diff --git a/LCG-UDG/Constants/FileHeaderConstants.cs b/LCG-UDG/Constants/FileHeaderConstants.cs
new file mode 100644
index 0000000..acf6b92
--- /dev/null
+++ b/LCG-UDG/Constants/FileHeaderConstants.cs
@@ -0,0 +1,78 @@
+namespace Rappen.XTB.LCG
+{
+    /// <summary>
+    /// Constants used for file header generation and template placeholders
+    /// </summary>
+    public static class FileHeaderConstants
+    {
+        /// <summary>
+        /// Template placeholder for tool name
+        /// </summary>
+        public const string ToolName = "{toolname}";
+
+        /// <summary>
+        /// Template placeholder for version
+        /// </summary>
+        public const string Version = "{version}";
+
+        /// <summary>
+        /// Template placeholder for organization URL
+        /// </summary>
+        public const string Organization = "{organization}";
+
+        /// <summary>
+        /// Template placeholder for filename
+        /// </summary>
+        public const string Filename = "{filename}";
+
+        /// <summary>
+        /// Template placeholder for creation date
+        /// </summary>
+        public const string CreateDate = "{createdate}";
+
+        /// <summary>
+        /// Template placeholder for legend
+        /// </summary>
+        public const string Legend = "{legend}";
+
+        /// <summary>
+        /// Template placeholder for namespace
+        /// </summary>
+        public const string Namespace = "{namespace}";
+
+        /// <summary>
+        /// Template placeholder for theme
+        /// </summary>
+        public const string Theme = "{theme}";
+
+        /// <summary>
+        /// Template placeholder for padding size
+        /// </summary>
+        public const string PaddingSize = "{paddingsize}";
+
+        /// <summary>
+        /// Template placeholder for data content
+        /// </summary>
+        public const string Data = "{data}";
+
+        /// <summary>
+        /// Label used for the "Created" line in file headers
+        /// </summary>
+        public const string CreatedLabel = "Created";
+
+        /// <summary>
+        /// Label used for the "Filename" line in file headers
+        /// </summary>
+        public const string FilenameLabel = "Filename";
+
+        /// <summary>
+        /// Double line ending used in file headers
+        /// </summary>
+        public const string LineEnding = "\r\n\r\n";
+
+        /// <summary>
+        /// Single line ending used in file headers
+        /// </summary>
+        public const string SingleLineEnding = "\r\n";
+    }
+}
diff --git a/LCG-UDG/Generation/Extensions.cs b/LCG-UDG/Generation/Extensions.cs
index 7ab3a47..a8fb5e0 100644
--- a/LCG-UDG/Generation/Extensions.cs
+++ b/LCG-UDG/Generation/Extensions.cs
@@ -1,17 +1,21 @@
-using System;
+using McTools.Xrm.Connection;
+using Microsoft.Xrm.Sdk.Metadata;
+using System;
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
 using System.Reflection;
 using System.Text;
+using System.Text.RegularExpressions;
 using System.Windows.Forms;
-using McTools.Xrm.Connection;
-using Microsoft.Xrm.Sdk.Metadata;
 
 namespace Rappen.XTB.LCG
 {
     public static class Extensions
     {
+        private const string DatePattern = @"\d{4}-\d{2}-\d{2} \d{2}:\d{2}:\d{2}";
+        private const string DateFormat = "yyyy-MM-dd HH:mm:ss";
+
         public static AttributeMetadata GetAttribute(this Dictionary<string, EntityMetadata> entities, string entity, string attribute)
         {
             if (entities == null
@@ -31,21 +35,70 @@ public static bool WriteFile(this string data, string filename, string orgurl, S
             var content = GetDataContent(data, settings, version);
             content = header + "\r\n\r\n" + content;
             content = content.BeautifyContent(settings.TemplateSettings.Template.IndentStr);
+
             if (settings.SaveConfigurationInCommonFile)
