diff --git a/.buildkite/beta-builds.yml b/.buildkite/beta-builds.yml
index 434463858bc6..b9e5d5019bcc 100644
--- a/.buildkite/beta-builds.yml
+++ b/.buildkite/beta-builds.yml
@@ -13,6 +13,7 @@ steps:
   #################
   - label: "Gradle Wrapper Validation"
     command: |
+      .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
       validate_gradle_wrapper
     plugins: [$CI_TOOLKIT]
 
@@ -27,14 +28,18 @@ steps:
 
       - label: "🕵️ Lint WordPress"
         key: wplint
-        command: ".buildkite/commands/lint.sh wordpress"
+        command: |
+          .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+          .buildkite/commands/lint.sh wordpress
         plugins: [$CI_TOOLKIT]
         artifact_paths:
           - "**/build/reports/lint-results*.*"
 
       - label: "🕵️ Lint Jetpack"
         key: jplint
-        command: ".buildkite/commands/lint.sh jetpack"
+        command: |
+          .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+          .buildkite/commands/lint.sh jetpack
         plugins: [$CI_TOOLKIT]
         artifact_paths:
           - "**/build/reports/lint-results*.*"
@@ -47,7 +52,9 @@ steps:
 
       - label: ":wordpress: :android: Beta Build"
         key: wpbuild
-        command: ".buildkite/commands/beta-build.sh wordpress"
+        command: |
+          .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+          .buildkite/commands/beta-build.sh wordpress
         depends_on: wplint
         plugins: [$CI_TOOLKIT]
         notify:
@@ -59,7 +66,9 @@ steps:
 
       - label: ":jetpack: :android: Beta Build"
         key: jpbuild
-        command: ".buildkite/commands/beta-build.sh jetpack"
+        command: |
+          .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+          .buildkite/commands/beta-build.sh jetpack
         depends_on: jplint
         plugins: [$CI_TOOLKIT]
         notify:
@@ -76,5 +85,7 @@ steps:
     depends_on:
       - wpbuild
       - jpbuild
-    command: ".buildkite/commands/create-github-release.sh"
+    command: |
+      .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+      .buildkite/commands/create-github-release.sh
     plugins: [$CI_TOOLKIT]
diff --git a/.buildkite/commands/checkout-editorial-branch.sh b/.buildkite/commands/checkout-editorial-branch.sh
index f495193ae32f..6cae072807ea 100755
--- a/.buildkite/commands/checkout-editorial-branch.sh
+++ b/.buildkite/commands/checkout-editorial-branch.sh
@@ -1,5 +1,7 @@
 #!/bin/bash -eu
 
+echo '--- :git: Checkout Editorial Branch'
+
 # EDITORIAL_BRANCH is passed as an environment variable from fastlane to Buildkite
 #
 if [[ -z "${EDITORIAL_BRANCH}" ]]; then
diff --git a/.buildkite/commands/checkout-release-branch.sh b/.buildkite/commands/checkout-release-branch.sh
index 7b6881194cf7..fe570fa93ad6 100755
--- a/.buildkite/commands/checkout-release-branch.sh
+++ b/.buildkite/commands/checkout-release-branch.sh
@@ -1,10 +1,8 @@
 #!/bin/bash -eu
 
-# RELEASE_VERSION is passed as an environment variable passed to Buildkite by ReleasesV2.
-if [[ -z "${RELEASE_VERSION}" ]]; then
-    echo "RELEASE_VERSION is not set."
-    exit 1
-fi
+echo "--- :git: Checkout Release Branch"
+
+RELEASE_VERSION="${1?Please provide a release version as an argument.}"
 
 # Buildkite, by default, checks out a specific commit. For many release actions, we need to be
 # on a release branch instead.
diff --git a/.buildkite/complete-code-freeze.yml b/.buildkite/complete-code-freeze.yml
index aea9b8822055..e2810cd52cf4 100644
--- a/.buildkite/complete-code-freeze.yml
+++ b/.buildkite/complete-code-freeze.yml
@@ -8,8 +8,7 @@ steps:
       echo '--- :robot_face: Use bot for git operations'
       source use-bot-for-git
 
-      echo '--- :git: Checkout Release Branch'
-      .buildkite/commands/checkout-release-branch.sh
+      .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
 
       echo '--- :ruby: Setup Ruby Tools'
       install_gems
diff --git a/.buildkite/finalize-release.yml b/.buildkite/finalize-release.yml
index 4253bd97c27f..c38a21e774c8 100644
--- a/.buildkite/finalize-release.yml
+++ b/.buildkite/finalize-release.yml
@@ -8,8 +8,7 @@ steps:
       echo '--- :robot_face: Use bot for git operations'
       source use-bot-for-git
 
-      echo '--- :git: Checkout Release Branch'
-      .buildkite/commands/checkout-release-branch.sh
+      .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
 
       echo '--- :ruby: Setup Ruby Tools'
       install_gems
diff --git a/.buildkite/publish-release.yml b/.buildkite/publish-release.yml
index 72b96d7ff4a1..9bacf47c4bc9 100644
--- a/.buildkite/publish-release.yml
+++ b/.buildkite/publish-release.yml
@@ -8,8 +8,7 @@ steps:
       echo '--- :robot_face: Use bot for git operations'
       source use-bot-for-git
 
