Clients having emails junked in outlook and Apple Mail

We use Exchange Server 2010 with Sophos Puremessage SPAM & ANTIVIRUS checking.

Our clients use Apple Mail & MS Outlook for Mac to access the server in cached mode.

Some of our internal messages i.e. emails from and to recipients within our organisation are junked and our end users don't notice this and IT Staff get ear ache about how the system is hindering them from working

Is there a central way to reduce or whitelist internal users? also many normal emails from other schools which we work close with also get junked. I have checked many servers including our own using MXTOOLBOX BLACKLIST checks and were not black listed and neither are any of the other schools.

I feel i simply need to turn down the sensitivity or to whitelist the domains

Any advise on this would be much appreciated
James WilkinsonNetwork Security AnalystAsked:
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Andy MIT Systems ManagerCommented:
Have you got the exchange in-built anti-spam agents enabled? If so then I would disable these as you already have Sophos doing your anti-spam and the two together could be causing issues.

If this is not the case have a look at the logs in Sophos - see if this is what's blocking the messages (it should also give you an idea as to why) though I don't believe it should be touching the internal emails at all as this will all be done on the exchange server itself. You could also check he message headers to see if any reason/score has been written into them and also what is actually looking at the message.

Once you've established what is actually flagging the emails as spam you can then adjust settings/whitelist as required. It could also be the client junk settings in Outlook/Mac Mail that is putting the emails into junk - we usually disable these where possible as they can cause issues as well.

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James WilkinsonNetwork Security AnalystAuthor Commented:
Great response time

Ill take a look into this, many thanks
James WilkinsonNetwork Security AnalystAuthor Commented:
I found the agents and they were all enabled. I have disabled content filtering agent as Sophos is doing that.

Should i disable all of them if Sophos is doing IP Block and Allow for all types of senders?
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Andy MIT Systems ManagerCommented:
Hi, sorry for delay in getting back to you.

Generally yes, if you have a third party anti-spam filter it's recommended to disable all built-in exchange anti-spam agents.
James WilkinsonNetwork Security AnalystAuthor Commented:
Hi Andy,

Thank you for your advise, i have disabled the Exchange agents and Sophos Puremessage is intercepting many more nasties now

Im unsure how i can stop certain things going into Junk but i am going to try get around the client machines and make sure that the junk filters are not on
James WilkinsonNetwork Security AnalystAuthor Commented:
Very helpful and rapid response
Andy MIT Systems ManagerCommented:
If all your machines are on a domain you can actually use Group Policy to disable Outlook's own junk-filtering system. Unfortunately I'm not aware of any way to do this on Macbooks so it will need manually amending on there.
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