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Windows Server 2000/2003 Thread, can't send emails to hotmail from exchange mailbox in Technical; When our child protection officer sends an email from her school email account (using both OWA and Outlook 2003) to ...
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    sandeep2504's Avatar
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    can't send emails to hotmail from exchange mailbox

    When our child protection officer sends an email from her school email account (using both OWA and Outlook 2003) to her hotmail account, it never arrives.

    When i send an from my school email account to her hotmail address it arrives successfully.

    When she sends an email from her school email account to my hotmail address it arrives sucessfully.

    I have checked the junk email folder on hotmail and other members of staff can send emails to and from hotmail accounts.

    I don't receive any failure reports either.

    I have checked Exchange Server Message Tracking and it all seems to be ok.

    Can anyone think why the above problem would be happening or suggest a way of troubleshooting the problem as i have no idea!

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    Is the address she's sending to the right one behind the pretty display name stuff?

    You can troubleshoot with SMTP logging which should show you any mail delivery conversation between your server and elsewhere - for E2K3 that's turned on in the SMTP virtual server properties somewhere.

  3. Thanks to PiqueABoo from:

    sandeep2504 (27th January 2010)

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    sandeep2504's Avatar
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    Quote Originally Posted by PiqueABoo View Post
    Is the address she's sending to the right one behind the pretty display name stuff?

    You can troubleshoot with SMTP logging which should show you any mail delivery conversation between your server and elsewhere - for E2K3 that's turned on in the SMTP virtual server properties somewhere.
    That sounds like it will do the job!

    I will try that.

    Thanks

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    Stupid question but she's not blocked her own school address has she?

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    Turn on delivery reports to see if it's getting delivered somewhere or declined somewhere that may give you a clue as to what's going on.

    Mike.

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    Hotmail, Yahoo and many others use RDNS and Blacklists to cut down on spam.

    Does your exchange smtp send outbound mail directly or through a smarthost?

    If you send directly using DNS and your exchange server cannot be identified by Hotmail the Hotmail servers will refuse it.
    As many mail operators refuse to generate NDRs (Non Delivery Reports) for certain types of mail refusals you may never actually be advised as to why your mail discarded!

    You need to test from a command prompt on the mailserver it self to try and identify why.

    You can follow this guide

    In most cases the Hotmail refusal is a temporary one but unless you have a static IP with a proper RDNS and MX record that point directly back to your outbound smtp relay you can find yourself block by them for days.

    Even if you use a smarthost (smtp.bt.net is BT's Leased Line customers relay) there is no guarantee, I have regularly had to call BT's IP services support over the Hotmail issue they get onto Hotmail and a few hours later if we are lucky it all works again.

    At home we have a dynamic IP so all outbound has to go via a paid for authenticated smtp relay as Hotmail absolutely refuse to accept mail from a Virgin Media IP block.

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    While this is all very interesting and a good investigation, why is your member of staff trying to send themself an email?

    Our e-safety team have just been out beating people for using personal email accounts for work, and I should think the CP staff should be particularly careful about this. Check your AUPs and e-safety policy.

    If it's work, she probably shouldn't be doing it anyway.

    If it's not work, it's not your problem ;-)

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    maniac's Avatar
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    Quote Originally Posted by theriver View Post
    While this is all very interesting and a good investigation, why is your member of staff trying to send themself an email?
    I quite often e-mail myself things from work, stuff I know I need, little reminders to do things etc. so it's not that unusual request I don't think.

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    Had this problem today turns out we had an open mail relay which is why we kept on getting blocked from sending to hotmail. You can check if you have an open mail relay from many sites goggle "test open mail relay"

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    Quote Originally Posted by maniac View Post
    I quite often e-mail myself things from work, stuff I know I need, little reminders to do things etc. so it's not that unusual request I don't think.
    Oh I quite agree that this is not uncommon - that's why it was raised at school . . . . .

    Cheers.

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    Quote Originally Posted by PiqueABoo View Post
    Is the address she's sending to the right one behind the pretty display name stuff?

    You can troubleshoot with SMTP logging which should show you any mail delivery conversation between your server and elsewhere - for E2K3 that's turned on in the SMTP virtual server properties somewhere.
    I don't suppose you know how to analyse these logs?

    I can't see anything obvious such as error xxxx or mail delivery failed in the logs.

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