Made of Everything You're Not

It’s crazy to me how important email is; it’s almost 2010 and I’m still, still, relying on email for communication more than anything else. Considering just how broken email is this, along with how I know it’s broken, this isn’t a little surprising. Managing the shear amount of email I get used to be pretty easy but now… it’s a little more painful but still manageable.

IMAP on Blackberry: The Poor Mans BES

When I had the day job I had access to a nice little network with Exchange 2003 and the latest Blackberry Enterprise Server (BES). It never really occurred to me how spoiled this would make me but, now that it’s gone, it’s pretty obvious how much I relied on it for my email management.

Why? Syncing. Loved the whole syncing aspect; open an email on your Blackberry and the email was marked as open in Exchange. Send an email from your Blackberry and it appeared in your sent folder in Outlook. Even better if you sent an email in Outlook, through Exchange, it was put in your sent folder on your Blackberry. Simple. This was great for things like filing and responding to emails. Put simply, using the Exchange/BES combo allowed you to keep all your communication in sync.

Then I get unplugged from the BES and have to setup a new solution. First, I went to POP3 (as I was most familiar with the protocol) but this was a cluster fuck of a bad idea. Yes, email was put on the Blackberry but it’s a one way method and nothing was kept in sync. I’d do something on the device and when I would go to Gmail nothing would be there; this couldn’t do.

I also tried the native Gmail Blackberry app but this too wasn’t ideal; I hated how it wasn’t truly a “native” app in that other apps would still open the default Blackberry message program to do anything email related. For example, if I clicked on an email on a web page while on the Blackberry it wouldn’t open the Gmail app but the native messaging one instead. I was surprised how much this happened and how much it bothered me but it did.

Then I learned that Gmail has IMAP support and have been using it ever since. So far, IMAP is the closest approximation of the BES experience I’ve found. It’s not without it’s issues or anything, and technically it’s not supported by Google, but it’s the best solution I’ve found.

Probably the biggest issue I have with the IMAP integration is that mail manipulated on the Gmail site doesn’t get synced to my Blackberry. This isn’t too bad since I usually only use the Gmail site for sending but if I want to keep things in sync I have to treat the Blackberry as the master.

To keep the calendar and contacts in sync requires the use of another Blackberry app called Google Sync. Google Sync it’s keeps your contacts and calendar synced up between Google Calendar and Gmail contacts and your Blackberry.

While it’s not a perfect solution I’ve been mostly happy with IMAP and Gmail on the Blackberry. It’s way, way, better than paying money for an outsourced BES / Exchange account.

Being the Director of Technology for a marketing agency is full of surprises. The best surprise was learning that everyone is an expert. Yup; regardless of experience, or knowledge, you’re going to run into all sorts of people who know everything about subjects that are incredibly complex and deep.

Don’t Embed Videos in Email

This was made apparent the other day when I received a link to an article called Hot Ecommerce Trend: Embedded Video in Email.

The article starts out with the general, and true, premise that linking to videos is a good way to improve click through rates:

Anna Yeaman reports one retailer boasting a 20-27% click through rate without linking to video, and 51-65% with links to video. And Forrester Research reports video in email can increase click through by 2-3X.

Of course there’s no mention of what the campaigns were about, or who the sample targets were in relation to previous email campaigns. But what the hell, it’s the Internet, so we grain of salt the numbers and don’t give them any real weight. Interestingly, though the article never comes right out and says it, from the tone of the article it looks like the idea is that if linking to a video is good embedding the video directly is better.

The article goes into some detail about the obvious challenges of actually embedding a video in an email, instead of just linking to the video, (like spam flagging and file size mostly) but just doesn’t offer a satisfactory response on how to accomplish it. Basically, it says embedding a video is a good thing to do but doesn’t provide any solutions to do it.

This is probably because, oh, I don’t know, IT’S NOT A GOOD THING TO DO (hmm, bold, italics, all caps? serious text). Just don’t do it if you want your email to, you know, be seen by people.

According to the article:

What’s so tough about embedding actual video in email?

Deliverability is the issue. Large video attachments are often a red flag for spam filters, and ISPs (Internet service providers) block “complex data” including Javascript for security reasons.

ISPs have banned Javascript Sending video in an e-mail has been a challenge for deliverability, since large video attachments often alert spam filters. The way that Goodmail gets around this issue is that their e-mail class, called CertifiedEmail, is a paid service that does not go through typical e-mail filters.

Forgiving for a second the nonsensical flow of the second paragraph, it seems there’s a service called Goodmail that, somehow, allows email to bypass the spam filters. Unfortunately, Goodmail is currently only in use by AOL at the moment so it’s not realistic unless you have a list of only AOL users. Does anyone, besides AOL, send to just AOL? Exactly.