             {
                 string selection = GetInlineConfiguration(settings);
                 content += "\r\n\r\n" + selection;
             }
-            try
+
+            if (File.Exists(filename))
             {
-                File.WriteAllText(filename, content);
-                return true;
+                var existingContent = File.ReadAllText(filename);
+                var contentWithoutDate = RemoveDateFromContent(content);
+                var existingContentWithoutDate = RemoveDateFromContent(existingContent);
+
+                if (contentWithoutDate.Trim().Equals(existingContentWithoutDate.Trim(), StringComparison.Ordinal))
+                {
+                    return false;
+                }
             }
-            catch (Exception e)
+
+            File.WriteAllText(filename, content);
+            return true;
+        }
+
+        private static string RemoveDateFromContent(string content)
+        {
+            var lines = content.Split(new[] { "\r\n", "\n" }, StringSplitOptions.None);
+            var result = new List<string>();
+            var skipConfiguration = false;
+
+            foreach (var line in lines)
             {
-                MessageBox.Show(e.Message, "Generate", MessageBoxButtons.OK, MessageBoxIcon.Error);
-                return false;
+                if (line.Contains(FileHeaderConstants.CreatedLabel) && line.Contains(":") &&
+                    Regex.IsMatch(line, DatePattern))
+                {
+                    continue;
+                }
+
+                if (line.Contains(FileHeaderConstants.FilenameLabel) && line.Contains(":"))
+                {
+                    continue;
+                }
+
+                // Skip configuration section
+                if (line.Contains("LCG-configuration-BEGIN"))
+                {
+                    skipConfiguration = true;
+                    continue;
+                }
+
+                if (line.Contains("LCG-configuration-END"))
+                {
+                    skipConfiguration = false;
+                    continue;
+                }
+
+                if (skipConfiguration)
+                {
+                    continue;
+                }
+
+                result.Add(line);
             }
+
+            return string.Join("\r\n", result);
         }
 
         private static string GetInlineConfiguration(Settings settings)
@@ -63,27 +116,27 @@ private static string GetInlineConfiguration(Settings settings)
         private static string GetFileHeader(string filename, string orgurl, Settings settings, string version)
         {
             var header = settings.TemplateSettings.Template.FileHeader
-                .Replace("{toolname}", settings.TemplateSettings.ToolName)
-                .Replace("{version}", version)
-                .Replace("{organization}", orgurl)
-                .Replace("{filename}", filename)
-                .Replace("{createdate}", DateTime.Now.ToString("yyyy-MM-dd HH:mm:ss"))
-                .Replace("{legend}", settings.Legend ? settings.TemplateSettings.Template.Legend : string.Empty)
-                .Replace("{namespace}", settings.NameSpace)
-                .Replace("\r\n\r\n", "\r\n");
+                .Replace(FileHeaderConstants.ToolName, settings.TemplateSettings.ToolName)
+                .Replace(FileHeaderConstants.Version, version)
+                .Replace(FileHeaderConstants.Organization, orgurl)
+                .Replace(FileHeaderConstants.Filename, filename)
+                .Replace(FileHeaderConstants.CreateDate, DateTime.Now.ToString(DateFormat))
+                .Replace(FileHeaderConstants.Legend, settings.Legend ? settings.TemplateSettings.Template.Legend : string.Empty)
+                .Replace(FileHeaderConstants.Namespace, settings.NameSpace)
+                .Replace(FileHeaderConstants.LineEnding, FileHeaderConstants.SingleLineEnding);
