them actually make a difference. And there are a bunch of block lists that will just block any IP that sends promotional messages. 

Lesley (12:07) – Just popping in here to mention that Alyssa uses the term block list instead of blacklist, just to move away from using black and white as terminology. They mean the same thing and this is something the email industry has moved towards in the past couple of years. 

Alyssa (12:24) – So anytime you’re doing like a lookup on the mail you send from your ESP, there’s a good chance. I think one popular one is like EmailTooltester or MxToolbox or something, I’m not sure. But if you’re doing one of those sorts of tests on your mail from an ESP and it says you’re on a blocklist in red, don’t just automatically freak out because there’s a good chance that’s normal and doesn’t mean anything. But there is also a chance that an ESP could be on a major block list. So, Iif you have figured out like, oh, this is a big deal, it’s spam house or something like that. It’s a really big one. Again, try to get to a deliverability expert. Once you get to that deliverability expert, see if they can put you on a different IP. That would be the big thing is to switch you to an IP that’s not on a block list. If that’s not happening, you’re confident that the ESP is on a major block list. That’s the problem. You’re seeing on Twitter, everyone’s saying like, ESP XYZ is all my emails are going to spam there. You’re probably not the problem like the ESP is. So at that point, honestly, I would look into leaving as harsh as that sounds. If email is a critical part of your business and you’re not, especially if you’re not getting any support or the answers you need, they’re not taking any steps to fix it or like talking to you about it. It’s just really important that you have your email list with a business who takes that really seriously, takes deliverability really seriously and knows how to talk to customers about it. So that’s kind of my harsh advice, but to prevent any of that from happening, I know whenever we pick an ESP, we usually look for like the shiny fun features, you know, the ones where you can design really beautiful emails or the one everyone’s talking about, which makes total sense or price, you know, the cheapest one. But one thing not enough people do is look into the deliverability of the ESP. And I always say the best way to do that is to, like I said, look at the way that they have, the way that they have invested in deliverability. Do they have a deliverability team? Again, a good way to see that is from maybe they’re about page or they’re linked in. Is there anyone at the company with a title with the word deliverability in it? It’s very important. Do they put out articles and blog posts about deliverability? Are they um, thinking about deliverability a lot and being experts in that space, things like that. If they’re not, which a lot of newer ESPs just haven’t gotten there yet, that’s just something they haven’t prioritized. Um, I personally wouldn’t put my email list there just because it’s really risky until, um, they’re more established in deliverability. 

Lesley (15:14) – Right. So a couple of things that I want to unpack there, but the first is, you know, most people are not going to be stalking employees of the ESP on LinkedIn to make sure there’s deliverability in their titles. So are there like good kind of very broad rules of thumb that we can just kind of, oh okay like you know this ESP is pretty established so I can kind of assume they’ve got deliverability sorted out. Is there some kind of like thing that I can just kind of assume there? 

Alyssa (15:42) – Yeah that’s a good question. I would say any ESP I know of that’s like five to ten you know at least years old. I can’t think of any of them that don’t have a deliverability team in house. I think by that point you learn that you have to have one. So that’s probably a good sign that, you know, they’ve been around for at least five years. I would, that’s probably the best. The other thing I would do, cause I’m a nerd that probably no one listening would do is there’s an organization M3AAWG that’s a handful. It’s called MAAWG. It’s a really, really, really hard organization to get into, but I would trust any ESP that’s in that organization. And it’s basically a working group of companies who take spam and abuse really seriously online. And so any ESP, that’s basically one of the big things that will determine your ESP’s deliverability is how seriously they take spam. It’s very hard to fight spam. Spammers are very smart. So the reason why your ESP might have bad deliverability is if they don’t have a team of people fighting spammers and building machine learning and building tools to stop spam. So basically if someone is in that organization, I know that they have really strict compliance and they’re fighting spam and so they are also going to have really great deliverability. So again, that’s kind of like the nerd in me. I don’t think most people are going to be doing that, but that’s another way you can look at it. If you’re able to find any information about, does this ESP have strict terms of use kind of, or are they paying close attention to spam or can literally anyone just join this ESP and start sending? Because that’s where you’re going to run into big deliverability issues. 

