diff --git a/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.ChatWithTranscriptModel.swift b/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.ChatWithTranscriptModel.swift
index 51092cc67..96b4d5813 100644
--- a/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.ChatWithTranscriptModel.swift
+++ b/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.ChatWithTranscriptModel.swift
@@ -117,7 +117,7 @@ extension SecureConversations.ChatWithTranscriptModel {
             guard let index = section.items
                 .enumerated()
                 .first(where: {
-                    guard case .outgoingMessage(let message) = $0.element.kind else { return false }
+                    guard case .outgoingMessage(let message, _) = $0.element.kind else { return false }
                     return message.payload.messageId == outgoingMessage.payload.messageId
                 })?.offset
             else { return }
@@ -197,7 +197,7 @@ extension SecureConversations.ChatWithTranscriptModel {
             messageId: ChatMessage.MessageId
         ) -> Bool {
             switch chatItem.kind {
-            case let .outgoingMessage(outgoingMessage):
+            case let .outgoingMessage(outgoingMessage, _):
                 return outgoingMessage.payload.messageId.rawValue.uppercased() == messageId.uppercased()
             case let .visitorMessage(message, _):
                 return message.id.uppercased() == messageId.uppercased()
@@ -311,6 +311,51 @@ extension SecureConversations.ChatWithTranscriptModel {
     }
     // swiftlint:enable function_body_length
 
+    // TODO: - This will be covered with unit tests in next PR
+    static func markMessageAsFailed(
+        _ outgoingMessage: OutgoingMessage,
+        in section: Section<ChatItem>,
+        message: String,
+        action: ActionCallback?
+    ) {
+        guard let index = section.items
+            .enumerated()
+            .first(where: { _, element in
+                Self.chatItemMatchesMessageId(
+                    chatItem: element,
+                    messageId: outgoingMessage.payload.messageId.rawValue
+                )
+            })?.offset
+        else { return }
+
+        let item = ChatItem(kind: .outgoingMessage(
+            outgoingMessage,
+            error: message
+        ))
+        section.replaceItem(at: index, with: item)
+        action?(.refreshRows([index], in: section.index, animated: false))
+    }
+
+    // TODO: - This will be covered with unit tests in next PR
+    static func removeMessage(
+        _ outgoingMessage: OutgoingMessage,
+        in section: Section<ChatItem>,
+        action: ActionCallback?
+    ) {
+        guard let index = section.items
+            .enumerated()
+            .first(where: { _, element in
+                Self.chatItemMatchesMessageId(
+                    chatItem: element,
+                    messageId: outgoingMessage.payload.messageId.rawValue
+                )
+            })?.offset
+        else { return }
+
+        section.removeItem(at: index)
+        action?(.deleteRows([index], in: section.index, animated: true))
+    }
+
     static private func shouldShowOperatorImage(
         for row: Int,
         in section: Section<ChatItem>
diff --git a/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.TranscriptModel.GVA.swift b/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.TranscriptModel.GVA.swift
index 8ae1e0206..3c2c52a76 100644
--- a/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.TranscriptModel.GVA.swift
+++ b/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.TranscriptModel.GVA.swift
@@ -100,7 +100,7 @@ private extension SecureConversations.TranscriptModel {
         let outgoingMessage = OutgoingMessage(payload: payload)
 
         appendItem(
-            .init(kind: .outgoingMessage(outgoingMessage)),
+            .init(kind: .outgoingMessage(outgoingMessage, error: nil)),
             to: pendingSection,
             animated: true
         )
diff --git a/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.TranscriptModel.swift b/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.TranscriptModel.swift
index b842f6287..3a29c149f 100644
--- a/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.TranscriptModel.swift
+++ b/GliaWidgets/SecureConversations/ChatTranscript/SecureConversations.TranscriptModel.swift
@@ -211,6 +211,9 @@ extension SecureConversations {
                 break
             case let .gvaButtonTapped(option):
                 gvaOptionAction(for: option)()
+            case let .retryMessageTapped(message):
+                // Will be handled in next PR
+                break
             }
         }
 
