Sending email through MS Outlook 2007

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#1 Mon, 03/16/2009 - 13:21
zer0

Sending email through MS Outlook 2007

hi, I have setup virtualmin to work as my email server. I have also setup outlook 2007 to serve as my email client. I am able to receive emails but when sending emails, sometimes it arrives at destination and sometimes it doesn't. In mail.log it shows that the email was sent

[code:1] Mar 16 16:48:07 eServer postfix/cleanup[24657]: 4DF897E2F2: message-id=<000001c9a680$e19605e0$a4c211a0$@ca> Mar 16 16:48:07 eServer postfix/qmgr[21538]: 4DF897E2F2: from=<user@domain.tld>, size=2549, nrcpt=2 (queue active) Mar 16 16:48:07 eServer postfix/smtp[24658]: 4DF897E2F2: to=<user2@hotmail.com>, relay=smtp.mts.net[142.161.2.118]:25, delay=0.42, delays=0.14/0.01/0.09/0.18, dsn=2.0.0, status=sent (250 ok: Message 67777821 accepted) Mar 16 16:48:07 eServer postfix/smtp[24658]: 4DF897E2F2: to=<user3@yahoo.ca>, relay=smtp.mts.net[142.161.2.118]:25, delay=0.42, delays=0.14/0.01/0.09/0.18, dsn=2.0.0, status=sent (250 ok: Message 67777821 accepted) [/code:1]

The in this case the one sent to hotmail never arrived, but in another attempt the one sent to hotmail arrived but the yahoo did not.

I'm not sure if this is due to configuration of postfix, or ms outlook.

Any help will be greatly appreciated.

Mon, 03/16/2009 - 13:50
andreychek

Yeah, I mean, it the message is showing as being &quot;Sent&quot;, it's a tough issue to resolve.

Sometimes in those cases, the message ends up in the persons spam folder -- do you have a way to access the account and test that?
-Eric

Tue, 03/17/2009 - 07:16 (Reply to #2)
ronald
ronald's picture

since when was hotmail and yahoo proven to be reliable addresses to test email on?
Yahoo often bounces emails first round and may deliver few days later. I have seen this time after time when sending mails to yahoo accounts.

Hotmail? 80% failure in my experience.

Tue, 03/17/2009 - 12:03 (Reply to #3)
zer0

but DNS shouldnt have any affect on the out going emails or any local emails right?

Tue, 03/17/2009 - 12:45 (Reply to #4)
Joe
Joe's picture

<div class='quote'>but DNS shouldnt have any affect on the out going emails or any local emails right?</div>

Wrong. As I mentioned previously, misconfigured DNS is a very spammy characteristic. Your message was classified as spam. DNS misconfiguration is a very common cause of that. How else can I say it, so you'll believe me and provide the information we need to help you fix things?

If you just look in the headers of the message marked as spam, as I explained above, we won't have to guess.

Or, you can continue to theorize and have no idea what's going on. But, I'm running out of ways to ask for the information we need to actually troubleshoot your problem...so, I'm gonna have to give up at some point.

Please just look in the spam mailbox of that user, and look at the headers of that message. SpamAssassin explains exactly why it marked something spam. You just have to look at it.

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Tue, 03/17/2009 - 13:26 (Reply to #5)
zer0

my apology. I miss understood.

here is the information in the header of the email marked as spam

<div class='quote'>
Received: from localhost by eServer with SpamAssassin (version 3.2.4); Tue, 17 Mar 2009 14:15:45 -0500
From: &quot;bilal.genvion&quot; &lt;bilal@genvion.ca&gt;
To: &lt;test@genvion.ca&gt;
Subject: test
Date: Tue, 17 Mar 2009 14:15:32 -0500
Message-Id: &lt;83b545db8cf4a700835b154df0b9b5b7@192.168.1.103&gt;
X-Spam-Flag: YES
X-Spam-Checker-Version: SpamAssassin 3.2.4 (2008-01-01) on eServer
X-Spam-Level: *****
X-Spam-Status: Yes, score=5.4 required=5.0 tests=LOCALPART_IN_SUBJECT, NO_RELAYS,TVD_SPACE_RATIO autolearn=no version=3.2.4
MIME-Version: 1.0
Content-Type: multipart/mixed; boundary=&quot;----------=_49BFF6E1.6488D12D&quot;
</div>

and this was in the body of the email

<div class='quote'>
Spam detection software, running on the system &quot;eServer&quot;, has
identified this incoming email as possible spam. The original message
has been attached to this so you can view it (if it isn't spam) or label
similar future email. If you have any questions, see
the administrator of that system for details.

Content preview: test23 [...]

Content analysis details: (5.4 points, 5.0 required)

pts rule name description
---- ---------------------- --------------------------------------------------
-0.0 NO_RELAYS Informational: message was not relayed via SMTP
2.5 LOCALPART_IN_SUBJECT Local part of To: address appears in Subject
2.9 TVD_SPACE_RATIO BODY: TVD_SPACE_RATIO

</div>

Thanx joe...
and sorry again...

