I think this bug is a core problem with Microsoft SL5 as the issue surfaces with Microsoft controls as well as Telerik controls. But I thought I'd bring it to attention as it might be valuable information for other developers to garnish.
Situation:
1. From a UserControl have a control (button, RadComboBox, etc.) that has the IsEnabled bound to an MVVM class property ... example
<telerik:RadComboBox x:Name="RentalTypeComboBox" Grid.ColumnSpan="2" Grid.Column="6" Grid.Row="1" Style="{StaticResource DomicoRadComboBoxFill}" DisplayMemberPath="RentalTypeName" ItemsSource="{Binding Path=RentalTypes, Mode=TwoWay}" SelectedItem="{Binding Path=RentalType, TargetNullValue='None', FallbackValue='N/A', Mode=TwoWay}" IsEnabled="{Binding Path=RentalTypeSelectionEnabled, Mode=TwoWay}"/>
2. Now instantiate (show) a ChildWindow ... this effectively disables the background by setting IsEnabled=False for all controls in the UserControl.
3. Once the user initiates the closing of the ChildWindow all the background control in UserControl should be reset to "IsEnabled" and then their current state gets re-applied. This works on all controls except when IsEnabled is used and it's Mode=TwoWay. If Mode=TwoWay the control will stay in a disabled state. Remove the Mode property like below and it works as expected:
<telerik:RadComboBox x:Name="RentalTypeComboBox" Grid.ColumnSpan="2" Grid.Column="6" Grid.Row="1" Style="{StaticResource DomicoRadComboBoxFill}" DisplayMemberPath="RentalTypeName" ItemsSource="{Binding Path=RentalTypes, Mode=TwoWay}" SelectedItem="{Binding Path=RentalType, TargetNullValue='None', FallbackValue='N/A', Mode=TwoWay}" IsEnabled="{Binding Path=RentalTypeSelectionEnabled}"/>
NOTE: It's important to understand that this issue WILL NOT surface under VS 2015 debug session, this issue ONLY surfaces when deployed to a real IIS web server. So if anyone tries to replicate under VS 2015 you will NOT be able to, you MUST deploy to an IIS web server to see this issue of IsEnabled with binding Mode=TwoWay when using showing a ChildWindow from a UserControl.
Cheers, Rob.