Next the article talks about sending to just gmail; provided the recipient signed up for YouTube video embedding in their gmail account settings they shouldn’t have a problem. This, too, suffers from the Goodmail problem of only working with one email provider. Not much of a solution really.

But, all of the above are minor issues that don’t really deal with the larger problem; email wasn’t made for embedded video. Sure, it can do it, in a kinda-sorta, if you squint and tilt your head kind of way, but it’s similar to how HTML isn’t a design language but has been re-purposed for that use.

Email was built for text; attachments weren’t even a possibility until 1996 with the introduction of RFC 2045. (The initial specification only allowed for text communication using 7bit US-ASCII as the encoding and had a limit on characters around 1,000 total.) Email with embedded video wasn’t even a thought at the time.

How much was video not considered an option? Just take a look at the complete lack of support for certain HTML tags required to embed a video in the popular email clients.

To be honest, there weren’t a lot of surprises here. The OBJECT and EMBED tags remain as poorly supported now as they were 3 years ago. This instantly wipes out Flash, Quicktime, and Windows Media formats. As predicted, Java support was also a no show.

So, what are your options then? That really depends on whether quality matters.

If quality actually means something to you then you definitely should avoid the much touted animated gif “trick”. Years ago this might have been a good idea but now, in the 21st century, it just looks dated. Once, videos and animated gifs were almost comparable but now the quality of online video just shines way too bright compared to an animated gif. It may be easy to do but definitely looks like amateur hour.

On the other hand, you could always link to the video. Why, for the love of god, this has to be stated plainly escapes me but c’mon people; just use an image and link to the video on your site. This has the added benefit of creating visitor to your property at the same time, and you never know, maybe they’ll think about sticking around.

To be honest, I don’t really see video in email EVER being a viable option. There are just too many problems inherit with the idea to make it possible, much less practical.

First, you have bandwidth, which is still one of the biggest barriers to doing anything cool online. Videos are big and delivering them via email is a sure way to drive people crazy. Have you ever tried to download an email with a big attachment? Same thing.

Second, as mentioned above the email clients don’t even support the HTML tags required to render a video even if it’s downloaded. This one is pretty big because those tags aren’t allowed for a reason: malware. If an EMBED or OBJECT tag is used the bad people have a bigger sandbox to play with. The rule of not opening attachments to help protect against malware goes right out the window. Changing the email client programs is just not going to happen.  Sorry.

So, let’s all get together and recognize that this isn’t going to happen. Ever.

In How to Not Suck at Email Campaigns I completely left out a HUGE part of not sucking; scrubbing your email list.

Sanitize email list

Scrubbing an email list before sending it out is something that rarely gets done but is actually pretty crucial.

See, email providers, the organizations that provide email like yahoo, gmail and hotmail, and some spam filters, actually look at the email addresses you send to and flag those they deem to be either role accounts or spam traps and they use that to determine part of your spam score. If your spam score is too high; you’re a spammer.

This assumes you have an honest list to begin with. If you’re buying lists of email addresses from people and sending emails to them you’re a spammer and nothing here is going to help you. Oh yeah, everyone else knows you’re a spammer too.

Fuck you.

Anyway, I first learned of the importance of scrubbing a list while preparing one of my clients email databases for a blast (they hired StreetWise to send email on their behalf). During the import process into the mailing solution we were using our account was put in lock down which essentially stopped the entire project dead in it’s tracks. After contacting the mailing solution I got the below response:

I do want to be clear that the list both contains spamtraps, role accounts (such as admin@) and other addresses with aspects that indicate that some part of the list may not be completely opt-in. Spamtrap addresses are those addresses that have generally been retired or are known by the domains postmaster to be inactive and as a result unlikely to be signing up for new mailing lists. These addresses may also be ones planted on a website specifically for email harvesting purposes. Sending to them indicates a lack of an opt-in process, the ideal option being a double opt-in confirmation method where members must both submit their email address and respond to a follow-up email before receiving regular mailings from the list.

Mail sent to spam traps, as with non opt-in mail in general, may result in a loss of deliverability for a sender. This may include domain blocks (refusal of the senders mail by a domain) or blacklisting by spam prevention agenies and further hurts the reputation of the sender.

Combined with negative feedback from the recipients (sent either to the sender, its ESP, or the users postmaster), not honoring opt-out requests, sending to a large amount of non-existent members, spamtrap addresses call into question the entire lists credibility.

So just what do you need to scrub for? Well, duplicates, MX records for the domain and syntax issues obviously but, more importantly, specific keywords in emails.

