diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/EditPostActivity.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/EditPostActivity.java
index 62c4cbcab00c..08ab3c6d64e1 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/EditPostActivity.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/EditPostActivity.java
@@ -559,6 +559,9 @@ public void run() {
     }
 
     private void purgeMediaToPostAssociationsIfNotInPostAnymore() {
+        boolean useAztec = AppPrefs.isAztecEditorEnabled();
+        boolean useGutenberg = AppPrefs.isGutenbergEditorEnabled();
+
         ArrayList<MediaModel> allMedia = new ArrayList<>();
         allMedia.addAll(mUploadStore.getFailedMediaForPost(mPost));
         allMedia.addAll(mUploadStore.getCompletedMediaForPost(mPost));
@@ -567,8 +570,16 @@ private void purgeMediaToPostAssociationsIfNotInPostAnymore() {
         if (!allMedia.isEmpty()) {
             HashSet<MediaModel> mediaToDeleteAssociationFor = new HashSet<>();
             for (MediaModel media : allMedia) {
-                if (!AztecEditorFragment.isMediaInPostBody(this, mPost.getContent(), String.valueOf(media.getId()))) {
-                    mediaToDeleteAssociationFor.add(media);
+                if (useAztec) {
+                    if (!AztecEditorFragment.isMediaInPostBody(this,
+                            mPost.getContent(), String.valueOf(media.getId()))) {
+                        mediaToDeleteAssociationFor.add(media);
+                    }
+                } else if (useGutenberg) {
+                    if (!PostUtils.isMediaInGutenbergPostBody(
+                            mPost.getContent(), String.valueOf(media.getId()))) {
+                        mediaToDeleteAssociationFor.add(media);
+                    }
                 }
             }
 
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/PostUtils.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/PostUtils.java
index 045530bbc208..71b517bb1ec8 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/PostUtils.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/PostUtils.java
@@ -1,6 +1,7 @@
 package org.wordpress.android.ui.posts;
 
 import android.content.Context;
+import android.support.annotation.NonNull;
 import android.support.v4.app.FragmentManager;
 import android.text.TextUtils;
 import android.text.format.DateUtils;
@@ -9,6 +10,7 @@
 import org.wordpress.android.R;
 import org.wordpress.android.WordPress;
 import org.wordpress.android.analytics.AnalyticsTracker;
+import org.wordpress.android.editor.Utils;
 import org.wordpress.android.fluxc.model.MediaModel;
 import org.wordpress.android.fluxc.model.PostModel;
 import org.wordpress.android.fluxc.model.SiteModel;
@@ -21,6 +23,7 @@
 import org.wordpress.android.util.HtmlUtils;
 import org.wordpress.android.util.LocaleManager;
 import org.wordpress.android.util.analytics.AnalyticsUtils;
+import org.wordpress.android.util.helpers.MediaFile;
 
 import java.text.BreakIterator;
 import java.text.SimpleDateFormat;
@@ -40,6 +43,9 @@ public class PostUtils {
     private static final HashSet<String> SHORTCODE_TABLE = new HashSet<>();
 
     private static final String GUTENBERG_BLOCK_START = "<!-- wp:";
+    private static final int SRC_ATTRIBUTE_LENGTH_PLUS_ONE = 5;
+    private static final String GB_IMG_BLOCK_HEADER_PLACEHOLDER = "<!-- wp:image {\"id\":%s} -->";
+    private static final String GB_IMG_BLOCK_CLASS_PLACEHOLDER = "class=\"wp-image-%s\"";
 
     /*
      * collapses shortcodes in the passed post content, stripping anything between the
@@ -378,6 +384,55 @@ public static boolean shouldShowGutenbergEditor(boolean isNewPost, PostModel pos
                    || TextUtils.isEmpty(post.getContent()));
     }
 
+    public static String replaceMediaFileWithUrlInGutenbergPost(@NonNull String postContent,
+                                                 String localMediaId, MediaFile mediaFile) {
+        if (mediaFile != null && contentContainsGutenbergBlocks(postContent)) {
+            String remoteUrl = org.wordpress.android.util.StringUtils
+                    .notNullStr(Utils.escapeQuotes(mediaFile.getFileURL()));
+            // TODO: replace the URL
+            if (!mediaFile.isVideo()) {
+                // replace gutenberg block id holder with serverMediaId, and url_holder with remoteUrl
+                String oldImgBlockHeader = String.format(GB_IMG_BLOCK_HEADER_PLACEHOLDER, localMediaId);
+                String newImgBlockHeader = String.format(GB_IMG_BLOCK_HEADER_PLACEHOLDER, mediaFile.getMediaId());
+                postContent = postContent.replace(oldImgBlockHeader, newImgBlockHeader);
+
+                // replace class wp-image-id with serverMediaId, and url_holder with remoteUrl
+                String oldImgClass = String.format(GB_IMG_BLOCK_CLASS_PLACEHOLDER, localMediaId);
+                String newImgClass = String.format(GB_IMG_BLOCK_CLASS_PLACEHOLDER, mediaFile.getMediaId());
+                postContent = postContent.replace(oldImgClass, newImgClass);
+
+                // let's first find this occurrence and keep note of the position, as we need to replace the
+                // immediate `src` value before
+                int iStartOfWpImageClassAttribute = postContent.indexOf(newImgClass);
+                if (iStartOfWpImageClassAttribute != -1) {
+                    // now search negatively, for the src attribute appearing right before
+                    int iStartOfImgTag = postContent.lastIndexOf("<img", iStartOfWpImageClassAttribute);
+                    if (iStartOfImgTag != -1) {
+                        Pattern p = Pattern.compile("<img[^>]*src=[\\\"']([^\\\"^']*)");
+                        Matcher m = p.matcher(postContent.substring(iStartOfImgTag));
+                        if (m.find()) {
+                            String src = m.group();
+                            int startIndex = src.indexOf("src=") + SRC_ATTRIBUTE_LENGTH_PLUS_ONE;
+                            String srcTag = src.substring(startIndex, src.length());
+                            // now replace the url
+                            postContent = postContent.replace(srcTag, remoteUrl);
+                        }
+                    }
+                }
+            } else {
+                // TODO replace in GB Video block?
+            }
+        }
+        return postContent;
+    }
+
+    public static boolean isMediaInGutenbergPostBody(@NonNull String postContent,
+                                            String localMediaId) {
+        // check if media is in Gutenberg Post
+        String imgBlockHeaderToSearchFor = String.format("<!-- wp:image {\"id\":%s} -->", localMediaId);
+        return postContent.indexOf(imgBlockHeaderToSearchFor) != -1;
+    }
+
     public static boolean isPostInConflictWithRemote(PostModel post) {
         // at this point we know there's a potential version conflict (the post has been modified
         // both locally and on the remote)
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/uploads/MediaUploadReadyProcessor.java b/WordPress/src/main/java/org/wordpress/android/ui/uploads/MediaUploadReadyProcessor.java
index 1b9f6bc976c4..b18bbcd1d83f 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/uploads/MediaUploadReadyProcessor.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/uploads/MediaUploadReadyProcessor.java
@@ -7,6 +7,7 @@
 import org.wordpress.android.editor.EditorFragment;
 import org.wordpress.android.fluxc.model.PostModel;
 import org.wordpress.android.ui.media.services.MediaUploadReadyListener;
+import org.wordpress.android.ui.posts.PostUtils;
 import org.wordpress.android.ui.prefs.AppPrefs;
 import org.wordpress.android.util.helpers.MediaFile;
 
