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 ...
27th January 2010, 03:28 PM #1
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!
27th January 2010, 03:40 PM #2
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.
Thanks to PiqueABoo from:
sandeep2504 (27th January 2010)
27th January 2010, 04:05 PM #3
That sounds like it will do the job!
Originally Posted by PiqueABoo
I will try that.
27th January 2010, 06:34 PM #4
Stupid question but she's not blocked her own school address has she?
27th January 2010, 06:42 PM #5
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.
27th January 2010, 07:45 PM #6
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.
27th January 2010, 10:24 PM #7
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 ;-)
27th January 2010, 10:43 PM #8
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.
Originally Posted by theriver
27th January 2010, 11:36 PM #9
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"
28th January 2010, 08:44 AM #10
Oh I quite agree that this is not uncommon - that's why it was raised at school . . . . .
Originally Posted by maniac
28th January 2010, 03:06 PM #11
I don't suppose you know how to analyse these logs?
Originally Posted by PiqueABoo
I can't see anything obvious such as error xxxx or mail delivery failed in the logs.
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