Why Is My Mail to this Person Not Getting Through?

Even after all these years, email spam remains a serious problem. With some people (like me) getting literally hundreds of unwanted messages per day, most internet service providers (as well as some individuals) take drastic steps to reduce the amount of junk mail arriving in their inboxes.

A problem with any anti-spam measure is that it will block some amount of legitimate email as well.

If email sent to one person is not getting through, but email sent to other people is generally working, it could be your email is being blocked by an anti-spam tool.

Become a Patron of Ask Leo! and go ad-free!

Summary

  • It’s easy for email to accidentally “look like” spam.
  • What recipients think is spam is not in your control.
  • Reputation of the sender, and any services used, matter more than ever.
  • Spam generally doesn’t cause bounces, but is discarded or placed in a spam folder instead.

Blocking legitimate mail

Legitimate email can get blocked in error for a couple of reasons:

  • The receiving system thinks your email looks too much like spam.
  • The receiving system thinks you have a reputation for sending spam.

Note that I said thinks. It’s the mistakes associated with that thinking that cause legitimate email to be mistaken for spam.

Looking like spam

Spam filters look at your email and assign points for various behaviors associated with email that “looks like” spam. As soon as you collect too many points (where “too many” is arbitrary, and up to the receiving system or the individual recipient to define), your email is flagged as spam. Some things to watch for in your email include:

  • Sexually explicit terms or phrases.
  • Certain drugs (typically linked to sexual performance or characteristics).
  • SHOUTING. Spam filters often consider shouting (typing in all caps) as sales copy.
  • Fake, inconsistent, or illegal return addresses; or, a “reply-to” address that does not match the “from” address. (If you don’t know how to even make that happen, don’t worry about it.)
  • HTML email. It’s not a huge mark against you, but some spam filters still consider HTML or “rich text” email as having a higher likelihood of being spam when compared to plain text email.
  • Marketing terms. Because so much spam is an attempt to get you to buy something, many filters look for various words and phrases associated with sales and marketing efforts.1

The more your email looks like spam...It’s important to realize that no one is saying that any of those things in your email is bad, or that any one of those things will cause your email to be blocked.

The unfortunate reality of the situation is that the more your email looks like spam, however innocuous, the more likely it is to be treated as spam.

The eye of the beholder

Despite this list of factors that might contribute to your email being considered spam, things aren’t nearly so cut and dried.

When someone hits the “This is SPAM” button in an online email interface (like Gmail, Outlook.com, and others), that system takes that to mean “Email that looks like this is spam to me.” If enough people mark similar email as spam, any email considered similar to that email stands a much higher chance of being automatically filtered as spam, regardless of what it contains.

For example, if a million people on an email service get an email that says “The sky is blue”, and half of them mark it as spam2, that particular email service may consider “The sky is blue” as an indicator of possible spam. Future emails that contain that phrase might be more likely to be filtered out as spam, and not arrive at their destined inboxes.

What that means is that anything could be labeled as spam, depending on what everyone considers spam to be at any point in time.

There’s almost nothing you can do about this.

Email reputation

Another factor in determining the authenticity of an email is the reputation of the email’s source.

In the past, email was blocked because it came from an IP address identified as related to spammers. Because spammers now use botnets to make it look like spam comes from millions of different IP addresses, this technique is less effective than it used to be. Unfortunately, it’s still in use.

Certain email providers have bad reputations. Hotmail used to be a hot source of spam, and simply sending from a Hotmail email address was considered a strike against you. While Hotmail (now Outlook.com) has improved, some ISPs and services simply have better reputations — and better deliverability — than others.

This is particularly true of mailing list providers: some have better reputations than others, and thus are able to more reliably deliver email. This is one reason I continue to use Aweber as the email service provider for The Ask Leo! Newsletter.

In any case, the only “cure” for a provider with a bad reputation is to switch to one with a good one.

