diff --git a/src/Umbraco.Infrastructure/Migrations/Upgrade/UmbracoPlan.cs b/src/Umbraco.Infrastructure/Migrations/Upgrade/UmbracoPlan.cs
index 3ba30b12df29..2d6d47e645dd 100644
--- a/src/Umbraco.Infrastructure/Migrations/Upgrade/UmbracoPlan.cs
+++ b/src/Umbraco.Infrastructure/Migrations/Upgrade/UmbracoPlan.cs
@@ -106,5 +106,6 @@ protected virtual void DefinePlan()
         To<V_13_0_0.ChangeWebhookUrlColumnsToNvarcharMax>("{21C42760-5109-4C03-AB4F-7EA53577D1F5}");
         To<V_13_0_0.AddExceptionOccured>("{6158F3A3-4902-4201-835E-1ED7F810B2D8}");
         To<V_13_3_0.AlignUpgradedDatabase>("{985AF2BA-69D3-4DBA-95E0-AD3FA7459FA7}");
+        To<V_13_5_0.ChangeRedirectUrlToNvarcharMax>("{CC47C751-A81B-489A-A2BC-0240245DB687}");
     }
 }
diff --git a/src/Umbraco.Infrastructure/Migrations/Upgrade/V_13_5_0/ChangeRedirectUrlToNvarcharMax.cs b/src/Umbraco.Infrastructure/Migrations/Upgrade/V_13_5_0/ChangeRedirectUrlToNvarcharMax.cs
new file mode 100644
index 000000000000..4f28b0fe8870
--- /dev/null
+++ b/src/Umbraco.Infrastructure/Migrations/Upgrade/V_13_5_0/ChangeRedirectUrlToNvarcharMax.cs
@@ -0,0 +1,41 @@
+using System.Linq.Expressions;
+using System.Text;
+using NPoco;
+using Umbraco.Cms.Core;
+using Umbraco.Cms.Infrastructure.Migrations.Expressions.Create.Column;
+using Umbraco.Cms.Infrastructure.Persistence;
+using Umbraco.Cms.Infrastructure.Persistence.Dtos;
+
+namespace Umbraco.Cms.Infrastructure.Migrations.Upgrade.V_13_5_0;
+
+public class ChangeRedirectUrlToNvarcharMax : MigrationBase
+{
+    public ChangeRedirectUrlToNvarcharMax(IMigrationContext context) : base(context)
+    {
+    }
+
+    protected override void Migrate()
+    {
+        // We don't need to run this migration for SQLite, since ntext is not a thing there, text is just text.
+        if (DatabaseType == DatabaseType.SQLite)
+        {
+            return;
+        }
+
+        string tableName = RedirectUrlDto.TableName;
+        string colName = "url";
+
+        // Determine the current datatype of the column within the database
+        string colDataType = Database.ExecuteScalar<string>($"SELECT TOP(1) CHARACTER_MAXIMUM_LENGTH FROM INFORMATION_SCHEMA.COLUMNS" +
+                                                            $" WHERE TABLE_NAME = '{tableName}' AND COLUMN_NAME = '{colName}'");
+
+        // 255 is the old length, -1 indicate MAX length
+        if (colDataType == "255")
+        {
+            // Upgrade to MAX length
+            Database.Execute($"Drop Index IX_umbracoRedirectUrl_culture_hash on {Constants.DatabaseSchema.Tables.RedirectUrl}");
+            Database.Execute($"ALTER TABLE {tableName} ALTER COLUMN {colName} nvarchar(MAX) NOT NULL");
+            Database.Execute($"CREATE INDEX IX_umbracoRedirectUrl_culture_hash ON {Constants.DatabaseSchema.Tables.RedirectUrl} (urlHash, contentKey, culture, createDateUtc)");
+        }
+    }
+}
diff --git a/src/Umbraco.Infrastructure/Persistence/Dtos/RedirectUrlDto.cs b/src/Umbraco.Infrastructure/Persistence/Dtos/RedirectUrlDto.cs
index 453ab1e308a2..3582a7eee569 100644
--- a/src/Umbraco.Infrastructure/Persistence/Dtos/RedirectUrlDto.cs
+++ b/src/Umbraco.Infrastructure/Persistence/Dtos/RedirectUrlDto.cs
@@ -38,6 +38,7 @@ internal class RedirectUrlDto
 
     [Column("url")]
     [NullSetting(NullSetting = NullSettings.NotNull)]
+    [SpecialDbType(SpecialDbTypes.NVARCHARMAX)]
     public string Url { get; set; } = null!;
 
     [Column("culture")]