For Each r As GridDataItem In gridSegment.Items

   If FileName.Text <> "" Then

       // Red the textbox if data is missing

   Else

      If timeIn.Text = "" AND timeOut.Text = "" AND Duration.Text = "" Then

        If Segment.Text <> 1 AND Segment.Text <> ??? Then
        
          // Red that row all textbox

        End If

     End If

   End If

Next

<Window x:Class="DataFormBugDemo.MainWindow"
                 xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
                 xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
                 xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
                 xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
                 xmlns:local="clr-namespace:DataFormBugDemo"
                 xmlns:telerik="http://schemas.telerik.com/2008/xaml/presentation"
                 mc:Ignorable="d"
                 Title="MainWindow" Height="450" Width="800">
    <Grid>
        <telerik:RadDataForm CurrentItem="{Binding Source={x:Static local:Setting.Instance}}" 
                             AutoEdit="True" AutoGenerateFields="True" AutoGeneratingField="RadDataForm_OnAutoGeneratingField"/>
    </Grid>
</Window>

using System.Windows;
using System.Windows.Data;
using Telerik.Windows.Controls;
using Telerik.Windows.Controls.Data.DataForm;

namespace DataFormBugDemo
{
    /// <summary>
    /// Interaction logic for MainWindow.xaml
    /// </summary>
    public partial class MainWindow : Window
    {

        public MainWindow()
        {
            StyleManager.ApplicationTheme = new Office2019Theme();
            Office2019Palette.LoadPreset(Office2019Palette.ColorVariation.Dark);
            InitializeComponent();
        }

        private void RadDataForm_OnAutoGeneratingField(object sender, AutoGeneratingFieldEventArgs e)
        {
            e.DataField.DataMemberBinding.NotifyOnSourceUpdated = true;
            e.DataField.DataMemberBinding.NotifyOnValidationError = true;
            e.DataField.DataMemberBinding.ValidatesOnDataErrors = true;
            e.DataField.DataMemberBinding.ValidatesOnNotifyDataErrors = true;
            e.DataField.DataMemberBinding.UpdateSourceTrigger = UpdateSourceTrigger.PropertyChanged;
            if (e.PropertyType == typeof(HotKey))
            {
                var dataField = new DataFormHotKeySettingsField()
                {
                    Label = e.DataField.Label,
                    DataMemberBinding = e.DataField.DataMemberBinding,
                    Description = e.DataField.Description
                };
                e.DataField = dataField;
            }
        }
    }
}

using System.Windows;
using System.Windows.Controls;
using System.Windows.Data;
using Telerik.Windows.Controls;

namespace DataFormBugDemo
{
    public class DataFormHotKeySettingsField : DataFormDataField
    {
        protected override DependencyProperty GetControlBindingProperty()
        {
            return HotKeyInputBox.HotKeyProperty;
        }

        protected override Control GetControl()
        {
            var dependencyProperty = GetControlBindingProperty();
            var inputBox = new HotKeyInputBox();
            if (DataMemberBinding != null)
            {
                var binding = DataMemberBinding;
                binding.Mode = BindingMode.TwoWay;
                inputBox.SetBinding(dependencyProperty, binding);
            }
            inputBox.SetBinding(IsEnabledProperty, new Binding("IsReadOnly") { Source = this, Converter = new InvertedBooleanConverter() });
            return inputBox;
        }
    }
}

using System.Windows;
using System.Windows.Controls;

namespace DataFormBugDemo
{
    class HotKeyInputBox : TextBox
    {
        public static readonly DependencyProperty HotKeyProperty = DependencyProperty.Register(
            "HotKey", typeof(HotKey), typeof(HotKeyInputBox), new PropertyMetadata(default(HotKey)));

        public HotKey HotKey
        {
            get { return (HotKey)GetValue(HotKeyProperty); }
            set { SetValue(HotKeyProperty, value); }
        }

        public static readonly DependencyProperty DisplayTextProperty = DependencyProperty.Register(
            "DisplayText", typeof(string), typeof(HotKeyInputBox), new PropertyMetadata(default(string)));

        public string DisplayText
        {
            get { return (string)GetValue(DisplayTextProperty); }
            set { SetValue(DisplayTextProperty, value); }
        }

        public HotKeyInputBox()
        {
            DisplayText = "None";
        }
    }
}

using System.Windows.Input;

namespace DataFormBugDemo
{
    public class HotKey
    {
        public bool IsEnabled { get; set; }

        public Key Key { get; set; }
    }
}

using PropertyChanged;

namespace DataFormBugDemo
{
    [AddINotifyPropertyChangedInterface]
    public class Setting
    {
        public static Setting Instance { get; }
        static Setting()
        {
            Instance = new Setting();
        }

        public string Name { get; set; } = "Test Name";

        public HotKey HotKey { get; set; } = new HotKey();
    }
}

<Application x:Class="DataFormBugDemo.App"
             xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
             xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
             xmlns:local="clr-namespace:DataFormBugDemo"
             xmlns:telerik="http://schemas.telerik.com/2008/xaml/presentation"
             StartupUri="MainWindow.xaml">
    <Application.Resources>
      <!-- HotKeyInputBox -->
      <ControlTemplate x:Key="HotKeyInputBoxTemplate" TargetType="local:HotKeyInputBox">
        <Grid>
          <Grid.ColumnDefinitions>
            <ColumnDefinition Width="Auto" />
            <ColumnDefinition Width="Auto" />
            <ColumnDefinition Width="Auto" />
          </Grid.ColumnDefinitions>
          <Border Grid.Column="0" BorderBrush="{Binding BorderBrush, RelativeSource={RelativeSource TemplatedParent}}" BorderThickness="{TemplateBinding BorderThickness}" Background="{TemplateBinding Background}"
                  Padding="0" Name="PART_Border" VerticalAlignment="Center">
            <StackPanel Orientation="Horizontal">
              <TextBlock Text="{TemplateBinding DisplayText}" HorizontalAlignment="{TemplateBinding HorizontalContentAlignment}" Foreground="{TemplateBinding Foreground}"
                         MinWidth="150" Margin="0" />
            </StackPanel>
          </Border>
        </Grid>
      </ControlTemplate>

      <Style TargetType="local:HotKeyInputBox">
        <Setter Property="Template" Value="{StaticResource HotKeyInputBoxTemplate}" />
        <Setter Property="HorizontalAlignment" Value="Stretch" />
        <Setter Property="HorizontalContentAlignment" Value="Left" />
        <Setter Property="BorderBrush" Value="{telerik:Office2019Resource ResourceKey=MainBorderBrush}" />
        <Setter Property="BorderThickness" Value="1" />
        <Setter Property="Background" Value="{telerik:Office2019Resource ResourceKey=SecondaryBackgroundBrush}" />
        <Setter Property="Foreground" Value="{telerik:Office2019Resource ResourceKey=MainForegroundBrush}" />
        <Setter Property="FocusVisualStyle" Value="{x:Null}" />

      </Style>
    </Application.Resources>
</Application>