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  1. #1

    Outgoing email to Outlook / Hotmail always received as spam

    Hi,

    Looking for a bit of help with outgoing mail being treated as spam.

    I have a mail server running on a VPS and any email sent to a Hotmail or Outlook account is regarded as spam at the receiver. Email goes out to other accounts such as Gmail no problem and lands in the inbox as expected.

    rDNS is configured on the mail server and valid SPF records are in place as confirmed by the allaboutspam.com test and the Outlook mail headers. I have checked as far as I can that the mail server IP is not on any blacklists using the many free online checkers. It's clean.

    My host was convinced that having configured rDNS the problem would go away but it hasn't. As far as they're concerned everything is as it should be.

    Any help appreciated as customers are not receiving emails in response to enquiries generated from hotmail and outlook accounts.

    Thanks in advance.

  2. #2
    Join Date
    Sep 2009
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    1,976
    Try to submit this form. We did it and we did not have problem in the pst 4-5 years. https://support.msn.com/eform.aspx?p...&wfxredirect=1
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  3. #3
    Join Date
    Oct 2005
    Location
    Summerville, SC
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    1,021
    check you email address in all of the following and see if anything shows up:

    http://mxtoolbox.com/
    http://mxtoolbox.com/diagnostic.aspx
    http://mxtoolbox.com/spf.aspx

    check your bounced email header with this link:
    http://mxtoolbox.com/EmailHeaders.aspx

    If those don't show anything wrong, you may want to contact hotmail(msn) and Microsoft and see what they can see from their end

  4. #4
    Quote Originally Posted by LVPSHosting View Post
    Try to submit this form. We did it and we did not have problem in the pst 4-5 years.

    (URL's as above - can't post with url inc)
    Thanks, have submitted that form, can't see it can hurt anything.

    Quote Originally Posted by Daniel B View Post
    check you email address in all of the following and see if anything shows up:

    (URL's as above - can't post with url inc)
    Ok thanks, the first two check out but according to the last link:

    Test Result
    SPF Record A Valid SPF Record was not found

    However, there is a TXT record of:

    v=spf1 +a +mx -all

    Just tried to add SPF record but unable to do so, no option in DNS through Plesk. As I understand it a TXT record does the same when SPF is not available as an option, no?

    Quote Originally Posted by Daniel B View Post
    check your bounced email header with this link:

    (URL's as above - can't post with url inc)

    If those don't show anything wrong, you may want to contact hotmail(msn) and Microsoft and see what they can see from their end
    Mail isn't bounced, it's junked by the recipient but even so, nothing untoward showing up from that link / header analysis.

    I really am at a total loss. Host seems to think all is fine.

    Hoping the form submitted above may help but any other suggestions appreciated and thanks again!

  5. #5
    Join Date
    Aug 2007
    Location
    Lincoln, UK
    Posts
    489
    See if you can get access to Microsoft SNDS for your IP address (https://postmaster.live.com/snds/), which might point you towards any problems.

    Also, check out if you're on the Symantec Brightmail blacklist. We spent ages trying to work out why a customer wasn't able to send emails to Hotmail/live.com and their IP address was on the Symantec Brightmail list for some reason.

    Unfortunately, no-one at Symantec seems to know what Brightmail is (they bought them out) and they don't act on submissions of the delisting form, or even get in touch with you if you ask for further information.

    I ended up having a go at someone from their SSL division (who'd annoyed me about an unrelated matter) and he eventually managed to locate someone to remove the IP address from the Brightmail blacklist. It took months!
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  6. #6
    Join Date
    Oct 2005
    Location
    Summerville, SC
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    1,021
    if all that is working I'm not sure what else it could be, as that's pretty much everything that would be flagging a spam label that I can think of.

    Just as a test, you could change your spf record to

    v=spf1 +a +mx +ipv4:your.outgoing.mail.ipaddress -all

    maybe hotmail/outlook want to see a specific IP allowed via the spf record (not sure why they would though, just an idea)

  7. #7
    It could simply be a matter of reputation. Have you been sending mail from this IP address for a long time? If not, a lot of providers will err on the side of caution until you've built up a reputation of sending clean mail.
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  8. #8
    Join Date
    Feb 2006
    Posts
    5,393
    @muran, are you utilizing DKIM? This is important since Microsoft has a tendency to mark any email without a valid DKIM signature as spam.
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  9. #9
    Wow, thanks for all your help and suggestions, much appreciated!

    Just an update:

    Microsoft have come back to me already from the form submission I carried out above. They have confirmed that there are no active blocks in place but that some messages were being filtered. They have conditionally mitigated my IP (subject to possible low daily email limit until it has established a good reputation).

    So, looks like I need to await propagation and hope this resolves the issue without impacting any customers on the platform.

    To answer a few questions:

    Pretty sure we are not on any blacklists @freethought and thanks for the link, will check that out. The email receoved from Microsoft has stated they will happily work with Symantec to resolve any remaining issues if necessary so hopefully that takes away any of the grief you experienced!

    I considered the change of the SPF as suggested @Daniel B but this would only have an effect on our own domain. Customers sending from their domains would still see a problem so I think I really need to fix this at a higher level if poss.

    @Thalagyrt we have been on the same platform for over 12 months and email has been a regular part of the business so 'reputation' should be up there really.

    I looked into DKIM sig @DWS2006 as this was thrown up as an error in the allaboutspam report. Drew a blank though, is this something I can set up at mailserver level so as to have an effect on all hosted domains (all using the same mail server)?

    Thanks guys!

  10. #10
    Join Date
    Feb 2006
    Posts
    5,393
    Quote Originally Posted by muran View Post
    I looked into DKIM sig @DWS2006 as this was thrown up as an error in the allaboutspam report. Drew a blank though, is this something I can set up at mailserver level so as to have an effect on all hosted domains (all using the same mail server)?
    I'm really surprised by the fact that DKIM does not appear to be supported natively in Plesk. There are some tutorials regarding manual setup http://blog.matoski.com/articles/spf...-plesk-debian/

    Not sure about automating this in Plesk, though if Plesk supports post-account-creation or post-domain-creation hooks it should be possible.
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  11. #11
    Join Date
    Aug 2007
    Location
    Lincoln, UK
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    489
    Quote Originally Posted by DWS2006 View Post
    Not sure about automating this in Plesk, though if Plesk supports post-account-creation or post-domain-creation hooks it should be possible.
    You should be able to use the Plesk Event Manager to do that.
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  12. #12
    Oh God I thought it was too good to be true!

    I now receive a further email from Microsoft stating:

    "Unfortunately, after reviewing the information you provided and in compliance with our mail policies, we are unable to offer immediate mitigation for your deliverability issue. However, we have some specific recommendations for you to consider that can help you to improve deliverability over time. "

    A total contradiction to the earlier email that stated:

    "Our investigation has determined that there are no active blocks against these IP(s); however, some messages were filtered. We have confirmed that these IP(s) are eligible for conditional mitigation, but may be subject to low daily email limits until they have established a good reputation. Please note that this mitigation does not guarantee that your mail will be delivered to a user's inbox."

    Trying to get clarification is like pulling teeth with the operatives answering the email just parroting the last reply without actually addressng my question as to why I have been told my IP is being mitigated and now that they can't mitigate it.

    Where to go now!?

    Will look further at DKIM but can't help thinking I shouldn't be having to do this!

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