diff --git a/src/Umbraco.Web.UI.Client/src/common/services/tinymce.service.js b/src/Umbraco.Web.UI.Client/src/common/services/tinymce.service.js
index da013d88ee..387b206514 100644
--- a/src/Umbraco.Web.UI.Client/src/common/services/tinymce.service.js
+++ b/src/Umbraco.Web.UI.Client/src/common/services/tinymce.service.js
@@ -588,12 +588,15 @@ function tinyMceService($rootScope, $q, imageHelper, $locale, $http, $timeout, s
 
 
                     var selectedElm = editor.selection.getNode(),
-                        currentTarget;
+                        currentTarget,
+                        imgDomElement;
 
                     if (selectedElm.nodeName === 'IMG') {
                         var img = $(selectedElm);
+                        imgDomElement = selectedElm;
 
                         var hasUdi = img.attr("data-udi") ? true : false;
+                        var hasDataTmpImg = img.attr("data-tmpimg") ? true : false;
 
                         currentTarget = {
                             altText: img.attr("alt"),
@@ -605,12 +608,16 @@ function tinyMceService($rootScope, $q, imageHelper, $locale, $http, $timeout, s
                         } else {
                             currentTarget["id"] = img.attr("rel");
                         }
+
+                        if(hasDataTmpImg){
+                            currentTarget["tmpimg"] = img.attr("data-tmpimg");
+                        }
                     }
 
                     userService.getCurrentUser().then(function (userData) {
                         if (callback) {
                             angularHelper.safeApply($rootScope, function() {
-                                callback(currentTarget, userData);
+                                callback(currentTarget, userData, imgDomElement);
                             });
                         }
                     });
@@ -618,25 +625,77 @@ function tinyMceService($rootScope, $q, imageHelper, $locale, $http, $timeout, s
             });
         },
 
-        insertMediaInEditor: function (editor, img) {
+        insertMediaInEditor: function (editor, img, imgDomElement) {
             if (img) {
+                // imgElement is only definied if updating an image
+                // if null/undefinied then its a BRAND new image
+                if(imgDomElement){
+                    // Check if the img src has changed
+                    // If it has we will need to do some resizing/recalc again
+                    var hasImageSrcChanged = false;
 
-                var data = {
-                    alt: img.altText || "",
-                    src: (img.url) ? img.url : "nothing.jpg",
-                    id: '__mcenew',
-                    'data-udi': img.udi
-                };
+                    if(img.url !==  editor.dom.getAttrib(imgDomElement, "src")){
+                        hasImageSrcChanged = true;
+                    }
 
-                editor.selection.setContent(editor.dom.createHTML('img', data));
+                    // If null/undefinied it will remove the attribute
+                    editor.dom.setAttrib(imgDomElement, "alt", img.altText);
 
-                $timeout(function () {
-                    var imgElm = editor.dom.get('__mcenew');
-                    sizeImageInEditor(editor, imgElm, img.url);
-                    editor.dom.setAttrib(imgElm, 'id', null);
-                    editor.fire('Change');
+                    // It's possible to pick a NEW image - so need to ensure this gets updated
+                    if(img.udi){
+                        editor.dom.setAttrib(imgDomElement, "data-udi", img.udi);
+                    }
 
-                }, 500);
+                    // It's possible to pick a NEW image - so need to ensure this gets updated
+                    if(img.url){
+                        editor.dom.setAttrib(imgDomElement, "src", img.url);
+                    }
+
+                    // Remove width & height attributes (ONLY if imgSrc changed)
+                    // So native image size is used as this needed to re-calc width & height
+                    // For the function sizeImageInEditor() & apply the image resizing querystrings etc..
+                    if(hasImageSrcChanged){
+                        editor.dom.setAttrib(imgDomElement, "width", null);
+                        editor.dom.setAttrib(imgDomElement, "height", null);
+
+                        //Re-calc the image dimensions
+                        sizeImageInEditor(editor, imgDomElement, img.url);
+                    }
+
+                } else{
+                    // We need to create a NEW DOM <img> element to insert
+                    // setting an attribute of ID to __mcenew, so we can gather a reference to the node, to be able to update its size accordingly to the size of the image.
+                    var data = {
+                        alt: img.altText || "",
+                        src: (img.url) ? img.url : "nothing.jpg",
+                        id: "__mcenew",
+                        "data-udi": img.udi
+                    };
+                    
+                    editor.selection.setContent(editor.dom.createHTML('img', data));
+                    
+                    // Using settimeout to wait for a DoM-render, so we can find the new element by ID.
+                    $timeout(function () {
+
+                        var imgElm = editor.dom.get("__mcenew");
+                        editor.dom.setAttrib(imgElm, "id", null);
+
+                        // When image is loaded we are ready to call sizeImageInEditor.
+                        var onImageLoaded = function() {
+                            sizeImageInEditor(editor, imgElm, img.url);
+                            editor.fire("Change");
+                        }
+
+                        // Check if image already is loaded.
+                        if(imgElm.complete === true) {
+                            onImageLoaded();
+                        } else {
+                            imgElm.onload = onImageLoaded;
+                        }
+
+                    });
+                    
+                }
             }
         },
 