             return header;
         }
 
         private static string GetDataContent(string data, Settings settings, string version)
         {
             return settings.TemplateSettings.Template.DataContainer
-                .Replace("{toolname}", settings.TemplateSettings.ToolName)
-                .Replace("{version}", version)
-                .Replace("{namespace}", settings.NameSpace)
-                .Replace("{theme}", string.IsNullOrEmpty(settings.Theme) ? settings.TemplateSettings.Template.DefaultTheme : settings.GetTheme())
-                .Replace("{legend}", settings.Legend ? settings.TemplateSettings.Template.Legend : string.Empty)
-                .Replace("{paddingsize}", settings.TableSize.ToString())
-                .Replace("{data}", data);
+                .Replace(FileHeaderConstants.ToolName, settings.TemplateSettings.ToolName)
+                .Replace(FileHeaderConstants.Version, version)
+                .Replace(FileHeaderConstants.Namespace, settings.NameSpace)
+                .Replace(FileHeaderConstants.Theme, string.IsNullOrEmpty(settings.Theme) ? settings.TemplateSettings.Template.DefaultTheme : settings.GetTheme())
+                .Replace(FileHeaderConstants.Legend, settings.Legend ? settings.TemplateSettings.Template.Legend : string.Empty)
+                .Replace(FileHeaderConstants.PaddingSize, settings.TableSize.ToString())
+                .Replace(FileHeaderConstants.Data, data);
         }
 
         private static string BeautifyContent(this string content, string indentstr)
diff --git a/LCG-UDG/Generation/GenerationUtils.cs b/LCG-UDG/Generation/GenerationUtils.cs
index 5e924a3..d966dd1 100644
--- a/LCG-UDG/Generation/GenerationUtils.cs
+++ b/LCG-UDG/Generation/GenerationUtils.cs
@@ -4,7 +4,6 @@
 using System.Collections.Generic;
 using System.Linq;
 using System.Text;
-using System.Windows.Forms;
 
 namespace Rappen.XTB.LCG
 {
@@ -12,45 +11,37 @@ public class GenerationUtils
     {
         public static bool GenerateFiles(List<EntityMetadataProxy> selectedentities, Settings settings, IConstantFileWriter fileWriter)
         {
-            try
+            var addedrelationships = new List<string>();
+            var commonentity = GetCommonEntity(selectedentities, settings);
+            var suffix = Settings.FileSuffix(settings.TemplateFormat);
+            if (commonentity != null)
             {
-                var addedrelationships = new List<string>();
-                var commonentity = GetCommonEntity(selectedentities, settings);
-                var suffix = Settings.FileSuffix(settings.TemplateFormat);
-                if (commonentity != null)
-                {
-                    var entity = GetClass(commonentity, null, settings, addedrelationships);
-                    var fileName = commonentity.GetNameTechnical(settings.FileName, settings) + suffix;
-                    fileWriter.WriteBlock(settings, entity, fileName);
-                }
-                if (settings.Groups?.Count > 0)
-                {
-                    foreach (var group in settings.Groups.Where(g => selectedentities.Any(e => e.Group == g)))
-                    {
-                        var groupstr = GetGroup(group, selectedentities.Where(e => e.Group == group).ToList(), settings, addedrelationships);
-                        fileWriter.WriteBlock(settings, groupstr, group.Name);
-                    }
-                }
-                foreach (var entitymetadata in selectedentities.Where(e => e.Group == null))
-                {
-                    var entity = GetClass(entitymetadata, commonentity, settings, addedrelationships);
-                    var fileName = entitymetadata.GetNameTechnical(settings.FileName, settings) + suffix;
-                    fileWriter.WriteBlock(settings, entity, fileName);
-                }
