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How do I get mail hosts such as gmail to not automatically dump sent mail into spam/junk folder

Posted on 2008-10-20
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Last Modified: 2013-12-18
How do I configure my sendmail so that when it sends mail out the mail does not automatically get dumped into junk/spam folders and lost to the ages.



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Question by:Illyankesh
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7 Comments
 
LVL 8

Expert Comment

by:Rance_Hall
ID: 22761810
usually this doesn't have anything to do with the specific mailer you are using.

each mail administrator is allowed to set up their own testing for what is and is not spam.

in order for your mail to not get tagged as spam then you need to find out what tests the other guy runs and make sure you pass them.

There are litterally dozens of things to check.

is the sending IP on a blacklist somewhere?

are your dns records complete/correct?

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Author Comment

by:Illyankesh
ID: 22762339
added dns to rackspace list including check for smtp
pretty sure the ip is not on a blacklist, where would be a place to check?
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LVL 26

Expert Comment

by:jar3817
ID: 22766746
80% of the time it's dns related. Make sure whatever IP address this mail is coming from had valid (non-dynamic looking) DNS. This means the IP should resolve to something like "mail.yourdomain.com" or "smtp.somewhere.net" rather than something generic with an embedded IP like host1-2-3-4.isp.net

Are we talking about email sent from a human or from some web script? Email sent from webapps in shared hosting environments can be tough to get to look legit as the email is generated from a process rather than submitted from a user.
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Author Comment

by:Illyankesh
ID: 22770490
ah ok, the dns will be tricky and that is probably it....so here goes.
I have a virtual host, which generates a webscript which then relays that message to my sendmail server...all of this is hosted at rackspace, and our registrar is godaddy.  I found our firewall listed with cbl, and petitioned to have it taken off the list after making a few changes with our dns, and what not, such as changing the server name from localhost.localdomain to one similar to what you mentioned however that seemed to break the email out...I don't get bounced responses anymore they just seem to vanish.

...Scratch my last, but I left it in the post anyways...
Ok update...
So I have updated the dns at rackspace, and have opened a ticket to get the virtual machine an external ip address which should help with the dns resolution.  I've changed a bunch of settings back to the originals, and turned on the dns masquerading, to masquerade as our main domain name. and have created the user no-reply.  I can now send mails to my company account which is hosted offsite with a third party hosting company.  I have also added the mx records to the rackspace mx records as well.
I'm pretty sure I'm missing something...like my marbles...but that is what i've got so far.
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Author Comment

by:Illyankesh
ID: 22771555
Here is a bounced email I just got back, or rather a failed to deliver email...
I have the correct mx records in both our registrar at godaddy, and the DNS listing at rackspace which is where these devices are actually located.  So I added our mail hosting mx server listing from our email provider to the mx records at our registrar, and to the rackspace dns listing.  AND I added that server listing to the smart host in the /etc/mail/sendmail.mc file.  Now I've managed to get a test mail from sending directly from the server... /usr/sbin/sendmail   to my gmail account to the inbox, and not the junk mail folder.

However I still get rejected by hotmail, and I'm assuming by other email services because of the error below.  So this thing looks like a giant DNS error....but I'm still open to feedback/hints if anyone has any ideas.....
Date: Tue, 21 Oct 2008 16:01:01 -0500
From: Mail Delivery Subsystem <MAILER-DAEMON@apisphere.con.@apisphere.com>
To: <root@no-reply@apisphere.con>
Subject: Returned mail: see transcript for details
Auto-Submitted: auto-generated (failure)
 
[-- Attachment #1 --]
[-- Type: text/plain, Encoding: 7bit, Size: 0.4K --]
 
The original message was received at Tue, 21 Oct 2008 16:01:01 -0500
from localhost.localdomain [127.0.0.1]
 
   ----- The following addresses had permanent fatal errors -----
<crymethenile@hotmail.com>
    (reason: 501 Invalid Address)
 
   ----- Transcript of session follows -----
... while talking to mx2.hotmail.com.:
>>> MAIL From:<root@no-reply@apisphere.con> SIZE=564
<<< 501 Invalid Address
501 5.6.0 Data format error
 
[-- Attachment #2 --]
[-- Type: message/delivery-status, Encoding: 7bit, Size: 0.3K --]
 
Reporting-MTA: dns; no-reply@apisphere.con
Received-From-MTA: DNS; localhost.localdomain
Arrival-Date: Tue, 21 Oct 2008 16:01:01 -0500
 
Final-Recipient: RFC822; crymethenile@hotmail.com
Action: failed
Status: 5.5.2
Diagnostic-Code: SMTP; 501 Invalid Address
Last-Attempt-Date: Tue, 21 Oct 2008 16:01:01 -0500
 
[-- Attachment #3 --]
[-- Type: message/rfc822, Encoding: 7bit, Size: 0.6K --]
 
Date: Tue, 21 Oct 2008 16:01:00 -0500
From: root <root@no-reply@apisphere.con>
 
This is only a test

Open in new window

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LVL 8

Expert Comment

by:Rance_Hall
ID: 22776197
Its clear from the above you have some server configuration problems, and you still have dns issues.

the mail server cant find hotmail.

this is a dns problem of some sort.

go fix it.

read up on dns troubleshooting and follow a sound step by step approach till you figure out whats busted.

start at the ping level, can you ping by hostname?



also your bounces are coming from
 MAILER-DAEMON@apisphere.con.@apisphere.com

This is a hostname configuration problem and it may or may not be interfering with your dns problem, but
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Accepted Solution

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Illyankesh earned 0 total points
ID: 22790631
Errors were a reverse dns lookup due to a load balancer, and the relay not having a resolvable external ip address.  Once an external ip address was assigned and the registrar updated that helped.  Unfortunatly the virtual machine that was acting as the relay was damaged, and was subsequently lost when trying to restore to a previous snapshot.  Unable to clone a new machine, and or restore to previous state was due to features expiring independently of the overall license.  Which still has some time on it albeit not much.

So, to circumnavigate that entire debacle, the virtual machine that does have a resolvable external ip address was reconfigured to send mail out directly, instead of relaying to a separate machine.  Email can now be sent from the sign up script successfully to yahoo, gmail, and hotmail, and is not flagged as spam, or junk.

Now the last step is to get away from our email hosting service acting as a relay since they limit us to 200 emails out per day.

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