Can't Send emails to hotmail

mealto

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Oct 20, 2006
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Correct me if I am wrong, but I am reading the use of "forwarding" as being synonymous with "relaying" which is what really creates the problems.

To resolve this problem, I have changed my outgoing SMTP servers in Outlook, Thunderbird, and the like to use the SMTP for the ISP that I am connected to, in my case Verizon.
Thanks for the clarification freedog. I was leaning in that direction and thought to try using my ISP's SMTP but mail still ends up in hotmail junk folder. It's really odd. I tried it again after reading your post and it worked! Not sure what is going on but thank you for your informative reply.
 

sparek-3

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If you are going to be using your ISP's SMTP server (and there's nothing wrong with that) to send mail from an @yourdomain.com (again, nothing wrong with that). If you have an SPF record, you will need to have the SPF record updated to reflect this. Otherwise, places that check SPF records will see your mail as coming from a source that is not specified in your SPF record.

Also keep in mind that if you are using mail.verizon.net as your outgoing mail server, this does not necessarily mean that the IP sending the mail is whatever mail.verizon.net resolves to. You would need to know the IP of the mail server at Verizon that is sending out your message and update your SPF record to reflect this.

This is where SPF can be tedious and this is why I don't think its a good idea to support blanket SPF records in DNS zones, because you don't know what mail servers a particular user is going to be using to send out mail. If a user has domaina.com set up on your server and you have your DNS templates set to automatically set up an SPF record, then if that user never uses mail.domaina.com to send out mail, and they always use mail.verizon.net, then their messages will never match the SPF records, causing it to always look like spam. To combat this, a module needs to be created in cPanel that allows end users to enter their own SPF IPs reflecting whatever IPs are being used to send out mail for their domain.

Hope this makes sense.
 

mealto

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Oct 20, 2006
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Yes, that makes a lot more sense now. So the managed VPS host added this in the Zone file:

"v=spf1 a mx ~all"

Is this the blanket statement that you were talking about? Any tips to modify / edit this?
 

sparek-3

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By blanket SPF record, I really just meant setting up an SPF record for every domain on the server. Some hosts have set up their DNS templates to automatically add an SPF records. However, this does not account for any circumstances where an account user using that domain, is using a different SMTP server to send out mail. This is really what I was referring to as a blanket SPF record.

I must say, that I'm not really an SPF expert. Perhaps the blanket SPF record would not cause problems, someone who understands SPF and mailing protocols may be able to verify or dispute my theory.

If I am understanding SPF correctly, an SPF record of:

v=spf1 a mx ~all

This is basically saying that the IP associated with this particular domain (I'll call it domain.com for argument's sake) and the IPs associated with the MX records for this domain, are the only IPs that are allowed to send mail from this domain. This would work fine if everyone who sends mail from an @domain.com address uses mail.domain.com or domain.com as their outgoing mail server. But if you have, for example, Verizon as your ISP and you are using mail.verizon.net as your ougoing mail server to send out mail from an @domain.com address, then any system that checks SPF (i.e. Gmail, Hotmail, AOL, etc) would view this message as a likely spam message, because the sending source is not listed in the SPF record. Now just how much weight is put on this failed SPF lookup remains to be determined. I'm not sure if Gmail really puts a lot of weight on it, but I do know they check for SPF.

Hope this helps.
 

mealto

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Oct 20, 2006
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v=spf1 a mx ~all

This is basically saying that the IP associated with this particular domain (I'll call it domain.com for argument's sake) and the IPs associated with the MX records for this domain, are the only IPs that are allowed to send mail from this domain. This would work fine if everyone who sends mail from an @domain.com address uses mail.domain.com or domain.com as their outgoing mail server. But if you have, for example, Verizon as your ISP and you are using mail.verizon.net as your ougoing mail server to send out mail from an @domain.com address, then any system that checks SPF (i.e. Gmail, Hotmail, AOL, etc) would view this message as a likely spam message, because the sending source is not listed in the SPF record. Now just how much weight is put on this failed SPF lookup remains to be determined. I'm not sure if Gmail really puts a lot of weight on it, but I do know they check for SPF.

