Ok, so you want to start emailing/have acquired a database/looked at your own database of email addresses that you ultimately want to email. If humans have inputted the data without any verification stage it will contain all manner of errors, human error is understandable and unavoidable.

What kind of mistakes could these “data inputers” have made? It’s best illustrated by an example…

If Alice was taking down a customer’s email address, say Reginald@hotmail.com they could have typed the following…

  • Reginald@@hotmail.com – typed a single character or letter twice
  • Reginald@htmail.com – neglected to type a character
  • Reginald@htomail.com – typed all characters but in the wrong order

Having noticed this problem in BrightMinds’ database I wrote a TSQL script to identify and correct these human errors.

The script reads your existing email database and identifies domains whose emails have recently been read. These are inserted into the table domainKey. Next, these domains are read sequentially in a cursor and the human error domains created. A reference table is then created – domainSynRef with two columns – realdomain and errordomain.

Of course some rearranged domains could well be real domains, the script checks for this but could do with some development. Clearly if anyone else wishes to use the it will need some light table name or structure modifications. The basic string manipulations though are still entirely valid.

So here’s an example for what it generates with the domain aol.co.uk…

aol.co.uk .aol.co.uk
aol.co.uk @aol.co.uk
aol.co.uk ..aol.co.uk
aol.co.uk aolcouk
aol.co.uk aolco.uk
aol.co.uk aol.couk
aol.co.uk aol@co@uk
aol.co.uk aol@co.uk
aol.co.uk aol.co@uk
aol.co.uk l.co.uk
aol.co.uk ao.co.uk
aol.co.uk aol.co.u
aol.co.uk aol.co.
aol.co.uk ol.co.uk
aol.co.uk al.co.uk
aol.co.uk aol.o.uk
aol.co.uk aol.c.uk
aol.co.uk aol.co.k
aol.co.uk aaol.co.uk
aol.co.uk aool.co.uk
aol.co.uk aoll.co.uk
aol.co.uk aol..co.uk
aol.co.uk aol.cco.uk
aol.co.uk aol.coo.uk
aol.co.uk aol.co..uk
aol.co.uk alo.co.uk
aol.co.uk ao.lco.uk
aol.co.uk aolc.o.uk
aol.co.uk aol.oc.uk
aol.co.uk aol.c.ouk
aol.co.uk aol.cou.k
aol.co.uk aol.co.ku
aol.co.uk a.loco.uk
aol.co.uk aoc.lo.uk
aol.co.uk aoloc..uk
aol.co.uk aol..ocuk
aol.co.uk aol.cu.ok
aol.co.uk aol.coku.

Quite comprehensive I think, could it be edited to introduce double errors such as Reginald@hhotmail..com? Sure, if you then write some more string statements after the cursor. Although there’s probably a stage when one has to think – if someone’s made this many errors, can we assume we can fix it?!

As always, suggestions/modifications/improvements very much welcome. I imagine a single run script and subsequent checking function would be better for a single email address input and would probably work better than my stored procedure, this is just what fitted best into our environment (checking c.300,000 email addresses).

The result? We gained over 1500 now valid email addresses. Try it out for yourself, download the stored procedure here.

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If you’ve chosen to send your own marketing emails without an ESP you’ll already understand the importance of gaining good sender reputation with ISPs and webmail domains. Choose not to follow their guidelines and your emails will likely end up in junk/spam folders or worse still your IPs blacklisted.

Unfortunately there’s no easy “X number of steps” way to gain instantly great email sending reputation with ISPs. What’s required is to follow massive amounts of guidelines in your email processing, design and send stages with strict attention to detail.

So to help us all I’ve put together a broad but detailed 7 step guide to gaining great email sender reputation. It’s a compilation of all major ISP and webmail provider’s bulk mail sender guidelines and will, if executed fully, lead to very good sender reputation.

Design & Setup – Before you start sending

1. SMTP Mail Server.

When building your SMTP Server, whether using Windows or UNIX/Linux you’ll need to ensure it’s on a separate, fixed IP address to your business and transactional emails. You’ll also need to setup a reverse DNS record against its domain. E.g if your fixed sender IP is 89.98.252.65 then ask your ISP to setup the reverse DNS record email.yourdomain.com and ‘point it to’ 89.98.252.65. The SMTP server also needs to send authenticated emails using the SPF/SenderID and DKIM/DomainKeys frameworks. A few months ago I wrote a post describing how to integrate DKIM/DomainKeys into Microsoft Exchange Server. There are plenty of guides out there explaining how to set both of these up on UNIX/Linux.

