Industry News & Analysis

Collecting email addresses

One of the primary ways to collect email addresses is from website visitors, and it’s actually a pretty good way to collect addresses. One of the more popular, and effective, techniques is through a pop-up window, asking for an address. Users need to provide an address or click a “no thanks” link or close the window. I’ve noticed, though, that many companies drop something passive aggressive in their “no thanks” button. “No, thanks, I don’t want to save money.” “I don’t need workout advice.”

Of course, I’m not the only one who’s noticed. Many people have commented on this phenomenon. I’ve heard it called confirmshaming and the Nielsen Norman Group called them manipulinks. Someone even started a tumblr for screenshots of the ways companies try to manipulate visitors into handing over their email address.

In deliverability terms, I don’t think this is a great strategy. Manipulating users into giving you an email address is never a good thing for finding enthusiastic engaged users. I’ve written before about how some opt-in schemes are closer to taking permission asking for it. Confirmshaming is not exactly taking permission, but it is senders attempting to get an email address from a user who might not otherwise be inclined to share personal information.

Interestingly enough, there is some small amount of research showing that these techniques, despite showing an increase in address acquisition, may drive down brand reputation.

Although manipulinks may in fact cause people to pause, consider, and even convert in higher numbers, there’s a hidden tradeoff involved.  This approach will negatively impact your user’s experience in ways that aren’t as easily quantified with A/B testing. The short-term gains seen by increased micro conversions will come at the expense of disrespecting users, which will likely result in long term losses. Are a few more newsletter signups worth lower NPS scores? Or a negative brand perception? Or a loss of credibility and users’ trust?


When companies use dirty tactics like this and then see conversion increases, it probably has less to do with “clever” manipulink text than with the fact that they’re straight up lying to their users. And that’s not just a needy pattern, it’s a dark patternStop Shaming Your Users for Micro Conversions

The article didn’t discuss deliverability related to collecting addresses through manipulinks. I’m not sure anyone has. But if these links contribute to a negative user experience on the website, it’s likely the negative feelings transfer to the emails. Even if the emails themselves are great and don’t continue the negative user experience, how engaged are these users? Do companies using manipulinks to collect email addresses see any difference in deliverability from companies that don’t?

Major webmail providers focus on user experience. We know address collection processes are and important factor in reaching the inbox. Starting off an email relationship by shaming could hurt inboxing. Anyone have data?

Edit: Brian points out that Google is already watching who is doing full overlays and downgrading sites based on the overlays.

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Social media connections are not opt-ins

It seems silly to have to say this, but connecting on social media is not permission to add an address to your newsletter or mailing list or prospecting list or spam list. Back in 2016, I wrote:

[Scraping addresses from LinkedIn] is really rude. Just because someone accepted your contact request on LinkedIn, doesn’t mean they want to be added to any mailing lists you may have. Let’s be honest, some people have hundreds or thousands of LinkedIn contacts. They’re not going to want to get mail from all of them.

This behavior risks your ESP account. I know of ESPs who have disconnected customers for importing all their LinkedIn contacts. Harvesting Addresses from LinkedIn

In that blog post I wrote a number of suggestions for how to screen LinkedIn connections before sending them mail.

  1. Not everyone will necessarily be happy to receive this mail from you. Consider how closely you are connected with the person. Ask yourself: Would this person appreciate a commercial email from me or my company? If you don’t know the person well enough, then it’s likely that the answer will be no. Put a little time and energy into making sure that your message is going to be wanted. If that means dropping people you’re not sure about off your contact list, then do it.
  2. Consider sending out personal mails, not importing the email addresses into your CRM system or sending them out through your ESP. Don’t make the message look like a mass mailing. This is a social network, make your contact actually social.
  3. Think about what YOU are bringing to the relationship with the recipient. Are you actually offering them any value? With the Christmas card I received the  message was “Our company is wonderful! We love ourselves. And we think we’re so great we’re going to send out this card telling you how we’re not sending out Christmas cards this year!” In Al’s case the message was adding him to a mailing list. In both cases, neither of us cared. There was nothing in it for us.
  4. If you want to announce a product and or service use the tools provided by the social networking service. LinkedIn has InMail, which allows recipients to set their contact preferences and mail through their system.
  5. If recipients object to your email, arguing with them is never helpful. You’re not going to convince them the mail is wanted, you’re just going to convince them that you’re an unrepentant spammer. Apologize, learn from it, move on.

Those are all still reasonable suggestions, ones that I’d offer to anyone who asked. But all those suggestions do is minimize the chance that the sender will get into trouble for sending spam. The fact is harvesting addresses and sending mail to them is spamming. Even if it’s B2B mail it’s still spam. Because it’s spam, even if you do everything I recommend you risk having some of those recipients object to the mail. Folks who object may complain to your ESP, they may disconnect from you on LinkedIn, they may block all future mail from your company, they may even convince their company to never do business with you. All of these are actual consequences I’ve seen happen.