Hope this helps.
I think I understand but funny enough, I am seeing the opposite. When I use my ISP's SMTP to send email, it goes to hotmail just fine. When I use mail.mydomain.com, it goes into the junk folder! Very odd huh? How do you suggest we move forward with this one?

At this point, I can nly guess that this dnsreport and dnsstuff error may be the culprit:

domain.com claims to be host host.domain.com [but that host is at xx.xx.xx.112 (may be cached), not xx.xx.xx.114].

Any other thoughts?
 
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sparek-3

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You probably have someone or had someone on your web hosting server (not necessarily your hosting account on that server) that was forwarding their mail to Hotmail. This resulted in Hotmail rejecting/blackholing your e-mail when it is sent from your web hosting server. As a result, Hotmail views any message that is coming from your web hosting server IP as spam or just does not accept it. Why? I don't know. I could go into a big long rant as to why eventually everyone is going to be blocking everyone and e-mail will not be a very good communication tool (hey, if you block all mail coming to your server, you're guaranteeing your users won't receive spam).

Your ISP's SMTP server is likely not list in a Hotmail blacklist or other form of rejection and that is why it is being accepted. As to why the SPF record is not having any affect, I suspect this is just the way Hotmail weighs SPF records. As much as SPF has been touted, I just really don't think its been fully accepted as a spam prevention tool. I think servers that do check SPF are configured more in the way of treating SPF matches as legitimate mail and SPFs that do not match, they are just ignoring the SPF and treating it like a normal message. So if your SPF matches your message is more likely to be accepted (although this does not explain why your messages sent from your web hosting server are going to the junk folder, perhaps Hotmail's internal blacklist takes precedence) but if you send a message and the SPFs do not match, then the fact that the sending IP and the SPF record do not match does not factor in the decision on how to mark the message, instead SPF is ignored and the message is treated just as if the SPF record did not exist.

This is a prime example (and I should note that I really don't know if this is how things are working or not) of how difficult it is to add something to a standard communication medium. In order for SPF to be effective, everyone has to use it, every domain has to have an SPF record, and every mail server has to be willing to completely disregard messages when the IPs and the SPF records do not match. But SPF is just not accepted enough for ISPs and mail servers to do this. If mail server reject messages from domains that do not have SPF records or from servers when the SPFs do not match, then they will be rejecting a lot of mail.

And again, I should stress that while it may sound like I'm stressing the importance of SPF, I'm still not sure if it is a viable solution. A lot has yet to be determined regarding SPF.
 

mealto

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Oct 20, 2006
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Just an update. Noticed that when we use PHP to send out an email through the Tell A Friend script on our site, the mail never gets to Hotmail, Yahoo or Gmail. It works when we send it to our own domains, mind you, these are hosted the same same VPS as the TAF script. We have also tried our TAF to a different domain and low and behold, NO EMAIL!

This is not looking good. Can anyone provide any info to help us the trouble shoot?
 

yawsh

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Jun 20, 2004
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I'm having the same problem.
I tried what ever since 3 weeks.. Noting works till now.

The server is sending emails to anywhere.. Except to hotmail accounts.

What I figured out that web mail can send emails to hotmail ... only PHP and to be specific, vBulletin forums are not sending emails to hotmail accounts and sending to others like yahoo, gmail ..etc

I tried upgrading PHP from 4.4.2 to 4.4.4 and did not work and I went back to 4.4.2

is there any resolution to that?
 

yawsh

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Jun 20, 2004
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Just wanted to add that even by sellecting SMTP to send emails from VB it did not work ..



Regards
Mohamed
 

mealto

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Oct 20, 2006
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This is not good. Does anyone know if this a PHP issue or a Cpanel issue?
 

deanstev

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Jun 10, 2004
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Well I am having this issue too, and I have to say, it is annoying me and my clients - I have tried various options, I have rDNS, SPF and have recompiled PHP etc... the server says that the email has sent (checking the log confirms this), but it never ever shows up at a hotmail or yahoo mailbox - Junk folder or not...

Anyone any ideas?
 

forlinuxsupport

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Dec 22, 2004
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hi

Try do this on your server.

Code:
dig -t MX hotmail.com
That should return a nice list of MX records.

Then try telnet wth port 25 onto each one of them.

On one of my boxes it just sits there and eventually times out. Which makes me think hotmail is just DROPPING the traffic from my box becuase it thinks I'm a spammer.

