diff --git a/.github/actions/perform_smoke_test/action.yaml b/.github/actions/perform_smoke_test/action.yaml
index 90e5cd93..89f63cad 100644
--- a/.github/actions/perform_smoke_test/action.yaml
+++ b/.github/actions/perform_smoke_test/action.yaml
@@ -208,7 +208,8 @@ runs:
         ./${{ inputs.cli-binary-location }} upload \
         --org-url-slug trunk \
         --junit-paths "${{ github.workspace }}/target/**/*junit.xml" \
-        --token ${{ inputs.production-api-token }}
+        --token ${{ inputs.production-api-token }} \
+        --test-collection-id 4B2wfoEU
 
     - name: Upload to production with public repo id
       id: production-upload-public-repo-id
diff --git a/.github/actions/test_ruby_gem_uploads/action.yaml b/.github/actions/test_ruby_gem_uploads/action.yaml
index 41a9e4af..900c6b02 100644
--- a/.github/actions/test_ruby_gem_uploads/action.yaml
+++ b/.github/actions/test_ruby_gem_uploads/action.yaml
@@ -27,6 +27,9 @@ inputs:
   test-collection-id:
     description: Optional 8 character alphanumeric ID for a test collection
     required: false
+  variant:
+    description: Optional variant label to distinguish uploads within a matrix
+    required: false
   knapsack-pro-test-suite-token-rspec:
     description: Optional Knapsack Pro test suite token for RSpec
     required: true
@@ -87,6 +90,7 @@ runs:
         TRUNK_ORG_URL_SLUG: ${{ inputs.trunk-org-slug }}
         TRUNK_API_TOKEN: ${{ inputs.trunk-token }}
         TRUNK_TEST_COLLECTION_ID: ${{ inputs.test-collection-id }}
+        TRUNK_VARIANT: ${{ inputs.variant }}
 
     - name: Run variant quarantine test without variant (should fail - not quarantined)
       id: run-variant-test-no-variant
@@ -171,6 +175,8 @@ runs:
         TRUNK_API_TOKEN: ${{ inputs.trunk-token }}
         TRUNK_ORG_URL_SLUG: ${{ inputs.trunk-org-slug }}
         TRUNK_PUBLIC_API_ADDRESS: ${{ inputs.trunk-public-api-address }}
+        TRUNK_TEST_COLLECTION_ID: ${{ inputs.test-collection-id }}
+        TRUNK_VARIANT: ${{ inputs.variant }}
         TRUNK_LOCAL_UPLOAD_DIR: bundles
       run: |
         set -euo pipefail
diff --git a/.github/workflows/pull_request.yml b/.github/workflows/pull_request.yml
index e5c7a008..90f0de3b 100644
--- a/.github/workflows/pull_request.yml
+++ b/.github/workflows/pull_request.yml
@@ -216,7 +216,8 @@ jobs:
           target/${{ matrix.platform.target }}/release/trunk-analytics-cli upload \
             --junit-paths ${{ github.workspace }}/target/**/*junit.xml \
             --org-url-slug trunk \
-            --token ${{ secrets.TRUNK_PROD_ORG_API_TOKEN }}
+            --token ${{ secrets.TRUNK_PROD_ORG_API_TOKEN }} \
+            --test-collection-id EWhNPVic
 
   trunk_check_runner:
     name: Trunk Check runner [linux]
diff --git a/.github/workflows/release_ruby_gem.yml b/.github/workflows/release_ruby_gem.yml
index b17096ca..253e7427 100644
--- a/.github/workflows/release_ruby_gem.yml
+++ b/.github/workflows/release_ruby_gem.yml
@@ -128,12 +128,29 @@ jobs:
     steps:
       - uses: actions/checkout@v4
 
-      - uses: ./.github/actions/test_ruby_gem_uploads
+      - name: Test ruby gem uploads → analytics-cli-ruby-gem (staging)
+        uses: ./.github/actions/test_ruby_gem_uploads
         with:
           ruby-version: ${{ matrix.ruby-version }}
           trunk-token: ${{ secrets.TRUNK_STAGING_ORG_API_TOKEN }}
+          trunk-public-api-address: https://api.trunk-staging.io
+          trunk-org-slug: trunk-staging-org
           test-collection-id: T5yKSn9h
           platform: ${{ matrix.platform.name }}
+          variant: ${{ matrix.platform.name }}-ruby${{ matrix.ruby-version }}
+          artifact-pattern: cross-gem-${{ matrix.platform.name }}
+          knapsack-pro-test-suite-token-rspec: ${{ secrets.KNAPSACK_PRO_TEST_SUITE_TOKEN_RSPEC }}
+
+      - name: Test ruby gem uploads → analytics-cli-ruby-gem (prod)
+        uses: ./.github/actions/test_ruby_gem_uploads
+        with:
+          ruby-version: ${{ matrix.ruby-version }}
+          trunk-token: ${{ secrets.TRUNK_PROD_ORG_API_TOKEN }}
+          trunk-public-api-address: https://api.trunk.io
+          trunk-org-slug: trunk
+          test-collection-id: BiBP2neA
+          platform: ${{ matrix.platform.name }}
+          variant: ${{ matrix.platform.name }}-ruby${{ matrix.ruby-version }}
           artifact-pattern: cross-gem-${{ matrix.platform.name }}
           knapsack-pro-test-suite-token-rspec: ${{ secrets.KNAPSACK_PRO_TEST_SUITE_TOKEN_RSPEC }}
 
diff --git a/.github/workflows/ruby.yml b/.github/workflows/ruby.yml
index ac0d4653..66360420 100644
--- a/.github/workflows/ruby.yml
+++ b/.github/workflows/ruby.yml
@@ -25,16 +25,61 @@ jobs:
       - name: Setup Ruby
         uses: ./.github/actions/setup_ruby
 
