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What's the deal with Outlook and Hotmail ?
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What's the deal with Outlook and Hotmail ?

HAMSWHAMSW Member

Hello everyone,

I'm very curious to know if Microsoft is actually trolling or I'm doing something wrong on my side...

I've got a VPS with custom mail server setup and a shared hosting plan with mail.baby as a relay, both having 10/10 and 9.5/10 email scores on mail-tester .com, emails from either of them are properly landing in inboxes with no issues even with big providers like gmail.

But when it comes to @Outlook or @Hotmail they just end up in spam no matter what I do.

Are Microsoft just listing everything other than their service and other big tech as spam so people are more inclined to buy their service or am I just doing something wrong on my end ?

Comments

  • ChuckChuck Member

    monopoly, do you play it?

    Thanked by 1HAMSW
  • FlorinMarianFlorinMarian Member, Host Rep

    https://sender.office.com/ should be your friend.
    We had the same with some of our IPs but succeed to get delisted. (I have no idea who and what did previously with the same IP addresses)

    Thanked by 3HAMSW MikeA 10thHouse
  • HAMSWHAMSW Member

    @FlorinMarian is IP reputation still taken into consideration even when using an email relay service like mail.baby ?

  • JasonMJasonM Member

    @HAMSW said: mail.baby as a relay

    mail.baby emails mostly end in user's spam folders be it ymail (yahoo), outlook, hotmail, or even yandex mail and sometimes even on gmail spam folders.

    Thanked by 1HAMSW
  • quagsquags Member

    Open a support request and I will look further into this and may be able to get more info from the hotmail postmaster on this. There is significant work in monitoring ip reputation, feedback loops across all sending ips and many factors may go into an email including ips showing up in the received headers before hand off.

    Thanked by 1HAMSW
  • HAMSWHAMSW Member

    @quags said:
    Open a support request and I will look further into this and may be able to get more info from the hotmail postmaster on this. There is significant work in monitoring ip reputation, feedback loops across all sending ips and many factors may go into an email including ips showing up in the received headers before hand off.

    Sent you a DM

  • nobizzlenobizzle Member

    Just tried the same.for my mxroute (own domain on mxroute to Outlook). Also directly into spam.

    Thanked by 1HAMSW
  • PixelsPixels Member

    @HAMSW said:
    Are Microsoft just listing everything other than their service and other big tech as spam so people are more inclined to buy their service or am I just doing something wrong on my end ?

    Yes. All delivery problems I've had were always with Microsoft.

    Thanked by 1HAMSW
  • FlorinMarianFlorinMarian Member, Host Rep

    @HAMSW said:
    @FlorinMarian is IP reputation still taken into consideration even when using an email relay service like mail.baby ?

    Hey!
    I don't know how to tell you because I anyway keep all my IPs with 0 listings everywhere (I even delist those listed by the old clients of the subnets).

    Thanked by 1HAMSW
  • HAMSWHAMSW Member

    Update : I've tried Zoho Mail and it also went straight into spam folder.

    Has anyone tried AWS ? probably gonna try it, if it also fails I guess it just gonna be freakin' Microsoft Exchange -.-

  • @HAMSW said:
    Update : I've tried Zoho Mail and it also went straight into spam folder.

    Has anyone tried AWS ? probably gonna try it, if it also fails I guess it just gonna be freakin' Microsoft Exchange -.-

    I've been using Amazon SES, and it's been great. No problem with gmail, outlook and yahoo.

    Thanked by 1HAMSW
  • raindog308raindog308 Administrator, Veteran

    @JasonM said: mail.baby emails mostly end in user's spam folders be it ymail (yahoo), outlook, hotmail, or even yandex mail and sometimes even on gmail spam folders.

    @interservermike

    Thanked by 1HAMSW
  • magicvpnmagicvpn Member

    @nobizzle said:
    Just tried the same.for my mxroute (own domain on mxroute to Outlook). Also directly into spam.