On another box it does through, but always lands up in JUNK mailbox.

Im dont have SPF setup, so I will try that and see what that does.

cheers
Andy
 

deanstev

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Jun 10, 2004
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how do you telnet port 25?
i typed telnet
then open
then mx1.hotmail.com
it just sits there....

Code:
[email protected] [~]# dig -t MX hotmail.com

; <<>> DiG 9.2.4 <<>> -t MX hotmail.com
;; global options:  printcmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 15885
;; flags: qr rd ra; QUERY: 1, ANSWER: 4, AUTHORITY: 0, ADDITIONAL: 0

;; QUESTION SECTION:
;hotmail.com.                   IN      MX

;; ANSWER SECTION:
hotmail.com.            373     IN      MX      5 mx2.hotmail.com.
hotmail.com.            373     IN      MX      5 mx3.hotmail.com.
hotmail.com.            373     IN      MX      5 mx4.hotmail.com.
hotmail.com.            373     IN      MX      5 mx1.hotmail.com.

;; Query time: 188 msec
;; SERVER: 209.59.139.5#53(209.59.139.5)
;; WHEN: Mon Nov 20 17:19:42 2006
;; MSG SIZE  rcvd: 109
 
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mealto

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Oct 20, 2006
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This is becoming a real pain. Just did more testing and only Gmail can see our emails. Both Yahoo and Hotmail accounts never even see our emails! When I use the SMTP from our ISP, everything works. Anyone have a fix?

We are trying to forward some email accounts to yahoo. Yahoo never receives those forwards.
 

sneader

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Aug 21, 2003
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how do you telnet port 25?
i typed telnet
then open
then mx1.hotmail.com
it just sits there....
From a command prompt, type:

telnet mx1.hotmail.com 25

That's it!

If you want to go further and actually deliver a message by command line, try this:

telnet mx1.hotmail.com 25

It should give you some type of greeting. Then type:

helo www4.yourdomain.com (or whatever the hostname of your server is)

It should say "OK" or something. Then type:

mail from:<[email protected]> (obviously put YOUR e-mail addr in there)

It should say "sender OK" or similar. Then type:

rcpt to:<[email protected]> (obviously put their hotmail address there)

It should say "recipient OK" or similar. Then type:

data

It should say to type your message and end with a line with a period by itself. So...

type some message here then press enter
. (notice this is a period on a line all by itself) and press enter

You should get a message ID and a confirmation that the message was accepted.


The real SMTP pros will jump in here and probably embellish this simple tutorial, but I have used this exact same syntax hundreds of times to help test mail servers, etc. and it works fine.

- Scott
 
Jan 12, 2006
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I had the same problem sending emails from webmail to hotmail accounts. Outlook has always sent emails to hotmail fine using IMAP.

I spent most of the early hours this morning trying to sort the webmail problem and i gave up in the end.

earlier i was in my php.ini file and i saw that extension=php_curl.dll was not commented out which was causing error_log entries.

I commented it out and restarted apache in WHM and now webmail sends emails to hotmail just as well as outlook does.

The above probably had no reference to the hotmail problem but some how mine works now so im a little confused to what i actually did.


Dan
 

mealto

Well-Known Member
Oct 20, 2006
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I had the same problem sending emails from webmail to hotmail accounts. Outlook has always sent emails to hotmail fine using IMAP.

I spent most of the early hours this morning trying to sort the webmail problem and i gave up in the end.

earlier i was in my php.ini file and i saw that extension=php_curl.dll was not commented out which was causing error_log entries.

I commented it out and restarted apache in WHM and now webmail sends emails to hotmail just as well as outlook does.

The above probably had no reference to the hotmail problem but some how mine works now so im a little confused to what i actually did.


Dan
Are you using yoru ISP's SMTP or your domain's SMTP when using Outlook to send emails? Reason I am asking is that if I use my ISP's SMTP, hotmail emails work fine. When I use SMTP from my web host, it gets auto junked in hotmail.
 
Jan 12, 2006
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im using port 26 on my SMTP server as my ISP blocks port 25 unless i use their smtp server.

But ive just tried sending an email to hotmail and it is yet to come through!!

Dan