When the sender is using a reputable ESP, the risks are even bigger. I also know of multiple cases where complaints resulted in the ESP disconnecting the customer for AUP violations. This is not something you want to happen.

B2B spam is still spam, and it’s not OK. Don’t be a spammer. Social media is called social for a reason.

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Still with the Microsoft problems

We took a quick trip to Dublin last week. I had every intention of blogging while on the trip, but… oops. I did get to meet with some clients, and had a great dinner while discussing email and delivery.

Coming back, I see a lot of folks still reporting delivery problems to Microsoft properties. I’ve been operating under the assumption this was temporary as kinks were worked out after the migration. I’m still pretty convinced not all of the problems are intentional. Even the best tested code can have issues that only show up under real load with real users. Reading between-some-lines tells me that the tech team is hard at work identifying and fixing issues. There will be changes and things will continue to improve.

With all that being said, I think it’s important to realize that delivering to the new system is not the same as delivering to the old system. This is a major overhaul of their email handling code, representing multiple years worth of planning and development inside Microsoft. It’s very likely that not all of the current delivery problems are the result of deployment. Some of the problems are likely a result of new standards and thresholds for reaching the inbox. What worked a year ago to get into the inbox just doesn’t any more.

What can we do?

The first step is always acceptance.

Accept that …

… the delivery problems aren’t a mistake on Microsoft’s part.

… more difficulty reaching the inbox is not an accident.

… Microsoft may not ever tell us exactly what to do.

In fact, this new round of problems at Microsoft feels a lot like deliverability in the mid-2000s. All we can see is delivery is bad. There is no guidance from postmaster pages or public statements. We’re getting little to no feedback from the ISPs. The support channels seem to be returning messages unrelated to the questions we’ve asked. It’s 2005 delivery all over again!

In many ways we’re luckier now, as we have history and experience to draw on, as well as working relationships with folks inside the ISPs. I have every confidence that the postmaster pages will be updated at some point. Senders will continue testing and figure out how to send mail that makes it to the inbox and that information will get shared through the industry. Microsoft will get to a point where their end is stable and tests give us consistent responses and we can develop meaningful models.

We’re going to have to listen to the ISPs, and not just to what they say on the surface. ISP employees are typically limited to what they can say publicly, but many of them indicate investigative pathways in their responses to questions. As well, there are now trusted intermediaries to disseminate information that will help improve the overall email ecosystem.

It’s not just Microsoft

As I’ve said before, I think we’re going to see changes to more places than Microsoft. AOL addresses are moving to the Yahoo MXs as of February 1, and that opens up a huge number of questions about delivery to AOL. Some of these changes are the result of GDPR, others just a normal service cycle. Whatever the reason, we’re back to having to work out what the black box is hiding. That means we’re going to have to pay attention to what our stats are telling us. More than that, though, we’re going to have to think about what new information we can collect and how to use it to improve delivery.

All in all, deliverability is changing and we’re all going to need to adapt.


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AOL Changes

We’ve known for a while that AOL email infrastructure is going to be merging with Yahoo’s, but apparently it’s happening sooner than anyone expected.

The MXes for will be migrated to Yahoo infrastructure around February 1st. Reading between the lines I expect that this isn’t a flag day, and much of the rest of the AOL email infrastructure will be in use for a while yet, but primary delivery decisions will be made on Yahoo infrastructure.

The AOL and Yahoo postmaster teams are pretty smart so I assume they’ll have made sure that their reputation data is consistent, and be doing everything else they can do to make the migration as painless as possible. But it’s a major change affecting a lot of email, and I wouldn’t be surprised to see some bumpiness.

If you’ve done anything … unwise … with delivery to AOL addresses, such as hard-wiring MXes for delivery to, you should probably look at undoing that in the next week or so. I’m guessing the changeover will happen at the DNS level, so if you’ve nailed down delivery IPs for you might end up trying – and probably failing – to deliver to the old AOL infrastructure.




When we say that you might just be sending too much email and fatiguing or annoying the recipient into unsubscribing or hitting spam, this is the sort of thing we mean.

Three emails (to the same email address) in four minutes might be a bit much.

If you can’t combine the content you want to send into a single personalized email, maybe spread deliveries out a bit? Or even not send all of it, perhaps.


Filters evolving

I started writing this blog post while sitting on a conference call with a bunch of senders discussing some industry wide problems folks are having with delivery. Of course the issue of Microsoft comes up. A lot of senders are struggling with reaching the inbox there and no one has any real, clear guidance on how to resolve it. And the MS employees who regularly answer questions and help folks have been quiet during this time.

