diff --git a/src/Umbraco.Core/ApplicationEventHandler.cs b/src/Umbraco.Core/ApplicationEventHandler.cs
index a725a08a8e..8d97baac95 100644
--- a/src/Umbraco.Core/ApplicationEventHandler.cs
+++ b/src/Umbraco.Core/ApplicationEventHandler.cs
@@ -74,7 +74,7 @@ namespace Umbraco.Core
         /// <returns></returns>
         private bool ShouldExecute(ApplicationContext applicationContext)
         {
-            if (applicationContext.IsConfigured && applicationContext.DatabaseContext.CanConnect)
+            if (applicationContext.IsConfigured && applicationContext.DatabaseContext.IsDatabaseConfigured)
             {
                 return true;
             }
@@ -84,7 +84,7 @@ namespace Umbraco.Core
                 return true;
             }
 
-            if (!applicationContext.DatabaseContext.CanConnect && ExecuteWhenDatabaseNotConfigured)
+            if (!applicationContext.DatabaseContext.IsDatabaseConfigured && ExecuteWhenDatabaseNotConfigured)
             {
                 return true;
             }
diff --git a/src/Umbraco.Core/CoreBootManager.cs b/src/Umbraco.Core/CoreBootManager.cs
index f5dbdcf957..c5d3e2a4c7 100644
--- a/src/Umbraco.Core/CoreBootManager.cs
+++ b/src/Umbraco.Core/CoreBootManager.cs
@@ -2,10 +2,12 @@
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
+using System.Threading;
 using System.Web;
 using AutoMapper;
 using Umbraco.Core.Cache;
 using Umbraco.Core.Configuration;
+using Umbraco.Core.Exceptions;
 using Umbraco.Core.IO;
 using Umbraco.Core.Logging;
 using Umbraco.Core.Models.Mapping;
@@ -261,6 +263,9 @@ namespace Umbraco.Core
 
 		    FreezeResolution();
 
+            //Here we need to make sure the db can be connected to
+		    EnsureDatabaseConnection();
+
             using (DisposableTimer.DebugDuration<CoreBootManager>(
                 () => string.Format("Executing {0} IApplicationEventHandler.OnApplicationStarted", ApplicationEventsResolver.Current.ApplicationEventHandlers.Count()),
                 () => "Finished executing IApplicationEventHandler.OnApplicationStarted"))
@@ -299,6 +304,32 @@ namespace Umbraco.Core
 			return this;
 		}
 
+        /// <summary>
+        /// We cannot continue if the db cannot be connected to
+        /// </summary>
+        private void EnsureDatabaseConnection()
+        {
+            if (ApplicationContext.IsConfigured == false) return;
+            if (ApplicationContext.DatabaseContext.IsDatabaseConfigured == false) return;
+
+            var currentTry = 0;
+            while (currentTry < 5)
+            {
+                if (ApplicationContext.DatabaseContext.CanConnect)
+                    break;
+
+                //wait and retry
+                Thread.Sleep(1000);
+                currentTry++;
+            }
+
+            if (currentTry == 5)
+            {
+                throw new UmbracoStartupFailedException("Umbraco cannot start. A connection string is configured but the Umbraco cannot connect to the database.");
+            }
+
+        }
+
         /// <summary>
         /// Freeze resolution to not allow Resolvers to be modified
         /// </summary>
diff --git a/src/Umbraco.Core/DatabaseContext.cs b/src/Umbraco.Core/DatabaseContext.cs
index fad96b849d..dfaebb0315 100644
--- a/src/Umbraco.Core/DatabaseContext.cs
+++ b/src/Umbraco.Core/DatabaseContext.cs
@@ -26,8 +26,6 @@ namespace Umbraco.Core
     {
         private readonly IDatabaseFactory _factory;
         private bool _configured;
-        private bool _canConnect;
-        private volatile bool _connectCheck = false;
         private readonly object _locker = new object();
         private string _connectionString;
         private string _providerName;
@@ -67,21 +65,9 @@ namespace Umbraco.Core
             get
             {
                 if (IsDatabaseConfigured == false) return false;
-
-                //double check lock so that it is only checked once and is fast
-                if (_connectCheck == false)
-                {
-                    lock (_locker)
-                    {
-                        if (_canConnect == false)
-                        {
-                            _canConnect = DbConnectionExtensions.IsConnectionAvailable(ConnectionString, DatabaseProvider);
-                            _connectCheck = true;
-                        }
-                    }
-                }
-
-                return _canConnect;
+                var canConnect = DbConnectionExtensions.IsConnectionAvailable(ConnectionString, DatabaseProvider);
+                LogHelper.Info<DatabaseContext>("CanConnect = " + canConnect);
+                return canConnect;
             }
         }
 
diff --git a/src/Umbraco.Core/Exceptions/UmbracoStartupFailedException.cs b/src/Umbraco.Core/Exceptions/UmbracoStartupFailedException.cs
new file mode 100644
index 0000000000..d27d38de9a
--- /dev/null
+++ b/src/Umbraco.Core/Exceptions/UmbracoStartupFailedException.cs
@@ -0,0 +1,18 @@
+using System;
+
+namespace Umbraco.Core.Exceptions
+{
+    /// <summary>
+    /// An exception that is thrown if the umbraco application cannnot boot
+    /// </summary>
+    public class UmbracoStartupFailedException : Exception
+    {
+        /// <summary>
+        /// Initializes a new instance of the <see cref="T:System.Exception"/> class with a specified error message.
+        /// </summary>
+        /// <param name="message">The message that describes the error. </param>
+        public UmbracoStartupFailedException(string message) : base(message)
+        {
+        }
+    }
+}
\ No newline at end of file
diff --git a/src/Umbraco.Core/TypeFinder.cs b/src/Umbraco.Core/TypeFinder.cs
index 962f0e3d91..abaf5ae5e0 100644
--- a/src/Umbraco.Core/TypeFinder.cs
+++ b/src/Umbraco.Core/TypeFinder.cs
@@ -700,7 +700,11 @@ namespace Umbraco.Core
 
         #endregion
 
-        public static Type GetTypeByName(string typeName)
+        //TODO: This isn't very elegant, and will have issues since the AppDomain.CurrentDomain
+        // doesn't actualy load in all assemblies, only the types that have been referenced so far.
+        // However, in a web context, the BuildManager will have executed which will force all assemblies
+        // to be loaded so it's fine for now.
+        internal static Type GetTypeByName(string typeName)
         {
             var type = Type.GetType(typeName);
             if (type != null) return type;
diff --git a/src/Umbraco.Core/Umbraco.Core.csproj b/src/Umbraco.Core/Umbraco.Core.csproj
index 67ce55b8f1..4e155e1b3d 100644
--- a/src/Umbraco.Core/Umbraco.Core.csproj
+++ b/src/Umbraco.Core/Umbraco.Core.csproj
@@ -312,6 +312,7 @@
     <Compile Include="Events\SaveEventArgs.cs" />
     <Compile Include="Events\SendToPublishEventArgs.cs" />
     <Compile Include="Exceptions\InvalidCompositionException.cs" />
+    <Compile Include="Exceptions\UmbracoStartupFailedException.cs" />
     <Compile Include="HideFromTypeFinderAttribute.cs" />
     <Compile Include="HttpContextExtensions.cs" />
     <Compile Include="IApplicationEventHandler.cs" />