diff --git a/src/Umbraco.Core/CoreBootManager.cs b/src/Umbraco.Core/CoreBootManager.cs
index 091f07bd19..0419fb0cd0 100644
--- a/src/Umbraco.Core/CoreBootManager.cs
+++ b/src/Umbraco.Core/CoreBootManager.cs
@@ -75,6 +75,8 @@ namespace Umbraco.Core
             //initialize the DatabaseContext
             dbContext.Initialize();
 
+            InitializeModelMappers();
+
             //now we need to call the initialize methods
             ApplicationEventsResolver.Current.ApplicationEventHandlers
                 .ForEach(x => x.OnApplicationInitialized(UmbracoApplication, ApplicationContext));
@@ -95,6 +97,14 @@ namespace Umbraco.Core
             ApplicationContext = ApplicationContext.Current = new ApplicationContext(dbContext, serviceContext);
         }
 
+        /// <summary>
+        /// This method allows for configuration of model mappers
+        /// </summary>
+        protected virtual void InitializeModelMappers()
+        {
+            //TODO: There will most likely be AutoMapper configs to put in here, we know they exist in web for now so we'll leave this here for future use
+        }
+
         /// <summary>
         /// Special method to initialize the ProfilerResolver
         /// </summary>
diff --git a/src/Umbraco.Tests/App.config b/src/Umbraco.Tests/App.config
index b4fa2f7a10..cfbefb6754 100644
--- a/src/Umbraco.Tests/App.config
+++ b/src/Umbraco.Tests/App.config
@@ -22,7 +22,6 @@
     <add key="umbracoDefaultUILanguage" value="en"/>
     <add key="umbracoProfileUrl" value="profiler"/>
     <add key="umbracoUseSSL" value="false"/>
-    <add key="umbracoUseMediumTrust" value="false"/>
   </appSettings>
   
   <connectionStrings>
diff --git a/src/Umbraco.Web.UI.Client/src/common/directives/umbavatar.directive.js b/src/Umbraco.Web.UI.Client/src/common/directives/umbavatar.directive.js
index d83fc90ed3..c39f5ce0a5 100644
--- a/src/Umbraco.Web.UI.Client/src/common/directives/umbavatar.directive.js
+++ b/src/Umbraco.Web.UI.Client/src/common/directives/umbavatar.directive.js
@@ -7,7 +7,16 @@ function avatarDirective() {
     return {
         restrict: "E",    // restrict to an element
         replace: true,   // replace the html element with the template
-        templateUrl: 'views/directives/umb-avatar.html'        
+        templateUrl: 'views/directives/umb-avatar.html',
+        scope: {
+            name: '@',
+            email: '@',
+            hash: '@',
+        },
+        link: function(scope, element, attr, ctrl) {
+            //set the gravatar url
+            scope.gravatar = "http://www.gravatar.com/avatar/" + scope.hash + "?s=40";
+        }
     };
 }
 
diff --git a/src/Umbraco.Web.UI.Client/src/views/directives/umb-avatar.html b/src/Umbraco.Web.UI.Client/src/views/directives/umb-avatar.html
index b69a0a711f..48a4a776ba 100644
--- a/src/Umbraco.Web.UI.Client/src/views/directives/umb-avatar.html
+++ b/src/Umbraco.Web.UI.Client/src/views/directives/umb-avatar.html
@@ -1,3 +1,3 @@
 <a href="#" title="{{name}}">
-    <img ng-src="{{email}}" />
+    <img ng-src="{{gravatar}}" />
 </a>
\ No newline at end of file
diff --git a/src/Umbraco.Web.UI.Client/src/views/directives/umb-leftcolumn.html b/src/Umbraco.Web.UI.Client/src/views/directives/umb-leftcolumn.html
index 4ac78128cd..72c1bd17b1 100644
--- a/src/Umbraco.Web.UI.Client/src/views/directives/umb-leftcolumn.html
+++ b/src/Umbraco.Web.UI.Client/src/views/directives/umb-leftcolumn.html
@@ -3,7 +3,7 @@
         <ul class="sections">
             
             <li class="avatar">
-                <umb-avatar name="{{user.name}}" email="{{user.email}}"></umb-avatar>
+                <umb-avatar name="{{user.name}}" email="{{user.email}}" hash="{{user.emailHash}}"></umb-avatar>
             </li>
 
             <li ng-repeat="section in sections">
diff --git a/src/Umbraco.Web.UI/umbraco/Views/directives/umb-leftcolumn.html b/src/Umbraco.Web.UI/umbraco/Views/directives/umb-leftcolumn.html
index 4ac78128cd..72c1bd17b1 100644
--- a/src/Umbraco.Web.UI/umbraco/Views/directives/umb-leftcolumn.html
+++ b/src/Umbraco.Web.UI/umbraco/Views/directives/umb-leftcolumn.html
@@ -3,7 +3,7 @@
         <ul class="sections">
             
             <li class="avatar">
-                <umb-avatar name="{{user.name}}" email="{{user.email}}"></umb-avatar>
+                <umb-avatar name="{{user.name}}" email="{{user.email}}" hash="{{user.emailHash}}"></umb-avatar>
             </li>
 
