Outrunning the Bear

bear
You’ve started to notice that your campaigns aren’t working as well as they used to. Your metrics suggest fewer people are clicking through, perhaps because more of your mail is ending up in junk folders. Maybe your outbound queues are bigger than they used to be.
You’ve not changed anything – you’re doing what’s worked well for years – and it’s not like you’ve suddenly had an influx of spamming customers (or, if you have, you’ve dealt with them much the same as you have in the past).
So what changed?
Everything else did. The email ecosystem is in a perpetual state of change.
There’s not a bright line that says “email must be this good to be delivered“.
rideInstead, most email filtering practice is based on trying to identify mail that users want, or don’t want, and delivering based on that. There’s some easy stuff – mail that can be easily identified as unwanted (malware, phishing, botnet spew) and mail that can easily be identified as wanted (SPF/DKIM authenticated mail from senders with clean content and a consistent history of sending mail that customers interact with and never mark as spam).
The hard bit is the greyer mail in the middle. Quite a lot of it may be wanted, but not easily identified as wanted mail. And a lot of it isn’t wanted, but not easily identified as spam. That’s where postmasters, filter vendors and reputation providers spend a lot of their effort on mitigation, monitoring recipient response to that mail and adapting their mail filtering to improve it.
Postmasters, and other filter operators, don’t really care about your political views or the products you’re trying to sell, nor do they make moral judgements about your legal content (some of the earliest adopters of best practices have been in the gambling and pornography space…). What they care about is making their recipients happy, making the best predictions they can about each incoming mail, based on the information they have. And one of the the most efficient ways to do that is to look at the grey area to see what mail is at the back of the pack, the least wanted, and focusing on blocking “mail like that”.
If you’re sending mail in that grey area – and as an ESP you probably are – you want to stay near the front or at least the middle of the grey area mailers, and definitely out of that “least wanted” back of the pack. Even if your mail isn’t great, competitors who are sending worse mail than you will probably feel more filtering pain and feel it sooner.
Some of those competitors are updating their practices for 2015, buying in to authentication, responding rapidly to complaints and feedback loop data, and preemptively terminating spammy customers – and by doing so they’re both sending mail that recipients want and making it easy for ISPs (and their postmasters and their machine learning systems) to recognize that they’re doing that.
Other competitors aren’t following this years best practices, have been lazy about providing customer-specific authentication, are letting new customers send spam with little oversight, and aren’t monitoring feedback and delivery to make sure they’re a good mail stream. They end up in the spam folder, their good customers migrate elsewhere because of “delivery issues” and bad actors move to them because they have a reputation for “not being picky about acquisition practices“. They risk spiraling into wholesale bulk foldering and becoming just a “bulletproof spam-friendly ESP”.
If you’re not improving your practices you’re probably being passed by your competitors who are, and you risk falling behind to the back of the pack.
And your competitors don’t need to outrun the bear, they just need to outrun you.

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URL reputation and shorteners

