diff --git a/WordPress/Classes/Utility/Migration/ContentMigrationCoordinator.swift b/WordPress/Classes/Utility/Migration/ContentMigrationCoordinator.swift
index 7b7daa42c266..252f15b2b661 100644
--- a/WordPress/Classes/Utility/Migration/ContentMigrationCoordinator.swift
+++ b/WordPress/Classes/Utility/Migration/ContentMigrationCoordinator.swift
@@ -12,21 +12,32 @@ class ContentMigrationCoordinator {
     private let dataMigrator: ContentDataMigrating
     private let userPersistentRepository: UserPersistentRepository
     private let eligibilityProvider: ContentMigrationEligibilityProvider
+    private let tracker: MigrationAnalyticsTracker
 
     init(coreDataStack: CoreDataStack = ContextManager.shared,
          dataMigrator: ContentDataMigrating = DataMigrator(),
          userPersistentRepository: UserPersistentRepository = UserDefaults.standard,
-         eligibilityProvider: ContentMigrationEligibilityProvider = AppConfiguration()) {
+         eligibilityProvider: ContentMigrationEligibilityProvider = AppConfiguration(),
+         tracker: MigrationAnalyticsTracker = .init()) {
         self.coreDataStack = coreDataStack
         self.dataMigrator = dataMigrator
         self.userPersistentRepository = userPersistentRepository
         self.eligibilityProvider = eligibilityProvider
+        self.tracker = tracker
     }
 
-    enum ContentMigrationCoordinatorError: Error {
+    enum ContentMigrationCoordinatorError: LocalizedError {
         case ineligible
         case exportFailure
         case localDraftsNotSynced
+
+        var errorDescription: String? {
+            switch self {
+            case .ineligible: return "Content export is ineligible"
+            case .exportFailure: return "Content export failed"
+            case .localDraftsNotSynced: return "Local drafts not synced"
+            }
+        }
     }
 
     // MARK: Methods
@@ -41,22 +52,27 @@ class ContentMigrationCoordinator {
     /// - Parameter completion: Closure called after the export process completes.
     func startAndDo(completion: ((Result<Void, ContentMigrationCoordinatorError>) -> Void)? = nil) {
         guard eligibilityProvider.isEligibleForMigration else {
+            tracker.trackContentExportEligibility(eligible: false)
             completion?(.failure(.ineligible))
             return
         }
 
         guard isLocalPostsSynced() else {
-            completion?(.failure(.localDraftsNotSynced))
+            let error = ContentMigrationCoordinatorError.localDraftsNotSynced
+            tracker.trackContentExportFailed(reason: error.localizedDescription)
+            completion?(.failure(error))
             return
         }
 
-        dataMigrator.exportData { result in
+        dataMigrator.exportData { [weak self] result in
             switch result {
             case .success:
+                self?.tracker.trackContentExportSucceeded()
                 completion?(.success(()))
 
             case .failure(let error):
                 DDLogError("[Jetpack Migration] Error exporting data: \(error)")
+                self?.tracker.trackContentExportFailed(reason: error.localizedDescription)
                 completion?(.failure(.exportFailure))
             }
         }
diff --git a/WordPress/Jetpack/Classes/System/JetpackWindowManager.swift b/WordPress/Jetpack/Classes/System/JetpackWindowManager.swift
index 4c1dc1f4c1cf..77f74cf2bcd8 100644
--- a/WordPress/Jetpack/Classes/System/JetpackWindowManager.swift
+++ b/WordPress/Jetpack/Classes/System/JetpackWindowManager.swift
@@ -101,12 +101,17 @@ private extension JetpackWindowManager {
     func showLoadWordPressUI(schemeUrl: URL) {
         let actions = MigrationLoadWordPressViewModel.Actions()
         let loadWordPressViewModel = MigrationLoadWordPressViewModel(actions: actions)
-        let loadWordPressViewController = MigrationLoadWordPressViewController(viewModel: loadWordPressViewModel)
-        actions.primary = {
+        let loadWordPressViewController = MigrationLoadWordPressViewController(
+            viewModel: loadWordPressViewModel,
+            tracker: migrationTracker
+        )
+        actions.primary = { [weak self] in
+            self?.migrationTracker.track(.loadWordPressScreenOpenTapped)
             UIApplication.shared.open(schemeUrl)
         }
-        actions.secondary = { [weak self] in
-            loadWordPressViewController.dismiss(animated: true) {
+        actions.secondary = { [weak self, weak loadWordPressViewController] in
+            self?.migrationTracker.track(.loadWordPressScreenNoThanksTapped)
+            loadWordPressViewController?.dismiss(animated: true) {
                 self?.showSignInUI()
             }
         }
diff --git a/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Common/Analytics/MigrationAnalyticsTracker.swift b/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Common/Analytics/MigrationAnalyticsTracker.swift
index 1036efb7106e..2ac2f3ddcff5 100644
--- a/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Common/Analytics/MigrationAnalyticsTracker.swift	
+++ b/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Common/Analytics/MigrationAnalyticsTracker.swift	
@@ -9,6 +9,22 @@ struct MigrationAnalyticsTracker {
         WPAnalytics.track(event)
     }
 