Lesley (17:17) – So I’m going to like sidetrack really quickly here, but one thing that I see sometimes people complain about on Twitter is like how difficult it is to get set up with a new account on certain ESPs. And I always see that and I’m like, no, don’t you get like how important the fact that they do make it hard is that you should be happy that they make it hard so that you know that everyone who does get through those filters means that they’re all legitimate and you’re going to be surrounded by good actors using your shared IPs and it’s actually a good thing. 

Alyssa (17:45) – I love that way of thinking. That’s so important. And I totally agree. At ConvertKit, it’s kind of scary how much money I turn down constantly every day. I’m like, nope, sorry. Like all these people want to pay to use ConvertKit. And I am saying no, because like out of all the data I’ve seen, I’m like, I just don’t fully feel like their mail is going to be beneficial to the reputation of our IPs and our domains. And I take that so seriously. So I agree. I think if you sign up for an ESP and it was really easy to get started, either they’re a pro at anti-abuse and they’re looking at a ton of things in the background and you don’t even know it. We have gotten farther in that, so that’s been great. But there are a lot of hoops to jump through. I wouldn’t be discouraged. I would be excited. Like you said, that this ESP is taking anti-abuse really seriously. And this means they’re going to have a much better reputation, um, when it comes to deliverability. 

Lesley (18:49) – So we’re going to have a quick intermission where I ask you a series of questions. Feel free to answer with a word or a sentence or however much you like. So first question, spam sandwiches or spam fried rice? 

Alyssa (18:57) – Fried rice. 

Lesley (18:58) – Do you play any musical instruments? 

Alyssa (19:01) – Kind of play the drums. I’m definitely not an expert, but I took lessons for a little bit and I really like it. I haven’t played in a long time, but it’s really fun. 

Lesley (19:10) – Do you have a drum kit at home? 

Alyssa (19:12) – So my husband is a music producer and he has a studio. It used to be in our backyard and then we moved, but he still has that same studio. So I used to be able to go outside and practice but now I can’t so I haven’t played in a really long time. 

Lesley (19:27) – Oh well. I was gonna ask you if your drumming was driving your family crazy but I bet he’s the one that drives you crazy. 

Alyssa (19:33) – Yeah usually. Or our little baby has his own guitar so that is the thing driving us crazy. 

Lesley (19:41) – Yeah it’s cute for like three seconds right? 

Alyssa (19:42) – Yes. 

Lesley (19:44) – Beach or mountains? 

Alyssa (19:46) – Beach for sure.

Lesley (19:48) – Best perk of working from home? 

Alyssa (19:52) – Oh goodness. I mean right now it’s just the fact that I can walk away from my desk and go say hi to my little cute baby that I’m obsessed with right now. But it’s also very distracting. But right now I would say that’s my favorite part of working from home and not having to be out of the house from him. 

Lesley (20:08) – And last question, would you rather shave your eyebrows for a year or get a bright pink mullet?

Alyssa (20:16) – I think bright pink mullet, I don’t know that I could pull it off but it would be kind of fun. I mean, it would be a statement. 

Lesley (20:31) – While we were talking, I put a bunch of your answers into ChatGPT and got it to write you a limerick. 

Alyssa (20:37) – Wow, oh my gosh that’s amazing. 

Lesley (20:40) – So yeah, let me read it to you. There once was a girl named Alyssa whose passions were sure to impress ya. She drummed with great flair and beach life she’d share, working from home, son’s laughter treasure.

Alyssa (20:52) – Oh my goodness, I love it so much. Thank you. That’s so cute. 

Lesley (20:58) – All right, let’s, let’s get back to the questions. Okay, next question. We send a lot of emails to business email addresses and suddenly a lot of the emails to business domains are bouncing. It seems like the regular Gmail addresses are fine. What’s going on? 

