diff --git a/src/Umbraco.Core/Persistence/Repositories/ContentRepository.cs b/src/Umbraco.Core/Persistence/Repositories/ContentRepository.cs
index 741634157d..60951f6086 100644
--- a/src/Umbraco.Core/Persistence/Repositories/ContentRepository.cs
+++ b/src/Umbraco.Core/Persistence/Repositories/ContentRepository.cs
@@ -618,6 +618,17 @@ namespace Umbraco.Core.Persistence.Repositories
             repo.ReplaceEntityPermissions(permissionSet);
         }
 
+        public void ClearPublished(IContent content)
+        {
+            // race cond!
+            var documentDtos = Database.Fetch<DocumentDto>("WHERE nodeId=@id AND published=@published", new { id = content.Id, published = true });
+            foreach (var documentDto in documentDtos)
+            {
+                documentDto.Published = false;
+                Database.Update(documentDto);
+            }
+        }
+
         public IContent GetByLanguage(int id, string language)
         {
             var sql = GetBaseQuery(false);
diff --git a/src/Umbraco.Core/Persistence/Repositories/Interfaces/IContentRepository.cs b/src/Umbraco.Core/Persistence/Repositories/Interfaces/IContentRepository.cs
index ac0fcebbe7..5cb470b7cd 100644
--- a/src/Umbraco.Core/Persistence/Repositories/Interfaces/IContentRepository.cs
+++ b/src/Umbraco.Core/Persistence/Repositories/Interfaces/IContentRepository.cs
@@ -27,6 +27,12 @@ namespace Umbraco.Core.Persistence.Repositories
         /// <param name="permissionSet"></param>
         void ReplaceContentPermissions(EntityPermissionSet permissionSet);
 
+        /// <summary>
+        /// Clears the published flag for a content.
+        /// </summary>
+        /// <param name="content"></param>
+        void ClearPublished(IContent content);
+
         /// <summary>
         /// Gets a specific language version of an <see cref="IContent"/>
         /// </summary>
diff --git a/src/Umbraco.Core/Publishing/PublishingStrategy.cs b/src/Umbraco.Core/Publishing/PublishingStrategy.cs
index 899567bf8d..1c33f87c5e 100644
--- a/src/Umbraco.Core/Publishing/PublishingStrategy.cs
+++ b/src/Umbraco.Core/Publishing/PublishingStrategy.cs
@@ -303,32 +303,7 @@ namespace Umbraco.Core.Publishing
         /// <returns>True if the unpublish operation was successfull and not cancelled, otherwise false</returns>
         public override bool UnPublish(IContent content, int userId)
         {
-            if (UnPublishing.IsRaisedEventCancelled(new PublishEventArgs<IContent>(content), this))
-            {
-                LogHelper.Info<PublishingStrategy>(
-                        string.Format("Content '{0}' with Id '{1}' will not be un-published, the event was cancelled.", content.Name, content.Id));
-                return false;
-            }
-                
-
-            //If Content has a release date set to before now, it should be removed so it doesn't interrupt an unpublish
-            //Otherwise it would remain released == published
-            if (content.ReleaseDate.HasValue && content.ReleaseDate.Value <= DateTime.Now)
-            {
-                content.ReleaseDate = null;
-
-                LogHelper.Info<PublishingStrategy>(
-                    string.Format(
-                        "Content '{0}' with Id '{1}' had its release date removed, because it was unpublished.",
-                        content.Name, content.Id));
-            }
-
-            content.ChangePublishedState(PublishedState.Unpublished);
-
-            LogHelper.Info<PublishingStrategy>(
-                string.Format("Content '{0}' with Id '{1}' has been unpublished.",
-                              content.Name, content.Id));
-            return true;
+            return UnPublishInternal(content, userId).Success;
         }
 
         /// <summary>
@@ -337,43 +312,47 @@ namespace Umbraco.Core.Publishing
         /// <param name="content">An enumerable list of <see cref="IContent"/></param>
         /// <param name="userId">Id of the User issueing the unpublish operation</param>
         /// <returns>A list of publish statuses</returns>
-        internal IEnumerable<Attempt<PublishStatus>> UnPublishInternal(IEnumerable<IContent> content, int userId)
+        private IEnumerable<Attempt<PublishStatus>> UnPublishInternal(IEnumerable<IContent> content, int userId)
         {
-            var result = new List<Attempt<PublishStatus>>();
+            return content.Select(x => UnPublishInternal(x, userId));
+        }
 
