Internal email going to Junk Email

I have a few users that when the send themselves emails from the copier they go to their Junk Email folder.
 I have tried disabling Junk Email in Outlook, uninstalling the antispam on the client computer, checking rules and alerts, and even recreating a new roaming profile. When it goes into Junk it gets "[SPAM]" added to the subject.
I have checked windows updates just in case and I have all they do and I dont get the issue. Just seeing if anyone else has any idea's on this one?
Mr_WormaldAsked:
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Mr_WormaldConnect With a Mentor Author Commented:
I am yet to do the updates but I have been informed that this has been working correctly today, I will wait until tomorrow until a post again.
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NetfloCommented:
Hi,

Your issue lies on the server side with the antispam software you have installed there. The settings you are tweaking on the client can only do so much. The fact that the word SPAM is being printed, indicates that something is being done on server side.

On your Exchange server, ensure that the scanners IP is excluded from scanning and put into the trusted internal zone.

Emails from the scanner should deliver as normal after that issue has been corrected.
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Mr_WormaldAuthor Commented:
Bes tot do this under OC - Hub Transport - Anit-SPam - IP Allow List?

How/Where do I add to Trusted Internal Zone?
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NetfloCommented:
First question to ask, what is doing your antispam? Exchange only? 3rd party antispam software on the server?

The antispam IP allow list will not help under OC, you need to take a look at SC
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apache09Commented:
If you dont require outlooks built in junk mail or is giving you grief when in use

Simply turn off Cached Exchange Mode under the users account settings

Disabling cached exchange mode, completly disables the junk Mail Functinality in OUtlook

Once disabled, emails should no longer go into junk mail
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Mr_WormaldAuthor Commented:
Disabling Cached Exchange Mode didnt change the outcome.

We have a WatchGuard that is AntiSpam for externally sent/received emails.

Exchange 2007 doesnt really look to be doing any antispam other then blocking one email address (Only Receipent Filtering is enabled under OC)

Client side is done by ESET Smart Security
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NetfloCommented:
Is your scanners SMTP setting, the internal Exchange 2007 server or your ISPs SMTP. If emails are getting stamped and filtered the copier may be configured to look at your ISPs SMTP, which is then routing back in, being scanned by the Watchguard and getting stamped.

Alternatively login to your Fireware XTM Policy Manager -> Subscription Services -> Spam Blocker -> Configure -> Highlight your 'SMTP Proxy In' and select Configure -> Click on the Exceptions tab and enter the senders email address of the copier, ensure the action is Allow to ensure it passes straight through. Press OK, OK and save your configuration.

Let me know how you get along.
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Mr_WormaldAuthor Commented:
Setting the WatchGuard has not made a difference?
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NetfloCommented:
Where is your copier sending emails to? Internal Exchange or ISP SMTP?
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Mr_WormaldAuthor Commented:
Internal Exchange
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NetfloCommented:
Okay, I would create a dedicated receive connector just from the copier IP, you'll need to assign an additional IP to your Exchange servers LAN interface too.

See the following article to create a new connector with relaxed security: http://exchangepedia.com/2007/01/exchange-server-2007-how-to-allow-relaying.html
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Mr_WormaldAuthor Commented:
Just a question before I do this, if it is the server would it not be happening for all users? not just a few as the original issue mentions?
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NetfloCommented:
Looking a little into ESET, I believe this is your issue on the client machines. Take a look at the following link, step 4: http://kb.eset.com/esetkb/index?page=content&id=SOLN2121

Have you disable the client side email security? Looks like its on, as Exchange would not tag messages with [SPAM] by default.
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Mr_WormaldAuthor Commented:
I have disabled and even removed ESET and still get the issue. I have even changed the tag it receives but still goes into junk with the original tag [SPAM], thats why I rasied it here as I didnt know if something else would tag the junk email.
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NetfloCommented:
Okay lets look at your Exchange server, what AV do you have running on there? Any antispam config or Exchange level scanning on there too?
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Mr_WormaldAuthor Commented:
We have ESET AV installed on excahnge server but I believe this is only client side scanning. ESET AVExchange has nothing enabled other than what has been requested I believe.
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NetfloCommented:
For a message stamped with spam via the copier, can you open up the message properties and copy all the information into here. Obviously omit and replace personally identifiable information.

See the following link for what I'm after: https://support.dalton.missouri.edu/index.php/wiki/Public%3ARetrieving_Email_Headers_-_Outlook/
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Mr_WormaldAuthor Commented:
Received: from printer.domainname.local(IP Address) by
 mailserver.domainname.local(IP Address) with Microsoft SMTP Server id 8.1.436.0;
 Mon, 3 Sep 2012 11:19:16 +1000
X-Priority: 3 (Normal)
From: Choice Homes <printer@emailaddress.com.au>
To: "UserName"
 <user@emailaddress.com.au>
Subject: Attached Image
Date: Mon, 3 Sep 2012 11:11:06 +1000
Message-ID: <20120903111106.0001.CanonTxNo.3430@printer.domainname.local>
MIME-Version: 1.0
X-Mailer: Canon MFP
Content-Type: multipart/mixed; boundary="ADAJNMAHDCDIDAGEDGDGAGALALAA"
Return-Path: printer@emailaddress.com.au
X-EsetId: 0CD7D423DAAF223157978F
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NetfloCommented:
Can I ask you to at the very least upgrade your Exchange 2007 to SP3. Ensure you have a full and valid backup before upgrading.

We're trying to troubleshoot a routing and email issue and I'd expect you to have your Exchange server on the latest service pack to rule out any known issues or bugs.
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