+    // MARK: - Content Export
+
+    func trackContentExportEligibility(eligible: Bool) {
+        let properties = ["eligible": String(eligible)]
+        self.track(.contentExportEligibility, properties: properties)
+    }
+
+    func trackContentExportSucceeded() {
+        self.track(.contentExportSucceeded)
+    }
+
+    func trackContentExportFailed(reason: String) {
+        let properties = ["error_type": reason]
+        self.track(.contentExportFailed, properties: properties)
+    }
+
     // MARK: - Content Import
 
     func trackContentImportEligibility(eligible: Bool) {
diff --git a/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Common/Analytics/MigrationEvent.swift b/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Common/Analytics/MigrationEvent.swift
index 4767016bcf58..c1de02f1f627 100644
--- a/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Common/Analytics/MigrationEvent.swift	
+++ b/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Common/Analytics/MigrationEvent.swift	
@@ -1,6 +1,11 @@
 import Foundation
 
 enum MigrationEvent: String {
+    // Content Export
+    case contentExportEligibility = "migration_content_export_eligibility"
+    case contentExportSucceeded = "migration_content_export_succeeded"
+    case contentExportFailed = "migration_content_export_failed"
+
     // Content Import
     case contentImportEligibility = "migration_content_import_eligibility"
     case contentImportSucceeded = "migration_content_import_succeeded"
@@ -37,6 +42,11 @@ enum MigrationEvent: String {
     case pleaseDeleteWordPressScreenHelpTapped = "migration_please_delete_wordpress_screen_help_tapped"
     case pleaseDeleteWordPressScreenCloseTapped = "migration_please_delete_wordpress_screen_close_tapped"
 
-    // WordPress Migratable Stat
+    // Load WordPress
+    case loadWordPressScreenShown = "migration_load_wordpress_screen_shown"
+    case loadWordPressScreenOpenTapped = "migration_load_wordpress_screen_open_tapped"
+    case loadWordPressScreenNoThanksTapped = "migration_load_wordpress_screen_no_thanks_tapped"
+
+    // WordPress Migratable State
     case wordPressDetected = "migration_wordpressapp_detected"
 }
diff --git a/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Load WordPress/MigrationLoadWordPressViewController.swift b/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Load WordPress/MigrationLoadWordPressViewController.swift
index 259ac3feab50..0fa9c7de23e2 100644
--- a/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Load WordPress/MigrationLoadWordPressViewController.swift	
+++ b/WordPress/Jetpack/Classes/ViewRelated/WordPress-to-Jetpack Migration/Load WordPress/MigrationLoadWordPressViewController.swift	
@@ -5,11 +5,13 @@ class MigrationLoadWordPressViewController: UIViewController {
     // MARK: - Dependencies
 
     private let viewModel: MigrationLoadWordPressViewModel
+    private let tracker: MigrationAnalyticsTracker
 
     // MARK: - Init
 
-    init(viewModel: MigrationLoadWordPressViewModel) {
+    init(viewModel: MigrationLoadWordPressViewModel, tracker: MigrationAnalyticsTracker = .init()) {
         self.viewModel = viewModel
+        self.tracker = tracker
         super.init(nibName: nil, bundle: nil)
     }
 
@@ -32,4 +34,9 @@ class MigrationLoadWordPressViewController: UIViewController {
         super.viewDidLoad()
         self.view.backgroundColor = MigrationAppearance.backgroundColor
     }
+
+    override func viewDidAppear(_ animated: Bool) {
+        super.viewDidAppear(animated)
+        self.tracker.track(.loadWordPressScreenShown)
+    }
 }