In some ways the current situation with Microsoft reminds me of what most deliverability was like a decade ago. Receivers were consistently making changes and they weren’t interacting with senders. There weren’t FBLs really. There weren’t postmaster pages. The reason knowing someone at an ISP was so important was because there was no other way to get information about blocking.

These days, we have a lot more institutional knowledge in the industry. The ISPs realized it was better to invest in infrastructure so senders could resolve issues without having to know the right person. Thus we ended up with postmaster pages and a proliferation of FBLs and best practices and collaboration between senders and receivers and the whole industry benefited.

It is challenging to attempt to troubleshoot deliverability without the benefit of having a contact inside ISPs. But it is absolutely possible. Many ISP folks have moved on over the years; in many cases due to layoffs or having their positions eliminated. The result is ISPs where there often isn’t anyone to talk to about filters.

The lack of contacts doesn’t mean there’s no one there and working. For instance, in the conference call one person asked if we thought Microsoft was going to fix their systems or if this is the new normal. I think both things are actually true. I think Microsoft is discovering all sorts of interesting things about their mail system code now that it’s under full load. I think they’re addressing issues as they come up and as fast as they can. I also think this is some level of a new normal. These are modern filters that implement the lessons learned over the past 20 years of spam filtering without the corresponding cruft.

Overall, I do think we’re in a period of accelerating filter evolution. Address filtering problems has always been a moving target, but we’ve usually been building on known information. Now, we’re kinda starting over. I don’t have a crystal ball and I don’t know exactly what the future will bring. But I think the world of deliverability is going to get challenging again.



That’s not how you do it…

Got an email this morning from a company advertising their newest webinar “The Two Pillars of Effective Large-Scale Email: Security and Deliverability.” The message came to a tagged address, so clearly I’d given them one at some point. But I didn’t recognize the name or company or anything. I did a search to seen when I may have interacted with this company in the past.

Looking through my old emails, it appears I contacted this company through their support form back in 2007. They were blocking a client’s newsletter. This is what I sent:

One of my clients has asked me to talk with you about your blocking schemes. They’re rather confused as their mail to a customer (one-to-one mail, not bulk) is ending up in the junk/spam folder. They’re not sure what they’re doing to get filtered.

Is there someone who can talk to me about your filtering schemes so I can explain to your mutual customer what is happening?

The response was pretty unhelpful.

I see that the email address insight@ESP is already in Michael’s allow list in his Email Defense filter settings — was this a recent addition? This should let any emails sent from that address through without being filtered first. Another suggestion would be to add the source IP address itself to his allow list if emails are still being caught. Let us know if this alleviates the situation.

That’s the last I heard from said company until this morning, when they sent me an ad.

A common question we’re asked is “How can I safely and securely utilize large-scale/mass emailing to communicate?”

Whether you’re sending newsletters, announcements, notifications, even sensitive or private information, there are two pillars you must have in place to ensure your communications are sent securely AND are delivered without being classified as spam.

One way to prevent communications from being classified as spam is to not grab addresses from a decade ago out of your support queue and use them for marketing out of the blue. Also, I’m much more likely to trust your opinion on delivery if you follow CAN SPAM. I mean, it’s nice you sent me a picture of the nice lady who sent the spam, but you forgot to put a postal address on the email.

Interestingly enough, the company actually has a pretty effective sounding AUP for their customers. They prohibit, among other things:

  • Automatically opting visitors or purchasers into their subscriber list. This includes “pre-checking” an opt in box on forms.
  • Automatically adding subscribers on one mailing list to unrelated mailing lists
  • Sending emails to subscribers that are unrelated to the purpose to which they opted in
  • Adding people to the mailing list without their permission
  • Sending messages to people who have requested to be removed from the mailing list
  • Using old lists without checking with the subscribers that their addresses are still valid and that they still wish to be subscribed.

Too bad they don’t apply their AUP to their own email program.

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Oh, Microsoft

Things have been a little unsettled at Microsoft webmail properties over the last few months. A number of ESPs reported significantly increased deferrals from Microsoft properties starting sometime late in November. Others saw reduced open rates across their customer base starting in late October. More recently, people are noticing higher complaint rates as well as an increase in mail being dropped on the floor. Additionally, Return Path announced certification changes at the end of November lowering the Microsoft overall complaint rate to 0.2%, half of what is was previously.

Overall, sending mail to Microsoft is a challenge lately. This is all correlated with visible changes which may seem unrelated to deliverability, but actually are. What are the changes we know about?

