April 09, 2004

Making Sure Your E-Mail Newsletters Get Read

A LawTech Guru feature article by Jeffrey Beard
(For reprint arrangements, please contact me via .)

How many of you send out e-mail newsletters to clients, friends, business acquaintances, and more? Probably some. Now how many of you are absolutely sure that the vast majority of your recipients actually see them? Probably none.

If you could think of a single feature of e-mail newsletters that would dramatically increase the odds that they actually get read, what would you pick? Is it fancy HTML formatting? Compelling subject lines? Savvy content, perhaps? A few years ago, I probably would have agreed with any of these, particularly content. However, in today's world, I just might opt for Getting Past the Spam Filters.

You see, legitimate e-mail newsletters tend to have much in common with spam: They are mass-mailed and often have disclaimers, instructions and links to unsubscribe, suppressed recipient lists, assurances they comply with anti-spam laws, and more. That sounds like spam to me, and more importantly, they look like spam to a number of spam filtering software and services. Unless the recipient "whitelists" your newsletter, thus telling the spam filter it's okay, a good chunk of your newsletters may be filtered into your recipients' e-mail spam folder, or worse, blocked or deleted automatically -- before they ever have a chance to see them.

So what can you do? Well, a little crash course in spam filtering software wouldn't hurt. I'll use SpamAssassin as an example since it's very popular (I personally use and love it). Earlier this year, I showed people how to make it more effective at identifying spam. Now I'm going to give you some insight on how to get past it. Don't worry, I'm not passing along any information that the spammers don't already know. They're waaaaay ahead of us.

First, go read "How to Avoid the SpamAssassin", by Janet Roberts. It's a quick read and it summarizes how SpamAssassin uses weighted characteristic tests to determine whether or not an e-mail is spam. Each e-mail characteristic found (and there are many) is given a differently-weighted numeric value and then all of them are totaled for a given e-mail. If that total value exceeds SpamAssassin's threshold, then it assumes the e-mail is spam and marks it accordingly. You should know that SpamAssassin's default value, one which most people probably do not change, is 5.0. Thus if your e-mail newsletter scores a 5.0 or higher, you're spam baby: Do not pass Go, do not go into the Inbox, do not collect $200, but go directly to jail (the Spam folder), and that's if you're lucky it isn't automatically deleted.

Now notice that Ms. Roberts also shows certain characteristics that SpamAssassin uses to reduce an e-mail's score, which are essentially mitigating factors for e-mail newsletters. That's a good place to start. See how many you could incorporate into your newsletter e-mailing process.

Granted, this is just analyzing a single spam identification program when there are many in use. Some work quite differently than SpamAssassin, in that they block all e-mail until either the recipient whitelists it (marks or approves it as okay) or the sender has to fill out a one-time verification to tell the spam software your e-mail is legit. If you're serious about increasing the fullness of your newsletter readership, it wouldn't be a bad idea to understand their basic principles of operation. An hour or so of Googling could be enough to point you in the right direction.

Here's something else to consider: Depending upon the spam software used on the other end, sending your newsletter as an Acrobat PDF file attachment might be more effective against spam filters than incorporating its entire content into the e-mail body. The flip side is that it introduces several new challenges, both for you and your recipients:

Their e-mail system may block attachments based upon (a) file type (i.e., the .PDF extension) or (b) by file size. Normally, PDF's don't carry viruses, but there have been several PDF viruses for which Adobe has been updating Acrobat to resist and antivirus programs should detect. Thus a network administrator could arbitrarily block PDF e-mail attachments for security reasons. Regarding size, text-based PDFs tend to be relatively small for the typically short newsletter. However, if you're sending longer newsletters or image-based PDFs, then be aware of the potential for your PDF newsletter to exceed your recipients' file attachment size limitation. Many e-mail systems are set to block or truncate file attachments that are larger than 5 or 10 MB, but some may be set to block attachments as small as 2 MB. Therefore, try to keep your PDF newsletter file as small as possible, and preferably under 1MB in consideration of your readers who may still be using slower dial-up connections to the Internet. You also may have a small segment of recipients who prefer to read this information on their mobile e-mail device, including BlackBerries, Palms, PocketPCs, and smartphones such as the Treo 600, where less means more.