@@ -265,7 +268,7 @@ extension SecureConversations.TranscriptModel {
         )
 
         appendItem(
-            .init(kind: .outgoingMessage(outgoingMessage)),
+            .init(kind: .outgoingMessage(outgoingMessage, error: nil)),
             to: pendingSection,
             animated: true
         )
diff --git a/GliaWidgets/Sources/Coordinators/Chat/ChatCoordinator.swift b/GliaWidgets/Sources/Coordinators/Chat/ChatCoordinator.swift
index 7790a57f3..3d1e7de97 100644
--- a/GliaWidgets/Sources/Coordinators/Chat/ChatCoordinator.swift
+++ b/GliaWidgets/Sources/Coordinators/Chat/ChatCoordinator.swift
@@ -162,6 +162,7 @@ extension ChatCoordinator {
             isWindowVisible: isWindowVisible,
             startAction: startAction,
             deliveredStatusText: viewFactory.theme.chat.visitorMessageStyle.delivered,
+            failedToDeliverStatusText: viewFactory.theme.chat.visitorMessageStyle.failedToDeliver,
             chatType: chatType,
             environment: .create(
                 with: environment,
diff --git a/GliaWidgets/Sources/Extensions/UITableView+Extensions.swift b/GliaWidgets/Sources/Extensions/UITableView+Extensions.swift
index a2cde55a7..73fa081a8 100644
--- a/GliaWidgets/Sources/Extensions/UITableView+Extensions.swift
+++ b/GliaWidgets/Sources/Extensions/UITableView+Extensions.swift
@@ -45,4 +45,20 @@ internal extension UITableView {
             self.scrollToRow(at: indexPath, at: .bottom, animated: animated)
         }
     }
+
+    func deleteRows(_ rows: [Int], in section: Int, animated: Bool) {
+        let refreshBlock = {
+            self.beginUpdates()
+            let indexPaths = rows.map { IndexPath(row: $0, section: section) }
+            self.deleteRows(at: indexPaths, with: .fade)
+            self.endUpdates()
+        }
+        if animated {
+            refreshBlock()
+        } else {
+            UIView.performWithoutAnimation {
+                refreshBlock()
+            }
+        }
+    }
 }
diff --git a/GliaWidgets/Sources/View/Chat/ChatView.swift b/GliaWidgets/Sources/View/Chat/ChatView.swift
index bb545c84b..27f661142 100644
--- a/GliaWidgets/Sources/View/Chat/ChatView.swift
+++ b/GliaWidgets/Sources/View/Chat/ChatView.swift
@@ -24,6 +24,7 @@ class ChatView: EngagementView {
     var linkTapped: ((URL) -> Void)?
     var selectCustomCardOption: ((HtmlMetadata.Option, MessageRenderer.Message.Identifier) -> Void)?
     var gvaButtonTapped: ((GvaOption) -> Void)?
+    var retryMessageTapped: ((OutgoingMessage) -> Void)?
 
     let style: ChatStyle
     let environment: Environment
@@ -310,6 +311,10 @@ extension ChatView {
         }
     }
 
+    func deleteRows(_ rows: [Int], in section: Int, animated: Bool) {
+        tableView.deleteRows(rows, in: section, animated: animated)
+    }
+
     func refreshAll() {
         tableView.reloadData()
     }
@@ -345,8 +350,8 @@ extension ChatView {
         switch item.kind {
         case .queueOperator:
             return .queueOperator(connectView)
-        case let .outgoingMessage(message):
-            return outgoingMessageContent(message)
+        case let .outgoingMessage(message, error):
+            return outgoingMessageContent(message, error: error)
         case let .visitorMessage(message, status):
             return visitorMessageContent(message, status: status)
         case let .operatorMessage(message, showsImage, imageUrl):
@@ -667,7 +672,10 @@ extension ChatView {
         return .systemMessage(view)
     }
 
-    private func outgoingMessageContent(_ message: OutgoingMessage) -> ChatItemCell.Content {
+    private func outgoingMessageContent(
+        _ message: OutgoingMessage,
+        error: String?
+    ) -> ChatItemCell.Content {
         let view = VisitorChatMessageView(
             with: style.visitorMessageStyle,
             environment: .create(with: environment)
@@ -692,6 +700,12 @@ extension ChatView {
         )
         view.fileTapped = { [weak self] in self?.fileTapped?($0) }
         view.linkTapped = { [weak self] in self?.linkTapped?($0) }
+        view.error = error
+        if error != nil {
+            view.messageTapped = { [weak self] in
+                self?.retryMessageTapped?(message)
+            }
+        }
         return .outgoingMessage(view)
     }
 
diff --git a/GliaWidgets/Sources/View/Chat/Message/VisitorChatMessageView.swift b/GliaWidgets/Sources/View/Chat/Message/VisitorChatMessageView.swift
index 68884867a..8f632fb55 100644
--- a/GliaWidgets/Sources/View/Chat/Message/VisitorChatMessageView.swift
+++ b/GliaWidgets/Sources/View/Chat/Message/VisitorChatMessageView.swift
@@ -6,7 +6,15 @@ class VisitorChatMessageView: ChatMessageView {
         set { statusLabel.text = newValue }
     }
 