Spam typically doesn’t bounce

Because bouncing email flagged as spam would give the real spammers too much information about how to bypass the spam filters, it’s simply not done. Email flagged as spam is simply not delivered, or is delivered to the recipient’s spam folder, where they may or may not find it.

A quick test to make sure that any email can get through is to use another provider — for example, a friend’s email account on a different service, or a free account on another service.

Podcast audio

Play

Footnotes & references

1: I’m not including examples, because this article does go out via email, and I don’t want it to get marked as spam. Smile

2: To be clear, I have no idea what percentage is needed to make something happen; I’m just using these numbers to illustrate the technique.

91 comments on “Why Is My Mail to this Person Not Getting Through?”

  1. Dear Sirs.:Please be advised that when corresponding with my sister, who has Earthlink as a service provider, she can retrieve my E-Mail messages, but is unable to send them to me, as they are returned, despite the fact that I have not blocked them off my address book as “spam”.I do not know what is the best alternative, for all mail has been “unblocked”,yet she cannot get through. Her E-Mail is: hsteyer@iopener.net Thanks for your assistance in this matter, and hope to get a favorable response.Tommy Steyer.

  2. When the messages are returned to her there should be some kind of diagnistic information included. If you can get that it would help diagnose the problem.

    • Why is it that I can receive email but when I try to email anyone they don’t get my email. I got a message that I was being blocked. Now they say my password is in correct if I try to go in get info to see how to get unblocked.
      Please help. I have Verizon do I go to them to help me.

      • I believe you do. That message you were blocked might also have had additional information that would be valuable to whomever you ask for help.

  3. When I log into my yahoo account, and i go into my mail it says “welcome Joshus” and it says i have 1 or how ever many e mail that i havent read, but as soon as i go into mail the whole site goes into a search site. See i cant get into my mail because of this im in serious need of help. How come I cant access my mail and why does the site go to the search site?

  4. help please. i have been chatting with this lad we had both been sending each other im messages . then i sent my pic. and every time i send him an im it says hes off line. but i no he is on most vdays. im thinking he might have blocked me or changed his screen name could this be so?

  5. I write to someone who has been a friend and he has to use a different name to get a message to me because he can’t send it from his other name. He says he’s blocked from my mail and I would like to know how to change that and get him unblocked. Thank You

  6. my x is stalking me via email and im – i block her but she just makes a new screen name ..AOL9 ..aol say they cant do anything other than me block all unknown senders which is not an option as my business mail comes to that account ?? Please help .

  7. MY SISTER CHANGED HER ADDRESS FROM AOL TO RR.COM AND SINCE THAN HAS NOT BEEN ABLE TO E-MAIL ME. WHY NOT???????

  8. Hello Leo,
    Why do my emails with a ‘Hotmail’address always get returned?
    My emails are returned stating….. the following address had ‘transient delivery errors’.

  9. I HAVE BEEN TRYING TO EMAIL SOME JOKES TO MY FRIEND (HIS EMAIL IS Vnb8@aol.com) BUT THEY KEEP COMING BACK AS UNKNOWN PLEASE HELP ME TO FIND OUT WHAT IS GOING ON LIKE HOW DO I GET UNBLOCKED IF THAT IS THE CASE

  10. Hi could you please help me i have tried to respond to a very important e-mail how can i get my resoponce to the person.

    This is what i got 196.25.211.150 but sender was rejected. Remote host said: 553 sorry, your mail from a host [206.190.38.35]

    How do I fix this thanks for your help

  11. Hi Leo,

    My emails with a ‘aol’ address always get returned?

    ‘county999@aol.com’ is one of them…

    We had recently been black listed due to spam being sent from our domain without our knowledge, this has since been rectified and we have been removed from these black list, I wonder if we are on aol’s black list, how do we get off the list?

    Many Thanks

    Chris Laming
    IT DIRECTOR

    • A few years ago Kim Komando said that her emails to AOL addresses were not getting through because people were clicking SPAM instead of unsubscribe. She had to contact AOL numerous times not to have her newsletter unblocked.