-                if (settings.TemplateSettings.Template.AddAllRelationshipsAfterEntities)
+                var entity = GetClass(commonentity, null, settings, addedrelationships);
+                var fileName = commonentity.GetNameTechnical(settings.FileName, settings) + suffix;
+                fileWriter.WriteBlock(settings, entity, fileName);
+            }
+            if (settings.Groups?.Count > 0)
+            {
+                foreach (var group in settings.Groups.Where(g => selectedentities.Any(e => e.Group == g)))
                 {
-                    var relationships = selectedentities.SelectMany(e => e.Relationships.Where(r => r.IsSelected));
-                    relationships = relationships.GroupBy(r => r.LogicalName).Select(r => r.FirstOrDefault());    // This will make it distinct by LogicalName
-                    var allrelationshipsstring = GetRelationships(relationships, settings, addedrelationships);
-                    fileWriter.WriteBlock(settings, allrelationshipsstring, "Relationships" + suffix);
+                    var groupstr = GetGroup(group, selectedentities.Where(e => e.Group == group).ToList(), settings, addedrelationships);
+                    fileWriter.WriteBlock(settings, groupstr, group.Name);
                 }
-                return fileWriter.Finalize(settings);
             }
-            catch (Exception ex)
+            foreach (var entitymetadata in selectedentities.Where(e => e.Group == null))
+            {
+                var entity = GetClass(entitymetadata, commonentity, settings, addedrelationships);
+                var fileName = entitymetadata.GetNameTechnical(settings.FileName, settings) + suffix;
+                fileWriter.WriteBlock(settings, entity, fileName);
+            }
+            if (settings.TemplateSettings.Template.AddAllRelationshipsAfterEntities)
             {
-                MessageBox.Show($"Error:\n{ex.Message}", "Error", MessageBoxButtons.OK, MessageBoxIcon.Error);
-                return false;
+                var relationships = selectedentities.SelectMany(e => e.Relationships.Where(r => r.IsSelected));
+                relationships = relationships.GroupBy(r => r.LogicalName).Select(r => r.FirstOrDefault());    // This will make it distinct by LogicalName
+                var allrelationshipsstring = GetRelationships(relationships, settings, addedrelationships);
+                fileWriter.WriteBlock(settings, allrelationshipsstring, "Relationships" + suffix);
             }
+            return fileWriter.Finalize(settings);
         }
 
         private static EntityMetadataProxy GetCommonEntity(List<EntityMetadataProxy> selectedentities, Settings settings)
diff --git a/LCG-UDG/LCG-UDG-Common.csproj b/LCG-UDG/LCG-UDG-Common.csproj
index 7834315..095d1db 100644
--- a/LCG-UDG/LCG-UDG-Common.csproj
+++ b/LCG-UDG/LCG-UDG-Common.csproj
@@ -92,6 +92,7 @@
     <Compile Include="About.designer.cs">
       <DependentUpon>About.cs</DependentUpon>
     </Compile>
+    <Compile Include="Constants\FileHeaderConstants.cs" />
     <Compile Include="EntityGroup.cs" />
     <Compile Include="Generation\FabienDehopreIdentifier.cs" />
     <Compile Include="Generation\UnicodeCharacterUtilities.cs" />
diff --git a/LCG-UDG/LCG.cs b/LCG-UDG/LCG.cs
index 81a328a..c93039f 100644
--- a/LCG-UDG/LCG.cs
+++ b/LCG-UDG/LCG.cs
@@ -127,20 +127,31 @@ private void btnGenerate_Click(object sender, EventArgs e)
             GetSettingsFromUI();
             GetSelectionFromUI();
             var filewriter = settings.GetWriter(ConnectionDetail.WebApplicationUrl);
-            if (GenerationUtils.GenerateFiles(entities.Where(ent => ent.Selected).ToList(), settings, filewriter))
+            try
             {
-                var message = filewriter.GetResult(settings);
-                if (isUML)
+                if (GenerationUtils.GenerateFiles(entities.Where(ent => ent.Selected).ToList(), settings, filewriter))