Alyssa (21:06) – That’s a good one that I definitely see happen every now and then. Um, so business email addresses and I’ll call the Gmail addresses like consumer email addresses have very different rules when it comes to deliverability. I would say the business ones are a lot harder to get to the inbox for because, you know, they’re meant for work. So especially if you’re sending really promotional emails, a lot of times the IT teams who manage those email addresses don’t want their employees receiving a bunch of promotional emails at work or especially if it’s like a school email address with students or anything like that. It gets really tricky. So the fact that you mentioned bouncing makes me think it is probably a block list issue and there are certain block lists that mostly impact business addresses and not consumer addresses. So that’s the first thing I would look at. I would do a lookup of your sending IP address. If you don’t know how to find that you can. Use a tool like I was mentioning earlier. Um, I believe MailTool tester is the one I see most often and you can see, you know, is your IP address on any block list? That’s a good place to start. A second place could be the content of your message. I have found that the business email addresses are much stricter about content and will bounce your messages quicker based on something in the content. And it can be something so, you know, small or something that you wouldn’t think about. So for example, if you’re using a URL in your message and they don’t like that URL, I’ve seen links, the link shortener cause problems like this where it can cause all your messages to bounce because the mailbox providers don’t like it. 

Lesley (22:40) –   Newsletter Glue cuts your publishing time in half by enabling your team to publish newsletter the way you publish articles in WordPress. Find out more at Now, back to the episode.

Alyssa (23:06) – Or even one I’ve seen recently was this is going, I hope it’s not too in the weeds, but it might be subscriber’s email address into a link in your message. Some people will do that to try and track things So they’ll have like custom code where they’ll have a URL and then inside the URL The subscriber’s email address will get populated into the URL mailbox providers, especially business ones really don’t like that So I’ve seen instances where someone’s doing that and their messages all bounce Because it’s seen as like just not good I think for privacy and things that someone’s email address is getting put into URL. So that’s just a small example, but I think the two things I would look into are an IP or domain block list or something about the content and the links in your message that aren’t being liked. 

Lesley (24:07) – So let’s say that this is starting to happen. How would I then go about troubleshooting and figuring out how I can stop it from happening? 

Alyssa (24:14) – That’s a good one. This is where I would really lean on your ESP. Hopefully you have an ESP, like I mentioned with a deliverability team, who can help you because this is where I would jump in or my teammates would jump in and we would do that digging in for you. It’s something that would be really hard, I think, for someone who’s not a deliverability expert to diagnose on their own. But one thing you could do that I failed to mention, if you’re able to access the bounce codes, the reasons why the people are bouncing, those usually are pretty descriptive and that will give you some insight into what’s happening. Usually it will straight up say, you know, you’re on a block list, proof point or something like that. And that’ll tell you what the problem is. Um, or it might say the content looks like spam, you know, blocked. And that gives you more insight that there’s something about the content they didn’t like. Not all ESPs share that information. So that would be another reason to reach out. I know if someone reached out to us at ConvertKit, we would tell them what was going on. So that would be my very first step in diagnosing. 

Lesley (25:02) – How do I get access to those bonds information?

Alyssa (25:04) – Yeah, it depends on the ESP. So some of them will show it probably within the subscribers profile sort of in the ESP. If it says they bounced, it might have more information. Sometimes it’ll be really vague. It’ll say like invalid address or spam block. So if that’s all it tells you, you might need to contact them and ask for the specific codes. And then again, like ConvertKit, for example, we don’t just show the raw bounce codes to customers. I think it would cause way more confusion than benefit. But if you reach out to us and say like, Hey, suddenly all my subscribers with that are B2B addresses are bouncing. What’s going on? We would look at the bounce codes for you and share what was going on and do all that digging and all the annoying hard work for you. So it’s either going to be in the ESP’s interface or you need to reach out to them and ask for that. 

Lesley (26:02) – Cool. That’s really helpful. 

Key Takeaway: Something that’s shining through for me based on everything that Alyssa is talking about, is how important the ESP support team really is. I interact with dozens of email service providers and I can tell you that the quality of support really varies from company to company. Some are really responsive, some have specific account managers dedicated to different customers, some can only be reached via email, some via live chat. And I think as you grow larger, this is something to take into consideration a lot before you switch ESPs, just so that you can be confident that if anything does indeed go wrong, you’re gonna have a partner on your side that’s willing to troubleshoot and dig deep with you. 