  12. When I reply to my mother’s email, she doesn’t receive my message. We both have Verizon accounts. My father receives his and they’re in the same house, just different email addresses. Any idea what’s happening?

    Thanks!

  13. Is there any way to verify if a hotmail e-mail is getting through or being blocked on another hotmail account?

    Thank you.

  14. if there is so much spam trouble, why dont isp’s start sending authentication ie your email program must log on the send an email.

  15. i can recieve mail from russia but not send. all other mail is getting through. please help me i am in love with a russian model!!!!

  16. Some ISPs doing a lookup on the IP address of the SMTP server sending the mail, are not just checking for blacklisted addresses, but looking at the resolved DNS name. If it looks like something that might by dynamically assigned (e.g. user-0cet4xp.cable.mindspring.com)it will reject it as a potential bot.

    This causes small businesses with a DSL or cable IP connection that have their own SMTP server headaches. They either have to get their ISP to change how the IP address is resolved (for static addresses only) or relay mail through the ISP’s SMTP relay.

  17. I have been having trouble recieving email from my sister-in-law in New Mexico. She has an MSN email address, I am recieving email from Florida and Missouri. Should I contact my server or what?
    I have contacted Microsoft about the problem, since they are the providers. It is getting very frustrating. I am hoping you can help me. She thinks I have blocked her from my computer, and she mentioned something about a filter in the letter she sent me about this problem. Please can you help me?

  18. —–BEGIN PGP SIGNED MESSAGE—–
    Hash: SHA1

    As outlined in the article, 9 times out of 10 it’s over-agressive spam
    filtering.

    I had this happen myself when someone sent me an email – their email
    service (MSN Hotmail) puts an ad at the bottom of every email, and the
    spam filter triggered on some of the words in that email.

    Yet another reason not to use a free email account that adds advertising
    to your emails.

    See if you can whitelist her somehow by adding to your address book or
    however else your ISP supports configuring your spam filters.

    Good luck!

    Leo
    —–BEGIN PGP SIGNATURE—–
    Version: GnuPG v1.4.6 (MingW32)

    iD8DBQFF6bnJCMEe9B/8oqERAnf1AJ9cdpWu36p7aYPEu3K8ZDOuufb22ACbBGhH
    vD0qvHvQ0IFxmyDzT4RfNfQ=
    =OvRv
    —–END PGP SIGNATURE—–

  19. I am having trouble with email. I cant figure out why. my fiance send me several emails from russia at my Aim email. I received nothing…
    Please help me with this.
    thank you!

  20. I have an email I rec’d from brother and wish to send to friends–internet explorer email refuses to send content of message, including to myself. people complain where is the message? how do I remedy this.

  21. I am unable to receive e-mails from [email address removed] or [email address removed]. They din’t bounce or show up as junk mail. Both accounts are usually used on the same computer. Any suggestions?

    Thanks

  22. I have been emailing my husband’s work email and numerous colleugues at his work and all of a sudden – my emails are being returned undelivered saying Barracuda spam firewall has refused?? can you clarify.

    Sounds like something about your email looks like spam. There’s no way for me to know what, you’ll need to check with the people at the other end.

    – Leo
    17-Oct-2008
  23. I have yahoo and I get the message that I have mail but nothing appears. This morning It said I have 11 emails but only got 4. I know my friend is trying to send me mail and I don’t get it. Thanks

  24. I am trying for days now to send an email or reply to any of my friends I have received the emails from. There is no chance for my emails to get through! Once I click send, this is the notification that popps up in my screen: “Are you sure you want to nevigate away from this page? You haven’t sent this message. Are you sure you want to discard it? Press OK to continue or Cancel to stay on the current page.” Regardless of what I press (either Ok or Cancel) it will take me to the HTTP 403 (The webside declined to show this webpage) and my message never gets through!