Today, most e-mail systems will handle both text and HTML-formatted e-mail newsletters contained in the body of the e-mail message. Once you choose to send a file attachment, and even after you get past their safeguards, your recipient has to be able to view it. One of the largest drawbacks to using PDF newsletters is requirement to have the free Acrobat Reader installed on your recipients' system. Believe it or not, there are still many businesses who do not install it as a matter of course. This is particularly problematic in locked-down environments which do not support it. This situation forces your recipients to either (a) play "Mother May I" with their IT department to get it installed, which naturally doesn't endear you to any of them, or (b) they opt not to receive your newsletter at work.

Do you have a web site, and if so, do you provide your newsletter online? This is yet another good method to get past spam filters and e-mail attachment limitations because it's not e-mail. Key formatting options here are HTML and PDF. But how do you entice people to visit your site on a regular basis? Let's compare: E-mail automatically "pushes" content from you to them once they subscribe. However, traditional web sites function as a "pull" that the end user has to initiate every time to visit the site via a browser. With the growing popularity of news aggregators, you may want to think about providing an RSS (Really Simple Syndication or Rich Site Summary) feed. This is a specially-formatted XML page (eXtensible Markup Language, which simplistically can be decribed as a cousin to HTML), which allows visitors to "pull" your content down to their PC via a program or service known as a "news aggregator". There are now many such programs and web sites which are able to pull, or aggregate, content from the millions of web sites and blogs featuring RSS news feeds. This information is nicely organized into a single program window on a PC or mobile device (PDA's, smartphones, etc.). News aggregators are commonly set up to automatically poll and download content to the recipient at predefined intervals, say, once every hour or day. Bingo! You've just made it automatic to deliver web content.

Nowadays, folks just don't have time to visit every web site they like. Aggregators allow people to read more of your content in less time and with less effort than manually visiting each site. It's a convenience and time management feature that appeals to an initially small percentage of the population, but which is growing at a good rate for these reasons. Consider this: As people's list of sites in their aggregator is growing quickly, you want to be one of the first ones added so you're near the top of the heap (that is, if they're not sorted alphabetically). Early adopters have first mover advantages here.

Another consideration is that many blogs (web logs) have built-in RSS feed generation features, but many traditional web site operators will need to utilize additional programs or programmers to add an RSS feed to their web site. The downside to generic RSS is that unlike e-mail subscription, you won't get a list of your subscribers, but possibly only their IP address, domain name, and web browser or news aggregator type as listed in your web site's traffic logs. To get user information, some news aggregators support "authenticated" RSS feeds. This is just a fancy way of saying it requires you to set up an RSS delivery system which in turn requires your subscribers to provide a login name and password before their aggregator can download your content. Thus with additional expense and effort on your end, you may get some additional marketing feedback. However, it's a limiting and potentially less convenient route to take for your readership.

Obviously, not all of the above approaches may work for you as a content producer due to the time, expertise, and expense involved. Like everyone else, you probably have a lot of other important things to do. They do, however, bring up a key point that is sometimes forgotten in all of the technology: Approach these issues from the perspective of your recipients. Ask what is going to work best for them, and can you reasonably deliver it? Do what you can without overextending yourself. If you have a very diverse recipient list, then you may want to include an occasional short survey regarding format and delivery. Also consider including an e-mail link so they can easily contact you with problems, questions, or suggestions, while keeping in mind how a spam filter may classify these characteristics when delivered via e-mail.

Indeed, there may be no silver bullet: Considering these issues and your readership's technological diversity, a single newsletter format may not satisfy all of their needs. Thus you may be able to increase your readership and their satisfaction by providing a combination of e-mail, PDF, and web-based newsletters at their option. As mentioned, this needs to be balanced against any additional time and expense required to produce it in multiple formats. Fortunately, this is where savvy product selection can help. Optimally, your publishing tool(s) should be able to generate the required formats directly from the same source, to avoid duplication of work. On the e-mail front, you'll likely need to maintain several e-mail address lists, one for each format. As your subscriber list grows, there are mailing list management programs available to help.

As an online content provider myself, one of my favorite mottos is "Content is King". However, that takes on a new meaning in this spam-infested era. In addition to focusing on the compelling content you want to provide, one also needs to be aware of the content and characteristics you don't. In this regard, a little tech savvy can go a long way -- all the way to your clients' and prospective clients' Inbox.

[Updated 4.10.04 to add further discussion of using PDF and web-based solutions.]