             <li ng-repeat="section in sections">
diff --git a/src/Umbraco.Web.UI/web.Template.Debug.config b/src/Umbraco.Web.UI/web.Template.Debug.config
index 937cee3f3a..de074b944e 100644
--- a/src/Umbraco.Web.UI/web.Template.Debug.config
+++ b/src/Umbraco.Web.UI/web.Template.Debug.config
@@ -28,8 +28,8 @@
   
   <system.web>
     <compilation debug="true" xdt:Transform="SetAttributes(debug)" />
+    <!-- We no longer support medium trust so just remove it -->
     <trust xdt:Transform="Remove" />
-    <trust level="Medium" originUrl=".*"  xdt:Transform="Insert" />
   </system.web>
 
   <runtime>
diff --git a/src/Umbraco.Web.UI/web.Template.config b/src/Umbraco.Web.UI/web.Template.config
index 5438ea097b..19dceac49d 100644
--- a/src/Umbraco.Web.UI/web.Template.config
+++ b/src/Umbraco.Web.UI/web.Template.config
@@ -45,7 +45,6 @@
     <add key="umbracoDefaultUILanguage" value="en" />
     <add key="umbracoProfileUrl" value="profiler" />
     <add key="umbracoUseSSL" value="false" />
-    <add key="umbracoUseMediumTrust" value="false" />
 
     <!-- Set this to true to enable storing the xml cache locally to the IIS server even if the app files are stored centrally on a SAN/NAS Alex Norcliffe 2010 02 for 4.1  -->
     <add key="umbracoContentXMLUseLocalTemp" value="false"/>
@@ -283,4 +282,4 @@
     </pages>
   </system.web.webPages.razor>
 
-</configuration>
+</configuration>
diff --git a/src/Umbraco.Web/Models/ContentEditing/UserDetail.cs b/src/Umbraco.Web/Models/ContentEditing/UserDetail.cs
index 74fe5e641c..70aaa0cd77 100644
--- a/src/Umbraco.Web/Models/ContentEditing/UserDetail.cs
+++ b/src/Umbraco.Web/Models/ContentEditing/UserDetail.cs
@@ -13,5 +13,11 @@ namespace Umbraco.Web.Models.ContentEditing
         [DataMember(Name = "locale", IsRequired = true)]
         [Required]
         public string Language { get; set; }
+
+        /// <summary>
+        /// The MD5 lowercase hash of the email which can be used by gravatar
+        /// </summary>
+        [DataMember(Name = "emailHash")]
+        public string EmailHash { get; set; }
     }
 }
\ No newline at end of file
diff --git a/src/Umbraco.Web/Models/Mapping/UserModelMapper.cs b/src/Umbraco.Web/Models/Mapping/UserModelMapper.cs
index f6eee6750c..ad5fde9b5b 100644
--- a/src/Umbraco.Web/Models/Mapping/UserModelMapper.cs
+++ b/src/Umbraco.Web/Models/Mapping/UserModelMapper.cs
@@ -1,4 +1,5 @@
 using System;
+using AutoMapper;
 using Umbraco.Core;
 using Umbraco.Core.Models.Membership;
 using Umbraco.Web.Models.ContentEditing;
@@ -7,36 +8,39 @@ namespace Umbraco.Web.Models.Mapping
 {
     internal class UserModelMapper
     {
-        public UserDetail ToUserDetail(IUser user)
+        /// <summary>
+        /// Configures the automapper mappings
+        /// </summary>
+        internal static void Configure()
         {
-            var detail = new UserDetail
-            {
-                Name = user.Name,
-                Email = user.Email,
-                Language = user.Language
-            };
-            var result = user.Id.TryConvertTo<int>();
+            Mapper.CreateMap<IUser, UserDetail>()
+                  .ForMember(detail => detail.UserId, opt => opt.MapFrom(user => GetIntId(user.Id)))
+                  .ForMember(
+                      detail => detail.EmailHash,
+                      opt => opt.MapFrom(user => user.Email.ToLowerInvariant().Trim().ToMd5()));
+            Mapper.CreateMap<IProfile, UserBasic>()
+                  .ForMember(detail => detail.UserId, opt => opt.MapFrom(profile => GetIntId(profile.Id)));
+        }
+
+        private static int GetIntId(object id)
+        {
+            var result = id.TryConvertTo<int>();
             if (result.Success == false)
             {
-                throw new InvalidOperationException("Cannot convert the profile to a " + typeof(UserDetail).Name + " object since the id is not an integer");
+                throw new InvalidOperationException(
+                    "Cannot convert the profile to a " + typeof(UserDetail).Name + " object since the id is not an integer");
             }
-            detail.UserId = result.Result;
-            return detail;
+            return result.Result;
+        } 
+
+        public UserDetail ToUserDetail(IUser user)
+        {
+            return Mapper.Map<UserDetail>(user);
         }
 