  25. I began hearing from people that they had not heard from me for a long time. I had been sending out jokes with up to 200 names in BCC. I remembered AOL kickbacks mentioning the reason being headers with more than 32kb in size. My 200 names were in groups of various size. I measured a test email with 85 names in my largest group and found [in properties, and before I put any text in] that the 85 names were 25.5 kb in size. I did my emails in three bunches with the 85 by itself, and the rest in two other emails. They all go trough now with out a probllem. Size was my problem.

  26. I’d been sending mails via my phone for months before I discovered that there were not really through and those ones sent to me by friends via phone I couldn’t get either and I’m still facing the problem now! You people should do something fast about it.

  27. I see a few comments about Hotmail rejecting their emails. I went through that a couple of times. Hotmail has overly aggressive spam filters and sometimes blacklists entire email companies if one their clients sends spam to Hotmail clients. My suggestion switch from Hotmail to GMail, which incidentally had quite good spam filtering.

  28. I keep getting a daemon message that they could
    not deliver my message because they had tried
    past their time limit. I am on Yahoo.com and I
    am emailing {email removed}. She does
    work for a doctor and sometime works at home.
    Sometimes I get thru. Is their server down or what is going on?

  29. Comcast (one example) will block email as spam based on the criteria Leo laid out. However, they don’t send anything back to the sender so the sender has no way of knowing whether the email is delivered. Email volume seems to be one of their triggers. Very frustrating when you are working on a project with someone.

  30. lately all forwarded main to hot mail & aol people comes back saying it cannot be delivered but i receive e mail from them. i have to fax them

    • Hi Adrienne,
      The place to ask Leo a question is at this link: http://askleo.com/ask-leo/

      To get an answer you will need to be a lot more specific. Include things like what kind of a computer you are using, what browser. Do the emails get to some people and not others? How do you know they are not getting through, and what error messages you get.

  31. Another criteria which I use (and this may be considered rude or drastic to some others) is that if the email contains no description in the “Subject” line, AND I don’t recognize the sender, it goes in the trash. I have rarely lost anything important by doing this.

  32. I have been sending emails to {removed}@comcast.net can you tell me if he is receiving these e mails and if not why is he not getting them

  33. just this morning I worked with someone who wasn’t getting email from a friend. It turned out that the friend’s email address had been put in the outlook blocked sender’s list. There were other email addresses in his list that he was surprised at, so we cleaned it up. This didn’t fix the problem of how they got in the list, but at least he gets email from my friend now.

  34. Leo, Thanks for this article. My email was not getting through to one person. I ran a test deleting the hyperlinks in the signature and it got through.

  35. I recently have not been getting emails from one customer I do business with. It will go to ac recipient that is copied on the email, but I won’t receive it. Could this customer if mine done anything to change their emails (spam) or anything else? What do I need to do so I can receive their emails in the future? Thank you in advance for your time and looking forward to your answer.

    • It’s almost impossible to say. You might try setting up an email account with a different provider and seeing if they can email you there.

  36. Leo, very often I try to email a company using their “contact us” information link and the email doesn’t go through. I click the send button and nothing happens. It’s kind of frustrating. Is there a way around this issue?

    • That would be a problem with that particular company’s website. It could be that their form simply is coded wrong and does not work. Very often they are using an old technology that does not work well with online email clients such as Yahoo. If you see a blue link for an email address then they are probably using that old technology which expects to open a default email client on your computer (such as old Outlook Express). If you are using an online service then there is nothing to open and the link fails.

      The solution is to simply copy the email address provided on the page, go to your Yahoo mail (or Gmail, or Outlook.com, etc.) and start an email. Paste in their address in the “to” field and you are ready to go.

      There is another, more complicated, method explained in this article: https://askleo.com/how_do_i_change_the_mailto_or_default_mail_program/

    • There’s no way to know. There are as many different technologies involved as there are companies and contact forms. It would depend on the specific contact form that’s not working for you. One thing I can say, though, is that most rely on JavaScript, so make sure that’s enabled, and that pop-up blockers are disabled.