@@ -17,8 +18,12 @@ public PostModel replaceMediaFileWithUrlInPost(@Nullable PostModel post, String
         if (post != null) {
             boolean showAztecEditor = AppPrefs.isAztecEditorEnabled();
             boolean showNewEditor = AppPrefs.isVisualEditorEnabled();
+            boolean showGutenbergEditor = AppPrefs.isGutenbergEditorEnabled();
 
-            if (showAztecEditor) {
+            if (showGutenbergEditor) {
+                post.setContent(
+                        PostUtils.replaceMediaFileWithUrlInGutenbergPost(post.getContent(), localMediaId, mediaFile));
+            } else if (showAztecEditor) {
                 post.setContent(AztecEditorFragment.replaceMediaFileWithUrl(WordPress.getContext(), post.getContent(),
                                                                             localMediaId, mediaFile));
             } else if (showNewEditor) {
@@ -36,8 +41,11 @@ public PostModel markMediaUploadFailedInPost(@Nullable PostModel post, String lo
         if (post != null) {
             boolean showAztecEditor = AppPrefs.isAztecEditorEnabled();
             boolean showNewEditor = AppPrefs.isVisualEditorEnabled();
+            boolean showGutenbergEditor = AppPrefs.isGutenbergEditorEnabled();
 
-            if (showAztecEditor) {
+            if (showGutenbergEditor) {
+                // TODO check if anything needs be done in Gutenberg
+            } else if (showAztecEditor) {
                 post.setContent(AztecEditorFragment.markMediaFailed(WordPress.getContext(), post.getContent(),
                                                                     localMediaId, mediaFile));
             } else if (showNewEditor) {
diff --git a/libs/editor/WordPressEditor/src/main/java/org/wordpress/android/editor/GutenbergEditorFragment.java b/libs/editor/WordPressEditor/src/main/java/org/wordpress/android/editor/GutenbergEditorFragment.java
index 106a2c754697..4bdf34aca937 100644
--- a/libs/editor/WordPressEditor/src/main/java/org/wordpress/android/editor/GutenbergEditorFragment.java
+++ b/libs/editor/WordPressEditor/src/main/java/org/wordpress/android/editor/GutenbergEditorFragment.java
@@ -45,7 +45,6 @@ public class GutenbergEditorFragment extends EditorFragmentAbstract implements
         EditorMediaUploadListener,
         IHistoryListener {
     private static final String KEY_HTML_MODE_ENABLED = "KEY_HTML_MODE_ENABLED";
-    private static final String GUTENBERG_BLOCK_START = "<!-- wp:";
     private static final String ARG_IS_NEW_POST = "param_is_new_post";
 
     private static boolean mIsToolbarExpanded = false;
@@ -345,29 +344,6 @@ private void toggleHtmlMode() {
         mWPAndroidGlueCode.toggleEditorMode();
     }
 
-    /*
-        Note the way we detect we're in presence of Gutenberg blocks logic is taken from
-        https://github.com/WordPress/gutenberg/blob/5a6693589285363341bebad15bd56d9371cf8ecc/lib/register.php#L331-L345
-
-        * Determine whether a content string contains blocks. This test optimizes for
-        * performance rather than strict accuracy, detecting the pattern of a block
-        * but not validating its structure. For strict accuracy, you should use the
-        * block parser on post content.
-        *
-        * @since 1.6.0
-        * @see gutenberg_parse_blocks()
-        *
-        * @param string $content Content to test.
-        * @return bool Whether the content contains blocks.
-
-        function gutenberg_content_has_blocks( $content ) {
-            return false !== strpos( $content, '<!-- wp:' );
-        }
-     */
-    public static boolean contentContainsGutenbergBlocks(String postContent) {
-        return (postContent != null && postContent.contains(GUTENBERG_BLOCK_START));
-    }
-
     /*
     * TODO: REMOVE THIS ONCE AZTEC COMPLETELY REPLACES THE VISUAL EDITOR IN WPANDROID APP
      */