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JackFlag for United Kingdom of Great Britain and Northern Ireland

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Can not email to Hotmail addresses

Hello,

I am having trouble emailing to Hotmail addresses, they fail with:

-------------------------------------------------------------------------------------------
Your message did not reach some or all of the intended recipients.

      Subject:      RE: change of address
      Sent:      29/10/2007 09:11

The following recipient(s) cannot be reached:

      'Email Address' on 29/10/2007 09:11
            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
            <infomedltd.co.uk #5.5.0 smtp;550 DY-002 Mail rejected by Windows Live Hotmail for policy reasons. The likely cause is a compromised or virus infected server/personal computer. If you are not an email/network admin please contact your E-mail/Internet Service Provider for help. Email/network admins, please visit http://postmaster.live.com for email delivery information and support>
--------------------------------------------------------------------------------------------------------

I try to go to: http://postmaster.live.com/ but it fails - server might be down.

Any help would be appreciated on why I can not email Hotmail contacts - its unfortunate as a lot of our customers use Hotmail.

Many thanks
Jack
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Jack
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ASKER

I tried a telnet to mail.hotmail.com 25 and this is the result:
Thanks, the page is working now.

-------------------------------------------------------------------------------------------------------
220 bay0-mc10-f12.bay0.hotmail.com Sending unsolicited commercial or bulk e-mail
 to Microsoft's computer network is prohibited. Other restrictions are found at
http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment lo
cated in California and other states. Mon, 29 Oct 2007 02:29:53 -0700

Connection to host lost.
--------------------------------------------------------------------------------------------------------

Is that normal?
Going by your DNS records you are on a dynamic IP address. Therefore I am not surprised that you are having problems sending Hotmail email. You will need to setup an SMTP connector to route email for them (And probably aol, yahoo, gmail etc) through your ISPs SMTP server.
If this is SBS, re-run the Internet and Email wizard and change the configuration to route through a smart host and enter your ISPs SMTP server in to the box when prompted.

Simon.

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ASKER

Hi Simon,

We are not on a dynamic IP address. By the way, this has only just started happening, all hotmail contacts were fine before.

Would you still recommend changing from DNS mail to SMTP?
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ASKER

I realise why you think I am on a Dynamic IP, the reason I use infomedltd.dyndns.org to forward email to thye IP of my SBS is that I am able to change the routing of email to different IP addresses should I have to. This company has moved locations many times in a short space, each time we get a new IP and this is my way of avoiding the propagation time and potential of loosing email.

Do you think I should just set a simple MX record to deliver mail straight to the Exchange and avoid all this, the company is settled here in its current location so I needn't worry so much.
It looks like a dynamic DNS address, and the server is announcing itself as just the domain.
You need to get everything corrected - change the MX records to an FQDN in your own domain - mail.infomedltd.co.uk for example, which will mean a new host set to that.
Then ask your ISP to set a reverse DNS to match that name.
Finally change the server to announce itself as that name.

Previous behaviour is not an indication that it was working correctly or will continue to work in the future. Fighting spam is a war, and that means things can change frequently.

Simon.

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Hi Simon,

I have contacted the domain hosts and will start making the changes. Am I likely to have any email down time while the changes are made?

Will my MX record jsut have one entry such as this?

10      mail.infomedltd.co.uk      --->      <mail server Public IP>      
MX records cannot be IP addresses
Therefore you will have to create a new host of type A, called mail, with your static IP address.
Then you can set the MX record to that.

There is nothing to stop you from leaving the existing MX records in place while the new records propagate - that will take up to 48 hours. Then remove the other entries later in the week.

Simon.

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So to confirm.... at the moment, the MX record is being updated by adding:
mail.infomedltd.co.uk but putting it at a lower priority than the current 10 infomedltd.dyndns.org & 30 mx2.mailhop.org.

So when the mail.infomedltd.co.uk has propagated and I have made the changes on Exchange and asked my ISP to change the reverse DNS settings, I can remove the 10 infomedltd.dyndns.org & 30 mx2.mailhop.org entires from the MX record?

Is this correct or am I going wrong in my understanding?

Thanks
Jack
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ASKER

My MX record now reads:

30      mail.infomedltd.co.uk      
40      infomedltd.dyndns.org

Both pointing to the same IP address which is the Exchange.

I thought it would be the other way around. So now I will wait for it to propagate, but now I will contact the ISP and get the reverse DNS sorted and then make the changes to the SBS that you asked me to do in another Q:

4. Change the SMTP banner to mail.infomedltd.co.uk - ESM, Servers, <your server>, Protocols, SMTP. Right click on the default SMTP VS and choose Properties. Click on the tab delivery and then advanced and change the FQDN. Be aware that each time you run the Connect to the Internet and email wizard (or whatever it is called) SBS will change it back to just infomedltd.co.uk, which is very annoying.

If I have gone wrong at any step, please say.

Does the priority number in the MX records make a difference? i.e for best practise, should 30 become 10 and 40 become 20?
Priority of the MX records doesn't matter. I don't like 0 as a priority. I usually use 10 and 20 or 10 and 50, but as long as one is higher than the other it should be fine.

Once the additional MX record have been propagated then you can remove the others.
You could leave the dynamic DNS host in the MX records. I have a dynamic DNS host in my own. That allows me to change where my email goes in the event of a failure of my ISP.

Simon.

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OK, MX records are:

30      mail.infomedltd.co.uk      
40      infomedltd.dyndns.org

Reverse DNS value for the Exchange IP: mail.infomedltd.co.uk

Exchange is announcing itself as:

220 mail.infomedltd.co.uk Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at  Tue, 30 Oct 2007 16:41:39 +0000

All changes were made today, so I expect this is all propagating. Hopefully this is why emailing to Hotmail gives the same Undelivered report (except it now says "mail.infomedltd.co.uk #5.5.0 " NOT "infomedltd.co.uk #5.5.0 "

If its still failing on Thursday I will let you know, or if iv gone wrong let me know ;)

Thanks
Jack
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ASKER

Still unable to email to Hotmail addresses, bouncing with the message in my last post.
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Sembee
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Ok, I am not sure how to do this so a few Q's...

Does it mean most mail will send via DNS and Hotmail via SMTP? Or all via SMTP?

Is this where I need to create a smarthost? If you could give me a quick guide that would be great.

Lastly, I checked on http://www.mxtoolbox.com diagnostics and it fails my reverse DNS. As far as I can see its all configured correctly now. Any ideas on that?

Thanks
Jack
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Actually reverse DNS is testing as OK now when I re-checked - last night it was failing.
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Its ok, found a guide, set the smarthost and all working.

Thanks for all your help.
Jack