diff --git a/src/Umbraco.Web/PropertyEditors/RichTextPropertyEditor.cs b/src/Umbraco.Web/PropertyEditors/RichTextPropertyEditor.cs
index 207e914061..c05a983346 100644
--- a/src/Umbraco.Web/PropertyEditors/RichTextPropertyEditor.cs
+++ b/src/Umbraco.Web/PropertyEditors/RichTextPropertyEditor.cs
@@ -8,6 +8,7 @@ using Umbraco.Core.PropertyEditors;
 using Umbraco.Core.Services;
 using Umbraco.Examine;
 using Umbraco.Web.Macros;
+using Umbraco.Web.Templates;
 
 namespace Umbraco.Web.PropertyEditors
 {
@@ -73,7 +74,8 @@ namespace Umbraco.Web.PropertyEditors
                 if (val == null)
                     return null;
 
-                var parsed = MacroTagParser.FormatRichTextPersistedDataForEditor(val.ToString(), new Dictionary<string, string>());
+                var propertyValueWithMediaResolved = TemplateUtilities.ResolveMediaFromTextString(val.ToString());
+                var parsed = MacroTagParser.FormatRichTextPersistedDataForEditor(propertyValueWithMediaResolved, new Dictionary<string, string>());
                 return parsed;
             }
 
diff --git a/src/Umbraco.Web/PropertyEditors/ValueConverters/RteMacroRenderingValueConverter.cs b/src/Umbraco.Web/PropertyEditors/ValueConverters/RteMacroRenderingValueConverter.cs
index 1868f9ce94..fbbf058c49 100644
--- a/src/Umbraco.Web/PropertyEditors/ValueConverters/RteMacroRenderingValueConverter.cs
+++ b/src/Umbraco.Web/PropertyEditors/ValueConverters/RteMacroRenderingValueConverter.cs
@@ -72,9 +72,10 @@ namespace Umbraco.Web.PropertyEditors.ValueConverters
 
             var sourceString = source.ToString();
 
-            // ensures string is parsed for {localLink} and urls are resolved correctly
+            // ensures string is parsed for {localLink} and urls and media are resolved correctly
             sourceString = TemplateUtilities.ParseInternalLinks(sourceString, preview, Current.UmbracoContext);
             sourceString = TemplateUtilities.ResolveUrlsFromTextString(sourceString);
+            sourceString = TemplateUtilities.ResolveMediaFromTextString(sourceString);
 
             // ensure string is parsed for macros and macros are executed correctly
             sourceString = RenderRteMacros(sourceString, preview);
diff --git a/src/Umbraco.Web/Templates/TemplateUtilities.cs b/src/Umbraco.Web/Templates/TemplateUtilities.cs
index 6da133413d..6c979e9a95 100644
--- a/src/Umbraco.Web/Templates/TemplateUtilities.cs
+++ b/src/Umbraco.Web/Templates/TemplateUtilities.cs
@@ -75,6 +75,9 @@ namespace Umbraco.Web.Templates
         private static readonly Regex ResolveUrlPattern = new Regex("(=[\"\']?)(\\W?\\~(?:.(?![\"\']?\\s+(?:\\S+)=|[>\"\']))+.)[\"\']?",
             RegexOptions.Compiled | RegexOptions.IgnoreCase | RegexOptions.IgnorePatternWhitespace);
 
+        private static readonly Regex ResolveImgPattern = new Regex(@"(<img[^>]*src="")([^""\?]*)([^""]*""[^>]*data-udi="")([^""]*)(""[^>]*>)",
+            RegexOptions.Compiled | RegexOptions.IgnoreCase | RegexOptions.IgnorePatternWhitespace);
+
         /// <summary>
         /// The RegEx matches any HTML attribute values that start with a tilde (~), those that match are passed to ResolveUrl to replace the tilde with the application path.
         /// </summary>
@@ -118,5 +121,46 @@ namespace Umbraco.Web.Templates
         {
             return text.CleanForXss(ignoreFromClean);
         }
+
+        /// <summary>
+        /// Parses the string looking for Umbraco image tags and updates them to their up-to-date image sources.
+        /// </summary>
+        /// <param name="text"></param>
+        /// <returns></returns>
+        /// <remarks>Umbraco image tags are identified by their data-udi attributes</remarks>
+        public static string ResolveMediaFromTextString(string text)
+        {
+            // don't attempt to proceed without a context
+            if (Current.UmbracoContext == null || Current.UmbracoContext.MediaCache == null)
+            {
+                return text;
+            }
+
+            return ResolveImgPattern.Replace(text, match =>
+            {
+                // match groups:
+                // - 1 = from the beginning of the image tag until src attribute value begins
+                // - 2 = the src attribute value excluding the querystring (if present)
+                // - 3 = anything after group 2 and before the data-udi attribute value begins
+                // - 4 = the data-udi attribute value
+                // - 5 = anything after group 4 until the image tag is closed
+                var src = match.Groups[2].Value;
+                var udi = match.Groups[4].Value;
+                if(src.IsNullOrWhiteSpace() || udi.IsNullOrWhiteSpace() || GuidUdi.TryParse(udi, out var guidUdi) == false)
+                {
+                    return match.Value;
+                }
+                var media = Current.UmbracoContext.MediaCache.GetById(guidUdi.Guid);
+                if(media == null)
+                {
+                    // image does not exist - we could choose to remove the image entirely here (return empty string),
+                    // but that would leave the editors completely in the dark as to why the image doesn't show
+                    return match.Value;
+                }
+
+                var url = media.Url;
+                return $"{match.Groups[1].Value}{url}{match.Groups[3].Value}{udi}{match.Groups[5].Value}";
+            });
+        }
     }
 }