  1. Towards the end of 2017, Microsoft moved their free webmail properties over to the same backend as Office365.
  2. Microsoft has updated their mobile interface to include this-is-spam buttons.
  3. FBL reports are generated now when users move mail to the bulk folder, even when using an IMAP client.
  4. Microsoft and Return Path decided to lower the acceptable complaint rate for certified IPs.

All of these changes are clear evidence Microsoft is investing in their email product and their filtering methodology.

Is it better?

I’m hearing mixed reports from folks. Many senders are seeing improvements in inboxing. However, it’s neither a consistent or linear progression. Things will improve for a while, then fall apart again. The overall trajectory is upwards, which is good; but there is frequent backsliding.

When will it be over?

I’m not sure. It may be that the new backend gives Microsoft some extra knobs and levers to dial in their filters and inboxing there will continue to be challenging. One thing I’m seeing on my clients is that Microsoft delivery is tracking closer to Gmail, or even a little worse. Senders that have traditionally struggled to reach the Gmail inbox are now starting to struggle to also reach the Microsoft inbox. This indicates that their filtering processes are focusing more on engagement and user interaction with email than before.

One bit of evidence for that is the move to more closely record feedback from mobile applications and generating FBL emails from IMAP clients. Sendgrid has a good blog post from last week discussing the increase in complaints. To me, this really confirms that Microsoft is looking at engagement and has improved their tools to better measure it.

A major problem with FBL reports is that they were only available when the ISP controlled the email interface. People who used a desktop or mobile mail client didn’t have a spam button, so even if they hated a particular mail, they couldn’t report it. Now, they have a report button in the mobile interface. On the desktop, reports are generated simply by moving messages to the spam folder. This means more complaints from recipients that couldn’t complain before.

At the same time they’re increasing the number of complaints generated, Microsoft has visibly lowered their complaint thresholds. This means more senders are going to struggle with inbox delivery, at least in the short term.

What does Microsoft say?

Many different folks attempted to discuss this with Microsoft employees, but there weren’t many answers forthcoming. One individual did report a response to one of their complaints that indicated Microsoft was seeing an overall increase in complaints. This may be due to the increase in reporting pathways, but it also might be due to the deluge of holiday mail. Many recipients react negatively to the holiday ramp up and hit spam or unsubscribe from more mail.

In all likelihood the increase in complaints is likely partially attributed to the increase in volume and the increase in reporting pathways.

What now?

As Microsoft has not published any specific information on their new filters, we’re left with seeing what has worked for senders to improve delivery. As always, send to users who want and expect your mail. Pay attention to engagement and remove recipients that show little interest in mail. Use other channels to encourage users to check their bulk folder and move the mail back to their inbox. If you’re doing all these things and not seeing improvement, talk to your deliverability team. They may see something you don’t. If your delivery team can’t help you, contact us and we’ll see what we can do.

Above all, don’t expect this to be resolved overnight. Microsoft has change how they’re doing things and it may take a few more weeks or months before their filters are dialed in exactly right. Expect changes to continue. I know it’s difficult to be patient, but sometimes there’s nothing else to do. Send good mail users want, and the filters will catch up.


That Should Be A Word

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What … is your name?

For some reason otherwise legitimate ESPs have over the years picked up a habit of obfuscating who they are.

I don’t mean those cases where they use a customers subdomain for their infrastructure or bounce address. If the customer is Harper Collins then mail “from” sent from a server claiming to be isn’t unreasonable. (Though something in the headers that identified the ESP would be nice).

No, I mean random garbage domains created by an ESP to avoid using their real domains in the mail they send and in their network infrastructure. This isn’t exactly snowshoe behaviour. They’re not really hiding anything terribly effectively from someone determined to identify them – the domains are registered with real contact information, and the IP addresses the mail is sent from are mostly SWIPped accurately – but they do prevent a casual observer from identifying the sender.

Silverpop has registered over 9,000 domains in .com that are just “mkt” followed by some random digits that they use for infrastructure hostnames, bounce addresses and click-tracking links. Apart from anything else, it’s a terrible waste of domain name space to use where they could just as well use or

For what they’re paying just for domain name registration and management they could probably hire multiple full time employees.

And Marketo has registered over 17,000 domains in .com that are just “mkto-” followed by what looks like a location code.

(I’m not picking on Marketo and Silverpop in particular – several other notable ESPs do the exact same thing – they’re just relevant to the end of the story).

Using garbage domains like this makes you look more like a snowshoe spammer at first glance than a legitimate ESP.

It also makes it much harder for a human glancing at your headers to correctly identify a responsible party …

… which is probably why abuse@marketo are rather tired of receiving misdirected complaints about spam sent by Silverpop from machines called something like