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 35593d3ab0c7..054fcb7d1323 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
@@ -3181,6 +3181,11 @@ public void onAddMediaClicked() {
         }
     }
 
+    @Override
+    public void onAddPhotoClicked() {
+        onPhotoPickerIconClicked(PhotoPickerIcon.ANDROID_CHOOSE_PHOTO);
+    }
+
     @Override
     public void onMediaDropped(final ArrayList<Uri> mediaUris) {
         mDroppedMediaUris = mediaUris;
diff --git a/libs/editor/WordPressEditor/src/main/java/org/wordpress/android/editor/EditorFragmentAbstract.java b/libs/editor/WordPressEditor/src/main/java/org/wordpress/android/editor/EditorFragmentAbstract.java
index 21b1d899c6a3..09c1265d10e8 100644
--- a/libs/editor/WordPressEditor/src/main/java/org/wordpress/android/editor/EditorFragmentAbstract.java
+++ b/libs/editor/WordPressEditor/src/main/java/org/wordpress/android/editor/EditorFragmentAbstract.java
@@ -179,6 +179,7 @@ public interface EditorFragmentListener {
         void onEditorFragmentInitialized();
         void onSettingsClicked();
         void onAddMediaClicked();
+        void onAddPhotoClicked();
         boolean onMediaRetryClicked(String mediaId);
         void onMediaUploadCancelClicked(String mediaId);
         void onMediaDeleted(String mediaId);
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 215e7899491e..43c9d3cebd40 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
@@ -20,6 +20,7 @@
 import android.view.ViewGroup;
 import android.view.WindowManager;
 import android.view.inputmethod.InputMethodManager;
+import android.webkit.URLUtil;
 
 import com.android.volley.toolbox.ImageLoader;
 
@@ -108,9 +109,14 @@ public View onCreateView(LayoutInflater inflater, ViewGroup container, Bundle sa
                 view.findViewById(R.id.gutenberg),
                 mHtmlModeEnabled,
                 new OnMediaLibraryButtonListener() {
-                    @Override public void onMediaLibraryButtonClick() {
+                    @Override public void onMediaLibraryButtonClicked() {
                         onToolbarMediaButtonClicked();
                     }
+
+                    @Override
+                    public void onUploadMediaButtonClicked() {
+                        mEditorFragmentListener.onAddPhotoClicked();
+                    }
                 },
                 getActivity().getApplication(),
                 BuildConfig.DEBUG,
@@ -444,7 +450,11 @@ public void appendMediaFile(final MediaFile mediaFile, final String mediaUrl, Im
             return;
         }
 
-        mWPAndroidGlueCode.appendMediaFile(mediaUrl);
+        if (URLUtil.isNetworkUrl(mediaUrl)) {
+            mWPAndroidGlueCode.appendMediaFile(mediaUrl);
+        } else {
+            mWPAndroidGlueCode.appendUploadMediaFile(String.valueOf(mediaFile.getId()), "file://" + mediaUrl);
+        }
     }
 
     @Override
@@ -496,15 +506,18 @@ public void onMediaUploadRetry(String localId, MediaType mediaType) {
 
     @Override
     public void onMediaUploadSucceeded(final String localMediaId, final MediaFile mediaFile) {
+        mWPAndroidGlueCode.mediaFileUploadSucceeded(localMediaId, mediaFile.getFileURL());
     }
 
     @Override
     public void onMediaUploadProgress(final String localMediaId, final float progress) {
+        mWPAndroidGlueCode.mediaFileUploadProgress(localMediaId, progress);
     }
 
     @Override
     public void onMediaUploadFailed(final String localMediaId, final MediaType
             mediaType, final String errorMessage) {
+        mWPAndroidGlueCode.mediaFileUploadFailed(localMediaId);
     }
 
     @Override
diff --git a/libs/gutenberg-mobile b/libs/gutenberg-mobile
index 18042baa0e55..15dfe2b88593 160000
--- a/libs/gutenberg-mobile
+++ b/libs/gutenberg-mobile
@@ -1 +1 @@
-Subproject commit 18042baa0e550e9484bcf35faca2a9c062de7217
+Subproject commit 15dfe2b88593e93765401ef0ac314e4842431fe6