Topic(s):   Feature Articles
Posted by Jeff Beard

Jeff-I think that this posting is best read together with your post on the efficacy of lawyer weblogs and your posting on content management. In one sense, no single method of communication to clients/colleagues/friends, etc., truly works with absolute efficiency. Therefore, we are left with the necessity of either (i) using a variety of media or (ii) concentrating on one method and living with the inefficiency.

I try to do stuff simply. For instance, I will be restarting my weblog, but I will periodically send out email messages to selected clients etc. that say, in essence "Look at this posting, it's very important to you." In this way, I focus most of my time on the production of the weblog, but don't forget the occasional reader.

Posted by: Stuart Levine at April 17, 2004 09:18 PM


FYI, I've recently revised my article as your comment inspired some additional analysis re: PDF and alternate delivery methods.

Some initial thoughts as to your situation, based purely on the limited info provided:

1) You're scanning in PDFs, so they are imaged-based and could be quite large. As I've added to the article, many e-mail systems block or truncate large attachments.

2) Some security patches to Outlook will block access to attachments. They're there, but the user is prevented from opening them. In these cases, Microsoft in its infinite wisdom took the sledgehammer approach to security instead of targeted surgery, and it's a problem on your recipients' end. They either have to solve it or you'll need to find another method of delivery. Consider adding a password-protected directory on your web server where they can bypass the e-mail problem and download it via their web browser.

3) Basic "is it plugged in"-type question: Do these recipients actually have a PDF viewer installed?

4) Even though you've attempted to make your Acrobat 6.0 PDFs backwards compatible with 5.0+, have you tested them on another PC running older versions of Acrobat? Perhaps some recipients are still running the Acrobat 4.x Reader.

5) Consider being ultra-backwards PDF compatible: If you still have it, or can obtain it, perhaps you might want to consider running the full version of Acrobat 4 or 5 on another PC lying around. That way, you'll know you're producing the PDFs at the lower common denominator.

6) Contact Adobe tech support, tell them your problems and that you won't give up until they provide some solutions. If first-level support can't provide them, then politely but firmly demand to get escalated support help. You're a paying customer, so don't accept any lame excuses. Stay on it until you get to a manager or one of the developer team.

7) Maybe the problem isn't the PDF file, but the e-mail delivery. Is it being blocked, quarantined, corrupted, deleted, etc. by the recipients' security and spam protections or the conversion trip through multiple e-mail servers? Is the PDF attachment okay, but the e-mail message you sent is being mis-identified as spam on their end? Again, see my suggestion in item #2 above for web delivery. It may not be the most convenient, but it might be a good workaround in those situations.

8) While the PDF format is convenient and cross-platform, you may want to consider an alternative file format, either image-based, or embedding the scanned documents into a word processor file format compatible with the recipient. I'm not saying this is pretty, but again it might work for you.

As I've mentioned in the article, focus on what works for your recipients to the best that you can. It may involve a little thinking outside the PDF box.

Again, these are my educated guesses based on minimal info. I know it's difficult, but the more information you can get from your recipients, the better able you'll be to solve this.

As for international adoption of PDF, I couldn't say, sorry. I'd suggest doing some Googling for those terms and see what you can find. Someone has probably already written about it somewhere.

I hope this helps and good luck.

Posted by: Jeff Beard at April 10, 2004 02:21 PM

Good article. Thanks.

Do you have any information about the reliability of Acrobat? Here's what I mean. I send more than 50 pdfs a week, to various clients all over the world.

All too often, the recipient will report that "the attachment will not open." I always press and cajole for details but they are rarely forthcoming. I am using 6.0 and I'm fairly sure that I'm using it right. I have it set to scan documents into pdf and make them compatible with 5.0 or higher.

It's bad enough that a small but substantial percentage of recipients report that they can't open the file. But I worry more about those that don't bother to report a problem.

At least one large-company-client does not get the pdf emails at all. The large emails are apparently blocked in some way. But then again, this person reports that she gets plenty of large emails from other senders, including pdfs.

I am fairly sure that 80 percent or more of the pdf emails are going through exactly as intended. But I would appreciate any ideas on pushing the number far closer to 100 percent.

Relatedly, do you have information about penetration of pdf into other countries? In the past year I have sent hundreds of pdfs to Japan, China, Russia, etc. but I have no idea whether pdf is commonly used in far off places.

Posted by: Robert C. Lehrman at April 10, 2004 08:28 AM