  37. I send emails to {email address removed} and they are never delivered I am regularly told they think it is spam by Mailer-Daemon@ yahoo.com this is very inconvenient as I am disabled and the only way I can get my groceries is by emailing the store. I normally email the store about 3 tines a week thank you

  38. Can’t receive any e- mails on my yahoo.com account , wondering if I have something turned off on my IPad in the settings that should be on??? I was receiving up till Oct. 10th now no emails………I am waiting on some to come in and it is aggravating. Some are receipts for a condo…..

    • Maybe you changed your password in your Yahoo account. Try checking your account from your computer and see if you can get in.

  39. Amazing that this 15 year old blog still holds true today!

    My emails started not getting through this past summer; the problem was intermittent; I never knew when it would not go through and it was frustrating! I changed email service providers and the problem still continues. The only one that sends me a delivery failure is Google, saying “Our system has detected an unusual rate of 421-4.7.0 unsolicited mail originating from your IP address. To protect our 421-4.7.0 users from spam, mail sent from your IP address has been temporarily 421-4.7.0 rate limited.” Others where I don’t get the mail delivery failure notice just don’t get delivered. I’ve been using alternate email addresses or the telephone to get my correspondence completed.

    I was told the problem is that some other user on the email hosting site is using their server to send huge amounts of spam. Google sees the spam coming from that server address and is blocking all email from that server even though my email is not spam. The only way around this would be to get an email provider that does not allow that kind of activity from their other users.

    I’ve also been told by the email host that the issue is with using proxy servers (which most hosting companies do) which switches the IP address every 10 minutes so if one of those servers gets blacklisted, every time you send an email through that server, Google will bounce it back, until the proxy server gets cleaned up. That’s why the problem has been intermittent.

    So G Suite and Office 365 were mentioned as alternatives for my small business. Is there any other solution to get email through than those two that would be cost effective for a very small professional office of three people?

  40. AT&T emails with sbcglobal.net addresses were not working for about 3 days, but they have started sending and receiving again today, with one exception.
    Neither SBCglobal.net nor outlook addresses will send to each other.

  41. Dear Leo,

    I’m facing a strange issue, where an email from one particular email id is not getting triggered but using the other id it’s getting triggered. In case , its marked as Spam, is there a way to remove it from the spam category. Regards, Jayant.

  42. I sent a Thank you notice to a Minister & his wife, & told them some information, in a short not

    e , why would a computer see that as spam, I don”t get it !

    • There’s no point in asking why. Spam algorithms are always changing based on what people click as “this is spam”. Not your Minister, but others. The systems start to learn that “mail like this, right now, looks like spam to a lot of people”. And yes, sometimes they get it wrong. And to top it off, it could all change next week.

  43. Dear Leo:
    I have been emailing an attorney for over a year, and the last snail I sent she didn’t reply for some time. She “claims” my email went to her “junk” folder. I don’t believe her. Why after a year would my emails stop reaching her inbox? Just sent another one a month ago. No reply.
    I think she’s ignoring my emails.
    What can you tell me?
    I would think as an attorney they’d have a way to mark all of their clients as “contacts” so that their emails are always recognized. I mean…. I’m sure her top priority clients emails aren’t ending up in her junk mail!

    • I can’t tell you much. Spam algorithms are always in flux so it’s very possible that your email COULD start landing in a spam folder. It’s also possible that they’re ignoring you. No way to know.

  44. It may also be your File > Mail > Compose Messages settings. If you have it on Rich Text that can prevent some users from receiving your attachments. Instead of an attachment they will get an icon that does not do anything. Change “Compose messages in this format” to HTML or Plain text.