+    var error: String? {
+        get { return errorLabel.text }
+        set { errorLabel.text = newValue }
+    }
+
+    var messageTapped: (() -> Void)?
+
     private let statusLabel = UILabel().makeView()
+    private let errorLabel = UILabel().makeView()
     private let contentInsets = UIEdgeInsets(top: 8, left: 88, bottom: 8, right: 16)
 
     init(
@@ -42,6 +50,13 @@ class VisitorChatMessageView: ChatMessageView {
             style.accessibility.isFontScalingEnabled,
             for: statusLabel
         )
+
+        errorLabel.font = style.error.font
+        errorLabel.textColor = UIColor(hex: style.error.color)
+        setFontScalingEnabled(
+            style.accessibility.isFontScalingEnabled,
+            for: errorLabel
+        )
     }
 
     override func defineLayout() {
@@ -55,6 +70,24 @@ class VisitorChatMessageView: ChatMessageView {
         addSubview(statusLabel)
         constraints += statusLabel.topAnchor.constraint(equalTo: contentViews.bottomAnchor, constant: 2)
         constraints += statusLabel.trailingAnchor.constraint(equalTo: trailingAnchor, constant: -contentInsets.right)
-        constraints += statusLabel.bottomAnchor.constraint(equalTo: bottomAnchor, constant: -contentInsets.bottom)
+
+        addSubview(errorLabel)
+        constraints += errorLabel.topAnchor.constraint(equalTo: statusLabel.bottomAnchor, constant: 0)
+        constraints += errorLabel.trailingAnchor.constraint(equalTo: trailingAnchor, constant: -contentInsets.right)
+        constraints += errorLabel.bottomAnchor.constraint(equalTo: bottomAnchor, constant: -contentInsets.bottom)
+
+        defineTapGestureRecognizer()
+    }
+
+    func defineTapGestureRecognizer() {
+        let tapRecognizer = UITapGestureRecognizer(
+            target: self,
+            action: #selector(tapped)
+        )
+        addGestureRecognizer(tapRecognizer)
+    }
+
+    @objc private func tapped() {
+        messageTapped?()
     }
 }
diff --git a/GliaWidgets/Sources/ViewController/Chat/ChatViewController.swift b/GliaWidgets/Sources/ViewController/Chat/ChatViewController.swift
index 74d54fc7e..32c51eb98 100644
--- a/GliaWidgets/Sources/ViewController/Chat/ChatViewController.swift
+++ b/GliaWidgets/Sources/ViewController/Chat/ChatViewController.swift
@@ -102,6 +102,10 @@ final class ChatViewController: EngagementViewController, PopoverPresenter {
             viewModel.event(.gvaButtonTapped(option))
         }
 
+        view.retryMessageTapped = { message in
+            viewModel.event(.retryMessageTapped(message))
+        }
+
         var viewModel = viewModel
 
         viewModel.action = { [weak self, weak view] action in
@@ -131,6 +135,8 @@ final class ChatViewController: EngagementViewController, PopoverPresenter {
                 view?.refreshRows(rows, in: section, animated: animated)
             case let .refreshSection(section, animated):
                 view?.refreshSection(section, animated: animated)
+            case let .deleteRows(rows, in: section, animated: animated):
+                view?.deleteRows(rows, in: section, animated: animated)
             case .refreshAll:
                 view?.refreshAll()
             case .scrollToBottom(let animated):
diff --git a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+ChoiceCards.swift b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+ChoiceCards.swift
index 94e300f28..c8abbdbcc 100644
--- a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+ChoiceCards.swift
+++ b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+ChoiceCards.swift
@@ -28,7 +28,7 @@ extension ChatViewModel {
         }
     }
 