Lesley (26:38) – Next question. I’m getting a large handful of mysterious replies from strangers telling me to fuck off or stop spamming me, and I look at what they were replying to, and it looks like a spammy email. What’s happening? I didn’t send those emails. 

Alyssa (26:55) – I love this question because. It’s one I do see happen every now and then. And I think it’s always so shocking to people. So what’s happening in this instance is that someone is spoofing your sending email address, um, and it can either happen with the way I see it happen most often is actually spammer is on your list. They receive your email and then they forward it on pieces of the header. They kind of pick and choose what they want. They completely change the message. Um, they make it this really spammy message and they make the from address say it’s from you. And then they send it onto their list of subscribers that they have. And yeah, then a bunch of people get spam that says it’s came from you, even though it didn’t. And then you’re gonna get a bunch of replies that says like, stop sending me spam. What is this? I didn’t sign up for this. So this is what we call spoofing. And the next step you’re gonna wanna take as soon as you can is to set up DMARC on your domain, which can get pretty technical, get a little hairy, but it’s what you have to do next. Um, so I would read up on that the website I usually give people to, um, look up how to set DMARC up is, um, And they have like a DMARC wizard that teaches you how to set up a DMARC record and just a bunch of other information about DMARC. Um, but what that will do, once you set it to be pretty strict, anytime a spammer tries to send mail from your domain, it should either go to spam or bounce depending on the settings you’ve put in place instead of making it through to the inbox like it is without DMARC. 

Lesley (28:50) – Should you want it to go to spam or inbox or like what, what is the ideal DMARC setup? 

Alyssa (28:56) – Yeah. So if you’re not under pressure to set up DMARC, the recommendation is always actually that you start with a DMARC record of a policy with that says none. And what that means is if a message fails DMARC, send it to the inbox actually, let it do nothing. And that gives you time to see like, where are my messages failing DMARC? And you can get all of that together. So DMARC sends you reports that tells you all the different places your emails are failing DMARC. So this is great for setup time because you can see like, oh. my ConvertKit emails are failing DMARC. I don’t want that. I want them to pass. I’m going to go set what I need to set up, which is a verified sending domain. And you can say like, oh no, these GSuite emails are failing DMARC. I’m going to go set up DMARC. You know, they’re the way I need to. And while you’re doing all this, your emails are still going to the inbox, even though you don’t have your ducks in a row yet. 

Lesley (29:38) –  Which means the spoofers can also keep sending emails to inbox. 

Alyssa (29:42) – Correct. Yes. So that’s one tricky part. If you’re under pressure, that P=none time needs to be as short as possible. You got to move on to the next step is P= quarantine, which means send messages to spam. Ideally you would get to P equals reject, which is completely bounce the messages because even that spammy stuff going to the spam folder is dangerous. You don’t want anyone clicking on phishing links. You don’t want people to see that from you in their spam folder. It’s just not a good look for your reputation. So I would try to get to P=reject as quickly as you can, but you also don’t want your legit emails to be bouncing. So that’s why this is all pretty tricky, but not totally undoable, especially if you don’t send email from very many places. If you just have a few places, then hopefully you can get those set up really quickly with DMARC and move on to P=reject. 

Lesley (30:37) –  Why do spoofers do this?

Alyssa (30:38) – Usually because they want to piggyback off of the healthy reputation of someone who has it. So deliverability is actually, you know, a hot commodity. It’s hard for a spammer to reach the inbox. They’re desperate to reach the inbox because if their messages are all going to spam, they’re not getting what they want. So a spammer is going to have a really hard time maintaining healthy domain reputation. They can spin up new domains, but new domains are treated as really risky. So they’re not going to go to the inbox very well. So they see your domain as a huge asset. If they can piggyback off of you and all your hard work that you put into your deliverability, they can reach the inbox. So that’s exactly why they do it. 

Lesley (31:16) – Well, the next question is my email stats look way off. According to the stats, a bunch of subscribers have opened and clicked on my emails dozens of times. What’s going on? 