    My mxroute just ends up in the inbox, not in spam.

    Thanked by 1HAMSW
  • HAMSWHAMSW Member

    @magicvpn said:

    @nobizzle said:
    Just tried the same.for my mxroute (own domain on mxroute to Outlook). Also directly into spam.

    My mxroute just ends up in the inbox, not in spam.

    Hmmmmm so it seems you have the better mxroute subscription :D

  • fendixfendix Member

    All my emails get delivered through MXRoute, whether it's Gmail, Outlook, or Yahoo. Even on my work email, with stricter filters than the standard Outlook ones, everything gets through.

    Have you ever opened a ticket?

    Thanked by 1HAMSW
  • It's a microsoft/outlook thing.

    they dice based on many factors, is not just if your IP is blacklisted or if you use any mail relay.

    they are just s*ckers that try to convince people to suscribe to their expensive mail service directly to avoid this issue.

    I have personally seen many doing so.

    Thanked by 1HAMSW
  • nobizzlenobizzle Member

    @magicvpn said:

    @nobizzle said:
    Just tried the same.for my mxroute (own domain on mxroute to Outlook). Also directly into spam.

    My mxroute just ends up in the inbox, not in spam.

    Mh, ok. I don't have a problem with Gmail though. Never had. No one is using Outlook anyway, so meh.

    Thanked by 1HAMSW
  • JosephFJosephF Member

    @nobizzle said:

    @magicvpn said:

    @nobizzle said:
    Just tried the same.for my mxroute (own domain on mxroute to Outlook). Also directly into spam.

    My mxroute just ends up in the inbox, not in spam.

    Mh, ok. I don't have a problem with Gmail though. Never had. No one is using Outlook anyway, so meh.

    Outlook users include Outlook.com, Live.com, Hotmail.com, MSN.com and other domains.

    Thanked by 1HAMSW
  • hsrhsr Member

    @HAMSW said:
    Update : I've tried Zoho Mail and it also went straight into spam folder.

    Has anyone tried AWS ? probably gonna try it, if it also fails I guess it just gonna be freakin' Microsoft Exchange -.-

    AWS SES aren't great for email deliverability, especially with Microsoft.

    Thanked by 1HAMSW
  • Before I gave up on self hosting outbound mail, getting listed on dnswl worked wonders for this scenario

    Thanked by 1HAMSW
  • nobizzlenobizzle Member

    @JosephF said:

    @nobizzle said:

    @magicvpn said:

    @nobizzle said:
    Just tried the same.for my mxroute (own domain on mxroute to Outlook). Also directly into spam.

    My mxroute just ends up in the inbox, not in spam.

    Mh, ok. I don't have a problem with Gmail though. Never had. No one is using Outlook anyway, so meh.

    Outlook users include Outlook.com, Live.com, Hotmail.com, MSN.com and other domains.

    as I said.. no one is using outlook anyway :wink:

  • emghemgh Member
    edited July 1

    nvm

  • Almost one month ago I achieved 1 year with MXRoute and I can't be happier than that.

    Got an lifetime plan and another very cheap plan with 6$/3 years.

  • kevindskevinds Member, LIR

    If I get a report of emails not being delivered, it is almost always Hotmail/Outlook..

    Only once has it not been for Hotmail/Outlook.

    Process is the same every single time too.. Submit/open a ticket, x hours later get a response that there is nothing wrong or we don't qualify for remediation, and they suggest using their tools that provide zero information.. Their tools just tell me not enough data..

    We reply to their response, after a 2-48 hours we get a reply that they have added remediation, this lasts 2-8 months, in which the cycle repeats.

    Over and over...

  • @HAMSW said: But when it comes to @Outlook or @Hotmail they just end up in spam no matter what I do.

    This is a common practice for Microsoft. I have suffered many times with email rejections and spam. I'd rather try to avoid them than to talk to robots with automated responses.

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