A bit of  a throwback post from Steve a few years ago. The problem has gotten a little better as some shortening companies are actually disabling spammed URLs, and blocking URLs with problematic content. I still don’t recommend using a public URL shortener in email messages, though.
Any time you put a URL in mail you send out, you’re sharing the reputation of everyone who uses URLs with that hostname. So if other people send unwanted email that has the same URL in it that can cause your mail to be blocked or sent to the bulk folder.
That has a bunch of implications. If you run an affiliate programme where your affiliates use your URLs then spam sent by your affiliates can cause your (clean, opt-in, transactional) email to be treated as spam. If you send a newsletter with advertisers URLs in it then bad behaviour by other senders with the same advertisers can cause your email to be spam foldered. And, as we discussed yesterday, if spammers use the same URL shortener you do, that can cause your mail to be marked as spam.
Even if the hostname you use for your URLs is unique to you, if it resolves to the same IP address as a URL that’s being used in spam, that can cause delivery problems for you.
What does this mean when it comes to using URL shorteners (such as bit.ly, tinyurl.com, etc.) in email you send out? That depends on why you’re using those URL shorteners.
The URLs in the text/html parts of my message are big and ugly
Unless the URL you’re using is, itself, part of your brand identity then you really don’t need to make the URL in the HTML part of the message visible at all. Instead of using ‘<a href=”long_ugly_url”> long_ugly_url </a>’ or ‘<a href=”shortened_url”> shortened_url </a>’ use ‘<a href=”long_ugly_url”> friendly phrase </a>’.
(Whatever you do, don’t use ‘<a href=”long_ugly_url”> different_url </a>’, though – that leads to you falling foul of phishing filters).
The URLs in the text/plain parts of my message are big and ugly
The best solution is to fix your web application so that the URLs are smaller and prettier. That will make you seem less dated and clunky both when you send email, and when your users copy and paste links to your site via email or IM or twitter or whatever. “Cool” or “friendly” URLs are great for a lot of reasons, and this is just one. Tim Berners-Lee has some good thoughts on this, and AListApart has two good articles on how to implement them.
If you can’t do that, then using your own, branded URL shortener is the next best thing. Your domain is part of your brand – you don’t want to hide it.
I want to use a catchy URL shortener to enhance my brand
That’s quite a good reason. But if you’re doing that, you’re probably planning to use your own domain for your URL shortener (Google uses goo.gl, Word to the Wise use wttw.me, etc). That will avoid many of the problems with using a generic URL shortener, whether you implement it yourself or use a third party service to run it.
I want to hide the destination URL from recipients and spam filters
Then you’re probably spamming. Stop doing that.
I want to be able to track clicks on the link, using bit.ly’s neat click track reporting
Bit.ly does have pretty slick reporting. But it’s very weak compared to even the most basic clickthrough reporting an ESP offers. An ESP can tell you not just how many clicks you got on a link, but also which recipients clicked and how many clicks there were for all the links in a particular email or email campaign, and how that correlates with “opens” (however you define that).
So bit.ly’s tracking is great if you’re doing ad-hoc posts to twitter, but if you’re sending bulk email you (or your ESP) can do so much better.
I want people to have a short URL to share on twitter
Almost all twitter clients will abbreviate a URL using some URL shortener automatically if it’s long. Unless you’re planning on using your own branded URL shortener, using someone else’s will just hide your brand. It’s all probably going to get rewritten as t.co/UgLy in the tweet itself anyway.
If your ESP offers their own URL shortener, integrating into their reporting system for URLs in email or on twitter that’s great – they’ll be policing users of that just the same as users of their email service, so you’re unlikely to be sharing it with bad spammers for long enough to matter.
All the cool kids are using bit.ly, so I need to to look cool
This one I can’t help with. You’ll need to decide whether bit.ly links really look cool to your recipient demographic (Spoiler: probably not) and, if so, whether it’s worth the delivery problems they risk causing.
And, remember, your domain is part of your brand. If you’re hiding your domain, you’re hiding your branding.
So… I really do need a URL shortener. Now what?
It’s cheap and easy to register a domain for just your own use as a URL shortener. Simply by having your own domain, you avoid most of the problems. You can run a URL shortener yourself – there are a bunch of freely available packages to do it, or it’s only a few hours work for a developer to create from scratch.
Or you can use a third-party provider to run it for you. (Using a third-party provider does mean that you’re sharing the same IP address as other URL shorteners – but everyone you’re sharing with are probably people like you, running a private URL shortener, so the risk is much, much smaller than using a freely available public URL shortener service.)
These are fairly simple fixes for a problem that’s here today, and is going to get worse in the future.

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Is Amazon SES a reputable place to send mail from

On the first installment of our Wednesday question series, I chose a question from twitter.

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Domains need to be warmed, too

One thing that came out of the ISP session at M3AAWG is that domains need to be warmed up, too. I can’t remember exactly which ISP rep said it, but there was general nodding across the panel when this was said.
This isn’t just the domain in the reverse DNS of the sending IP, but also domains used in the Return Path (Envelope From) and visible from.
From the ISP’s perspective, this makes tons of sense. Some of the most prolific snowshoe spammers use new domains and new IPs for every send. They’re not trying to establish a reputation, rather they’re trying to avoid one. ISPs respond by distrusting any mail from a new IP with a new domain.

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