diff --git a/WordPress/Classes/Services/MediaCoordinator.swift b/WordPress/Classes/Services/MediaCoordinator.swift
index 51fb39421019..6dd41a8c1142 100644
--- a/WordPress/Classes/Services/MediaCoordinator.swift
+++ b/WordPress/Classes/Services/MediaCoordinator.swift
@@ -5,11 +5,7 @@ import WordPressFlux
 /// items, independently of a specific view controller. It should be accessed
 /// via the `shared` singleton.
 ///
-class MediaCoordinator: NSObject, Uploader {
-    func resume() {
-    }
-
-
+class MediaCoordinator: NSObject {
     @objc static let shared = MediaCoordinator()
 
     private(set) var backgroundContext: NSManagedObjectContext = {
@@ -606,6 +602,20 @@ extension MediaCoordinator: MediaProgressCoordinatorDelegate {
     }
 }
 
+extension MediaCoordinator: Uploader {
+    func resume() {
+        let service = MediaService(managedObjectContext: mainContext)
+
+        service.getFailedMedia { [weak self] media in
+            guard let self = self else {
+                return
+            }
+
+            media.forEach() { self.retryMedia($0) }
+        }
+    }
+}
+
 extension Media {
     var uploadID: String {
         return objectID.uriRepresentation().absoluteString
diff --git a/WordPress/Classes/Services/MediaService.h b/WordPress/Classes/Services/MediaService.h
index 7bdccb53987c..c993e8d103fd 100644
--- a/WordPress/Classes/Services/MediaService.h
+++ b/WordPress/Classes/Services/MediaService.h
@@ -37,6 +37,12 @@ typedef NS_ERROR_ENUM(MediaServiceErrorDomain, MediaServiceError) {
                  thumbnailCallback:(nullable void (^)(Media * __nonnull media, NSURL * __nonnull thumbnailURL))thumbnailCallback
                         completion:(nullable void (^)(Media * __nullable media, NSError * __nullable error))completion;
 
+/**
+ Get all Media that failed to upload.
+ 
+ @param result a block that will be invoked to return the requested media.
+ */
+- (void)getFailedMedia:(nonnull void (^)( NSArray<Media *>* _Nonnull media))result;
 
 /**
  Get the Media object from the server using the blog and the mediaID as the identifier of the resource
diff --git a/WordPress/Classes/Services/MediaService.m b/WordPress/Classes/Services/MediaService.m
index f2103300cacd..ee6c19d9ced1 100644
--- a/WordPress/Classes/Services/MediaService.m
+++ b/WordPress/Classes/Services/MediaService.m
@@ -509,6 +509,24 @@ - (void)deleteMedia:(nonnull NSArray<Media *> *)mediaObjects
 
 #pragma mark - Getting media
 
+- (void)getFailedMedia:(void (^)( NSArray<Media *>* media))result {
+    [self.managedObjectContext performBlock:^{
+        NSString *entityName = NSStringFromClass([Media class]);
+        NSFetchRequest *request = [NSFetchRequest fetchRequestWithEntityName:entityName];
+        
+        request.predicate = [NSPredicate predicateWithFormat:@"remoteStatusNumber == %d", MediaRemoteStatusFailed];
+        
+        NSError *error = nil;
+        NSArray *results = [self.managedObjectContext executeFetchRequest:request error:&error];
+        
+        if (!results) {
+            result(@[]);
+        } else {
+            result(results);
+        }
+    }];
+}
+
 - (void) getMediaWithID:(NSNumber *) mediaID inBlog:(Blog *) blog
                 success:(void (^)(Media *media))success
                 failure:(void (^)(NSError *error))failure
diff --git a/WordPress/Classes/Services/PostCoordinator.swift b/WordPress/Classes/Services/PostCoordinator.swift
index d555b727f9ea..fb5785da8b00 100644
--- a/WordPress/Classes/Services/PostCoordinator.swift
+++ b/WordPress/Classes/Services/PostCoordinator.swift
@@ -248,9 +248,14 @@ class PostCoordinator: NSObject {
 