-      echo '--- :git: Checkout Release Branch'
-      .buildkite/commands/checkout-release-branch.sh
+      .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
 
       echo '--- :ruby: Setup Ruby tools'
       install_gems
diff --git a/.buildkite/release-builds.yml b/.buildkite/release-builds.yml
index abefd4942a40..1bfe1e5e9371 100644
--- a/.buildkite/release-builds.yml
+++ b/.buildkite/release-builds.yml
@@ -13,6 +13,7 @@ steps:
   #################
   - label: "Gradle Wrapper Validation"
     command: |
+      .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
       validate_gradle_wrapper
     priority: 1
     plugins: [$CI_TOOLKIT]
@@ -28,7 +29,9 @@ steps:
 
       - label: "🕵️ Lint WordPress"
         key: wplint
-        command: ".buildkite/commands/lint.sh wordpress"
+        command: |
+          .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+          .buildkite/commands/lint.sh wordpress
         priority: 1
         plugins: [$CI_TOOLKIT]
         artifact_paths:
@@ -36,7 +39,9 @@ steps:
 
       - label: "🕵️ Lint Jetpack"
         key: jplint
-        command: ".buildkite/commands/lint.sh jetpack"
+        command: |
+          .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+          .buildkite/commands/lint.sh jetpack
         priority: 1
         plugins: [$CI_TOOLKIT]
         artifact_paths:
@@ -50,7 +55,9 @@ steps:
 
       - label: ":wordpress: :android: Release Build"
         key: wpbuild
-        command: ".buildkite/commands/release-build.sh wordpress"
+        command: |
+          .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+          .buildkite/commands/release-build.sh wordpress
         priority: 1
         depends_on: wplint
         plugins: [$CI_TOOLKIT]
@@ -63,7 +70,9 @@ steps:
 
       - label: ":jetpack: :android: Release Build"
         key: jpbuild
-        command: ".buildkite/commands/release-build.sh jetpack"
+        command: |
+          .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+          .buildkite/commands/release-build.sh jetpack
         priority: 1
         depends_on: jplint
         plugins: [$CI_TOOLKIT]
@@ -81,6 +90,8 @@ steps:
     depends_on:
       - wpbuild
       - jpbuild
-    command: ".buildkite/commands/create-github-release.sh"
+    command: |
+      .buildkite/commands/checkout-release-branch.sh "$RELEASE_VERSION"
+      .buildkite/commands/create-github-release.sh
     priority: 1
     plugins: [$CI_TOOLKIT]
diff --git a/.buildkite/update-release-notes.yml b/.buildkite/update-release-notes.yml
index bc781f42589b..5443723ab506 100644
--- a/.buildkite/update-release-notes.yml
+++ b/.buildkite/update-release-notes.yml
@@ -9,7 +9,6 @@ steps:
       echo '--- :robot_face: Use bot for git operations'
       source use-bot-for-git
 
-      echo '--- :git: Checkout Editorial Branch'
       .buildkite/commands/checkout-editorial-branch.sh
 
       echo '--- :ruby: Setup Ruby Tools'
diff --git a/fastlane/lanes/release.rb b/fastlane/lanes/release.rb
index 0605bbd0417c..42c70f25737f 100644
--- a/fastlane/lanes/release.rb
+++ b/fastlane/lanes/release.rb
@@ -548,19 +548,30 @@ def commit_version_bump
   end
 
   def trigger_buildkite_release_build(branch:, beta:)
+    environment = {
+      RELEASE_VERSION: current_release_version
+    }
+
     pipeline_file = beta ? 'beta-builds.yml' : 'release-builds.yml'
     message = beta ? 'Beta Builds' : 'Release Builds'
 
-    build_url = buildkite_trigger_build(
-      buildkite_organization: 'automattic',
-      buildkite_pipeline: 'wordpress-android',
-      branch: branch,
-      pipeline_file: pipeline_file,
-      message: message
-    )
+    # If we're running on CI, we can directly start the release pipeline jobs within the same build
+    if is_ci
+      buildkite_pipeline_upload(
+        pipeline_file: pipeline_file,
+        environment: environment
+      )
+    else
+      build_url = buildkite_trigger_build(
+        buildkite_organization: 'automattic',
+        buildkite_pipeline: 'wordpress-android',
+        branch: branch,
+        pipeline_file: pipeline_file,
+        message: message
+      )
 
-    message = "This build triggered a build on <code>#{branch}</code>:<br>- #{build_url}"
-    buildkite_annotate(style: 'info', context: 'trigger-release-build', message: message) if is_ci
+      UI.success("Release build triggered on #{branch}: #{build_url}")
+    end
   end
 
   def create_backmerge_pr(source_branch: "release/#{current_release_version}", target_branch: nil)