+      - name: Build CLI
+        run: cargo build -p trunk-analytics-cli
+
       - name: Test ruby package
         if: "!cancelled()"
         run: |
           bundle install
           bundle exec rake test
         working-directory: rspec-trunk-flaky-tests
+        env:
+          TRUNK_LOCAL_UPLOAD_DIR: ../upload_bundle
+
+      - name: Upload ruby package results → analytics-cli-ruby-gem (staging)
+        if: "!cancelled()"
+        run: |
+          ./target/debug/trunk-analytics-cli upload \
+            --org-url-slug trunk-staging-org \
+            --token ${{ secrets.TRUNK_STAGING_ORG_API_TOKEN }} \
+            --test-reports ./upload_bundle/trunk_output.bin \
+            --test-collection-id T5yKSn9h
+        env:
+          TRUNK_PUBLIC_API_ADDRESS: https://api.trunk-staging.io
+
+      - name: Upload ruby package results → analytics-cli-ruby-gem (prod)
+        if: "!cancelled()"
+        run: |
+          ./target/debug/trunk-analytics-cli upload \
+            --org-url-slug trunk \
+            --token ${{ secrets.TRUNK_PROD_ORG_API_TOKEN }} \
+            --test-reports ./upload_bundle/trunk_output.bin \
+            --test-collection-id BiBP2neA
+        env:
+          TRUNK_PUBLIC_API_ADDRESS: https://api.trunk.io
+
+      - name: Upload ruby package results → analytics-cli-smoke-tests (staging)
+        if: "!cancelled()"
+        run: |
+          ./target/debug/trunk-analytics-cli upload \
+            --org-url-slug trunk-staging-org \
+            --token ${{ secrets.TRUNK_STAGING_ORG_API_TOKEN }} \
+            --test-reports ./upload_bundle/trunk_output.bin \
+            --test-collection-id z2dzjLHm
         env:
           TRUNK_PUBLIC_API_ADDRESS: https://api.trunk-staging.io
-          TRUNK_ORG_URL_SLUG: trunk-staging-org
-          TRUNK_API_TOKEN: ${{ secrets.TRUNK_STAGING_ORG_API_TOKEN }}
+
+      - name: Upload ruby package results → analytics-cli-smoke-tests (prod)
+        if: "!cancelled()"
+        run: |
+          ./target/debug/trunk-analytics-cli upload \
+            --org-url-slug trunk \
+            --token ${{ secrets.TRUNK_PROD_ORG_API_TOKEN }} \
+            --test-reports ./upload_bundle/trunk_output.bin \
+            --test-collection-id 4B2wfoEU
+        env:
+          TRUNK_PUBLIC_API_ADDRESS: https://api.trunk.io
 
       - name: Validate ruby platform gem
         if: "!cancelled()"
@@ -112,7 +157,8 @@ jobs:
           name: ruby-gem-pr
           path: .github/actions/test_ruby_gem_uploads/
 
-      - uses: ./.github/actions/test_ruby_gem_uploads
+      - name: Test ruby gem uploads → analytics-cli-ruby-gem (staging)
+        uses: ./.github/actions/test_ruby_gem_uploads
         with:
           ruby-version: "3.4"
           trunk-token: ${{ secrets.TRUNK_STAGING_ORG_API_TOKEN }}
@@ -122,3 +168,39 @@ jobs:
           platform: x86_64-linux
           artifact-pattern: ""
           knapsack-pro-test-suite-token-rspec: ${{ secrets.KNAPSACK_PRO_TEST_SUITE_TOKEN_RSPEC }}
+
+      - name: Test ruby gem uploads → analytics-cli-ruby-gem (prod)
+        uses: ./.github/actions/test_ruby_gem_uploads
+        with:
+          ruby-version: "3.4"
+          trunk-token: ${{ secrets.TRUNK_PROD_ORG_API_TOKEN }}
+          trunk-public-api-address: https://api.trunk.io
+          trunk-org-slug: trunk
+          test-collection-id: BiBP2neA
+          platform: x86_64-linux
+          artifact-pattern: ""
+          knapsack-pro-test-suite-token-rspec: ${{ secrets.KNAPSACK_PRO_TEST_SUITE_TOKEN_RSPEC }}
+
+      - name: Test ruby gem uploads → analytics-cli-smoke-tests (staging)
+        uses: ./.github/actions/test_ruby_gem_uploads
+        with:
+          ruby-version: "3.4"
+          trunk-token: ${{ secrets.TRUNK_STAGING_ORG_API_TOKEN }}
+          trunk-public-api-address: https://api.trunk-staging.io
+          trunk-org-slug: trunk-staging-org
+          test-collection-id: z2dzjLHm
+          platform: x86_64-linux
+          artifact-pattern: ""
+          knapsack-pro-test-suite-token-rspec: ${{ secrets.KNAPSACK_PRO_TEST_SUITE_TOKEN_RSPEC }}
+
+      - name: Test ruby gem uploads → analytics-cli-smoke-tests (prod)
+        uses: ./.github/actions/test_ruby_gem_uploads
+        with:
+          ruby-version: "3.4"
+          trunk-token: ${{ secrets.TRUNK_PROD_ORG_API_TOKEN }}
+          trunk-public-api-address: https://api.trunk.io
+          trunk-org-slug: trunk
+          test-collection-id: 4B2wfoEU
+          platform: x86_64-linux
+          artifact-pattern: ""
+          knapsack-pro-test-suite-token-rspec: ${{ secrets.KNAPSACK_PRO_TEST_SUITE_TOKEN_RSPEC }}