diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/services/PostUploadNotifier.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/services/PostUploadNotifier.java
index 3f1077408df1..a20070bc1651 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/services/PostUploadNotifier.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/services/PostUploadNotifier.java
@@ -7,6 +7,7 @@
 import android.content.Intent;
 import android.graphics.Bitmap;
 import android.graphics.BitmapFactory;
+import android.support.annotation.NonNull;
 import android.support.v4.app.NotificationCompat;
 import android.text.TextUtils;
 import android.util.SparseArray;
@@ -20,6 +21,7 @@
 import org.wordpress.android.ui.posts.PostsListActivity;
 import org.wordpress.android.util.AppLog;
 import org.wordpress.android.util.CrashlyticsUtils;
+import org.wordpress.android.util.StringUtils;
 import org.wordpress.android.util.SystemServiceFactory;
 import org.wordpress.android.util.WPMeShortlinks;
 
@@ -53,10 +55,8 @@ public PostUploadNotifier(Context context, PostUploadService service) {
         mNotificationBuilder.setSmallIcon(android.R.drawable.stat_sys_upload);
     }
 
-    public void updateNotificationNewPost(PostModel post, String title, String message) {
-        if (title != null) {
-            mNotificationBuilder.setContentTitle(title);
-        }
+    public void createNotificationForPost(@NonNull PostModel post, String message) {
+        mNotificationBuilder.setContentTitle(buildNotificationTitleForPost(post));
         if (message != null) {
             mNotificationBuilder.setContentText(message);
         }
@@ -68,6 +68,16 @@ public void updateNotificationNewPost(PostModel post, String title, String messa
         mService.startForeground(notificationId, mNotificationBuilder.build());
     }
 
+    public boolean isDisplayingNotificationForPost(@NonNull PostModel post) {
+        return mPostIdToNotificationData.get(post.getId()) != null;
+    }
+
+    public void updateNotificationMessage(@NonNull PostModel post, String message) {
+        NotificationData notificationData = mPostIdToNotificationData.get(post.getId());
+        mNotificationBuilder.setContentText(StringUtils.notNullStr(message));
+        doNotify(notificationData.notificationId, mNotificationBuilder.build());
+    }
+
     public void updateNotificationIcon(PostModel post, Bitmap icon) {
         NotificationData notificationData = mPostIdToNotificationData.get(post.getId());
 
@@ -231,4 +241,9 @@ public void setCurrentMediaItem(PostModel post, int currentItem) {
         mNotificationBuilder.setContentText(String.format(mContext.getString(R.string.uploading_total),
                 currentItem, notificationData.totalMediaItems));
     }
+
+    private String buildNotificationTitleForPost(PostModel post) {
+        String postTitle = TextUtils.isEmpty(post.getTitle()) ? mContext.getString(R.string.untitled) : post.getTitle();
+        return String.format(mContext.getString(R.string.posting_post), postTitle);
+    }
 }
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/services/PostUploadService.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/services/PostUploadService.java
index 0eb89c0aab7f..39c9f619a31c 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/services/PostUploadService.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/services/PostUploadService.java
@@ -167,6 +167,7 @@ public int onStartCommand(Intent intent, int flags, int startId) {
         }
 
         uploadNextPost();
+        showNotificationsForPendingMediaPosts();
         // We want this service to continue running until it is explicitly stopped, so return sticky.
         return START_STICKY;
     }
@@ -214,6 +215,16 @@ private PostModel getNextUploadablePost() {
         return null;
     }
 
+    private void showNotificationsForPendingMediaPosts() {
+        for (PostModel postModel : mPostsList) {
+            if (MediaUploadService.hasPendingMediaUploadsForPost(postModel)) {
+                if (!mPostUploadNotifier.isDisplayingNotificationForPost(postModel)) {
+                    mPostUploadNotifier.createNotificationForPost(postModel, getString(R.string.uploading_post_media));
+                }
+            }
+        }
+    }
+
     /**
      * Removes a post from the queued post list given its local ID.
      * @return the post that was removed - if no post was removed, returns null
@@ -266,14 +277,16 @@ protected void onPostExecute(Boolean pushActionWasDispatched) {
         protected Boolean doInBackground(PostModel... posts) {
             mPost = posts[0];
 
