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macfreq

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I'm using KMS 6.3.1 on Mac OS X Server 10.4.9 and I have DNS services running for local machines and have other traffic forwarded to my ISPs DNS servers.
The problem: When I try to send an NEW email to an account at Hotmail or Gmail KMS says it relayed the message, but the person never receives the email. And I don't get a bounce back message.
If the Hotmail user sends the email and I reply to it, he gets the reply fine.

Any ideas on what the problem is?

Thanks,

Tom
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scubaman99

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are the messages going into their "spam" folders, or are they just disappearing?
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macfreq

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Well, it looks like it's for Hotmail only. I looked in the spam folders for gmail and the emails were going there. Is there anything special about Hotmail?
BTW, this weekend I setup a SPF entry in my DNS settings for my email server to make sure it appeared as a legit server.
Not sure why Hotmail is not receiving.
In the Mail log I get the following result "Result: relayed, Status: 2.0.0"
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JamesG

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We were having sporadic problems like this with Hotmail, Yahoo, and AOL.

These services are "disappearing" the message, and not bouncing it, because they think you are a spammer (to oversimplify the explanation).

The first thing you should do is check and make sure you have a Reverse DNS entry. This is done with your ISP, and is not in your DNS services. You can verify at http://www.dnsstuff.com

We are now successfully sending to Hotmail after this change. If this doesn't work, you may need to pursue SPF and trusted sender services.



James
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macfreq

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I think I have the Reverse DNS is setup properly. Dnsstuff.com doesn't report any problems. The reverse lookup reports my ISP's connection name. Should it report back my email server's name (i.e. mail.domain.com) instead of static-IPADDRESS.ptldor.fios.verizon.net.?
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winkelman

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macfreq wrote on Tue, 15 May 2007 23:33

I think I have the Reverse DNS is setup properly. Dnsstuff.com doesn't report any problems. The reverse lookup reports my ISP's connection name. Should it report back my email server's name (i.e. mail.domain.com) instead of static-IPADDRESS.ptldor.fios.verizon.net.?


The Reverse DNS should report back the same as what your mail server is identifying itself with...
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macfreq

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OK, I have the reverse DNS records setup properly with Verizon and it checks out. But Hotmail still doesn't deliver my email. I can receive email from a Hotmail account and reply back with no problems.
Gmail is kind of working, any new email is being sent directly to the Spam folder, unless I add the account to my contact list. Annoying for first emails. But I can live with that. Hotmail on the other hand ignores the message al together.
Is there a setting in KMS that I'm missing, a header setting, that is being set when I reply but not being set when I initiate an email with Hotmail?

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akkab

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rDNS isn't enough

since 2004 Microsoft (hotmail) started using antispam technologies to take down spam from forged domains and mailbots.
one of these technology is SPF (Sender policy framework) its a TXT (or SPF if dns server can handle it) record added to your domain DNS, unlike MX that tells what server (MTA) receives mail for a domain, SPF tells what server SENDS mail for specific domain
you must have a valid SPF record in your DNS
goto http://www.openspf.org/ to learn more and a wizard helps u creating the text string.

EDIT: this link helps u validate your spf record once published in dns.

but even if this solves mail disappearing when sent to hotmail, this doesn't guarantee you your mail doesn't end in junk folder. their obscure spam policies make sending legitimate messages like playing lottery.

I once found an article in internet reporting that mail sent from Microsoft developpement team ended in hotmail junk folder Very Happy

ps: excuse my english , it's not my natural language

[Updated on: Sun, 20 May 2007 18:58]

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blasto

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try using kerio webmail, interestingly webmail delivers messages to hotmail... temporary solution till someone finds a permanent one...
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macfreq

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I have an SPF record already setup from the domain. The openspf.org site is a little confusing but I put together an entry that I think is right.
The entry is:
v=spf1 a mx ptr mx:mail.mydomain.com ~all

Is this a correct entry?
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macfreq

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I tried sending from the web mail interface a few days ago and tried again today with the same results, no mail shows up. I have even tried adding the contact for the sending email address to my contacts list in Hotmail and I still don't get email.
Frustrating!!
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akkab

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macfreq wrote on Mon, 21 May 2007 02:33

I have an SPF record already setup from the domain. The openspf.org site is a little confusing but I put together an entry that I think is right.
The entry is:
v=spf1 a mx ptr mx:mail.mydomain.com ~all

Is this a correct entry?



it depends on your DNS/MTA configuration, but you can validate your entry on "Test an SPF record" in this page
elsewhere the HELO/EHLO message of ur MTA must be a FQDN and correspond to your domain or a subdomain
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akkab

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blasto wrote on Sun, 20 May 2007 21:35

try using kerio webmail, interestingly webmail delivers messages to hotmail... temporary solution till someone finds a permanent one...



if webmail succedded in sending to hotmail while (i guess) mail client did not is that your are maybe using a different server in your outgoing smtp config (your isp's) what server isn't designated in SPF record as legitimate sender for your domain.
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winkelman

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I don't have any SPF or Caller-ID records setup and I can send to Hotmail just fine (just tested it). So I don't think there lies your problem...
akkab

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winkelman wrote on Mon, 21 May 2007 09:57

I don't have any SPF or Caller-ID records setup and I can send to Hotmail just fine (just tested it). So I don't think there lies your problem...



maybe but read this
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