diff --git a/src/Umbraco.Core/Configuration/Models/ContentSettings.cs b/src/Umbraco.Core/Configuration/Models/ContentSettings.cs
index 2d2ec674b9..28c9ad1427 100644
--- a/src/Umbraco.Core/Configuration/Models/ContentSettings.cs
+++ b/src/Umbraco.Core/Configuration/Models/ContentSettings.cs
@@ -28,6 +28,7 @@ public class ContentSettings
     internal const bool StaticDisableUnpublishWhenReferenced = false;
     internal const bool StaticAllowEditInvariantFromNonDefault = false;
     internal const bool StaticShowDomainWarnings = true;
+    internal const bool StaticShowUnroutableContentWarnings = true;
 
     /// <summary>
     ///     Gets or sets a value for the content notification settings.
@@ -141,4 +142,10 @@ public class ContentSettings
     /// </summary>
     [DefaultValue(StaticShowDomainWarnings)]
     public bool ShowDomainWarnings { get; set; } = StaticShowDomainWarnings;
+
+    /// <summary>
+    /// Gets or sets a value indicating whether to show unroutable content warnings.
+    /// </summary>
+    [DefaultValue(StaticShowUnroutableContentWarnings)]
+    public bool ShowUnroutableContentWarnings { get; set; } = StaticShowUnroutableContentWarnings;
 }
diff --git a/src/Umbraco.Core/Events/AddUnroutableContentWarningsWhenPublishingNotificationHandler.cs b/src/Umbraco.Core/Events/AddUnroutableContentWarningsWhenPublishingNotificationHandler.cs
new file mode 100644
index 0000000000..ad457d287c
--- /dev/null
+++ b/src/Umbraco.Core/Events/AddUnroutableContentWarningsWhenPublishingNotificationHandler.cs
@@ -0,0 +1,119 @@
+using Microsoft.Extensions.Logging;
+using Microsoft.Extensions.Options;
+using Umbraco.Cms.Core.Configuration.Models;
+using Umbraco.Cms.Core.Models;
+using Umbraco.Cms.Core.Models.PublishedContent;
+using Umbraco.Cms.Core.Notifications;
+using Umbraco.Cms.Core.PublishedCache;
+using Umbraco.Cms.Core.Routing;
+using Umbraco.Cms.Core.Services;
+using Umbraco.Cms.Core.Services.Navigation;
+using Umbraco.Cms.Core.Web;
+using Umbraco.Extensions;
+
+namespace Umbraco.Cms.Core.Events;
+
+public class AddUnroutableContentWarningsWhenPublishingNotificationHandler : INotificationAsyncHandler<ContentPublishedNotification>
+{
+    private readonly IPublishedRouter _publishedRouter;
+    private readonly IUmbracoContextAccessor _umbracoContextAccessor;
+    private readonly ILanguageService _languageService;
+    private readonly ILocalizedTextService _localizedTextService;
+    private readonly IContentService _contentService;
+    private readonly IVariationContextAccessor _variationContextAccessor;
+    private readonly ILoggerFactory _loggerFactory;
+    private readonly UriUtility _uriUtility;
+    private readonly IPublishedUrlProvider _publishedUrlProvider;
+    private readonly IPublishedContentCache _publishedContentCache;
+    private readonly IDocumentNavigationQueryService _navigationQueryService;
+    private readonly IEventMessagesFactory _eventMessagesFactory;
+    private readonly ContentSettings _contentSettings;
+
+    public AddUnroutableContentWarningsWhenPublishingNotificationHandler(
+        IPublishedRouter publishedRouter,
+        IUmbracoContextAccessor umbracoContextAccessor,
+        ILanguageService languageService,
+        ILocalizedTextService localizedTextService,
+        IContentService contentService,
+        IVariationContextAccessor variationContextAccessor,
+        ILoggerFactory loggerFactory,
+        UriUtility uriUtility,
+        IPublishedUrlProvider publishedUrlProvider,
+        IPublishedContentCache publishedContentCache,
+        IDocumentNavigationQueryService navigationQueryService,
+        IEventMessagesFactory eventMessagesFactory,
+        IOptions<ContentSettings> contentSettings)
+    {
+        _publishedRouter = publishedRouter;
+        _umbracoContextAccessor = umbracoContextAccessor;
+        _languageService = languageService;
+        _localizedTextService = localizedTextService;
+        _contentService = contentService;
+        _variationContextAccessor = variationContextAccessor;
+        _loggerFactory = loggerFactory;
+        _uriUtility = uriUtility;
+        _publishedUrlProvider = publishedUrlProvider;
+        _publishedContentCache = publishedContentCache;
+        _navigationQueryService = navigationQueryService;
+        _eventMessagesFactory = eventMessagesFactory;
+        _contentSettings = contentSettings.Value;
+    }
+
+    public async Task HandleAsync(ContentPublishedNotification notification, CancellationToken cancellationToken)
+    {
+        if (_contentSettings.ShowUnroutableContentWarnings is false)
+        {
+            return;
+        }
+
+        foreach (IContent content in notification.PublishedEntities)
+        {
+            string[]? successfulCultures;
+            if (content.ContentType.VariesByCulture() is false)
+            {
+                // successfulCultures will be null here - change it to a wildcard and utilize this below
+                successfulCultures = ["*"];
+            }
+            else
+            {
+                successfulCultures = content.PublishedCultures.ToArray();
+            }
+
+            if (successfulCultures?.Any() is not true)
+            {
+                return;
+            }
+
+            if (!_umbracoContextAccessor.TryGetUmbracoContext(out IUmbracoContext? umbracoContext))
+            {
+                return;
+            }
+
+            UrlInfo[] urls = (await content.GetContentUrlsAsync(
+                _publishedRouter,
+                umbracoContext,
+                _languageService,
+                _localizedTextService,
+                _contentService,
+                _variationContextAccessor,
+                _loggerFactory.CreateLogger<IContent>(),
+                _uriUtility,
+                _publishedUrlProvider,
+                _publishedContentCache,
+                _navigationQueryService)).ToArray();
+
+
+            EventMessages eventMessages = _eventMessagesFactory.Get();
+            foreach (var culture in successfulCultures)
+            {
+                if (urls.Where(u => u.Culture == culture || culture == "*").All(u => u.IsUrl is false))
+                {
+                    eventMessages.Add(new EventMessage("Content published", "The document does not have a URL, possibly due to a naming collision with another document. More details can be found under Info.", EventMessageType.Warning));
+
+                    // only add one warning here, even though there might actually be more
+                    break;
+                }
+            }
+        }
+    }
+}
diff --git a/src/Umbraco.Core/Routing/NewDefaultUrlProvider.cs b/src/Umbraco.Core/Routing/NewDefaultUrlProvider.cs
index f7eeb1a1b4..3818bc2776 100644
--- a/src/Umbraco.Core/Routing/NewDefaultUrlProvider.cs
+++ b/src/Umbraco.Core/Routing/NewDefaultUrlProvider.cs
@@ -145,8 +145,10 @@ public class NewDefaultUrlProvider : IUrlProvider
 