-            String postTitle = TextUtils.isEmpty(mPost.getTitle()) ? getString(R.string.untitled) : mPost.getTitle();
-            String uploadingPostTitle = String.format(getString(R.string.posting_post), postTitle);
             String uploadingPostMessage = String.format(
                     getString(R.string.sending_content),
                     mPost.isPage() ? getString(R.string.page).toLowerCase() : getString(R.string.post).toLowerCase()
             );
 
-            mPostUploadNotifier.updateNotificationNewPost(mPost, uploadingPostTitle, uploadingPostMessage);
+            if (mPostUploadNotifier.isDisplayingNotificationForPost(mPost)) {
+                mPostUploadNotifier.updateNotificationMessage(mPost, uploadingPostMessage);
+            } else {
+                mPostUploadNotifier.createNotificationForPost(mPost, uploadingPostMessage);
+            }
 
             mSite = mSiteStore.getSiteByLocalId(mPost.getLocalSiteId());
             if (mSite == null) {
@@ -606,11 +619,14 @@ private String uploadImageFile(MediaFile mediaFile, SiteModel site) {
         }
     }
 
-    private void cancelPostUploadMatchingMedia(MediaModel media) {
+    private void cancelPostUploadMatchingMedia(MediaModel media, String mediaErrorMessage) {
         PostModel postToCancel = removeQueuedPostByLocalId(media.getLocalPostId());
         if (postToCancel == null) return;
 
-        // TODO: Update post upload messaging at this point
+        SiteModel site = mSiteStore.getSiteByLocalId(postToCancel.getLocalSiteId());
+        String message = getErrorMessage(postToCancel, mediaErrorMessage);
+        mPostUploadNotifier.updateNotificationError(postToCancel, site, message, true);
+
         mFirstPublishPosts.remove(postToCancel.getId());
         EventBus.getDefault().post(new PostEvents.PostUploadCanceled(postToCancel.getLocalSiteId()));
         finishUpload();
@@ -705,14 +721,15 @@ private void handleMediaUploadCompleted(OnMediaUploaded event) {
         if (event.isError()) {
             AppLog.e(T.MEDIA, "Media upload failed for post " + event.media.getLocalPostId() + " : " +
                     event.error.type + ": " + event.error.message);
-            cancelPostUploadMatchingMedia(event.media);
+            String errorMessage = getErrorMessageFromMediaError(event.error);
+            cancelPostUploadMatchingMedia(event.media, errorMessage);
             return;
         }
 
         if (event.canceled) {
             AppLog.i(T.MEDIA, "Upload cancelled for post with id " + event.media.getLocalPostId()
                             + " - a media upload for this post has been cancelled, id: " + event.media.getId());
-            cancelPostUploadMatchingMedia(event.media);
+            cancelPostUploadMatchingMedia(event.media, getString(R.string.error_media_canceled));
             return;
         }
 
diff --git a/WordPress/src/main/res/values/strings.xml b/WordPress/src/main/res/values/strings.xml
index d8813ce2aebb..a64468971a34 100644
--- a/WordPress/src/main/res/values/strings.xml
+++ b/WordPress/src/main/res/values/strings.xml
@@ -391,6 +391,7 @@
     <string name="update_verb">Update</string>
     <string name="sending_content">Uploading %s content</string>
     <string name="uploading_total">Uploading %1$d of %2$d</string>
+    <string name="uploading_post_media">Uploading media…</string>
 
     <!-- new account view -->
     <string name="signing_in">Logging in…</string>
@@ -1090,6 +1091,7 @@
     <string name="error_media_load">Unable to load media</string>
     <string name="error_media_request_too_large">Media too large, can\'t be uploaded</string>
     <string name="error_media_save">Unable to save media</string>
+    <string name="error_media_canceled">Uploading media were canceled</string>
     <string name="error_blog_hidden">This blog is hidden and couldn\'t be loaded. Enable it again in settings and try again.</string>
     <string name="fatal_db_error">An error occurred while creating the app database. Try reinstalling the app.</string>
     <string name="error_copy_to_clipboard">An error occurred while copying text to clipboard</string>