Tue, 03/17/2009 - 13:50 (Reply to #6)
Joe
Joe's picture

You have a broken hostname. It is &quot;localhost&quot;. This is never right. If you installed with the install.sh automated install script, it shouldn't have let you proceed until you set a valid fully qualified domain name...but I guess it failed to detect this problem somehow.

So, you need to fix that. In Webmin-&gt;Networking-&gt;Hostname and DNS Client you can set the hostname. It needs to be a sane fully qualified domain name, and it needs to resolve via DNS.

If you are running Debian 5 or Ubuntu you might have to update /etc/mailname (I hate this new convention; this is a really stupid idea that I think the Ubuntu folks came up with...the seem to be full of stupid ideas on the server-side...they broke the Apache configuration in really stupid ways last year, too) to also include this new name. On most systems, Postfix gets the name from the system hostname, so it only needs to be set in one location.

I'm not actually sure what &quot;TVD_SPACE_RATIO&quot; is, but if your hostname were sane, it wouldn't have been enough to push this into being ranked spam and it would have been delivered correctly.

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Tue, 03/17/2009 - 14:38 (Reply to #7)
ronald
ronald's picture

also note:

ERROR: Some of your MX records returned by your nameservers are IP addresses. This is not ok per the RFCs and you should change them.
The problem records are:
205.200.9.230
This can cause problems !

ERROR: I could not get any A records for www.genvion.ca!

Looking for A record through squish:

50.0% of queries will end in failure at 204.174.223.72 (ns1.domainpeople.com) - no such record

50.0% of queries will end in failure at 64.40.96.140 (ns2.domainpeople.com) - no such record

Tue, 03/17/2009 - 14:46 (Reply to #8)
Joe
Joe's picture

Ah, DNS is misconfigured! I wonder why no one thought of that earlier? ;-)

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Wed, 03/18/2009 - 04:05 (Reply to #9)
zer0

Ahhh ic... I tried to configure the DNS with limited knowledge, and domainpeople require you to configure DNS from scratch, unlike godaddy.

Here is how i initially set up the DNS

A record pointing to MY IP
MX record pointing to MY IP

and thats it... I guess I need to do more.

Joe, There is no Webmin-&gt;Networking-&gt;Hostname and DNS Client. Hostname and DNS Client do not exist under the Networking.

Wed, 03/18/2009 - 04:28 (Reply to #10)
zer0

Joe, nevermind i found it... Webmin&gt;&gt;Networking&gt;&gt;Network Configuration&gt;&gt;Hostname and DNS Clients

The name of my machine (which I gave it when installing ubuntu 8.04) is entered for the Hostname, should it be something else?

Thanx

Wed, 03/18/2009 - 09:04 (Reply to #11)
Joe
Joe's picture

<div class='quote'>The name of my machine (which I gave it when installing ubuntu 8.04) is entered for the Hostname, should it be something else?</div>

It should be a fully qualified domain name that resolves via DNS.

You also need to update the /etc/mailname, as I mentioned.

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Wed, 03/18/2009 - 11:28 (Reply to #12)
zer0

hey it worked...I fixed the DNS (i think) Thank you everyone

also, Joe, I changed the hostname from eServer to domain.com i think that changed the name of my ubuntu machine.

I'm just wondering if its possible to change the machine name without affecting anything?

Thanx

Wed, 03/18/2009 - 11:43 (Reply to #13)
Joe
Joe's picture

<div class='quote'>I'm just wondering if its possible to change the machine name without affecting anything?</div>

I thought we were hoping to effect things...like, you know, making mail work. ;-)

Since you aren't hosting DNS locally, there isn't a lot that's effected by changing the name. Nothing comes to mind, actually...but I might be wrong.

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Wed, 03/18/2009 - 12:23 (Reply to #14)
zer0

Thanx Joe.
Also my domain controller has the same domain... will that cause problems?

Wed, 03/18/2009 - 13:30 (Reply to #15)
Joe
Joe's picture

<div class='quote'>Also my domain controller has the same domain... will that cause problems? </div>

Almost certainly, though I don't know what a &quot;domain controller&quot; is. You can't sanely have two systems with the same name on the same network (where &quot;the Internet&quot; counts as one network).

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Wed, 03/18/2009 - 13:39 (Reply to #16)
Joe
Joe's picture

Oh, unless you actually mean &quot;the same domain&quot;. You can have an unlimited number of systems in the same domain (virtualmin.com, www.virtualmin.com, mail.virtualmin.com, joe.virtualmin.com, jamie.virtualmin.com, etc. etc., all are in the virtualmin.com domain)...but they can't have the same name.

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Fri, 03/20/2009 - 05:18 (Reply to #17)
zer0

my email server hostname is &quot;abcd.ca&quot; and my domain in active directory is also abcd.ca, but the name of the windows server machine is different.

i hope they wont cause any confusion

Fri, 03/20/2009 - 13:12 (Reply to #18)
Joe
Joe's picture

<div class='quote'>my email server hostname is &quot;abcd.ca&quot; and my domain in active directory is also abcd.ca, but the name of the windows server machine is different.

i hope they wont cause any confusion</div>

I think only I'm confused. I don't see how two systems with different names could cause problems.