Alyssa (31:27) – Yeah, this one is so tricky. Um, email is very imperfect. So there are automatic opens and clicks that can happen pretty often. There are two different problems or situations, but automatic opens is a huge one right now with the new Apple privacy changes. I don’t know how long I can call them new. I mean, I think it’s been like a year or two, but in Apple’s, you know, change that they made whenever that was a year or so ago, if you’re using Apple mail apps and you have opted into their like privacy protection, which I think most people did that use that. They automatically open any message that you receive that has an open tracking pixel in it. So for a lot of senders these days, their open rates are extremely inflated. They’re seeing a lot of automatic opens. And I think most people have gotten used to that new normal. You know, people used to be like, oh, my open rates are 20% or 30%. That’s amazing. And now everyone’s open rates are like 40 or 50 or 60%. Yeah, depending on the situation. So automatic opens, I think are here to stay. Kind of the new normal for senders. And now when you’re trying to figure out if your open rates are healthy or if there’s a problem, you just sort of have to look at the trend. And if you see a set and drop, then you’re like, oh, there’s probably a deliverability problem. But then open or automatic clicks are sort of a different beast and they fluctuate a lot depending on the sender’s content, what their list is like. So in the industry, a lot of times we call them non-human interactions. And those are really common with any sort of business address, like we mentioned, because they’re checking the links in your email for security, for safety. The IT teams of these businesses are not really concerned about your click rate. They’re concerned about the safety and security of their employees and their business. They don’t want phishing emails going through to their employees. So a lot of times they’re going to check all the links in your email and make sure they’re safe and then put them in the inbox. And I’ve seen that that will happen more often depending on the content of your message or the domain reputation of your message. So there are some things you can do to try and prevent those automatic clicks if you’re seeing them a lot, but that is why they happen. It’s checking for security usually, and there’s not a whole lot senders can do about it, except what we’ve seen help is number one, always use HTTPS links in your emails instead of HTTP. That helps a little bit to keep your domain reputation really healthy with a clean list, the better your reputation, the less likely they are to check all the links because they’re going to trust you more. And then three, just paying really close, um, attention to your content. Like I mentioned, if you have those like link shorteners, bitly links, um, if your content looks spammy to the mailbox provider, they might be more likely to click those links if you’re like, buy now, act now, download here, you know, those sorts of things. So yeah, that would be my advice is to take those steps to prevent automatic clicks. 

Lesley (34:41) – How manual are these security teams? Like is it manual? Is it automatic? Is it a combination of both? 

Alyssa (34:46) – Yeah, every one is going to be different. I would say it’s mostly automatic, but they sort of have like dials they can do of like how strict they want to be with certain things. And I think each, you know, organization is going to be completely different and it will really depend on how vulnerable they are for attacks and things like that. Like I mentioned any like government address or school address or anything like a bank or hospital. I’ve seen those are

some of the most strict and hard to get your mail delivered there. That makes sense. You’re going to see a lot of automatic clicks. Yeah. But you know, just a normal sort of like small business, maybe a restaurant or something, they’re not going to be as strict about security. 

Lesley (35:25) – I’d be pretty surprised if a restaurant has a security, email security team. 

Alyssa (35:28) – That would be very impressive. 

Lesley (35:33) – Alright, so we are on to our final question. I just switched ESPs and my open rates have dropped and I’m going to spam. What can I do? 

Alyssa (35:42) – Oh, yes, this is, this is a sad one that I do see happen every now and then. And I actually have an example that I’m working with someone on this now, and it just enforces how important a ramp up plan is kind of how we mentioned at the beginning of the episode when it comes to moving ESPs. So whenever we have a larger customer join ConvertKit, our team builds a ramp up plan for them. Or we say, okay, your first send, you’re going to send to 5,000 people. We want it to be your most engaged people. And then your second send, you’re going to add in maybe 10,000 more people and so on. And we build out this plan. Some people don’t love to go that slow. You know, they’re like, I want to send now. It’s hard to be patient. And sometimes we can make some tweaks and sometimes we have to say like, this is our expert advice. You can do what you want to do, but this is the expert advice. 

Lesley (36:34) – Hey, this is Lesley from a few weeks after the podcast recording with an important added detail. Alyssa talks multiple times about a ramp up plan which starts by sending emails to 5k subscribers, to 10k and so on.