To start you want to get rid of any email address containing the keywords below (* is wildcard):

junk*
admin@*
root@*
postmaster@*
blackhole*
confirm@*
fuck*
donotreply*
help@*
nobody@*
*@poop.com
support@*
sysadmin@*
*spam*
dev@*
devnull@*

That’s not a complete list of course; just the ones I’ve personally discovered to date. I plan on compiling a database of them once I get more and so should anyone who’s serious about not sucking at bulk email blasts.

There’s also spam trap email addresses. These are email addresses people sign up for that allow them to sign up for accounts and other services without actually giving their real email address.

They are insanely popular (and pretty annoying too).

So far I’ve only had to deal with a few though. You want to remove any email address from the below domain:

*@spamgourmet.com
*@sneakemail.com
*@mailinator.com
*@trashymail.com
*@mailexpire.com
*@temporaryinbox.com
*@spambox.us
*@spamhole.com
*@pookmail.com
*@spamfree24.*
*@kasmail.com

This is especially important on lists you’re sending on behalf of your clients. I have yet to have a client freely admit to having email addresses that haven’t been opted into properly; they always swear that their list is clean. I’ve seen HUGE corporations, we’re talking hundreds of millions of dollar companies, hand over lists that decreased over 20% once it’s scrubbed.

Cool thing is, though, that the client usually has no idea. Usually, someone told them they have a list of email addresses somewhere and, odd as this may sound, they’re actually thrilled to be told their list isn’t “good”. Makes you look like you know your shit

One of the most frequent IT related tasks I have to deal with are email issues. Spam is a big part of my life, on both sides of the fence. I have to deal with legitimate email from clients getting flagged as spam on my network and I also have to make sure email StreetWise sends out on behalf of our clients doesn’t get flagged as spam.

Spam

Over the years I’ve put together a list of requirements for making sure email campaigns go as smoothly as possible. Since no one can seem to get email campaigns right I figured I write it all down and post it and hope someone gets something out of it. Enjoy!

Check Spam Score

A Spam Score is a number assigned by the spam-scanning rules. The higher the score, the more “spamlike” the message appears. It’s very important to how your email ranks so you can fix the before you send out the blast.

There’s a great tool called Mail-Check that will evaluate an email and report on it’s supposed spam score. It has an integrated SpamAssassin engine that performs a series of tests against your email to determine how much like spam it looks like.

The tool is in no way fool proof though. Be sure to use it as just a single source of information and don’t make too many decisions based on the results.

Send Email Slowly

The basic idea behind this idea is that an email provider looks at how many emails is coming in from a particular domain and, if there’s a lot of email coming in at , will assume it’s either a spammer or a virus. Not a good label to have on your domain.

How slowly should email be sent? Unfortunately, that’s a difficult question and the amount of email you need to send greatly affects the answer. For example, if you have 1,000 emails to send you probably don’t need to worry about sending too fast. On the other hand if you have 250,000 emails to send slowing down the send process is HUGELY beneficial.

I’ve heard that the best approach is to throttle your sending by recipient domain. Now, I’ve never done this myself, but throttling by domain is supposed to be helpful because you can keep a consistent flow of email coming from the mail server but since there isn’t a constant stream of email to one provider they don’t know a bulk mailing is being sent to their network.

Get Whitelisted

This ones a bit of a no brainer but you NEED to get your email domain whitelisted by the email service providers you’re sending to. This should include, at the very least, Yahoo!, gMail, MSN (hotmail) and AOL as well as the email recipients. This can be pretty tricky to do because the methods for getting whitelisted by the companies above tend to change fairly frequently. A good method to help would be to send individual requests to “postmaster@DOMAIN.tld”, where DOMAIN.tld is the email providor you want to get whitelisted from, and explain your opt-in process and ask to be added to their whitelist.

It’s also a good idea to ask your email recipients to add your email address to their personal whitelists. This helps because most email providers allow email through that is on their blacklist but on a users personal whitelist.

Setup and Maintain Your Email Server Properly

A lot of newbies make the mistake of thinking that if they can send email they should send email. This is pure folly. There are a few things you should do on the server level to ensure you’re not going to look like a spammer. Off the top of my head here are a couple requirements that have to be implemented:

All e-mail servers must have valid reverse DNS records. Doing this allows email providers the ability to look you up and make sure you’re not sending from a blackhole. A lot of spammers won’t go through the trouble of setting up a reverse DNS record because they have to be ready to move at a moments notice. Setting one up shows you’re serious.

