diff --git a/src/Umbraco.Cms.Persistence.SqlServer/Services/SqlServerSyntaxProvider.cs b/src/Umbraco.Cms.Persistence.SqlServer/Services/SqlServerSyntaxProvider.cs
index 64ed9e3566..a1b9d2d8f0 100644
--- a/src/Umbraco.Cms.Persistence.SqlServer/Services/SqlServerSyntaxProvider.cs
+++ b/src/Umbraco.Cms.Persistence.SqlServer/Services/SqlServerSyntaxProvider.cs
@@ -272,6 +272,13 @@ where tbl.[name]=@0 and col.[name]=@1;",
         return !constraintName.IsNullOrWhiteSpace();
     }
 
+    public override bool DoesPrimaryKeyExist(IDatabase db, string tableName, string primaryKeyName)
+    {
+        IEnumerable<SqlPrimaryKey>? keys = db.Fetch<SqlPrimaryKey>($"select * from sysobjects where xtype='pk' and  parent_obj in (select id from sysobjects where name='{tableName}')")
+            .Where(x => x.Name == primaryKeyName);
+        return keys.FirstOrDefault() is not null;
+    }
+
     public override bool DoesTableExist(IDatabase db, string tableName)
     {
         var result =
@@ -453,4 +460,9 @@ _sqlInspector ??= new SqlInspectionUtilities();
     }
 
     #endregion
+
+    private class SqlPrimaryKey
+    {
+        public string Name { get; set; } = null!;
+    }
 }
diff --git a/src/Umbraco.Cms.Persistence.Sqlite/Services/SqliteSyntaxProvider.cs b/src/Umbraco.Cms.Persistence.Sqlite/Services/SqliteSyntaxProvider.cs
index 3803d96490..af9147b29a 100644
--- a/src/Umbraco.Cms.Persistence.Sqlite/Services/SqliteSyntaxProvider.cs
+++ b/src/Umbraco.Cms.Persistence.Sqlite/Services/SqliteSyntaxProvider.cs
@@ -174,6 +174,14 @@ public class SqliteSyntaxProvider : SqlSyntaxProviderBase<SqliteSyntaxProvider>
         return false;
     }
 
+    public override bool DoesPrimaryKeyExist(IDatabase db, string tableName, string primaryKeyName)
+    {
+        IEnumerable<string> items = db.Fetch<string>($"select sql from sqlite_master where type = 'table' and name = '{tableName}'")
+            .Where(x => x.Contains($"CONSTRAINT {primaryKeyName} PRIMARY KEY"));
+
+        return items.Any();
+    }
+
     public override string GetFieldNameForUpdate<TDto>(Expression<Func<TDto, object?>> fieldSelector, string? tableAlias = null)
     {
         var field = ExpressionHelper.FindProperty(fieldSelector).Item1 as PropertyInfo;
diff --git a/src/Umbraco.Infrastructure/Migrations/MigrationBase_Extra.cs b/src/Umbraco.Infrastructure/Migrations/MigrationBase_Extra.cs
index 49775bcd0a..b548112d8f 100644
--- a/src/Umbraco.Infrastructure/Migrations/MigrationBase_Extra.cs
+++ b/src/Umbraco.Infrastructure/Migrations/MigrationBase_Extra.cs
@@ -110,6 +110,11 @@ namespace Umbraco.Cms.Infrastructure.Migrations
             return indexes.Any(x => x.Item2.InvariantEquals(indexName));
         }
 
+        protected bool PrimaryKeyExists(string tableName, string primaryKeyName)
+        {
+            return SqlSyntax.DoesPrimaryKeyExist(Context.Database, tableName, primaryKeyName);
+        }
+
         protected bool ColumnExists(string tableName, string columnName)
         {
             ColumnInfo[]? columns = SqlSyntax.GetColumnsInSchema(Context.Database).Distinct().ToArray();
diff --git a/src/Umbraco.Infrastructure/Migrations/Upgrade/V_10_5_0/AddPrimaryKeyConstrainToContentVersionCleanupDtos.cs b/src/Umbraco.Infrastructure/Migrations/Upgrade/V_10_5_0/AddPrimaryKeyConstrainToContentVersionCleanupDtos.cs
index 331a6fced6..d1185bec46 100644
--- a/src/Umbraco.Infrastructure/Migrations/Upgrade/V_10_5_0/AddPrimaryKeyConstrainToContentVersionCleanupDtos.cs
+++ b/src/Umbraco.Infrastructure/Migrations/Upgrade/V_10_5_0/AddPrimaryKeyConstrainToContentVersionCleanupDtos.cs
@@ -10,18 +10,28 @@ public class AddPrimaryKeyConstrainToContentVersionCleanupDtos : MigrationBase
 