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Sat, 03/21/2009 - 03:44 (Reply to #19)
zer0

and your confusion has answered my question. Thank you joe, and everyone else...

you guys are awesome!!!

Mon, 03/16/2009 - 14:59
Joe
Joe's picture

If DNS is misconfigured in any serious way, it could prevent delivery...making mail from your server look &quot;spammy&quot;.

Beyond that, not much comes to mind. The log tells us that the mail was handed off...once it goes to another server, we're just guessing about problems.

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Tue, 03/17/2009 - 03:42
zer0

thanx for reply guys,

yeah all the emails that i sent out i sent them to my external email addresses to test them. only once (the 2nd or 3rd try but not the first, first was in inbox) they ended up in spam. I am using my ISP's SMTP server, which should deliver it to inbox.

Tue, 03/17/2009 - 10:22
zer0

hi,
actually it could be some other issue because I cant even send mail localy.

[code:1]
Mar 17 14:15:32 eServer postfix/pickup[22040]: CA3767E2F3: uid=33 from=&lt;bilal@genvion.ca&gt;
Mar 17 14:15:32 eServer postfix/cleanup[22316]: CA3767E2F3: message-id=&lt;83b545db8cf4a700835b154df0b9b5b7@192.168.1.103&gt;
Mar 17 14:15:33 eServer postfix/qmgr[22041]: CA3767E2F3: from=&lt;user@domain.tld&gt;, size=459, nrcpt=1 (queue active)
Mar 17 14:15:33 eServer postfix/trivial-rewrite[22317]: warning: do not list domain domain.ca in BOTH mydestination and virtual_alias_domains
Mar 17 14:15:33 eServer dovecot: imap-login: Login: user=&lt;user.domain&gt;, method=PLAIN, rip=192.168.1.103, lip=192.168.1.103, secured
Mar 17 14:15:33 eServer dovecot: IMAP(user.domain): Disconnected: Logged out
Mar 17 14:15:34 eServer dovecot: imap-login: Login: user=&lt;user.domain&gt;, method=PLAIN, rip=192.168.1.103, lip=192.168.1.103, secured
Mar 17 14:15:34 eServer dovecot: IMAP(user.domain): Disconnected: Logged out
Mar 17 14:15:45 eServer postfix/local[22318]: CA3767E2F3: to=&lt;user2.domain@domain.tld&gt;, orig_to=&lt;user2@domain.tld&gt;, relay=local, delay=13, delays=0.24/0.03/0/12, dsn=2.0.0, status=sent (delivered to command: /usr/bin/procmail-wrapper -o -a $DOMAIN -d $LOGNAME)
Mar 17 14:15:45 eServer postfix/qmgr[22041]: CA3767E2F3: removed
[/code:1]

The email never arrived.

All the services are running, any help will be appreciated.

Thanx

Tue, 03/17/2009 - 11:15 (Reply to #23)
Joe
Joe's picture

What appears in the procmail.log in this case?

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Tue, 03/17/2009 - 11:20
zer0

procmail.log

<div class='quote'>
From root@genvion.ca Tue Mar 17 07:52:04 2009
Subject: Anacron job 'cron.daily' on eServer
Folder: /home/administrator/Maildir/new/1237294325.12339_0.eServer 429
Time:1237294325 From:root@genvion.ca To:root@genvion.ca User:administrator Size:477 Dest:/home/administrator/Maildir/new/1237294325.12339_0.eServer Mode:None
From bilal@genvion.ca Tue Mar 17 14:15:33 2009
Subject: test
Folder: /home/genvion/homes/test/Maildir/.spam/new/1237317345.22320_ 2286
Time:1237317345 From:bilal@genvion.ca To:test@genvion.ca User:test.genvion Size:2334 Dest:/home/genvion/homes/test/Maildir/.spam/new/1237317345.22320_0.eServer Mode:Spam
</div>

Tue, 03/17/2009 - 11:35 (Reply to #25)
Joe
Joe's picture

So the first one from root to administrator was delivered successfully. The second one from bilal was detected as spam for some reason. You'll want to look in the .spam folder and look at the headers for why spamassassin called it spam. I always suspect DNS misconfiguration, but there are other possibilities.

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Tue, 03/17/2009 - 11:43
zer0

i dont know why it classified it as spam, since its local from same domain, and its also in the spamassasin's whitelist. As for DNS, i'm not using BIND, infact I unchecked it from the module list. I'm using the Domainpeople.com (where i got the domain from) DNS.

Anything else that I can check?

maybe since its https(secure) it could be causing problems? (noob guesses)

Tue, 03/17/2009 - 12:01 (Reply to #27)
Joe
Joe's picture

<div class='quote'>i dont know why it classified it as spam</div>

That's why I told you how to check. ;-)

We can't fix it without knowing what's wrong.

<div class='quote'>As for DNS, i'm not using BIND, infact I unchecked it from the module list. I'm using the Domainpeople.com (where i got the domain from) DNS.</div>

This is irrelevant. DNS can be misconfigured, regardless of where the servers are.

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