diff --git a/.circleci/config.yml b/.circleci/config.yml
index 0af04b0..295f74b 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -1,8 +1,8 @@
 version: 2.1
 
 orbs:
-  # This uses the iOS Orb located at https://github.com/wordpress-mobile/circleci-orbs
-  ios: wordpress-mobile/ios@0.0.25
+  # Using 1.0 of our Orbs means it will use the latest 1.0.x version from https://github.com/wordpress-mobile/circleci-orbs
+  ios: wordpress-mobile/ios@1.0
 
 workflows:
   test_and_validate:
@@ -14,7 +14,21 @@ workflows:
           scheme: WordPressShared
           device: iPhone XS
           ios-version: "12.2"
+          bundle-install: true
+          pod-install: true
       - ios/validate-podspec:
           name: Validate Podspec
           xcode-version: "10.2.0"
           podspec-path: WordPressShared.podspec
+          bundle-install: true
+      - ios/publish-podspec:
+          name: Publish to Trunk
+          xcode-version: "10.2.0"
+          podspec-path: WordPressShared.podspec
+          bundle-install: true
+          post-to-slack: true
+          filters:
+            tags:
+              only: /.*/
+            branches:
+              ignore: /.*/
diff --git a/Gemfile b/Gemfile
index 427d2bd..c1535c5 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,4 +1,4 @@
 source 'https://rubygems.org' do
-  gem 'cocoapods', '1.6.1'
+  gem 'cocoapods', '~> 1.8.0'
   gem 'xcpretty'
 end
diff --git a/Gemfile.lock b/Gemfile.lock
index 78c85e1..0a8bea7 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -1,35 +1,40 @@
 GEM
   remote: https://rubygems.org/
   specs:
-    CFPropertyList (3.0.0)
+    CFPropertyList (3.0.1)
     activesupport (4.2.11.1)
       i18n (~> 0.7)
       minitest (~> 5.1)
       thread_safe (~> 0.3, >= 0.3.4)
       tzinfo (~> 1.1)
+    algoliasearch (1.27.1)
+      httpclient (~> 2.8, >= 2.8.3)
+      json (>= 1.5.1)
     atomos (0.1.3)
-    claide (1.0.2)
-    cocoapods (1.6.1)
+    claide (1.0.3)
+    cocoapods (1.8.4)
       activesupport (>= 4.0.2, < 5)
       claide (>= 1.0.2, < 2.0)
-      cocoapods-core (= 1.6.1)
-      cocoapods-deintegrate (>= 1.0.2, < 2.0)
+      cocoapods-core (= 1.8.4)
+      cocoapods-deintegrate (>= 1.0.3, < 2.0)
       cocoapods-downloader (>= 1.2.2, < 2.0)
       cocoapods-plugins (>= 1.0.0, < 2.0)
       cocoapods-search (>= 1.0.0, < 2.0)
       cocoapods-stats (>= 1.0.0, < 2.0)
-      cocoapods-trunk (>= 1.3.1, < 2.0)
+      cocoapods-trunk (>= 1.4.0, < 2.0)
       cocoapods-try (>= 1.1.0, < 2.0)
       colored2 (~> 3.1)
       escape (~> 0.0.4)
-      fourflusher (>= 2.2.0, < 3.0)
+      fourflusher (>= 2.3.0, < 3.0)
       gh_inspector (~> 1.0)
       molinillo (~> 0.6.6)
       nap (~> 1.0)
       ruby-macho (~> 1.4)
-      xcodeproj (>= 1.8.1, < 2.0)
-    cocoapods-core (1.6.1)
+      xcodeproj (>= 1.11.1, < 2.0)
+    cocoapods-core (1.8.4)
       activesupport (>= 4.0.2, < 6)
+      algoliasearch (~> 1.0)
+      concurrent-ruby (~> 1.1)
       fuzzy_match (~> 2.0.4)
       nap (~> 1.0)
     cocoapods-deintegrate (1.0.4)
@@ -38,19 +43,21 @@ GEM
       nap
     cocoapods-search (1.0.0)
     cocoapods-stats (1.1.0)
-    cocoapods-trunk (1.3.1)
+    cocoapods-trunk (1.4.1)
       nap (>= 0.8, < 2.0)
       netrc (~> 0.11)
     cocoapods-try (1.1.0)
     colored2 (3.1.2)
     concurrent-ruby (1.1.5)
     escape (0.0.4)
-    fourflusher (2.2.0)
+    fourflusher (2.3.1)
     fuzzy_match (2.0.4)
     gh_inspector (1.1.3)
+    httpclient (2.8.3)
     i18n (0.9.5)
       concurrent-ruby (~> 1.0)
-    minitest (5.11.3)
+    json (2.2.0)
+    minitest (5.12.2)
     molinillo (0.6.6)
     nanaimo (0.2.6)
     nap (1.1.0)
@@ -60,7 +67,7 @@ GEM
     thread_safe (0.3.6)
     tzinfo (1.2.5)
       thread_safe (~> 0.1)
-    xcodeproj (1.8.2)
+    xcodeproj (1.13.0)
       CFPropertyList (>= 2.3.3, < 4.0)
       atomos (~> 0.1.3)
       claide (>= 1.0.2, < 2.0)
@@ -73,8 +80,8 @@ PLATFORMS
   ruby
 
 DEPENDENCIES
-  cocoapods (= 1.6.1)!
+  cocoapods (~> 1.8.0)!
   xcpretty!
 