     protected override void Migrate()
     {
-        IEnumerable<ContentVersionCleanupPolicyDto> contentVersionCleanupPolicyDtos =
-            Database
-                .Fetch<ContentVersionCleanupPolicyDto>()
-                .OrderByDescending(x => x.Updated)
-                .DistinctBy(x => x.ContentTypeId);
-
+        IEnumerable<ContentVersionCleanupPolicyDto>? contentVersionCleanupPolicyDtos = null;
         if (TableExists(ContentVersionCleanupPolicyDto.TableName))
         {
+            if (PrimaryKeyExists(ContentVersionCleanupPolicyDto.TableName, "PK_umbracoContentVersionCleanupPolicy"))
+            {
+                return;
+            }
+
+            contentVersionCleanupPolicyDtos =
+                Database
+                    .Fetch<ContentVersionCleanupPolicyDto>()
+                    .OrderByDescending(x => x.Updated)
+                    .DistinctBy(x => x.ContentTypeId);
+
             Delete.Table(ContentVersionCleanupPolicyDto.TableName).Do();
         }
 
         Create.Table<ContentVersionCleanupPolicyDto>().Do();
-        Database.InsertBatch(contentVersionCleanupPolicyDtos);
+
+        if (contentVersionCleanupPolicyDtos is not null)
+        {
+            Database.InsertBatch(contentVersionCleanupPolicyDtos);
+        }
     }
 }
diff --git a/src/Umbraco.Infrastructure/Persistence/Dtos/ContentVersionCleanupPolicyDto.cs b/src/Umbraco.Infrastructure/Persistence/Dtos/ContentVersionCleanupPolicyDto.cs
index 128c59594b..4dd1a14fb5 100644
--- a/src/Umbraco.Infrastructure/Persistence/Dtos/ContentVersionCleanupPolicyDto.cs
+++ b/src/Umbraco.Infrastructure/Persistence/Dtos/ContentVersionCleanupPolicyDto.cs
@@ -1,4 +1,3 @@
-using System.Data;
 using NPoco;
 using Umbraco.Cms.Core;
 using Umbraco.Cms.Infrastructure.Persistence.DatabaseAnnotations;
@@ -13,7 +12,7 @@ internal class ContentVersionCleanupPolicyDto
     public const string TableName = Constants.DatabaseSchema.Tables.ContentVersionCleanupPolicy;
 
     [Column("contentTypeId")]
-    [PrimaryKeyColumn(AutoIncrement = false)]
+    [PrimaryKeyColumn(AutoIncrement = false, Name = "PK_umbracoContentVersionCleanupPolicy")]
     [ForeignKey(typeof(ContentTypeDto), Column = "nodeId")]
     public int ContentTypeId { get; set; }
 
diff --git a/src/Umbraco.Infrastructure/Persistence/SqlSyntax/ISqlSyntaxProvider.cs b/src/Umbraco.Infrastructure/Persistence/SqlSyntax/ISqlSyntaxProvider.cs
index d9b76a4942..a71ccf5bed 100644
--- a/src/Umbraco.Infrastructure/Persistence/SqlSyntax/ISqlSyntaxProvider.cs
+++ b/src/Umbraco.Infrastructure/Persistence/SqlSyntax/ISqlSyntaxProvider.cs
@@ -188,6 +188,8 @@ public interface ISqlSyntaxProvider
     /// </remarks>
     bool TryGetDefaultConstraint(IDatabase db, string? tableName, string columnName, [MaybeNullWhen(false)] out string constraintName);
 
+    bool DoesPrimaryKeyExist(IDatabase db, string tableName, string primaryKeyName) => throw new NotImplementedException();
+
     string GetFieldNameForUpdate<TDto>(Expression<Func<TDto, object?>> fieldSelector, string? tableAlias = null);
 
     /// <summary>
diff --git a/src/Umbraco.Infrastructure/Persistence/SqlSyntax/SqlSyntaxProviderBase.cs b/src/Umbraco.Infrastructure/Persistence/SqlSyntax/SqlSyntaxProviderBase.cs
index 48b882d604..15cb68bfc5 100644
--- a/src/Umbraco.Infrastructure/Persistence/SqlSyntax/SqlSyntaxProviderBase.cs
+++ b/src/Umbraco.Infrastructure/Persistence/SqlSyntax/SqlSyntaxProviderBase.cs
@@ -209,6 +209,8 @@ public abstract class SqlSyntaxProviderBase<TSyntax> : ISqlSyntaxProvider
 
     public abstract bool TryGetDefaultConstraint(IDatabase db, string? tableName, string columnName, [MaybeNullWhen(false)] out string constraintName);
 
+    public virtual bool DoesPrimaryKeyExist(IDatabase db, string tableName, string primaryKeyName) => throw new NotImplementedException();
+
     public virtual string GetFieldNameForUpdate<TDto>(
         Expression<Func<TDto, object?>> fieldSelector,
         string? tableAlias = null) => this.GetFieldName(fieldSelector, tableAlias);