This was was hard to crack, most people complain that email messages end up in their junk mail folder despite configuration to the contrary. My issue was the other way around. I operate my Outlook client on a 'white-list' the politically correct Microsoft name for this is 'safe senders only'. In this mode everything goes to my junk mail unless I have added an email address or whole domain to my 'safe senders list'. There are nice short cut features that allow you to automatically consider people in your contacts list to be considered safe. That way my inbox is focused on real email and the occasional sales receipt that I want to see can be found in mu junk mail and I can choose to add them to my safe senders if I feel it's appropriate. Well, after a rebuild I configured my Outlook 2010 as I normally do and found that some items of mail were flowing into my inbox despite not being on my safe senders list. After much research here's what was going on:
I actually operate two email addresses, my Yahoo account and my GMail account. Typically I hand out my Yahoo address to online sales transactions and subscriptions and save my GMail account for friends and family. In Outlook 2010 Microsoft have provided the obfuscated ability to set different junk mail options per account. The reason I say obfuscated is that there is hardly any indication of this. When you select 'junk mail options' the title of the child window shows the account that you are configuring and this will always show the account that is set to default (in my case GMail since that is my sending account). Now, if you go into account management and make my Yahoo account the default account and then go into the Junk mail options you will find that the title of the child windows reflects the fact that you are now looking at junk mail settings pertaining to the Yahoo account. And... there is the problem, the junk mail option was set to 'LOW' (which is the default). I corrected that, switched the default email account back to GMail and problem solved. You can debate the wisdom of having two different junk mail policies but I think the hidden nature of this configuration is questionable.