Workaround for this bug is setting Style.Triggers for this scenario. <Style BasedOn="{StaticResource RadRibbonSplitButtonStyle}" TargetType="telerik:RadRibbonSplitButton"> <Style.Triggers> <MultiTrigger> <MultiTrigger.Conditions> <Condition Property="IsChecked" Value="True"/> <Condition Property="IsEnabled" Value="True"/> <Condition Property="CurrentSize" Value="Medium"/> </MultiTrigger.Conditions> <MultiTrigger.Setters> <Setter Property="Foreground" Value="{DynamicResource CheckedBrush}"/> </MultiTrigger.Setters> </MultiTrigger> </Style.Triggers> </Style>