Punctuation Reputation

Are your attempts to avoid email content filters getting you filtered even more?

I’ve commonly seen publishers use punctuation in certain words trying to bypass content filters. Thinking those words such as free, profits, savings, winners, sale, profitable, no cost are going to automatically get them filtered.

Unfortunately by using punctuation to obfuscate words those publishers have just made their messages look exactly like the messages spammers send.

Examples such as:


Regardless of how much your subscribers want your information, to the ISP filtering you’re message you’ve just labeled yourself as a spammer by employing the same tricks spammers use to try and get their messages delivered. Not to mention the credibility and readability issues you have with subscribers if they receive your message.

Bottom line:

Don’t use punctuation in words to try and bypass content filters. In the long run it will hurt your email deliverability.


  1. Matt

    8/9/2006 11:58 am

    I totally agree. I see a few of my favorite and reputable ezine writers employ this sort of thing.

    Do you have any suggestions on what you can do instead?

  2. Tom Kulzer

    8/9/2006 12:19 pm


    Use the regular word or a different one 😉

    It’s extremly rare for a content filter to dump your message to a spam folder for a single word or even a couple of words. The side effects of having legit mail look like spam by using punctuation or other tricks in the middle of words is more harmful than the few that might get spam foldered.

  3. Philip Richards

    8/9/2006 1:31 pm

    WELL!! You sure have caused me a lot of work. Now I have to go back and change all those no cost and free entries. (o:

  4. Jacquie Hale

    8/9/2006 1:49 pm

    Actually, when I was first testing out aweber with an HTML broadcast. I sent a one sentence message to myself without any of the questionable words and Norton AntiSpam removed it from my regular email.

    I have since stopped using Norton at all, but I realize many of my readers do use it. Any help on that front?

    Do you find that HTML message are more likely to be filtered?

    Thanks for your great product!

  5. Tom Kulzer

    8/9/2006 2:07 pm


    I have some follow up posts regarding proper testing of messages for deliverability. Unfortunately many people test messages in ways that do not replicate real world conditions for deliverability.

    More than likely in your testing the HTML message didn’t have a plain text portion as well. This greatly enhances your chances of getting filtered. Also, one sentence isn’t the type of content you would send to subscribers so it’s not an accurate test. Another common mistake in testing is when testing to yourself, you often are sending the email to the same email address that is listed in the “FROM” email address. This is also another large spam sign for many content based filters.

    Yes, HTML only messages are more likely to be filtered. See Marc’s post, “Are you sending HTML without plain text alternatives?” for more information. We also have some deliverability statistics that show deliverability dependent on different types of messages delivered.

  6. Steve Elliott

    8/9/2006 11:05 pm

    Hi Tom,
    Thanks for the post, my personal technique is to use simple ‘text only’ emails and send a nicely formatted pdf attachment with the message containg the bulk of the information. I also find that putting my own name in the subject field gets a better result, for example: “Latest newsletter about Italian Property Overseas (from Steve Elliott)”


  7. Barbra Sundquist

    8/10/2006 2:34 am

    Guilty as charged! And I thought I was being so clever to use punctuation on “iffy” words. What you have pointed out makes perfect sense, and I’m going to stop the practice. Very helpful tip, thank you.

  8. Wild Fiction

    8/10/2006 4:29 pm

    This is a good blog and I completely agree with what you say. Type it as it is.

    Your job: Provide the email to the mailing list. Provide what they expect and signed up for. Use correct grammar and English if that’s what they want and expect.

    Their job (the spam filters): Work on algorithms to differentiate your emails from spammers.

    If you start using spammer’s tricks for spam avoidence then the Spam Filters can’t differentiate you.

  9. Dave Franzwa

    8/13/2006 3:43 pm

    Hi Tom,

    Thanks again for you insights. I’ve been in the process of undoing some of those camo-techniques myself, lately.

    I probably don’t have them all squashed yet, but step-by-bloody-step and I’ll get there.

    In fact, I published an article just this am that alluded to the issue of negotiating with robots. It’s more related to SEO, but a robot is a robot. You’ll can find it linked under my name (above).

    Keep up the great work

  10. David Beroff

    8/17/2006 10:21 am

    I’ve followed these ideas with my own mailings for several years now, and I’ve also used the spam checking system that AWeber provides to review my autoresponder messages in the last few months. While I generally aim for a score of “0”, let me add one comment to your post, and that is to learn to *accept* a few “dings” when they appear. A very concrete example is when I promote our own copy of Sonic Opt-In. The spam score noted that “Opt-In”, with that capitalization, is more likely to trigger filters. I even went to the author, Jay Jennings, and asked him if we could change the product’s name (to Sonic Squeeze Page) so that I wouldn’t potentially trigger this. In the end, though, I learned to relax, and simply accept the score of 0.8 (which is still well below the recommended threshhold of 5).

    Thanks for your post, Tom!

  11. Diana Mirkin

    8/27/2006 6:46 am

    We write a health and fitness newsletter, by an M.D., and occasionally have articles that mention medically correct terms for body parts, such as “breast” or “penis”, and sometimes medications such as “Viagra” or “testosterone”. These routinely got rejected for so many of our subscribers that I started to put a * in the middle of the words. They are in the text, not in headlines. What else can I do, other than just stop using these pieces in the newsletter?

  12. Tom Kulzer

    8/31/2006 12:35 pm


    You’re unfortunately in a market space that is so commonly spammed that heavy content filters are a way of life. Your best avenue for good deliverability is to keep your emails extremely short with the goal to get recipients to click thru to a webpage that contains the meat of your content.

    Definitely don’t resort to tricks to try to get past filters using obfuscation. In the long run it just makes your messages look unprofessional and will eventually get you filtered even more heavily.