 extension PostCoordinator: Uploader {
     func resume() {
-        // Resume the upload of all posts that are not synched.
-        //
-        // 1. Query posts with status == .failed
-        // 2. Call retrySave() for each post
+        let service = PostService(managedObjectContext: mainContext)
+
+        service.getFailedPosts { [weak self] posts in
+            guard let self = self else {
+                return
+            }
+
+            posts.forEach() { self.retrySave(of: $0 ) }
+        }
     }
 }
diff --git a/WordPress/Classes/Services/PostService.h b/WordPress/Classes/Services/PostService.h
index 7ae2ad6fad02..f9b20b36fed9 100644
--- a/WordPress/Classes/Services/PostService.h
+++ b/WordPress/Classes/Services/PostService.h
@@ -43,6 +43,13 @@ extern const NSUInteger PostServiceDefaultNumberToSync;
               success:(void (^)(AbstractPost *post))success
               failure:(void (^)(NSError *))failure;
 
+/**
+ Get all posts that failed to upload.
+ 
+ @param result a block that will be invoked to return the requested posts.
+ */
+- (void)getFailedPosts:(nonnull void (^)( NSArray<AbstractPost *>* _Nonnull posts))result;
+
 /**
  Sync an initial batch of posts from the specified blog.
  Please note that success and/or failure are called in the context of the
diff --git a/WordPress/Classes/Services/PostService.m b/WordPress/Classes/Services/PostService.m
index 664a9b9031ee..8a12ef61575a 100644
--- a/WordPress/Classes/Services/PostService.m
+++ b/WordPress/Classes/Services/PostService.m
@@ -65,6 +65,26 @@ - (Page *)createDraftPageForBlog:(Blog *)blog {
     return page;
 }
 
+
+- (void)getFailedPosts:(void (^)( NSArray<AbstractPost *>* posts))result {
+    [self.managedObjectContext performBlock:^{
+        NSString *entityName = NSStringFromClass([AbstractPost class]);
+        NSFetchRequest *request = [NSFetchRequest fetchRequestWithEntityName:entityName];
+        
+        request.predicate = [NSPredicate predicateWithFormat:@"remoteStatusNumber == %d", AbstractPostRemoteStatusFailed];
+        
+        NSError *error = nil;
+        NSArray *results = [self.managedObjectContext executeFetchRequest:request error:&error];
+        
+        if (!results) {
+            result(@[]);
+        } else {
+            result(results);
+        }
+    }];
+}
+
+
 - (void)getPostWithID:(NSNumber *)postID
               forBlog:(Blog *)blog
               success:(void (^)(AbstractPost *post))success
diff --git a/WordPress/Classes/Uploads/UploadsManager.swift b/WordPress/Classes/Uploads/UploadsManager.swift
index 646ca2c6865e..84f0bf612dd3 100644
--- a/WordPress/Classes/Uploads/UploadsManager.swift
+++ b/WordPress/Classes/Uploads/UploadsManager.swift
@@ -1,24 +1,11 @@
 import Foundation
+import Reachability
 
 /// Takes care of coordinating all uploaders used by the app.
 ///
-@objc
 class UploadsManager: NSObject {
     private let uploaders: [Uploader]
-    private lazy var reachabilityObserver: NSObjectProtocol = {
-        return NotificationCenter.default.addObserver(forName: .reachabilityChanged, object: nil, queue: nil) { [weak self] notification in
-
-            guard let self = self else {
-                return
-            }
-
-            let internetIsReachable = notification.userInfo?[Foundation.Notification.reachabilityKey] as? Bool ?? false
-
-            if internetIsReachable {
-                self.resume()
-            }
-        }
-    }()
+    private let reachability: Reachability = Reachability.forInternetConnection()
 
     // MARK: Initialization & Finalization
 
@@ -31,17 +18,24 @@ class UploadsManager: NSObject {
         self.uploaders = uploaders
 
         super.init()
+
+        setupReachableBlock()
     }
 
-    deinit {
-        NotificationCenter.default.removeObserver(reachabilityObserver)
+    // MARK: Reachability
+
+    private func setupReachableBlock() {
+        reachability.reachableBlock = { _ in
+            self.resume()
+        }
+
+        reachability.startNotifier()
     }
 
     // MARK: Interacting with Uploads
 
     /// Resumes all uploads handled by the uploaders.
     ///
-    @objc
     func resume() {
         for uploader in uploaders {
             uploader.resume()