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Why do a majority of my clients emails end up in the intended recipients outlook "junk" folder

Posted on 2009-05-13
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Last Modified: 2012-05-06
My client has an SBS 2003 server and is sending his emails via exchange. The exchange in turn relays the messages off his ISP's SMTP server (this has reverse DNS setup correctly and is definately not on any blacklists).

When messages are recieved at the far end - if the user is using Outlook - invariably messages from the clients domain end up being put by Outlook directly into Junk.

What can we do to minimise this ? - Could the problem be related to his domain ? how can i check the reputation of his domain ?
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Question by:MentalSolutions
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by:MattiasN
ID: 24373824
Very good site to checkwether or not your servers is blacklisted:

MXtoolbox
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by:TonySt
ID: 24373850
Is the ISP's SMTP server blacklisted ??
Outlook on the End users system thinks emails from your client are Spam.  Do they look like spam ?? Do they contain keywords that are normally associated with spam ??  If they are not "spam-like" then the problem is at the end-users side.  They must have some rule or condition thats causing junk mail classification.  You need to investigate these:

1.  End users junk mail settings are to high.  They have to be missing other important mail also.
2.  End user could put your clients address or domain on thier "approved sender list"
3.  Find out if the end user is using a blacklist and if the ISP is on it.
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Author Comment

by:MentalSolutions
ID: 24373854
i know that site and the server / domain definately isnt blacklisted.

Its something wierd in Outlook - for example when he sends me an email - the message passes nicely through my comprehensive "Mailfoundry" spam filter but outlook drops it into JUNK


its most odd - how does outlook identify messages as spam ?
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Author Comment

by:MentalSolutions
ID: 24373891
Hi Tony - tanks for your thoughts

the ISP SMTP server definately ISNT blacklisted

for points 1 and 2 - its not realistic to contact everyone he might potentially email and ask them to adjust their junk mail settings - this happens with most contacts with default outlook settings (which is basically most contacts)
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by:TonySt
ID: 24373894
I'm confused, Your outook drops his email into junk AND also when he sends it to some other user it drops into junk also ??
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by:MentalSolutions
ID: 24373934
yes - pretty much anyone he sends messages to outlook drops it into junk

I was using him sending me messages directly as an example  - to stress the fact that the message sailed through the mailfoundry and was not quaranteened as SPAM - so not on RBL, greylist, redlist and all the other checks the mailfoundry does - and yet when it reaches the desktop, my OL2007 eats it as JUNK.

Its very odd
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by:TonySt
ID: 24373987
Well, if he's being dropped into junk by virtually everyone, then either there is something about his email, his server, or his ISP that is causing that classificiation.  What is he sending thats being dumped??  a normal text "Hi how are you email"  or an HTML ad  with pictures and prices etc ??
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by:kory1006
ID: 24374015
Have you checked the junk email settings in Outlook to make sure he isnt on the blocked senders list?  If you go under Tools, then Options, you should see the Preferences tab... in there is the Junk E-Mail button.  Under the Blocked Senders tab, make sure the user isnt listed there, and for all other purposes add him to the safe senders tab.
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by:TonySt
ID: 24374054

@kory1006
he already said that there are several contacts on his clients contact list that are treating the emails as spam.
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by:kory1006
ID: 24374122
TonySt

using him as an example...  Outlook has its own junk email filter and for whatever reason may be blocking his client.

But as you already stated it sounds like something with his ISPs SMTP server.  Sender ID settings maybe?  But who knows.
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Author Comment

by:MentalSolutions
ID: 24374160
is there a way of seeing WHY outlook has classified something as SPAM ?
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by:Mestha
ID: 24374236
There is no way of knowing why a message was classified as spam. Think about it for a moment. What is to stop a spammer from doing the same thing and then being able to tune their messages to get through? No antispam provider will tell you what the content triggers are.

Are the messages graphical? Using stationary or images as part of the signature? If the message is sent in plain text does it get through?

Simon.
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by:TonySt
ID: 24374243
You have to start by processof elimination.  First shut off your outlook spam filter and have him send you an email.  if that works correctly then outlook is treating him as spam as opposed to a black list issue
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Author Comment

by:MentalSolutions
ID: 24374341
Simon

actually i dont think that is strictly correct -for example a dedicated Barracuda Spam filter will tell you WHY it thought a message was spam - it runs it through a number of tests and each test causes "scores" then all the scores are added together and if this breaches a threshold score the message is deemed to be spam. Obviously this score breakdown is not forwarded back to the spam sender but it is available locally for an administrator to see why certain messages are being classed as spam.

in this case my clients messages are passing straight through some very expensive and sophisticated spam filters - it is ONLY outlook that thinks they are junk
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by:TonySt
ID: 24376945
You still have not told us if ALL emails are being dumped or just some.  Do straight text only emails get dumped or just ones with pictures, links, ect.
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Author Comment

by:MentalSolutions
ID: 24377038
sorry I thought i had answered that

basically its not EVERY message just the majority

there does not seem to be any correlation between the type of message and it getting intercepted. Plain text "hello world" messages are the bulk of what he sends - im not sure if he does any HTML type messages at all
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by:TonySt
ID: 24377126
Are you using an exchange server ??  If you are check the "Message Delivery Properties"  "Intelligent Message Filtering" settings.    There is a threshhold setting there that places email into a users junk mail folder based on a "SCL" rating.  Check to see what the levels for SLC and UCE are.  Not long ago I had to re-adjust ours because the latest exchange service pack did not mix well with outlook 2007.
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Author Comment

by:MentalSolutions
ID: 24377161
I appreciate that - but the main problem is sending to people all over the world who i have no control over their exchange servers etc

It is coming out of an exchange server (on an SBS2003 box) at this end - but the changes you are suggesting pertain to the recipient end do they not ?
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TonySt earned 500 total points
ID: 24377402
In order to diagnose whats going on, we have to figure out where its being dumped.  While I realize that you have no control over the rest of the planet, it still could be a exchange setting causing this problem.  
In any case, you are lucky enough to have your system dumping his mail also so we have something to look at to figure out what going on.  MicroSoft has in the past provided service pack and updates to the entire world and suddenly things stop working everywhere.  I had to reset The SCL on my server after a service pack install Outlook 2007 started dumping all out email into junk until I stopped it.
To be honest with you, if its not a "global" setting. Or something that Microsoft changed during a service pack or update to either exchange or outlook, then the ONLY other possibility is Blacklisting.
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Author Comment

by:MentalSolutions
ID: 24380598
it is MOST odd - I agree with your strategy though - in the morning I will attempt to send myself 20-30 messages of every concievable type to see what percentage are being intercepted. Possibly I could send you some tests from their account too if you dont mind Tony
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