  45. Google asked me to change my password, I did.
    Now when I try to send an email it asks for my password and will not accept either the new or old password.
    Now I cannot send an email.
    No matter what i have done, I still have no email.
    the Best.
    Paul Echlin

  46. I have been emailing my sister at a couple different addresses for years. During the last six months or so she has been unable to receive mail from me whether I respond of of her sent email or I create and send new. I am able to send and respond to other people. Does this seem to mean that she has blocked my emails with a spam filter. Could there be any other reason?
    Thank you, Barbara Dickinson

  47. Big frustration here. Most of my family members have gmail addresses (I don’t, mine is a tiny rural co-op ISP). Recently, I’ve been getting “undeliverable” messages from gmail that look like this: The attached message could not be delivered to the recipients listed below. The original message was rejected at Wed, 06 Feb 2019 19:28:24 +0000
    Delivery attempt from MAG: smtp687.redcondor.net to receiving MTA failed.
    —– The following addresses had permanent fatal errors —–

    550-5.7.1 [208.80.206.87 12] Our system has detected that this message is
    550-5.7.1 likely unsolicited mail. To reduce the amount of spam sent to Gmail,
    550-5.7.1 this message has been blocked. Please visit
    550-5.7.1 https://support.google.com/mail/?p=UnsolicitedMessageError
    550 5.7.1 for more information. m5si4771761pfm.149 – gsmtp
    My Mom was BCC’d on a personal message, a reply to a friend about legislation in my Mom’s home state. I did not want to expose her address on my friend’s machine. A few days ago, my personal email to family members about an online meeting was similarly blocked to all gmail addresses. My research indicates that gmail will not help me unless I have a gmail address myself, and I don’t want to give Google my PII. My newsletter mass mailing for business clients is scheduled soon and I fear the worst. (I recently coped with the SPF_FAIL problem via a DNS configuration change.) I would appreciate suggestions for coping with this new gmail-specific problem.

  48. Hi Leo and Team Leo,

    I’ve been receiving some emails from my company’s payroll company (ADP) to my personal email (AOL). I’ve been forwarding some of these emails back to my work email address (emails are setup thru company website and we use Mozilla Thunderbird to read and send email at the office). For some reason the emails from my personal inbox are not arriving in my work inbox. They are not in a spam folder either. In case you’re wondering, I do get emails directly from ADP to my work email at times with no issue and I’ve also sent emails back and forth between my personal and work email accounts before without any issue. For some reason, these particular ones from my AOL account are a problem. What’s odd to me is AOL says, your message was sent- there have not been any bounce back messages or error codes. These emails are just floating out there in cyberspace. As a test, I forwarded one of the missing ADP emails from my personal account to my co-worker (has the same work email set up as I do) and she received it no problem. Then she forwarded it to my work email and I received it. I thought that was strange, but even stranger yet, a minute later, I received this same missing email from my personal AOL account at my work inbox! So, my questions are, 1. Do you have any suggestions for me as to what I could do to fix this or why it’s happening? I’m not sure why Thunderbird would think this is spam.. there’s nothing confidential and no one was BCC’d on anything. 2. Is it possible that when it accepted this same email that was forwarded from my co-worker that the Spam Assassin or Spam Pal in Thunderbird learned that it was ok to accept email from ADP? Or do you think it learns per individual email- not necessarily all emails that will come from ADP? Thanks so much for listening.. looking forward to your reply.

    • This sounds more like your work email system is interfering. I’d contact whoever manages your work email to see if they can figure out what’s going on.

Leave a reply:

Before commenting please:

  • Read the article. Comments indicating you've not read the article will be removed.
  • Comment on the article. New question? Start with search, at the top of the page. Off-topic comments will be removed.
  • No personal information. Email addresses, phone numbers and such will be removed.
  • Add to the discussion. Comments that do not — typically off-topic or content-free comments — will be removed.

All comments containing links will be moderated before publication. Anything that looks the least bit like spam will be removed.

I want comments to be valuable for everyone, including those who come later and take the time to read.