                 {
-                    this.ShowFileLinkMessage(
-                        message,
-                        settings.CommonFilePath, 10000);
+                    var message = filewriter.GetResult(settings);
+                    if (isUML)
+                    {
+                        this.ShowFileLinkMessage(
+                            message,
+                            settings.CommonFilePath, 10000);
+                    }
+                    else
+                    {
+                        this.ShowSuccessMessage(message, 10000);
+                    }
                 }
                 else
                 {
-                    this.ShowSuccessMessage(message, 10000);
+                    this.ShowInfoMessage("No file needed, probably because no changes.", 5000);
                 }
             }
+            catch (Exception ex)
+            {
+                ShowErrorDialog(ex, $"Generate {settings.TemplateFormat}");
+            }
         }
 
         private void btnLoadEntities_Click(object sender, EventArgs e)
diff --git a/LCG-UDG/Settings/Settings.cs b/LCG-UDG/Settings/Settings.cs
index 259a40e..5e0d664 100644
--- a/LCG-UDG/Settings/Settings.cs
+++ b/LCG-UDG/Settings/Settings.cs
@@ -1,6 +1,8 @@
-using System.Collections.Generic;
+using Rappen.XRM.Helpers.Extensions;
+using System.Collections.Generic;
 using System.IO;
 using System.Windows.Forms;
+using System.Xml.Serialization;
 using XrmToolBox.Extensibility;
 
 namespace Rappen.XTB.LCG
@@ -176,11 +178,41 @@ internal string GetTheme()
     public class EntityFilter
     {
         public bool Expanded { get; set; } = false;
+
+        [XmlIgnore]
         public CheckState Custom { get; set; } = CheckState.Checked;
+
+        [XmlElement("Custom")]
+        public string CustomSerialized
+        {
+            get => Custom.ToString();
+            set => Custom = value.ToCheckState(CheckState.Checked);
+        }
+
+        [XmlIgnore]
         public CheckState Managed { get; set; } = CheckState.Checked;
+
+        [XmlElement("Managed")]
+        public string ManagedSerialized
+        {
+            get => Managed.ToString();
+            set => Managed = value.ToCheckState(CheckState.Checked);
+        }
+
         public bool ExcludeIntersect { get; set; }
+
         internal CheckState Selected { get; set; }
+
+        [XmlIgnore]
         public CheckState Records { get; set; } = CheckState.Checked;
+
+        [XmlElement("Records")]
+        public string RecordsSerialized
+        {
+            get => Records.ToString();
+            set => Records = value.ToCheckState(CheckState.Checked);
+        }
+
         public bool Uncountable { get; set; }
     }
 
@@ -188,12 +220,67 @@ public class AttributeFilter
     {
         public bool Expanded { get; set; } = false;
         public bool CheckAll { get; set; }
+
+        [XmlIgnore]
         public CheckState Custom { get; set; } = CheckState.Checked;
+
+        [XmlElement("Custom")]
+        public string CustomSerialized
+        {
+            get => Custom.ToString();
+            set => Custom = value.ToCheckState(CheckState.Checked);
+        }
+
+        [XmlIgnore]
         public CheckState Managed { get; set; } = CheckState.Checked;
+
+        [XmlElement("Managed")]
+        public string ManagedSerialized
+        {
+            get => Managed.ToString();
+            set => Managed = value.ToCheckState(CheckState.Checked);
+        }
+
+        [XmlIgnore]
         public CheckState PrimaryKeyName { get; set; } = CheckState.Checked;
+
+        [XmlElement("PrimaryKeyName")]
+        public string PrimaryKeyNameSerialized
+        {
+            get => PrimaryKeyName.ToString();
+            set => PrimaryKeyName = value.ToCheckState(CheckState.Checked);
+        }
+
+        [XmlIgnore]
         public CheckState Required { get; set; } = CheckState.Checked;
