Word to the Wise

We make email better.

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We make email better.

Word to the Wise helps email marketers create more effective email messages, programs and infrastructures. We advise you how to skillfully navigate the constant business, technology, and policy challenges so your messages reach your customers.

We can help you with your email strategy, deliverability challenges and many other email issues.

Latest stories

The Case of the 500-mile Email

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I stumbled across this story again this morning, and it’s such a lovely delivery yarn I thought I’d share it. It’s from Trey Harris, and it’s set in the mid 90s. Here's a problem that *sounded* impossible... I almost regret posting the story to a wide audience, because it makes a great tale over drinks at a conference. :-) The story is slightly altered in order to protect...

iOS17 filtering click tracking links

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I’ve heard quite a bit of concern about what iOS 17’s automatic removal of click-tracking parameters means, but less discussion of what it actually does. Broadly it’s Apple trying to improve user-privacy by making it harder to do cross-site tracking at scale. Cross-site tracking is the basis of a lot of privacy-violating tracking technologies, and tracking parameters added to...

They Must Have Changed Something…

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One of the most common refrains I hear from folks with delivery problems is that the filters must have changed because their mail suddenly started to go to the bulk folder. A few years ago, I posted about how even when there is no change in the sender’s behavior, reputation can slowly erode until mail suddenly goes to the Gmail bulk folder. Much of that still applies – although the...

Is this email address disposable?

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As a consumer there are several different sorts of email address that are described as “disposable” or “temporary”. Some of them are what we might call tagged addresses – addresses that are unique, created to be given to a specific vendor. If it’s misused by the vendor, or if it’s leaked to spammers, then the address can be disabled, either by rejecting...

C is for Cookie

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Trekkie Monster. He’s obsessed by social media and isn’t owned by Children’s Television Workshop. What is a Cookie? I’m not talking about biscuits, nor about web cookies, at least not exactly. When you’re talking to a protocol developer a cookie is a thing you’re given, that you hang on to for a while, then give back. If you leave your suitcase with your hotel...

Unresolvable RFC.5321 domain at Yahoo

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Seen this recently? 451 Message temporarily deferred due to unresolvable RFC.5321 from domain; see This is Yahoo doing some extra work to identify that the 5321.From domain1The return-path, aka the 821.From, 5321.From, or bounce address is the email address you send from at the protocol level, not the email address in the From: header, and it’s the address any bounces will be sent to. of...

Is .edu a canary?

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Several times recently I’ve heard about something unusual happening email delivery-wise at academic domains that was new, and wasn’t being seen at non-academic domains on the same lists. Most recently it was aggressive following of all links in an email at delivery time, seen at several .edu domains, all using the same mail provider. Not that unusual a thing in itself, we know that...

Want a link on WttW?

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There is an ever increasing amount of spam I am getting from various companies asking for links here on WttW. The Answer is No. We do not have paid links. We do not have sponsored posts. Any links on the site are done at our whim and because we have something to say about your company. The only place we offer links is on the ESPs and Purchased Lists post. And, I gotta tell you, if you buy my...

Is email dead?

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These last few years have been something, huh? Something had to give and, in my case, that something was blogging. There were a number of reasons I stopped writing here, many of them personal, some of them more global. I will admit, I was (and still am a little) burned out as it seemed I was saying and writing the same things I’d been saying and writing for more than a decade. Taking time...

“Friendly From” addresses

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When we’re looking at the technical details of email addresses there are two quite different contexts we talk about. One is an “821 address” or “5321 address”. This is the email address as it’s used by the SMTP protocol, as part of the “MAIL FROM: <>” or “RCPT TO: <>” commands sent to the mailserver. It’s defined in RFC 821...

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