  13. The Frank Haywood Newsletter » Ever received email with words like FR’EE in them?

    9/11/2006 3:30 am

    […] September 11, 2006Ever received email with words like FR’EE in them? If so, it was probably spam am I right?  However I’ve noticed an increasing number of mailing lists that I’m on have started sending me email that looks like spam.  With mangled words in the body like FR’EE, F.REE, FR,EE and so on.   This is crazy as well as annoying, because even though I’m opted in to receive those mailings, when I receive them they look like spam.  In fact I accidentally deleted one the other day while quickly going through an account.   They also hurt readability as it causes me to stop part way through a sentence even if only for a fraction of a second, but it halts the flow of the text.   So why have the authors started to do it?   Well, they want to use the magic words (now overused in my opinion) that trigger attention.  Words like "free" and "sex", and my personal favourite phrase "free sex".   Sorry.   Anyway, if they use those in their emails, guess what?  They trigger a spam filter and the email either gets marked as spam or put in the spam folder or deleted or any combination of those things.   The reasoning is, they break up the spammy words by putting punctuation in them.  D’oh!  Talk about shooting yourself in the foot!   So now, even though the email is a legitimate opted-in newsletter, it looks like spam.  Because guess what?  Putting punctuation in words is exactly what the spammers do to get them past spam filters.  And admins running those spam filters know this, so they get an even higher spam rating.   Isn’t that just daft?  I read a bit of advice a couple of years ago about working on the web, and it simply said "keep it real".  That’s good advice.   Just ignore what’s going on with spam and deliverability, and do what you do best.  Ultimately your message will get across.   This has been a topic on my mind for a while now, but this piece was written after I read an article by Tom Kutzer of Aweber called Punctuation Reputation.  Go and have a read.  Filed under Blog by Frank Haywood […]

  14. Mark Widawer

    9/17/2006 11:50 am

    When I write autoresponder and broadcast messages, I write in a totally natural voice, and to the recipient personally. In other words, the ‘first person’.
    I don’t care one bit about writing spammy text — even when I am offering something free to my list or something with a bonus.
    But when I’m done, I do care. I click the spam-assassin button in Aweber, I always score under 1, and usually a flat zero.
    Your advice is perfect.

  15. Daniel from Argentina

    12/5/2006 10:33 am

    Hi! I’ve been in internet business since 1999
    well, we sell a singing multimedia course
    and actually have more than 50,000 subscribers into our list

    But, after a doing campaing only 8 to 10% gets read by the
    recipient’s owner.. that’s really bad for keep in business..

    nowadays we’re having BIG deliverability
    problems in spanish language so our question
    is if AWEBER offers a solution to this spanish
    language market (which is really big)

    Or if anyone of you did campaing using aweber
    in spanish..

    I mean..spam score check to spanish spam triggers words,
    like GRATIS, PROMOCION, and so..

    We’re thinking to use AWEBER for our next ‘inminent’
    christmass’s campaing but we need some kind of
    security or recomendation at least.

    Oh! almost forgot this.. what about the exclamation symbols?
    would those kind of symbols, like ? ! $ %’, trigger
    the spam filters too? ‘cos we are using them in our

    Thanks you all!

  16. » A Love-Hate Relationship with Email - AWeber Blog

    2/13/2007 9:22 am

    […] Avoid Intentional Misspellings […]

  17. David Kamau

    10/17/2007 9:18 am

    Good tip. But could you go step farther and offer alternative suggestions? When I use certain words on my autoresponders messages, the spam rating goes up (meaning they will likely cause my message to be flagged). Once I add punctuations (or slight misspellings) into the same keywords, spam rating goes down, sometimes to zero.

    I’m confused here. Additional suggestions would be nice.

  18. Justin Premick

    10/17/2007 10:46 am


    When looking at the Spam score for one of your messages, just focus on keeping your score relatively low – below 5.

    Don’t micro-manage it – taking a message with a score of say, 2 and obfuscating words to get the score down to 1 won’t help you get delivered. As Tom notes, it’ll look to an ISP like you’re using spammer tricks (and in their eyes, who but a spammer would do that?), and it’ll look bad to your subscribers as well.

    Write your message the way you want people to read it, and as long as your Spam score is below 5, send it. If it’s above 5, look at the criteria and see why – the cause will almost always be something other than just certain words appearing in your message.

  19. Murray

    10/17/2007 6:58 pm

    Hi Justin: I am reqlly confussed about how effective the filtering system really is.

    Legetimate emails, like the ones mentioned above are filtered everyday, but the junk from Africa still gets through. I know, because 2-3 a week still hits my mailbox, no matter how much blocking I do.

    What’s the deal here?

  20. Justin Premick

    10/18/2007 8:26 am


    ISPs and spammers are constantly trying to keep ahead of each other, and sometimes false positives (legitimate mail getting filtered) do occur, as well as spam getting through.

    Keep in mind that the 2-3 pieces of spam that you’re seeing per week represent only a fraction of the unsolicited mail that’s actually sent to your address. Your ISP takes care of much of it without ever even putting it in your inbox or your junk folder.

  21. Is the word "free" safe to use again?

    6/4/2009 12:04 pm

    […] in the email, you absolutely should not try to "fool" a spam filter with weird spacing or punctuation. You’d be trying to fool people who have $350 billion to throw at catching you. Which of these do […]

  22. Sean Breslin

    11/24/2009 5:56 pm

    I have always hated that punctuation method in emails, still do! Will not use it myself, I would rather be filtered.

    Although that does defeat the object, of sending the email!

    Will the problem get worse?

  23. Olivier

    11/1/2011 5:18 am

    Many thanks for this usefgul contents. I shall ask you if I have trouble implementing these things for my emailing. I´ll keep an eye on what gets said here on this subject.