-    private func respond(to choiceCardId: String, with selection: String?) {
+    func respond(to choiceCardId: String, with selection: String?) {
         // In the case of upgrading a secure conversation to a live chat,
         // there's a bug (MSG-483) that sends the welcome message web socket event before the
         // start engagement event. This means that we display it in the `pendingSection`
diff --git a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+CustomCard.swift b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+CustomCard.swift
index b813184a7..f9aaa9897 100644
--- a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+CustomCard.swift
+++ b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+CustomCard.swift
@@ -18,7 +18,10 @@ extension ChatViewModel {
         )
 
         let payload = environment.createSendMessagePayload(option.text, attachment)
-        let outgoingMessage = OutgoingMessage(payload: payload)
+        let outgoingMessage = OutgoingMessage(
+            payload: payload,
+            relation: .customCard(messageId: messageId)
+        )
 
         registerReceivedMessage(messageId: payload.messageId.rawValue)
 
@@ -31,7 +34,7 @@ extension ChatViewModel {
 
             self.updateCustomCard(
                 messageId: messageId,
-                selectedOption: option,
+                selectedOptionValue: option.value,
                 isActive: false
             )
             self.replace(
@@ -43,29 +46,32 @@ extension ChatViewModel {
             self.action?(.scrollToBottom(animated: true))
         }
 
-        let failure: (CoreSdkClient.SalemoveError) -> Void = { [weak self] error in
+        let failure: () -> Void = { [weak self] in
             guard let self = self else { return }
             self.updateCustomCard(
                 messageId: messageId,
-                selectedOption: nil,
+                selectedOptionValue: nil,
                 isActive: true
             )
-            self.engagementAction?(.showAlert(.error(error: error.error)))
+            self.markMessageAsFailed(
+                outgoingMessage,
+                in: self.messagesSection
+            )
         }
 
         interactor.send(messagePayload: payload) { result in
             switch result {
             case let .success(message):
                 success(message)
-            case let .failure(error):
-                failure(error)
+            case .failure:
+                failure()
             }
         }
     }
 
-    private func updateCustomCard(
+    func updateCustomCard(
         messageId: MessageRenderer.Message.Identifier,
-        selectedOption: HtmlMetadata.Option?,
+        selectedOptionValue: String?,
         isActive: Bool
     ) {
         guard let index = messagesSection.items
@@ -85,7 +91,7 @@ extension ChatViewModel {
             _
         ) = customCardItem.kind else { return }
 
-        message.attachment?.selectedOption = selectedOption?.value
+        message.attachment?.selectedOption = selectedOptionValue
         let item = ChatItem(kind: .customCard(
             message,
             showsImage: showsImage,
diff --git a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+GVA.swift b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+GVA.swift
index 99de9bfe8..3e3cffd73 100644
--- a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+GVA.swift
+++ b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+GVA.swift
@@ -128,8 +128,11 @@ private extension ChatViewModel {
                         in: self.messagesSection
                     )
                 }
-            case let .failure(error):
-                self.engagementAction?(.showAlert(.error(error: error.error)))
+            case .failure:
+                self.markMessageAsFailed(
+                    outgoingMessage,
+                    in: self.messagesSection
+                )
             }
         }
     }
diff --git a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+ViewModel.swift b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+ViewModel.swift
index 11397a2d3..f3bcc2798 100644
--- a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+ViewModel.swift
+++ b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel+ViewModel.swift
@@ -18,6 +18,7 @@ extension ChatViewModel: ViewModel {
             messageId: MessageRenderer.Message.Identifier
         )
         case gvaButtonTapped(GvaOption)
+        case retryMessageTapped(OutgoingMessage)
     }
 
     enum Action {
@@ -37,6 +38,7 @@ extension ChatViewModel: ViewModel {
         case refreshRow(Int, in: Int, animated: Bool)
         case refreshRows([Int], in: Int, animated: Bool)
         case refreshSection(Int, animated: Bool = false)
+        case deleteRows([Int], in: Int, animated: Bool)
         case refreshAll
         case scrollToBottom(animated: Bool)
         case updateItemsUserImage(animated: Bool)
diff --git a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel.Mock.swift b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel.Mock.swift
index cf51b1b5d..47e58d434 100644
--- a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel.Mock.swift
+++ b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel.Mock.swift
@@ -11,6 +11,7 @@ extension ChatViewModel {
         isWindowVisible: ObservableValue<Bool> = .init(with: true),
         startAction: StartAction = .startEngagement,
         deliveredStatusText: String = "Delivered",
+        failedToDeliverStatusText: String = "Failed",
         chatType: ChatViewModel.ChatType = .nonAuthenticated,
         environment: Environment = .mock,
         maximumUploads: () -> Int = { 2 }
@@ -25,6 +26,7 @@ extension ChatViewModel {
             isWindowVisible: isWindowVisible,
             startAction: startAction,
             deliveredStatusText: deliveredStatusText,
+            failedToDeliverStatusText: failedToDeliverStatusText,
             chatType: chatType,
             environment: environment,
             maximumUploads: maximumUploads
diff --git a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel.swift b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel.swift
index 57b5064c7..22378cf87 100644
--- a/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel.swift
+++ b/GliaWidgets/Sources/ViewModel/Chat/ChatViewModel.swift
@@ -32,6 +32,7 @@ class ChatViewModel: EngagementViewModel {
 
