Whenever no selection is made from all checkboxes I want the user to see an orange border around the checkboxes. This is not a validation error, but a warning this is not the intended use. My style in XAML looks like this

<Style x:Key="WarningNoSelection" TargetType="{x:Type Border}">
   <Style.Triggers>
      <MultiDataTrigger>
         <MultiDataTrigger.Conditions>
            <Condition Binding="{Binding Path=AdminRole}"     Value="False" />
            <Condition Binding="{Binding Path=DataRole}"      Value="False" />
            <Condition Binding="{Binding Path=WebServer}"     Value="False" />
            <Condition Binding="{Binding Path=ResourceRole}"  Value="False" />
            <Condition Binding="{Binding Path=DataEntryRole}" Value="False" />
         </MultiDataTrigger.Conditions>
         <MultiDataTrigger.Setters>
            <Setter Property="BorderBrush" Value="Orange"/>
         </MultiDataTrigger.Setters>
      </MultiDataTrigger>
   </Style.Triggers>
</Style>

With the debugger described here. I found that the trigger was working but stil no orange border around my checkboxes. The problem was the BorderBrush property specified in the Border Tag. After removing that I got my orange border when no checkbox was checked.

<!--
<Border BorderBrush="Silver" Style="{StaticResource WarningNoSelection}" BorderThickness="1">
-->
<Border Style="{StaticResource WarningNoSelection}" BorderThickness="1">
    <StackPanel>
        <CheckBox Content="Admin"     IsChecked="{Binding Path=AdminRole}" />
        <CheckBox Content="Data"      IsChecked="{Binding Path=DataRole}" />
        <CheckBox Content="WebServer" IsChecked="{Binding Path=WebServer}" />
        <CheckBox Content="Resource"  IsChecked="{Binding Path=ResourceRole}" />
        <CheckBox Content="DataEntry" IsChecked="{Binding Path=DataEntryRole}" />
    </StackPanel>
</Border>