2. Clean Lists

Design your newsletter subscribes process to follow a ‘double opt-in’ mechanism to minimise junk/wrong/spam-trapping email addresses. In other words ensure that when someone signs up to your service, send them an initial email that contains a verification link. When clicked the user’s email address is verified and added to the mailing list. This stops us trying to send emails to fictionaladdress@hotmail.com and punishing our reputation when we receive a hard bounce from hotmail.com. Don’t know what a hard bounce is? You’ll want to learn about them.

3. Unsubscribes, bounces and bad formats

Double, triple and quadruple check that your system processes unsubscribe requests quickly and correctly. Likewise for soft and hard bounces; ISPs are well known to assess sender credibility heavily on the number of bounces they generate. Lots of bounces means a poorly compiled or maintained emailing list.

If you collect email addresses by phone, post or acquisition make sure you have some form of bad format checking in place to prevent typical errors like barry@hotmail..com or barry@@hotmail.com. If you want to get extra fancy, script it to dynamically replace historical (pre double opt-in) email addresses like homail, ohtmail, hptmail with hotmail. I’ve written my own in TSQL and will publish it shortly.

Monitor your new subscribers for spamflag addresses – abuse@, postmaster@ and nospam@ addresses should all be automatically unsubscribed.

4. Sign up to email feedback loops (FBLs) and whitelist services.

FBLs simply notify the email sender when the recipient clicks on the ‘This is Spam’ button while reading your email. Since these recipients have deemed our email to be spam (and the ISP concerned knows this) we need to unsubscribe them to ensure we build good reputation. Many of you will have signed up with the big ones AOL, Hotmail and Yahoo but do make the very small effort in signing up for the rest. Word to the wise maintains a good list of all known feedback loops and whitelists along with a script to make processing their spam notifications a little easier. If processing these FBL notifications becomes a drag be sure to read my solution on how to automate it.

Starting up – When you start sending

5. Test your messages

Use design tools such as Email on Acid and Litmus to test your designs in multiple email clients to ensure they all look the same. Also paste the HTML into content checkers to get a “spam score” as well as suggestions on how to avoid the spam filters. SpamCheck and Contactology are both pretty useful.

6. Start small and often

Nobody wants to hear this, especially when they’re planning on sending 250,000 emails a week but it really is very important for those first few weeks. ISPs are fully aware of your sending trends and will consider a sudden increase in sending rates highly suspicious. Try to send small to begin with and slowly raise the sending rate.

Try also to be consistent with the times you send your emails. This may be difficult, especially if you occasionally respond to current affairs or the weather etc. Sending zero emails on Monday followed by 50,000 on Tuesday looks like a potential email server hijacking and may result in your mail servers being temporarily blocked by ISPs. Is there anything wrong with some people receiving ‘Monday Newsletter’, some ‘Tuesday Newsletter’ etc? Of course not, in fact depending on seasonality, staffing levels and demand it’s arguably quite appealing.

7. Design well

Follow CAN-SPAM requirements. It’s a complex list of requirements laid down in 2003 that were meant to stop SPAM. Clearly it failed but for us non-spammers that simply want our messages read by our subscribers we need to comply. OpenMoves is a decent post outlining the basic requirements.

Send Multi-part MIME emails rather than just HTML; ISPs look at simple HTML emails as likely manifesting covert “Click here for FREE Viagra” banners. Likewise, low text/html ratios look suspicious so ensure you pack a great deal of text into your emails. Product descriptions bulked out with product reviews works very well.  Avoid using attachments and keep your “From Name” and “From Address” consistent. Never link to another domain or port from within your emails.

Design for when images are enabled and disabled and use your imagination to think about how best to push your message. If you use a broad image in a table then don’t just use alt text, place <font> tags around the image to enlarge the alt text and make it unmissable. Look at the images below – which one do you think will get more clicks?

Rubbish, bland alt tags

Vibrant Alt Tags

Beyond the technical design, good, well thought out and tested design results in better customer engagement – better open rates, click throughs and conversions. Importantly though it also results in far fewer unsubscribe requests. Ensure you send genuinely engaging emails. Weekly “Hey look at our samey products that we’ve sent you a million times before” will pull in reliable revenue but you’ll likely see the clickers and converters are not your most recent or valuable customers. Likewise, people won’t be engaged if you just talk solely about your products with wholly one-sided conversation (there are curious exceptions).