 BUNDLED WITH
-   1.17.2
+   2.0.2
diff --git a/Podfile b/Podfile
index b740e4d..e7da527 100644
--- a/Podfile
+++ b/Podfile
@@ -1,4 +1,4 @@
-source 'https://github.com/CocoaPods/Specs.git'
+source 'https://cdn.cocoapods.org/'
 
 inhibit_all_warnings!
 use_frameworks!
diff --git a/Podfile.lock b/Podfile.lock
index 5ae69cf..a368937 100644
--- a/Podfile.lock
+++ b/Podfile.lock
@@ -34,7 +34,7 @@ DEPENDENCIES:
   - Specta (= 1.0.7)
 
 SPEC REPOS:
-  https://github.com/cocoapods/specs.git:
+  trunk:
     - CocoaLumberjack
     - Expecta
     - FormatterKit
@@ -50,6 +50,6 @@ SPEC CHECKSUMS:
   OHHTTPStubs: 9cbce6364bec557cc3439aa6bb7514670d780881
   Specta: 3e1bd89c3517421982dc4d1c992503e48bd5fe66
 
-PODFILE CHECKSUM: 55afbed6130408cd4c9f1a07c4c6c6f0e7241262
+PODFILE CHECKSUM: 67eadfaf0746636eac9749cc8f835112af82f302
 
-COCOAPODS: 1.6.1
+COCOAPODS: 1.8.4
diff --git a/WordPressShared.podspec b/WordPressShared.podspec
index e489e02..c5bde12 100644
--- a/WordPressShared.podspec
+++ b/WordPressShared.podspec
@@ -1,6 +1,6 @@
 Pod::Spec.new do |s|
   s.name          = "WordPressShared"
-  s.version       = "1.8.7"
+  s.version       = "1.8.8"
   s.summary       = "Shared components used in building the WordPress iOS apps and other library components."
 
   s.description   = <<-DESC
diff --git a/WordPressShared/Core/Analytics/WPAnalytics.h b/WordPressShared/Core/Analytics/WPAnalytics.h
index c3011f7..449dc1b 100644
--- a/WordPressShared/Core/Analytics/WPAnalytics.h
+++ b/WordPressShared/Core/Analytics/WPAnalytics.h
@@ -27,6 +27,7 @@ typedef NS_ENUM(NSUInteger, WPAnalyticsStat) {
     WPAnalyticsStatAppUpgraded,
     WPAnalyticsStatApplicationClosed,
     WPAnalyticsStatApplicationOpened,
+    WPAnalyticsStatAutoUploadPostInvoked,
     WPAnalyticsStatAutomatedTransferCustomDomainDialogShown,
     WPAnalyticsStatAutomatedTransferCustomDomainDialogCancelled,
     WPAnalyticsStatAutomatedTransferCustomDomainSuggestionQueried,
@@ -479,8 +480,12 @@ typedef NS_ENUM(NSUInteger, WPAnalyticsStat) {
     WPAnalyticsStatStatsDateTappedBackward,
     WPAnalyticsStatStatsDateTappedForward,
     WPAnalyticsStatStatsInsightsAccessed,
+    WPAnalyticsStatStatsItemSelectedAddInsight,
     WPAnalyticsStatStatsItemTappedAuthors,
     WPAnalyticsStatStatsItemTappedClicks,
+    WPAnalyticsStatStatsItemTappedInsightMoveDown,
+    WPAnalyticsStatStatsItemTappedInsightMoveUp,
+    WPAnalyticsStatStatsItemTappedInsightRemove,
     WPAnalyticsStatStatsItemTappedInsightsAddStat,
     WPAnalyticsStatStatsItemTappedInsightsCustomizeDismiss,
     WPAnalyticsStatStatsItemTappedInsightsCustomizeTry,
@@ -488,6 +493,7 @@ typedef NS_ENUM(NSUInteger, WPAnalyticsStat) {
     WPAnalyticsStatStatsItemTappedLatestPostSummarySharePost,
     WPAnalyticsStatStatsItemTappedLatestPostSummaryPost,
     WPAnalyticsStatStatsItemTappedLatestPostSummaryViewPostDetails,
+    WPAnalyticsStatStatsItemTappedManageInsight,
     WPAnalyticsStatStatsItemTappedPostsAndPages,
     WPAnalyticsStatStatsItemTappedSearchTerms,
     WPAnalyticsStatStatsItemTappedTagsAndCategories,