     private string GetLegacyRouteFormatById(Guid key, string? culture)
     {
+        var isDraft = _umbracoContextAccessor.GetRequiredUmbracoContext().InPreviewMode;
 
-        return _documentUrlService.GetLegacyRouteFormat(key, culture, _umbracoContextAccessor.GetRequiredUmbracoContext().InPreviewMode);
+
+        return _documentUrlService.GetLegacyRouteFormat(key, culture, isDraft);
 
 
     }
@@ -163,9 +165,22 @@ public class NewDefaultUrlProvider : IUrlProvider
             throw new ArgumentException("Current URL must be absolute.", nameof(current));
         }
 
+        // This might seem to be some code duplication, as we do the same check in GetLegacyRouteFormat
+        // but this is strictly neccesary, as if we're coming from a published notification
+        // this document will still not always be in the memory cache. And thus we have to hit the DB
+        // We have the published content now, so we can check if the culture is published, and thus avoid the DB hit.
+        string route;
+        var isDraft = _umbracoContextAccessor.GetRequiredUmbracoContext().InPreviewMode;
+        if(isDraft is false && string.IsNullOrWhiteSpace(culture) is false && content.Cultures.Any() && content.IsInvariantOrHasCulture(culture) is false)
+        {
+            route = "#";
+        }
+        else
+        {
+            route = GetLegacyRouteFormatById(content.Key, culture);
+        }
 
         // will not use cache if previewing
-        var route = GetLegacyRouteFormatById(content.Key, culture);
 
         return GetUrlFromRoute(route, content.Id, current, mode, culture);
     }
diff --git a/src/Umbraco.Infrastructure/DependencyInjection/UmbracoBuilder.CoreServices.cs b/src/Umbraco.Infrastructure/DependencyInjection/UmbracoBuilder.CoreServices.cs
index 50ae0d7deb..bd101ad37b 100644
--- a/src/Umbraco.Infrastructure/DependencyInjection/UmbracoBuilder.CoreServices.cs
+++ b/src/Umbraco.Infrastructure/DependencyInjection/UmbracoBuilder.CoreServices.cs
@@ -411,8 +411,8 @@ public static partial class UmbracoBuilderExtensions
             .AddNotificationHandler<AssignedUserGroupPermissionsNotification, AuditNotificationsHandler>();
 
         // Handlers for publish warnings
-        builder
-            .AddNotificationHandler<ContentPublishedNotification, AddDomainWarningsWhenPublishingNotificationHandler>();
+        builder.AddNotificationHandler<ContentPublishedNotification, AddDomainWarningsWhenPublishingNotificationHandler>();
+        builder.AddNotificationAsyncHandler<ContentPublishedNotification, AddUnroutableContentWarningsWhenPublishingNotificationHandler>();
 
         // Handlers for save warnings
         builder