@@ -1402,7 +1461,7 @@ function tinyMceService($rootScope, $q, imageHelper, $locale, $http, $timeout, s
             });
 
             //Create the insert media plugin
-            self.createMediaPicker(args.editor, function (currentTarget, userData) {
+            self.createMediaPicker(args.editor, function (currentTarget, userData, imgDomElement) {
 
                 var startNodeId, startNodeIsVirtual;
                 if (!args.model.config.startNodeId) {
@@ -1425,7 +1484,7 @@ function tinyMceService($rootScope, $q, imageHelper, $locale, $http, $timeout, s
                     startNodeIsVirtual: startNodeIsVirtual,
                     dataTypeKey: args.model.dataTypeKey,
                     submit: function (model) {
-                        self.insertMediaInEditor(args.editor, model.selection[0]);
+                        self.insertMediaInEditor(args.editor, model.selection[0], imgDomElement);
                         editorService.close();
                     },
                     close: function () {
diff --git a/src/Umbraco.Web.UI.Client/src/views/common/infiniteeditors/mediapicker/mediapicker.controller.js b/src/Umbraco.Web.UI.Client/src/views/common/infiniteeditors/mediapicker/mediapicker.controller.js
index 837c0ebc9d..24b8b999fa 100644
--- a/src/Umbraco.Web.UI.Client/src/views/common/infiniteeditors/mediapicker/mediapicker.controller.js
+++ b/src/Umbraco.Web.UI.Client/src/views/common/infiniteeditors/mediapicker/mediapicker.controller.js
@@ -98,11 +98,15 @@ angular.module("umbraco")
                         gotoStartNode();
                     }
                 } else {
-                    //if a target is specified, go look it up - generally this target will just contain ids not the actual full
-                    //media object so we need to look it up
+                    // if a target is specified, go look it up - generally this target will just contain ids not the actual full
+                    // media object so we need to look it up
                     var id = $scope.target.udi ? $scope.target.udi : $scope.target.id;
                     var altText = $scope.target.altText;
-                    entityResource.getById(id, "Media")
+                    
+                    // ID of a UDI or legacy int ID still could be null/undefinied here
+                    // As user may dragged in an image that has not been saved to media section yet
+                    if(id){
+                        entityResource.getById(id, "Media")
                         .then(function (node) {
                             $scope.target = node;
                             if (ensureWithinStartNode(node)) {
@@ -113,6 +117,12 @@ angular.module("umbraco")
                             }
                         },
                             gotoStartNode);
+                    }
+                    else {
+                        // No ID set - then this is going to be a tmpimg that has not been uploaded
+                        // User editing this will want to be changing the ALT text
+                        $scope.openDetailsDialog();
+                    }
                 }
             }
 
@@ -508,4 +518,4 @@ angular.module("umbraco")
 
             onInit();
 
-        });
\ No newline at end of file
+        });
diff --git a/src/Umbraco.Web.UI.Client/src/views/prevalueeditors/mediafolderpicker.controller.js b/src/Umbraco.Web.UI.Client/src/views/prevalueeditors/mediafolderpicker.controller.js
index ddfca295d4..1f39c2423e 100644
--- a/src/Umbraco.Web.UI.Client/src/views/prevalueeditors/mediafolderpicker.controller.js
+++ b/src/Umbraco.Web.UI.Client/src/views/prevalueeditors/mediafolderpicker.controller.js
@@ -27,7 +27,7 @@ function mediaFolderPickerController($scope, editorService, entityResource) {
     $scope.add = function() {
         var mediaPickerOptions = {
             view: "mediapicker",
-            multiPicker: true,
+            multiPicker: false, // We only want to allow you to pick one folder at a given time
             disableFolderSelect: false,
             onlyImages: false,
             onlyFolders: true,
diff --git a/src/Umbraco.Web/PropertyEditors/GridPropertyEditor.cs b/src/Umbraco.Web/PropertyEditors/GridPropertyEditor.cs
index 0b37638afd..2c2c69d181 100644
--- a/src/Umbraco.Web/PropertyEditors/GridPropertyEditor.cs
+++ b/src/Umbraco.Web/PropertyEditors/GridPropertyEditor.cs
@@ -1,5 +1,6 @@
 using Newtonsoft.Json;
 using System;
+using System.Collections.Generic;
 using System.Linq;
 using Umbraco.Core;
 using Umbraco.Core.Logging;
@@ -86,26 +87,63 @@ namespace Umbraco.Web.PropertyEditors
                 if (rawJson.IsNullOrWhiteSpace())
                     return null;
 
-                var grid = JsonConvert.DeserializeObject<GridValue>(rawJson);
+                var grid = DeserializeGridValue(rawJson, out var rtes);
 