     private let downloader: FileDownloader
     private let deliveredStatusText: String
+    private let failedToDeliverStatusText: String
     private(set) var messageText = "" {
         didSet {
             validateMessage()
@@ -71,6 +72,7 @@ class ChatViewModel: EngagementViewModel {
         isWindowVisible: ObservableValue<Bool>,
         startAction: StartAction,
         deliveredStatusText: String,
+        failedToDeliverStatusText: String,
         chatType: ChatType,
         environment: Environment,
         maximumUploads: () -> Int
@@ -106,6 +108,7 @@ class ChatViewModel: EngagementViewModel {
 
         self.downloader = FileDownloader(environment: .create(with: environment))
         self.deliveredStatusText = deliveredStatusText
+        self.failedToDeliverStatusText = failedToDeliverStatusText
         super.init(
             interactor: interactor,
             screenShareHandler: screenShareHandler,
@@ -198,10 +201,9 @@ class ChatViewModel: EngagementViewModel {
 
             pendingMessages.forEach { [weak self] outgoingMessage in
                 self?.interactor.send(messagePayload: outgoingMessage.payload) {  [weak self] result in
+                    guard let self else { return }
                     switch result {
                     case let .success(message):
-                        guard let self else { return }
-
                         self.replace(
                             outgoingMessage,
                             uploads: [],
@@ -210,9 +212,11 @@ class ChatViewModel: EngagementViewModel {
                         )
 
                         self.action?(.scrollToBottom(animated: true))
-                    case let .failure(error):
-                        guard let self else { return }
-                        self.engagementAction?(.showAlert(.error(error: error.error)))
+                    case .failure:
+                        self.markMessageAsFailed(
+                            outgoingMessage,
+                            in: self.messagesSection
+                        )
                     }
                 }
             }
@@ -276,6 +280,8 @@ extension ChatViewModel {
             sendSelectedCustomCardOption(option, for: messageId)
         case .gvaButtonTapped(let option):
             gvaOptionAction(for: option)()
+        case .retryMessageTapped(let message):
+            retryMessageSending(message)
         }
     }
 }
@@ -460,11 +466,11 @@ extension ChatViewModel {
                         )
                         self.action?(.scrollToBottom(animated: true))
                     }
-                case let .failure(error):
-                    self.engagementAction?(.showAlert(.error(
-                        error: error.error,
-                        dismissed: endSession
-                    )))
+                case .failure:
+                    self.markMessageAsFailed(
+                        outgoingMessage,
+                        in: self.messagesSection
+                    )
                 }
             }
         case .enqueued:
@@ -518,6 +524,29 @@ extension ChatViewModel {
         )
     }
 
+    func markMessageAsFailed(
+        _ outgoingMessage: OutgoingMessage,
+        in section: Section<ChatItem>
+    ) {
+        SecureConversations.ChatWithTranscriptModel.markMessageAsFailed(
+            outgoingMessage,
+            in: section,
+            message: failedToDeliverStatusText,
+            action: action
+        )
+    }
+
+    func removeMessage(
+        _ outgoingMessage: OutgoingMessage,
+        in section: Section<ChatItem>
+    ) {
+        SecureConversations.ChatWithTranscriptModel.removeMessage(
+            outgoingMessage,
+            in: section,
+            action: action
+        )
+    }
+
     @discardableResult
     private func validateMessage() -> Bool {
         let canSendText = !messageText.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty
@@ -549,7 +578,7 @@ extension ChatViewModel {
             // processing time.
             for chatItem in messagesSection.items.reversed() {
                 switch chatItem.kind {
-                case let .outgoingMessage(outgoingMessage)
+                case let .outgoingMessage(outgoingMessage, _)
                     where outgoingMessage.payload.messageId.rawValue.uppercased() == message.id.uppercased():
                     isMatchingOutgoingMessage = true
                 default:
@@ -611,7 +640,7 @@ extension ChatViewModel {
         // avoid message duplication. Currently pending messages
         // stay in pending section whole session.
         for pendingMessage in self.pendingSection.items {
-            if case let .outgoingMessage(outgoingPendingMessage) = pendingMessage.kind,
+            if case let .outgoingMessage(outgoingPendingMessage, _) = pendingMessage.kind,
                 outgoingPendingMessage.payload.messageId.rawValue.uppercased() == message.id.uppercased() {
                 return
             }
@@ -788,6 +817,67 @@ extension ChatViewModel {
     }
 }
 