+
+        [XmlElement("Required")]
+        public string RequiredSerialized
+        {
+            get => Required.ToString();
+            set => Required = value.ToCheckState(CheckState.Checked);
+        }
+
+        [XmlIgnore]
         public CheckState Logical { get; set; } = CheckState.Unchecked;
+
+        [XmlElement("Logical")]
+        public string LogicalSerialized
+        {
+            get => Logical.ToString();
+            set => Logical = value.ToCheckState(CheckState.Unchecked);
+        }
+
+        [XmlIgnore]
         public CheckState Internal { get; set; } = CheckState.Unchecked;
+
+        [XmlElement("Internal")]
+        public string InternalSerialized
+        {
+            get => Internal.ToString();
+            set => Internal = value.ToCheckState(CheckState.Unchecked);
+        }
+
         public bool ExcludeCreMod { get; set; } = true;
         public bool ExcludeOwner { get; set; } = true;
         internal bool AreUsed { get; set; } = false;
@@ -204,8 +291,27 @@ public class RelationshipFilter
     {
         public bool Expanded { get; set; } = false;
         public bool CheckAll { get; set; }
+
+        [XmlIgnore]
         public CheckState Custom { get; set; } = CheckState.Checked;
+
+        [XmlElement("Custom")]
+        public string CustomSerialized
+        {
+            get => Custom.ToString();
+            set => Custom = value.ToCheckState(CheckState.Checked);
+        }
+
+        [XmlIgnore]
         public CheckState Managed { get; set; } = CheckState.Checked;
+
+        [XmlElement("Managed")]
+        public string ManagedSerialized
+        {
+            get => Managed.ToString();
+            set => Managed = value.ToCheckState(CheckState.Checked);
+        }
+
         public bool Type1N { get; set; } = false;
         public bool TypeN1 { get; set; } = true;
         public bool TypeNN { get; set; } = true;
diff --git a/LCGCmd/LCGHelper.cs b/LCGCmd/LCGHelper.cs
index 58efecc..7deac94 100644
--- a/LCGCmd/LCGHelper.cs
+++ b/LCGCmd/LCGHelper.cs
@@ -47,13 +47,20 @@ public void GenerateConstants()
             LoadEntities();
             RestoreSelectedEntities();
             var writer = Settings.GetWriter(this.crmConnection.WebApplicationUrl);
-            if (GenerationUtils.GenerateFiles(entities, Settings, writer))
+            try
             {
-                Console.Write(writer.GetResult(Settings));
+                if (GenerationUtils.GenerateFiles(entities, Settings, writer))
+                {
+                    Console.Write(writer.GetResult(Settings));
+                }
+                else
+                {
+                    Console.WriteLine("Not saved, probably because no changes.");
+                }
             }
-            else
+            catch (Exception ex)
             {
-                Console.WriteLine("Error");
+                MessageBox.Show($"Error:\n{ex.Message}", "Error", MessageBoxButtons.OK, MessageBoxIcon.Error);
             }
         }
 
diff --git a/LCGTests/DatePreservationTests.cs b/LCGTests/DatePreservationTests.cs
new file mode 100644
index 0000000..3a8dfc0
--- /dev/null
+++ b/LCGTests/DatePreservationTests.cs
@@ -0,0 +1,118 @@
+using System;
+using System.IO;
+using Microsoft.VisualStudio.TestTools.UnitTesting;
+using Rappen.XTB.LCG;
+
+namespace LateboundConstantGeneratorTests
+{
+    [TestClass]
+    public class DatePreservationTests
+    {
+        private string _testFilePath;
+
+        [TestInitialize]
+        public void Setup()
+        {
+            _testFilePath = Path.GetTempFileName();
+        }
+
+        [TestCleanup]
+        public void Cleanup()
+        {
+            if (File.Exists(_testFilePath))
+            {
+                File.Delete(_testFilePath);
+            }
+        }
+
+        [TestMethod]
+        public void WriteFile_WhenContentUnchanged_ShouldPreserveOriginalDate()
