Outlook can't send email to one contact, but web based mssgs work fine Solved

  1.    11 Aug 2016 #1

    Outlook can't send email to one contact, but web based mssgs work fine

    As the title says, I use Microsoft Outlook '07 to access my Roadrunner and AOL POP accounts. If I send email from either account to one particular friend who uses windstream.net, and accesses his mail through Windstream's web mail page, it disappears without any trace that I can find. Not only doesn't he receive my newly composed messages, but he does not receive my direct replies either. That rules out a misspell. There is no evidence other contacts are not receiving my emails. I first thought maybe he had me blocked, however if I go to either of my two accounts' web based email pages, he receives my messages just fine.

    And I always receive his emails. The only odd thing that might be a clue is that, since this began, about half of the email he sends me now, whether I view them in Outlook or on the web, is in plain format with system fonts. Sometimes they come to me in HTML.

    I never get any delivery failure notification either. The last time he got one of my emails is when I sent out a July monthly newsletter to about a hundred people including him. I usually get the same few failure notifications because some of our members' addresses have changed or can't be found... the usual reasons, and I need to update my distribution list. But he got that letter in July, and that's the last time I've been able to send him anything through Outlook on either AOL or Roadrunner. But both of those ISPs always deliver mail to him if I use their respective web pages to send it. What could be going on? I'm thinking it's something with his Windsream.net service. But if he had me blocked, it would also reject me when I send from the web.

    This is an odd one. can anyone help?

      My ComputerSystem Spec

  2.    26 Aug 2016 #2

    Well, about a week ago it started working again, and this one fellow can receive emails I send via Outlook with my roadrunner account.

    However last night I sent out a newsletter to about 225 members of my aeromodelling club, and now I can't even send email to my wife. First, it appeared in her junk folder, then not at all. This is the same time last month my problem started. Today I've had several kicked back as "Containing possible spam." The newsletter I sent out contained one PDF of about 4.5MB. It also contained lots of pictures and videos... of airplanes. Any ideas?
    Last edited by RknRusty; 27 Aug 2016 at 10:50.
      My ComputerSystem Spec

  3.    27 Aug 2016 #3

    This sounds like an issue with the ISPs and their "blacklist" anti-spam software.
    They may be reacting to some combination of words &/or pictures that match a spam pattern.

    For example, last week, I transferred some money to my sister-in-law's bank account. My bank's website has a feature that allows an automatic email to be sent to the recipient, advising of the transfer.

    Her ISP rejected the message as matching that of a "Nigerian Prince" scam!
      My ComputerSystem Spec

  4.    27 Aug 2016 #4

    Haha, that's funny. Just a moment ago I told one of the guys on my mailing list I was trying to prove I'm not a Nigerian Lawyer. Don't know if he got it or not, I asked him to ping me if he did.

    I'm going to call Time Warner, who provides my keyhole into the internet, and see if they can help clear my name.
    Strange how I'm only semi blocked. Once in a while, a message gets through. Two of about 10 tries got through to my wife's email last night.

    Thanks for your reply.
      My ComputerSystem Spec

  5. Berton's Avatar
    Posts : 5,877
    Win10 Home and Pro, Win10 Insider Preview, WinXP Home Premium, Linux Mint
       27 Aug 2016 #5

    The newsletter I sent out contained one PDF of about 450MB
    An attachment of 450MB is pretty large, many ISPs, both sending and receiving, will have limits on attachment size, may be as little as 2MB. I'd think it better to use something like DropBox to upload then send the link to it. Actually, that seems to be quite a large file size for a .pdf file, must be a lot of images in it.
      My ComputerSystem Spec

  6.    27 Aug 2016 #6

    Oops, I meant 4.5MB. Yeah, 450MB would never make it out of the door. I'll edit my post.

    I think I'll start sending everyone a dropbox link to the newsletter, rather than an attachment.

      My ComputerSystem Spec

  7.    06 Oct 2016 #7

    This thread is Semi-Solved, but I'm starting a new one to un-muddy the water, so to speak.
    Thanks for the replies.
      My ComputerSystem Spec


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