All e-mail servers must be secured to prevent unauthorized or  anonymous use. Preventing Joe Spammer from sending email from your domain shows the email services that the email really came from you. If, for example, they see that anyone can send email from your sever the email services has no reason to trust it actually came from you.

Setup a Sender Policy Framework (SPF) DNS record for your domain. The SPF is an open standard specifying a technical method to prevent sender address forgery. This basically means that setting up an SPF record in your DNS shows the email provider that email coming from a server is being sent on your behalf.

Avoid Evil

This is a topic that’s pretty absurd it even has to be mentioned but, sigh…, it has to be mentioned. (I guess I’m a bit of an idealist, but it seems to me that this stuff is just kind of  evil.)

Anyway, right off, you’ve got to be compliant with the federal Can Spam Act of 2003. If you’re going to be sending bulk email it’s important to understand the rules, especially when sending on behalf of your business and clients.

For the love God, don’t try to hide, forge or misrepresent the sender of the e-mail and sending site of the e-mail in any way. I’ve had this asked of me more times than I can count and it always ends badly; it’s an easy way to get yourself on a blacklist.

The last evil thing might not be too evil but I hate when I get an email and it doesn’t say where they you got the my email address and why they’re sending them an email. It’s an easy thing to do, especially since the act of having that information requires honesty about the list, plus it makes your recipients feel secure.

Write Good Email Content

Much like in Search Engine Optimization a lot of what makes a good email is good content (by content I’m talking about the entire email here; not just the copy). Here’s just a couple must dos:

1. Use alt-tags on ALL images.
2. Use short, descriptive, subject lines. Avoid special characters like the plauge.
3. Avoid using a lot of spammy key words and characters. For example; free, $, Prize, etc.
4. Keep the top header under 100 pixels tall and place a “View Email Online” link first and foremost.
5. Avoid center aligned content; it’s best to keep the email body left aligned on a white background. Spam filters tend to flag colored backgrounds higher than white.
6. Include a plain text version of your email with every blast.

Unsubscribing Should be EASY

This is probably the most important piece in my opinion. It has to be easy, like ridiculously easy, for a user to remove themselves from your list. Bulk mailings should contain simple and obvious unsubscribe mechanisms. AOL recommend that this be in the form of a working link to a one-click unsubscribe system; however, a valid “reply to:” address may be used instead.

There are all sorts of methods for the unsubscribe flow; just pick one that requires the least investment for the user. Avoid the impulse to create a survey asking why a user doesn’t want your email anymore. The fact they don’t want it anymore should be enough. Anything more and you run the risk of pissing people off.

Summary

Looking over the above I’m sure I forgot some things. Still, it should be a good starting point.

It’s important to remember that there really is no silver bullet when it comes to email marketing. Sadly, the reality is that even if all of the above is done there’s still a chance your email will be flagged as spam. Most email providers take their users interests very seriously, while taking the stance that everyone else is evil until proven not evil. Even if they don’t consider you evil they’ll revert a good mailing to evil status after only a handful of complaints.

Additional Reading

AOL Whitelist Information
Email Secrets of a Top Converting Website
Create Better Performing Assets

I was walking down the hall the other day when I heard one of the employees complaining about how much email they get. Apparently, this particular employee gets over 50 legitimate emails a day!

That got me thinking about how much I get so I kept my email for an entire week. Usually, I’ll delete anything I don’t need to keep and file those I do, but instead I kept a gnarly Inbox for 7 whole days.

Gates of Hell

When 7 days had passed I compiled a list of the daily emails I get:

20 emails from my direct boss
10 emails from each member of my team
5 emails from the Creative Director
10 emails from Velvet Hammer employees (SW manages their IT)
10 emails from the CEO of StreetWise
4 emails notifying me backups have happened on my server*
around 100 emails warning me about suspicous activities on all my servers combined (around 4*)
4 emails notifying me about log changes to my servers*
1 Windows SBS Server Performance Report
4 emails notifying me of system changes on my Linux servers (if something changes that is)
3 email inbox quarantine summaries from Postini
20+ bounceback emails from random email campaigns
around 20 emails notifying me about the firewall banning an IP address
Task Reminder from my companies collaboration system
4 emails notifying me about cPanel changes on my servers
3 Website Pulse Daily Monitoring Log emails
4 cron.daily notification emails for various cron scripts I run
2 emails notifying me the firewall tried to update itself and the status of the attempt
4 emails notifying me that yum tried to update itself
3 emails notifying me cPanel updated it’s license ping

By my count that’s over 200 legitimate emails I get on a daily basis. This doesn’t include spam or any of the abnormal emails I can get.

I’m sure this isn’t any kind of record or anything but the next time you’re thinking you have it bad just remember me