+        {
+            // Arrange
+            var settings = new Settings();
+            settings.NameSpace = "TestNamespace";
+            var originalDate = "2023-01-15 10:30:45";
+            var originalContent = TestContentHelper.GetExpectedTestContent(Path.GetFileName(_testFilePath), originalDate);
+
+            // Write original file
+            File.WriteAllText(_testFilePath, originalContent);
+
+            // Act - Write the same content again
+            var dataContent = TestContentHelper.GetTestDataContent();
+            var result = dataContent.WriteFile(_testFilePath, "https://test.crm.dynamics.com", settings);
+
+            // Assert
+            Assert.IsTrue(result);
+            var finalContent = File.ReadAllText(_testFilePath);
+            Assert.IsTrue(finalContent.Contains(originalDate), "Original date should be preserved");
+            Assert.IsFalse(finalContent.Contains(DateTime.Now.ToString("yyyy-MM-dd")), "Current date should not be used");
+        }
+
+        [TestMethod]
+        public void WriteFile_WhenContentChanged_ShouldUpdateDate()
+        {
+            // Arrange
+            var settings = new Settings();
+            settings.NameSpace = "TestNamespace";
+            var originalDate = "2023-01-15 10:30:45";
+            var originalContent = TestContentHelper.GetExpectedTestContent(Path.GetFileName(_testFilePath), originalDate);
+
+            // Write original file
+            File.WriteAllText(_testFilePath, originalContent);
+
+            // Act - Write different content
+            var dataContent = TestContentHelper.GetModifiedTestDataContent();
+            var result = dataContent.WriteFile(_testFilePath, "https://test.crm.dynamics.com", settings);
+
+            // Assert
+            Assert.IsTrue(result);
+            var finalContent = File.ReadAllText(_testFilePath);
+            Assert.IsFalse(finalContent.Contains(originalDate), "Original date should not be preserved when content changes");
+            Assert.IsTrue(finalContent.Contains(DateTime.Now.ToString("yyyy-MM-dd")), "Current date should be used when content changes");
+            Assert.IsTrue(finalContent.Contains("modified_entity"), "Modified content should be present");
+        }
+
+        [TestMethod]
+        public void WriteFile_WhenOnlyFilenameChanged_ShouldPreserveOriginalFilename()
+        {
+            // Arrange
+            var settings = new Settings();
+            settings.NameSpace = "TestNamespace";
+            var originalDate = "2023-01-15 10:30:45";
+            var originalFilename = "OriginalFile.cs";
+            var originalContent = TestContentHelper.GetExpectedTestContent(originalFilename, originalDate);
+
+            // Write original file
+            File.WriteAllText(_testFilePath, originalContent);
+
+            // Act - Write content with different filename
+            var dataContent = TestContentHelper.GetTestDataContent();
+            var result = dataContent.WriteFile(_testFilePath, "https://test.crm.dynamics.com", settings);
+
+            // Assert
+            Assert.IsTrue(result);
+            var finalContent = File.ReadAllText(_testFilePath);
+            Assert.IsTrue(finalContent.Contains(originalFilename), "Original filename should be preserved");
+            Assert.IsFalse(finalContent.Contains("ModifiedFile.cs"), "Modified filename should not be used");
+            Assert.IsTrue(finalContent.Contains(originalDate), "Original date should also be preserved");
+        }
+
+        [TestMethod]
+        public void WriteFile_WhenFileDoesNotExist_ShouldUseCurrentDate()
+        {
+            // Arrange
+            var settings = new Settings();
+            settings.NameSpace = "TestNamespace";
+            var dataContent = TestContentHelper.GetNewTestDataContent();
+
+            // Act - Write to new file