-                // Find all controls that use the RTE editor
-                var controls = grid.Sections.SelectMany(x => x.Rows.SelectMany(r => r.Areas).SelectMany(a => a.Controls));
-                var rtes = controls.Where(x => x.Editor.Alias.ToLowerInvariant() == "rte");
+                var userId = _umbracoContextAccessor.UmbracoContext?.Security.CurrentUser.Id ?? Constants.Security.SuperUserId;
 
-                foreach(var rte in rtes)
+                //process the rte values
+                foreach (var rte in rtes)
                 {
                     // Parse the HTML
                     var html = rte.Value?.ToString();
 
-                    var userId = _umbracoContextAccessor.UmbracoContext?.Security.CurrentUser.Id ?? Constants.Security.SuperUserId;
+                    var parseAndSavedTempImages = TemplateUtilities.FindAndPersistPastedTempImages(html, mediaParentId, userId, _mediaService, _contentTypeBaseServiceProvider, _logger);
+                    var editorValueWithMediaUrlsRemoved = TemplateUtilities.RemoveMediaUrlsFromTextString(parseAndSavedTempImages);
 
-                    var parsedHtml = TemplateUtilities.FindAndPersistPastedTempImages(html, mediaParentId, userId, _mediaService, _contentTypeBaseServiceProvider, _logger);
-                    rte.Value = parsedHtml;
+                    rte.Value = editorValueWithMediaUrlsRemoved;
                 }
 
                 // Convert back to raw JSON for persisting
                 return JsonConvert.SerializeObject(grid);
             }
+
+            /// <summary>
+            /// Ensures that the rich text editor values are processed within the grid
+            /// </summary>
+            /// <param name="property"></param>
+            /// <param name="dataTypeService"></param>
+            /// <param name="culture"></param>
+            /// <param name="segment"></param>
+            /// <returns></returns>
+            public override object ToEditor(Property property, IDataTypeService dataTypeService, string culture = null, string segment = null)
+            {
+                var val = property.GetValue(culture, segment);
+                if (val == null) return string.Empty;
+
+                var grid = DeserializeGridValue(val.ToString(), out var rtes);
+
+                //process the rte values
+                foreach (var rte in rtes.ToList())
+                {
+                    var html = rte.Value?.ToString();
+
+                    var propertyValueWithMediaResolved = TemplateUtilities.ResolveMediaFromTextString(html);
+                    rte.Value = propertyValueWithMediaResolved;
+                }
+
+                return grid;
+            }
+
+            private GridValue DeserializeGridValue(string rawJson, out IEnumerable<GridValue.GridControl> richTextValues)
+            {
+                var grid = JsonConvert.DeserializeObject<GridValue>(rawJson);
+
+                // Find all controls that use the RTE editor
+                var controls = grid.Sections.SelectMany(x => x.Rows.SelectMany(r => r.Areas).SelectMany(a => a.Controls));
+                richTextValues = controls.Where(x => x.Editor.Alias.ToLowerInvariant() == "rte");
+
+                return grid;
+            }
         }
     }
 }
diff --git a/src/Umbraco.Web/PropertyEditors/RichTextPropertyEditor.cs b/src/Umbraco.Web/PropertyEditors/RichTextPropertyEditor.cs
index d29b96c1db..3eed40c8bf 100644
--- a/src/Umbraco.Web/PropertyEditors/RichTextPropertyEditor.cs
+++ b/src/Umbraco.Web/PropertyEditors/RichTextPropertyEditor.cs
@@ -114,16 +114,16 @@ namespace Umbraco.Web.PropertyEditors
                 if (editorValue.Value == null)
                     return null;
 
-                var editorValueWithMediaUrlsRemoved = TemplateUtilities.RemoveMediaUrlsFromTextString(editorValue.Value.ToString());
-                var parsed = MacroTagParser.FormatRichTextContentForPersistence(editorValueWithMediaUrlsRemoved);
-
                 var userId = _umbracoContextAccessor.UmbracoContext?.Security.CurrentUser.Id ?? Constants.Security.SuperUserId;
 
                 var config = editorValue.DataTypeConfiguration as RichTextConfiguration;
                 var mediaParent = config?.MediaParentId;
                 var mediaParentId = mediaParent == null ? Guid.Empty : mediaParent.Guid;
 
-                parsed = TemplateUtilities.FindAndPersistPastedTempImages(parsed, mediaParentId, userId, _mediaService, _contentTypeBaseServiceProvider, _logger);
+                var parseAndSavedTempImages = TemplateUtilities.FindAndPersistPastedTempImages(editorValue.Value.ToString(), mediaParentId, userId, _mediaService, _contentTypeBaseServiceProvider, _logger);
+                var editorValueWithMediaUrlsRemoved = TemplateUtilities.RemoveMediaUrlsFromTextString(parseAndSavedTempImages);
+                var parsed = MacroTagParser.FormatRichTextContentForPersistence(editorValueWithMediaUrlsRemoved);
+
                 return parsed;
             }
         }