-            //Only update content thats already been published
-            foreach (var item in content.Where(x => x.Published == true))
+        private Attempt<PublishStatus> UnPublishInternal(IContent content, int userId)
+        {
+            // content should (is assumed to ) be the newest version, which may not be published
+            // don't know how to test this, so it's not verified
+            // NOTE
+            // if published != newest, then the published flags need to be reseted by whoever is calling that method
+            // at the moment it's done by the content service
+
+            //Fire UnPublishing event
+            if (UnPublishing.IsRaisedEventCancelled(new PublishEventArgs<IContent>(content), this))
             {
-                //Fire UnPublishing event
-                if (UnPublishing.IsRaisedEventCancelled(new PublishEventArgs<IContent>(item), this))
-                {
-                    LogHelper.Info<PublishingStrategy>(
-                        string.Format("Content '{0}' with Id '{1}' will not be published, the event was cancelled.", item.Name, item.Id));
-                    result.Add(Attempt.Fail(new PublishStatus(item, PublishStatusType.FailedCancelledByEvent)));
-                    continue;
-                }
-
-                //If Content has a release date set to before now, it should be removed so it doesn't interrupt an unpublish
-                //Otherwise it would remain released == published
-                if (item.ReleaseDate.HasValue && item.ReleaseDate.Value <= DateTime.Now)
-                {
-                    item.ReleaseDate = null;
-
-                    LogHelper.Info<PublishingStrategy>(
-                        string.Format("Content '{0}' with Id '{1}' had its release date removed, because it was unpublished.",
-                                      item.Name, item.Id));
-                }
-
-                item.ChangePublishedState(PublishedState.Unpublished);
-
                 LogHelper.Info<PublishingStrategy>(
-                    string.Format("Content '{0}' with Id '{1}' has been unpublished.",
-                                  item.Name, item.Id));
-
-                result.Add(Attempt.Succeed(new PublishStatus(item)));
+                    string.Format("Content '{0}' with Id '{1}' will not be unpublished, the event was cancelled.", content.Name, content.Id));
+                return Attempt.Fail(new PublishStatus(content, PublishStatusType.FailedCancelledByEvent));
             }
 
-            return result;
+            //If Content has a release date set to before now, it should be removed so it doesn't interrupt an unpublish
+            //Otherwise it would remain released == published
+            if (content.ReleaseDate.HasValue && content.ReleaseDate.Value <= DateTime.Now)
+            {
+                content.ReleaseDate = null;
+
+                LogHelper.Info<PublishingStrategy>(
+                    string.Format("Content '{0}' with Id '{1}' had its release date removed, because it was unpublished.",
+                                  content.Name, content.Id));
+            }
+
+            // if newest is published, unpublish
+            if (content.Published)
+                content.ChangePublishedState(PublishedState.Unpublished);
+
+            LogHelper.Info<PublishingStrategy>(
+                string.Format("Content '{0}' with Id '{1}' has been unpublished.",
+                              content.Name, content.Id));
+
+            return Attempt.Succeed(new PublishStatus(content));
         }
 
         /// <summary>
diff --git a/src/Umbraco.Core/Services/ContentService.cs b/src/Umbraco.Core/Services/ContentService.cs
index f86739aeb8..c4181a80a4 100644
--- a/src/Umbraco.Core/Services/ContentService.cs
+++ b/src/Umbraco.Core/Services/ContentService.cs
@@ -1698,6 +1698,13 @@ namespace Umbraco.Core.Services
         /// <returns>True if unpublishing succeeded, otherwise False</returns>
         private bool UnPublishDo(IContent content, bool omitCacheRefresh = false, int userId = 0)
         {
+            var newest = GetById(content.Id); // ensure we have the newest version
+            if (content.Version != newest.Version) // but use the original object if it's already the newest version
+                content = newest;
+            var published = content.Published ? content : GetPublishedVersion(content.Id); // get the published version
+            if (published == null)
+                return false; // already unpublished
+
             var unpublished = _publishingStrategy.UnPublish(content, userId);
             if (unpublished)
             {
@@ -1706,6 +1713,9 @@ namespace Umbraco.Core.Services
                 {
                     content.WriterId = userId;
                     repository.AddOrUpdate(content);
+                    // is published is not newest, reset the published flag on published version
+                    if (published.Version != content.Version)
+                        repository.ClearPublished(published);
                     repository.DeleteContentXml(content);
 
                     uow.Commit();