+            var result = dataContent.WriteFile(_testFilePath, "https://test.crm.dynamics.com", settings);
+
+            // Assert
+            Assert.IsTrue(result);
+            var finalContent = File.ReadAllText(_testFilePath);
+            Assert.IsTrue(finalContent.Contains(DateTime.Now.ToString("yyyy-MM-dd")), "Current date should be used for new files");
+            Assert.IsTrue(finalContent.Contains("new_entity"), "New content should be present");
+        }
+    }
+}
diff --git a/LCGTests/LCGTests.csproj b/LCGTests/LCGTests.csproj
index ed52ed1..cb9f110 100644
--- a/LCGTests/LCGTests.csproj
+++ b/LCGTests/LCGTests.csproj
@@ -228,8 +228,10 @@
   </ItemGroup>
   <ItemGroup>
     <Compile Include="CSharpUtilTests.cs" />
-    <Compile Include="Properties\AssemblyInfo.cs" />
+    <Compile Include="DatePreservationTests.cs" />
     <Compile Include="LCGHelperTest.cs" />
+    <Compile Include="TestContentHelper.cs" />
+    <Compile Include="Properties\AssemblyInfo.cs" />
   </ItemGroup>
   <ItemGroup>
     <None Include="app.config" />
@@ -239,6 +241,9 @@
     <None Include="testdata\LateboundConstantsGeneratorConfiguration.xml">
       <CopyToOutputDirectory>Always</CopyToOutputDirectory>
     </None>
+    <Content Include="testdata\ExpectedTestContent.cs">
+      <CopyToOutputDirectory>Always</CopyToOutputDirectory>
+    </Content>
   </ItemGroup>
   <ItemGroup>
     <ProjectReference Include="..\LCGCmd\LCGCmd.csproj">
diff --git a/LCGTests/TestContentHelper.cs b/LCGTests/TestContentHelper.cs
new file mode 100644
index 0000000..950a932
--- /dev/null
+++ b/LCGTests/TestContentHelper.cs
@@ -0,0 +1,42 @@
+using System;
+using System.IO;
+
+namespace LateboundConstantGeneratorTests
+{
+    public static class TestContentHelper
+    {
+        private static readonly string TestDataPath = Path.Combine(AppDomain.CurrentDomain.BaseDirectory, "testdata");
+        
+        public static string GetExpectedTestContent(string filename, string date)
+        {
+            var templatePath = Path.Combine(TestDataPath, "ExpectedTestContent.cs");
+            var template = File.ReadAllText(templatePath);
+            return string.Format(template, filename, date);
+        }
+        
+        public static string GetTestDataContent()
+        {
+            return @"public class TestClass
+{
+    public const string EntityName = ""test_entity"";
+}";
+        }
+        
+        public static string GetModifiedTestDataContent()
+        {
+            return @"public class TestClass
+{
+    public const string EntityName = ""modified_entity"";
+    public const string NewProperty = ""new_value"";
+}";
+        }
+        
+        public static string GetNewTestDataContent()
+        {
+            return @"public class TestClass
+{
+    public const string EntityName = ""new_entity"";
+}";
+        }
+    }
+}
diff --git a/LCGTests/testdata/ExpectedTestContent.cs b/LCGTests/testdata/ExpectedTestContent.cs
new file mode 100644
index 0000000..55184fe
--- /dev/null
+++ b/LCGTests/testdata/ExpectedTestContent.cs
@@ -0,0 +1,16 @@
+// *********************************************************************
+// Created by : Latebound Constants Generator 1.2023.5.901 for XrmToolBox
+// Tool Author: Jonas Rapp https://jonasr.app/
+// GitHub     : https://github.com/rappen/LCG-UDG/
+// Source Org : https://test.crm.dynamics.com
+// Filename   : {0}
+// Created    : {1}
+// *********************************************************************
+
+namespace TestNamespace
+{{
+    public class TestClass
+    {{
+        public const string EntityName = ""test_entity"";
+    }}
+}}
diff --git a/Rappen.XTB.Helper b/Rappen.XTB.Helper
index 7b60f84..7905fb3 160000
--- a/Rappen.XTB.Helper
+++ b/Rappen.XTB.Helper
@@ -1 +1 @@
-Subproject commit 7b60f8449564d3080ae165292eb53d951e8bc348
+Subproject commit 7905fb35e1e96387da39baff67414cf861d68ae8