diff --git a/WordPress/Classes/Services/PostCoordinator.swift b/WordPress/Classes/Services/PostCoordinator.swift
index de08dcd4b403..2ea04cc4724e 100644
--- a/WordPress/Classes/Services/PostCoordinator.swift
+++ b/WordPress/Classes/Services/PostCoordinator.swift
@@ -452,6 +452,9 @@ class PostCoordinator: NSObject {
             retryDelay = min(32, retryDelay * 1.5)
             return retryDelay
         }
+        func setLongerDelay() {
+            retryDelay = max(retryDelay, 20)
+        }
         var retryDelay: TimeInterval
         weak var retryTimer: Timer?
 
@@ -509,10 +512,11 @@ class PostCoordinator: NSObject {
     }
 
     private func startSync(for post: AbstractPost) {
-        guard let revision = post.getLatestRevisionNeedingSync() else {
-            let worker = getWorker(for: post)
+        if let worker = workers[post.objectID], worker.error != nil {
             worker.error = nil
             postDidUpdateNotification(for: post)
+        }
+        guard let revision = post.getLatestRevisionNeedingSync() else {
             return DDLogInfo("sync: \(post.objectID.shortDescription) is already up to date")
         }
         startSync(for: post, revision: revision)
@@ -610,14 +614,16 @@ class PostCoordinator: NSObject {
             worker.error = error
             postDidUpdateNotification(for: operation.post)
 
-            if !PostCoordinator.isTerminalError(error) {
-                let delay = worker.nextRetryDelay
-                worker.retryTimer = Timer.scheduledTimer(withTimeInterval: delay, repeats: false) { [weak self, weak worker] _ in
-                    guard let self, let worker else { return }
-                    self.didRetryTimerFire(for: worker)
-                }
-                worker.log("scheduled retry with delay: \(delay)s.")
+            if PostCoordinator.isTerminalError(error) {
+                worker.setLongerDelay()
+            }
+
+            let delay = worker.nextRetryDelay
+            worker.retryTimer = Timer.scheduledTimer(withTimeInterval: delay, repeats: false) { [weak self, weak worker] _ in
+                guard let self, let worker else { return }
+                self.didRetryTimerFire(for: worker)
             }
+            worker.log("scheduled retry with delay: \(delay)s.")
 
             if let error = error as? PostRepository.PostSaveError, case .deleted = error {
                 operation.log("post was permanently deleted")
diff --git a/WordPress/Classes/ViewRelated/Post/PostEditor.swift b/WordPress/Classes/ViewRelated/Post/PostEditor.swift
index 0016190ac30e..f86694d5d20d 100644
--- a/WordPress/Classes/ViewRelated/Post/PostEditor.swift
+++ b/WordPress/Classes/ViewRelated/Post/PostEditor.swift
@@ -147,6 +147,7 @@ extension PostEditor where Self: UIViewController {
             showPostTrashedOverlay()
         } else {
             showAutosaveAvailableAlertIfNeeded()
+            showTerminalUploadErrorAlertIfNeeded()
         }
 
         var cancellables: [AnyCancellable] = []
@@ -273,6 +274,39 @@ extension PostEditor where Self: UIViewController {
         self.post = post // Even if it's the same instance, it's how you currently refresh the editor
         self.createRevisionOfPost()
     }
+
+    // MARK: - Failed Media Uploads
+
+    private func showTerminalUploadErrorAlertIfNeeded() {
+        let hasTerminalError = post.media.contains {
+            guard let error = $0.error else { return false }
+            return MediaCoordinator.isTerminalError(error)
+        }
+        if hasTerminalError {
+            let notice = Notice(title: Strings.failingMediaUploadsMessage, feedbackType: .error, actionTitle: Strings.failingMediaUploadsViewAction, actionHandler: { [weak self] _ in
+                self?.showMediaUploadDetails()
+            })
+            DispatchQueue.main.asyncAfter(deadline: .now() + .milliseconds(700)) {
+                ActionDispatcherFacade().dispatch(NoticeAction.post(notice))
+            } // Delay to let the editor show first
+        }
+    }
+
+    private func showMediaUploadDetails() {
+        let viewController = PostMediaUploadsViewController(post: post)
+        let nav = UINavigationController(rootViewController: viewController)
+        nav.navigationBar.isTranslucent = true // Reset to default
+        viewController.navigationItem.leftBarButtonItem = UIBarButtonItem(systemItem: .close, primaryAction: UIAction { [weak self] _ in
+            self?.dismiss(animated: true)
+        })
+        if let sheetController = nav.sheetPresentationController {
+            sheetController.detents = [.medium(), .large()]
+            sheetController.prefersGrabberVisible = true
+            sheetController.preferredCornerRadius = 16
+            nav.additionalSafeAreaInsets = UIEdgeInsets(top: 8, left: 0, bottom: 0, right: 0)
+        }
+        self.present(nav, animated: true)
+    }
 }
 
 private var cancellablesKey: UInt8 = 0
@@ -305,4 +339,8 @@ private enum Strings {
     static let trashedPostSheetCancel = NSLocalizedString("postEditor.recoverTrashedPostAlert.cancel", value: "Cancel", comment: "Editor, alert for recovering a trashed post")
     static let trashedPostSheetRecover = NSLocalizedString("postEditor.recoverTrashedPostAlert.restore", value: "Restore", comment: "Editor, alert for recovering a trashed post")
     static let trashedPostRestored = NSLocalizedString("postEditor.recoverTrashedPost.postRecoveredNoticeTitle", value: "Post restored as a draft", comment: "Editor, notice for successful recovery a trashed post")
+
+    static let failingMediaUploadsMessage = NSLocalizedString("postEditor.postHasFailingMediaUploadsSnackbar.message", value: "Some media items failed to upload", comment: "A message for a snackbar informing the user that some media files requires their attention")
+
+    static let failingMediaUploadsViewAction = NSLocalizedString("postEditor.postHasFailingMediaUploadsSnackbar.actionView", value: "View", comment: "A 'View' action for a snackbar informing the user that some media files requires their attention")
 }
diff --git a/WordPress/Classes/ViewRelated/Post/PostMediaUploadsView.swift b/WordPress/Classes/ViewRelated/Post/PostMediaUploadsView.swift
index a9e4f4a306e3..22818819b471 100644
--- a/WordPress/Classes/ViewRelated/Post/PostMediaUploadsView.swift
+++ b/WordPress/Classes/ViewRelated/Post/PostMediaUploadsView.swift
@@ -1,6 +1,19 @@
 import Foundation
 import SwiftUI
 
+final class PostMediaUploadsViewController: UIHostingController<PostMediaUploadsView> {
+    private let viewModel: PostMediaUploadsViewModel
+
+    init(post: AbstractPost) {
+        self.viewModel = PostMediaUploadsViewModel(post: post) // Manange lifecycle
+        super.init(rootView: PostMediaUploadsView(viewModel: viewModel))
+    }
+
+    required dynamic init?(coder aDecoder: NSCoder) {
+        fatalError("init(coder:) has not been implemented")
+    }
+}
+
 /// Displays upload progress for the media for the given post.
 struct PostMediaUploadsView: View {
     @ObservedObject var viewModel: PostMediaUploadsViewModel