Where’s this leading? Well webmail clients compile and analyse email open rates and click through rates by domain and judge your spam content on this. If 80% of GoogleMail recipients open an email from yourdomain.com then GoogleMail will deem yourdomain.com to be highly engaging and so decrease its likelihood of ending up in the Spam/Junk folder. If only 5% of them open the email, GoogleMail can assume that what you send is not really worth cluttering their inboxes. The lesson here? Only send your emails to those that want to read them.

Keeping that reputation

As already mentioned, try to remain consistent with broadcast levels and times. Does sending 50,000 emails on Monday and 10 across the rest of the week look suspicious? Yes, very, so stagger the send. The time of day you send is more likely to influence the open rate rather than directly affect your reputation. For example I know that most of my emails are opened at about 9.30pm, even if I send them at 2am. So I can achieve a better open and click through rate by sending them at around 9pm. Better open and click rates mean better reputation. For other businesses, especially B2B, it’s likely to be different.

Should you send all your marketing emails from one IP? Yes, to begin with at least because it simplifies IP reputation assessments by the ISPs. However, once you’re up to speed it’s worth sending through a second IP via another ISP. Imagine if your ISP suddenly changed your IP range, went bust or just felt like being irritating – you could lose your IP and so all that built up good reputation – disaster! So like with the first IP, create a reverse DNS record and begin sending low volume. Slowly build the volume and split the sending across both IPs.

Monitor your deliverability across domains by collating the number of emails sent and comparing it to the number of emails opened by domain. This, monitored weekly, gives a great view into your deliverability by domain. To increase the definition, look at the same data over a single day. This will reveal whether you’re reaching short term sending limits with some domains. To check whether you have any long term issues, be sure to check MX Toolbox’s Blacklist Checker.

Sending emails is not an easy exercise to get right but as with so many things in life, if we tick all the boxes and follow the correct guidelines, we can create really very successful email marketing programmes.

If anyone feels like contributing to this then please email me and I’ll add your suggestions!

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One of the biggest nightmares for email marketing folk is email client image blocking. It’s a security feature designed to stop email senders from tempting their recipients’ computers into downloading unknown content. Could someone wrap a virus into JPG, embedded in an HTML email? Sure. It also helps stop kinky viagra spam emails being viewed by little Timmy.

Ignoring the expensive options to guarantee image blocking is switched off (Goodmail etc) we can only really do two things. Firstly, we can encourage recipients to disable image blocking on one of our emails early in the relationship. Once image blocking is disabled for the sender, that setting will normally be saved permanently. The other option is to take full advantage of Alt tags. These are the short blurbs of text or ‘Micro-copy’ shown instead of images when the images are unavailable or blocked.

Annoyingly, not all email clients/web clients actually support showing Alt tags (grumble). Here is a list of most current email clients and whether they support displaying Alt tags…

Supports Alt Tag Display Doesn’t support Alt Tag Display
Hotmail Desktop Client Entourage 2004
Outlook 2003 Entourage 2008
Outlook Express Mac Mail
Thunderbird 2 Outlook 2007
Thunderbird 3 Outlook 2010
AOL Online Windows Mail
Gmail Online Hotmail Online
Yahoo Classic Online
Yahoo New Online
iPhone Client

The important things to point out are that Outlook 2007 and 2010 do not show Alt tags and neither do any of the Mac clients. On the bright side though all the webmail clients do show them. As a random observation, isn’t it a little strange that whilst the Microsoft Hotmail Client displays Alt tags, Hotmail online does not?!

So here are my suggestions for getting your recipients to permanently disable image blocking…

  • For one of your first communication triggered emails, try sending something with a tempting subject line and a body made almost wholly of 1 image. Include text above the image politely reminding the user to disable image blocking. Simple but some recipients will disable image blocking.
  • Instead of using dull, informative Alt tags like ‘logo’ and ‘menu image’ try using ‘Disable Image Blocking’ for every alt tag seen in a typical email client viewing pane. This is clearly a powerful call to action and I’ll be running a randomised test of precisely this very soon. I will post the results.
  • Remember to think long term and ensure you write your Alt tags to get your recipients to do what you want them to do. If you write ’50% off’ you’re clearly more likely to get a click than a disabled image block. Do you think ‘unbeatable offer image’ or ‘disable image blocking’ would perform better? Which will provide better long term click through for future email campaigns?
  • As ever – experiment, measure and experiment again.
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