However, if you run an active newsletter to, let’s say 50k subscribers, you can’t simply not email the other 45k subscribers while you ramp up.

I messaged Alyssa about this after the podcast and she clarified that what you really want to do is send from both email service providers at the same time. So, for example, if you are migrating from Mailchimp to ActiveCampaign. You might keep sending 45k emails from Mailchimp and start with 5k emails from ActiveCampaign. Then for your next newsletter, you might send 40k emails from Mailchimp and 10k emails from ActiveCampaign. And you’ll keep ramping up the number of emails you send from ActiveCampaign until you’re sending all your emails from ActiveCampaign and none from Mailchimp.

This has some important implications for your migration plan as it means there will need to be at least a month or two of overlap between subscriptions, so you’ll need to budget that in. And it also means that you’ll be having to spend additional time writing or building the newsletters in both email service providers. So again, you’ll have to budget in the time to do all of that. I hope that helps. Now, back to the recording.

Alyssa (38:13) – So there’s a customer I am working with right now who didn’t do any ramp up plan. They just wanted to go for it and they did end up with some of their messages going to the spam folder. And you know, then there’s the customers that they do ramp up and they don’t have any problems. So it’s just a good example that this is an issue. We don’t want, you know, you to ramp up just for our own fun and entertainment, but it really does help. So my top advice to prevent this would be like we mentioned, start slow, send your most engaged people first off of the new ESP and then ramp up from there. Some other things to pay attention to, DMARC, like we mentioned earlier, if you have a DMARC record on your domain, there’s some steps you’re gonna need to take in this new ESP to reach the inbox. So make sure you’ve taken those. I can only speak for a ConvertKit that’s called a verified sending domain, but at other ESPs, they have it called something else. So make sure you’ve done all that, that your messages are authenticating properly. I would send yourself a test from the new ESP first to make sure all that looks good and that your message is going to the inbox. And then from there, it really is mostly about that ramping up slowly so that you don’t cause any big red flags at those mailbox providers. But if this has already happened to you, so now you need to know what to do next. Um, I would again, take a pause a little bit from sending, maybe take at least a week off of sending from this new ESP if possible, and then start that ramp up plan over, um, hopefully not too much damage has been done a lot of times in that very first send. When you saw some emails go to spam, it’s sort of Gmail or Microsoft or whoever just having a big question mark. They’re like, I don’t know what to do with this. This is all new to me. You’re sending me my new ESP. So we’re just going to put some in spam, some in the inbox and they’re trying to figure it out. And so it shouldn’t have caused huge damage to you, but I would now start with a ramp up plan where you’re sending to your most engaged and then go up from there. 

Lesley (40:13) – How large does my list have to be for me to be concerned with having a ramp up plan when I switch?

Alyssa (40:18) – I would say 20K is usually the sweet spot that I look at, especially if you have really great open rates. Like if you have a list of 10K and you have 50 or 60% open rates or something, you should be fine to just send a message out of your new ESP. Yeah, exactly. If you have a 15K list with a 10% open rate, there’s probably some other things that need to happen also. But I wouldn’t be, I would definitely want you to take some steps before you just sent to your full list. 

Lesley (40:50) – If for example, I’m just moving my ESP and I’m concerned about this, would you say, I mean it’s hard for you to speak for other ESPs of course, but would you say that most ESPs would have in place like a ramp up for all their customers? 

Alyssa (41:00) – That’s a good question. ESPs I’ve worked for, which is only two, a ConvertKit will make it for anyone who needs it. At the previous ESP I worked for, I believe it only happened for pretty large enterprise customers. I honestly don’t know what other ESPs do. I would say some of the really, really large ones don’t do this. 

Lesley (41:16) – Let’s say I wanted to do that myself. How can I go about warming up my domain and warming up all of this stuff by myself without the help of a dedicated deliverability specialist in my ESP? 