         public UserBasic ToUserBasic(IProfile profile)
         {
-            var user = new UserBasic
-                {
-                    Name = profile.Name
-                };
-            var result = profile.Id.TryConvertTo<int>();
-            if (result.Success == false)
-            {
-                throw new InvalidOperationException("Cannot convert the profile to a " + typeof(UserBasic).Name + " object since the id is not an integer");
-            }
-            user.UserId = result.Result;
-            return user;
+            return Mapper.Map<UserDetail>(profile);
         }
     }
 }
\ No newline at end of file
diff --git a/src/Umbraco.Web/Umbraco.Web.csproj b/src/Umbraco.Web/Umbraco.Web.csproj
index cd7fae9060..14a549d9a5 100644
--- a/src/Umbraco.Web/Umbraco.Web.csproj
+++ b/src/Umbraco.Web/Umbraco.Web.csproj
@@ -95,6 +95,9 @@
       <Project>{07fbc26b-2927-4a22-8d96-d644c667fecc}</Project>
       <Name>UmbracoExamine</Name>
     </ProjectReference>
+    <Reference Include="AutoMapper">
+      <HintPath>..\packages\AutoMapper.2.2.1\lib\net40\AutoMapper.dll</HintPath>
+    </Reference>
     <Reference Include="ClientDependency.Core, Version=1.7.0.2, Culture=neutral, processorArchitecture=MSIL">
       <SpecificVersion>False</SpecificVersion>
       <HintPath>..\packages\ClientDependency.1.7.0.2\lib\ClientDependency.Core.dll</HintPath>
@@ -309,7 +312,6 @@
     <Compile Include="Models\Mapping\ContentTypeModelMapper.cs" />
     <Compile Include="Models\Mapping\MediaModelMapper.cs" />
     <Compile Include="Models\Mapping\UserModelMapper.cs" />
-    <Compile Include="Mvc\BackOfficeArea.cs" />
     <Compile Include="Trees\LegacyTreeApiController.cs" />
     <Compile Include="Trees\ISearchableTree.cs" />
     <Compile Include="Trees\LegacyTreeDataAdapter.cs" />
diff --git a/src/Umbraco.Web/WebBootManager.cs b/src/Umbraco.Web/WebBootManager.cs
index 1e51f126d9..a166b96702 100644
--- a/src/Umbraco.Web/WebBootManager.cs
+++ b/src/Umbraco.Web/WebBootManager.cs
@@ -20,6 +20,7 @@ using Umbraco.Web.Editors;
 using Umbraco.Web.Media;
 using Umbraco.Web.Media.ThumbnailProviders;
 using Umbraco.Web.Models;
+using Umbraco.Web.Models.Mapping;
 using Umbraco.Web.Mvc;
 using Umbraco.Web.PropertyEditors;
 using Umbraco.Web.PublishedCache;
@@ -111,6 +112,15 @@ namespace Umbraco.Web
             ProfilerResolver.Current.SetProfiler(new WebProfiler());
         }
 
+        /// <summary>
+        /// Configure the model mappers
+        /// </summary>
+        protected override void InitializeModelMappers()
+        {
+            base.InitializeModelMappers();
+            UserModelMapper.Configure();
+        }
+
         /// <summary>
         /// Adds custom types to the ApplicationEventsResolver
         /// </summary>
diff --git a/src/Umbraco.Web/packages.config b/src/Umbraco.Web/packages.config
index d370ef28d5..9f5ddf7b61 100644
--- a/src/Umbraco.Web/packages.config
+++ b/src/Umbraco.Web/packages.config
@@ -1,5 +1,6 @@
 <?xml version="1.0" encoding="utf-8"?>
 <packages>
+  <package id="AutoMapper" version="2.2.1" targetFramework="net45" />
   <package id="ClientDependency" version="1.7.0.2" targetFramework="net40" />
   <package id="CodeSharp.Package.AspNetWebPage" version="1.0" targetFramework="net40" />
   <package id="Examine" version="0.1.51.2941" targetFramework="net40" />
diff --git a/src/umbraco.businesslogic/GlobalSettings.cs b/src/umbraco.businesslogic/GlobalSettings.cs
index dd77f843b1..1ba730ecfb 100644
--- a/src/umbraco.businesslogic/GlobalSettings.cs
+++ b/src/umbraco.businesslogic/GlobalSettings.cs
@@ -101,31 +101,6 @@ namespace umbraco
 			get { return Umbraco.Core.SystemUtilities.GetCurrentTrustLevel(); }
         }
 
-
-        /// <summary>
-        /// Forces umbraco to be medium trust compatible
-        /// </summary>
-        /// <value>If true, umbraco will be medium-trust compatible, no matter what Permission level the server is on.</value>
-        [Obsolete("This property is no longer used and will be removed in future versions")]
-        public static bool UseMediumTrust
-        {
-			get
-			{
-				try
-				{
-					var trustLevel = SystemUtilities.GetCurrentTrustLevel();
-					if (trustLevel == AspNetHostingPermissionLevel.High || trustLevel == AspNetHostingPermissionLevel.Unrestricted)
-						return false;
-					else
-						return bool.Parse(ConfigurationManager.AppSettings["umbracoUseMediumTrust"]);
-				}
-				catch
-				{
-					return false;
-				}
-			}
-        }
-
         /// <summary>
         /// Saves a setting into the configuration file.
         /// </summary>