+// MARK: Message sending retry
+
+extension ChatViewModel {
+    // TODO: - This will be covered with unit tests in next PR
+    private func retryMessageSending(_ outgoingMessage: OutgoingMessage) {
+        removeMessage(
+            outgoingMessage,
+            in: messagesSection
+        )
+
+        let item = ChatItem(with: outgoingMessage)
+        appendItem(item, to: messagesSection, animated: true)
+        action?(.scrollToBottom(animated: true))
+
+        interactor.send(messagePayload: outgoingMessage.payload) { [weak self] result in
+            guard let self else { return }
+
+            switch result {
+            case let .success(message):
+                if !self.hasReceivedMessage(messageId: message.id) {
+                    self.registerReceivedMessage(messageId: message.id)
+
+                    self.updateSelectedOption(with: outgoingMessage)
+
+                    self.replace(
+                        outgoingMessage,
+                        uploads: [],
+                        with: message,
+                        in: self.messagesSection
+                    )
+                    self.action?(.scrollToBottom(animated: true))
+                }
+            case .failure:
+                self.markMessageAsFailed(
+                    outgoingMessage,
+                    in: self.messagesSection
+                )
+            }
+        }
+    }
+
+    // Updates Response Card or Custom Card selected option
+    // TODO: - This will be covered with unit tests in next PR
+    private func updateSelectedOption(with outgoingMessage: OutgoingMessage) {
+        let selectedOption = outgoingMessage.payload.attachment?.selectedOption
+
+        switch outgoingMessage.relation {
+        case let .customCard(messageId):
+            updateCustomCard(
+                messageId: messageId,
+                selectedOptionValue: selectedOption,
+                isActive: false
+            )
+        case let .singleChoice(messageId):
+            respond(to: messageId.rawValue, with: selectedOption)
+        case .none:
+            return
+        }
+    }
+}
+
 // MARK: General
 
 extension ChatViewModel {
diff --git a/GliaWidgets/Sources/ViewModel/Chat/Data/ChatItem.swift b/GliaWidgets/Sources/ViewModel/Chat/Data/ChatItem.swift
index 198ec5e49..d75a3978f 100644
--- a/GliaWidgets/Sources/ViewModel/Chat/Data/ChatItem.swift
+++ b/GliaWidgets/Sources/ViewModel/Chat/Data/ChatItem.swift
@@ -30,7 +30,7 @@ class ChatItem {
     init(
         with message: OutgoingMessage
     ) {
-        kind = .outgoingMessage(message)
+        kind = .outgoingMessage(message, error: nil)
     }
 
     init?(
@@ -78,7 +78,7 @@ class ChatItem {
 extension ChatItem {
     enum Kind {
         case queueOperator
-        case outgoingMessage(OutgoingMessage)
+        case outgoingMessage(OutgoingMessage, error: String?)
         case visitorMessage(ChatMessage, status: String?)
         case operatorMessage(ChatMessage, showsImage: Bool, imageUrl: String?)
         case choiceCard(ChatMessage, showsImage: Bool, imageUrl: String?, isActive: Bool)
diff --git a/GliaWidgets/Sources/ViewModel/Chat/Data/OutgoingMessage.swift b/GliaWidgets/Sources/ViewModel/Chat/Data/OutgoingMessage.swift
index 16c235e77..bd0ad29fa 100644
--- a/GliaWidgets/Sources/ViewModel/Chat/Data/OutgoingMessage.swift
+++ b/GliaWidgets/Sources/ViewModel/Chat/Data/OutgoingMessage.swift
@@ -3,18 +3,32 @@ import GliaCoreSDK
 