Alyssa (41:25) – Yeah, that’s tough, but you can definitely do it. So I would start with a four week plan and I would. Kind of like we mentioned earlier, divide your listing for, let’s just say you’re 20K, that’s easy to stick with. So if it was a 20K person, I would say week one, send to your 5,000 most engaged people. Week two, do 10K, three, 15K, week four, 20K. That’s nice and easy to keep up with. It’ll be great for your mailbox providers to just get little doses of your mail and see that it’s all going well. And that’s easy for you to maintain on your own. So that’s sort of the structure I would follow. Obviously, if it’s not 20k exactly, your listeners can tweak it depending on their numbers. But that’s a good process. That’s pretty simple. You don’t really need an expert to help you with that. And it should help you get to the inbox and stay out of that spam folder. 

Lesley (42:29) – Awesome. That’s so helpful. 

Alyssa (42:34) – Yeah, no problem. 

Lesley (42:35) – So we’ve reached the end of our questions. I personally learned a lot and I hope everybody listening as well has found at least a couple of questions, if not more, that really speaks to them, resonates to them. Maybe they have PTSD or maybe it’s something they’re about to do soon and can implement all of the best practices that you talked about. So before we end, I’d love to ask you three quick questions. So the first question is, what’s an underrated email tool you wish more people used and talked about and why? 

Alyssa (43:05) – There’s a tool I use fairly often in my job that I think customers or email senders could get more use out of too. It’s called Kickbox,, and it’s an email validation tool. So there’s lots of validation tools out there. I just personally like Kickbox. And I use it for customers when they’re moving over to ConvertKit. I’ll run their list through it and make sure they don’t have any bounced addresses on their list or risky addresses on their list. But you know, individuals can use it in a lot of different ways. If you are moving to a new ESP, you can run it to make sure that you don’t send a bad addresses at the new ESP, but also you can add their code to your signup form and it will do real time email validation, which I think is really cool. So if someone types in a typo in real time, like, it’ll pop up and say, did you mean Alyssa at for example? Yeah. So, um, it’s a great one when it comes to email health. So highly recommend it.

Lesley (44:05) –  Cool. I’m gonna check it out. What’s your favorite must subscribe, must read newsletter? 

Alyssa (44:10) – It changes all the time for me, but right now the one I’ve been loving is by Eli Weiss and it’s called All Things Customer Experience and Retention because leading up to this kind of role shift that convert it to creator growth, I was looking a lot into retention, just customer retention, customer experience. And it’s so interesting. It was just a whole new world for me of. How do you give customers an amazing experience and keep them retained because they’re so well taken care of. So he has a really great newsletter all about customer retention. I do think he is mostly specialized in like physical products. So that’s a little different than SAS, but I’ve still learned so much from all the different companies he highlights and the things that they do for customer attention. So I’ve been loving that one. 

Lesley (44:54) – That’s really cool. I should check it out. And last question. What’s your favorite piece of advice for a news that’s a publishes? 

Alyssa (45:00) – I feel like we kind of said it, but I’ll say it again, because I think it’s important, get those replies from your subscribers and do it in an authentic way. Um, but that really can help deliverability. And it also is just great for your subscriber relationship. I love replying to the subscribers who reply to me. I’m sure as your newsletter gets bigger, that’s harder to do, but it really is great to keep that you know, back and forth conversation going with subscribers. You can learn from your subscribers. It boosts your reputation. And then again, if you use it the way I did, whenever I’m like, what do I write about this week? I go look and see what are some of the replies I’ve gotten lately. And that’s been so helpful. So I think replies are just a big strength when it comes to deliverability, but also relationships. 

Lesley (45:50) – Awesome. Such great advice. 

Alyssa (45:51) – Thanks. 

Lesley (45:52) – Thank you. Yeah. So we’re at the end of our podcast. Thanks so much for coming on the show. Where can people go to learn more about you and get in touch? 

Alyssa (46:03) – Yeah. So I have a website if you need to like fill out a contact form, I am on Twitter. I believe it’s elissa_dulin there. There is the Deliverability Defined podcast that we’re still recording currently. Um, it’s a really fun podcast and we have a lot of conversations like this one. So that’s another good place to.

Lesley (46:24) – Awesome! Yeah and I highly recommend the podcast as well. I’ve heard of a few episodes and really enjoyed it. Thanks again Alyssa for coming on the show. It’s been so great having you. 

Alyssa (46:33) – Thank you so much!

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