 class OutgoingMessage: Equatable {
     let files: [LocalFile]
+    /// Defines if the message is associated with Single Choice Response card
+    /// or Custom Response card. Used for reloading an associated card.
+    let relation: Relation
     var payload: CoreSdkClient.SendMessagePayload
 
     init(
         payload: CoreSdkClient.SendMessagePayload,
-        files: [LocalFile] = []
+        files: [LocalFile] = [],
+        relation: Relation = .none
     ) {
         self.payload = payload
         self.files = files
+        self.relation = relation
     }
 
     static func == (lhs: OutgoingMessage, rhs: OutgoingMessage) -> Bool {
         lhs.payload == rhs.payload &&
-        lhs.files == rhs.files
+        lhs.files == rhs.files &&
+        lhs.relation == rhs.relation
+    }
+}
+
+extension OutgoingMessage {
+    enum Relation: Equatable {
+        case none
+        case singleChoice(messageId: CoreSdkClient.Message.Id)
+        case customCard(messageId: MessageRenderer.Message.Identifier)
     }
 }
diff --git a/GliaWidgetsTests/Lib/ChatItem/ChatItem+Equatable.swift b/GliaWidgetsTests/Lib/ChatItem/ChatItem+Equatable.swift
index 289362f83..2ef59b5f3 100644
--- a/GliaWidgetsTests/Lib/ChatItem/ChatItem+Equatable.swift
+++ b/GliaWidgetsTests/Lib/ChatItem/ChatItem+Equatable.swift
@@ -6,7 +6,7 @@ extension ChatItem.Kind: Equatable {
         case (.queueOperator, .queueOperator):
             return true
 
-        case (.outgoingMessage(let lhsMessage), .outgoingMessage(let rhsMessage)):
+        case (.outgoingMessage(let lhsMessage, _), .outgoingMessage(let rhsMessage, _)):
             return lhsMessage.payload.messageId == rhsMessage.payload.messageId
 
         case (.visitorMessage(let lhsMessage, _), .visitorMessage(let rhsMessage, _)):
diff --git a/GliaWidgetsTests/Sources/ChatViewModel/ChatViewModelTests.swift b/GliaWidgetsTests/Sources/ChatViewModel/ChatViewModelTests.swift
index 8a10fab61..bc8d80a78 100644
--- a/GliaWidgetsTests/Sources/ChatViewModel/ChatViewModelTests.swift
+++ b/GliaWidgetsTests/Sources/ChatViewModel/ChatViewModelTests.swift
@@ -24,7 +24,8 @@ class ChatViewModelTests: XCTestCase {
             isCustomCardSupported: false,
             isWindowVisible: .init(with: true),
             startAction: .none,
-            deliveredStatusText: "Delivered",
+            deliveredStatusText: "Delivered", 
+            failedToDeliverStatusText: "Failed",
             chatType: .nonAuthenticated,
             environment: .init(
                 fetchFile: { _, _, _ in },
@@ -744,7 +745,7 @@ class ChatViewModelTests: XCTestCase {
 
         let outgoingMessage = OutgoingMessage(payload: .mock(messageIdSuffix: messageIdSuffix))
         viewModel.pendingSection.append(
-            .init(kind: .outgoingMessage(outgoingMessage))
+            .init(kind: .outgoingMessage(outgoingMessage, error: nil))
         )
 
         viewModel.interactorEvent(.receivedMessage(.mock(id: outgoingMessage.payload.messageId.rawValue)))
diff --git a/GliaWidgetsTests/ViewModel/Chat/Mocks/ChatItem.Kind.Mock.swift b/GliaWidgetsTests/ViewModel/Chat/Mocks/ChatItem.Kind.Mock.swift
index da5b313be..132d4744d 100644
--- a/GliaWidgetsTests/ViewModel/Chat/Mocks/ChatItem.Kind.Mock.swift
+++ b/GliaWidgetsTests/ViewModel/Chat/Mocks/ChatItem.Kind.Mock.swift
@@ -14,7 +14,7 @@ extension ChatItem.Kind {
     static func mock(kind: Internal) -> ChatItem.Kind {
         switch kind {
         case .queueOperator: return .queueOperator
-        case .outgoingMessage: return .outgoingMessage(.mock())
+        case .outgoingMessage: return .outgoingMessage(.mock(), error: nil)
         case .visitorMessage: return .visitorMessage(.mock(), status: nil)
         case .operatorMessage:
             return .operatorMessage(