diff --git a/.github/workflows/deploy.yml b/.github/workflows/deploy.yml
index 5dbc319b501f..d2cebadd8ba8 100644
--- a/.github/workflows/deploy.yml
+++ b/.github/workflows/deploy.yml
@@ -769,24 +769,21 @@ jobs:
           CF_API_KEY: ${{ secrets.CLOUDFLARE_TOKEN }}
           HOST: ${{ env.DEPLOY_ENV == 'production' && vars.WEB_PRODUCTION_HOST || vars.WEB_STAGING_HOST }}
 
+      # The staging host is verified by webDeployStagingWorker, which deploys after this job.
       - name: Verify deploy
+        if: ${{ env.DEPLOY_ENV == 'production' }}
         run: |
           APP_VERSION=$(jq -r .version < package.json)
           ./.github/scripts/verifyDeploy.sh "$HOST" "$APP_VERSION"
         env:
-          HOST: ${{ env.DEPLOY_ENV == 'production' && vars.WEB_PRODUCTION_HOST || vars.WEB_STAGING_HOST }}
+          HOST: ${{ vars.WEB_PRODUCTION_HOST }}
 
-  webDeployCloudflareWorkers:
-    name: Deploy Web to Cloudflare Workers (${{ matrix.environment }})
+  webDeployTestStaging:
+    name: Deploy Web to test-staging.new.expensify.com
     needs: [prep, webBuild, buildStorybook]
     if: ${{ always() && needs.webBuild.result == 'success' && needs.prep.outputs.DEPLOY_ENV == 'staging' }}
     # Trial hosting for the web build, so a failure here must not fail the staging deploy.
     continue-on-error: true
-    strategy:
-      fail-fast: false
-      matrix:
-        # `staging` serves no traffic until staging.new.expensify.com is routed to its Worker in Cloudflare.
-        environment: [test-staging, staging]
     runs-on: blacksmith-2vcpu-ubuntu-2404
     steps:
       - name: Checkout
@@ -812,10 +809,65 @@ jobs:
       - name: Extract web build
         run: tar -xzf "${{ needs.webBuild.outputs.TAR_FILENAME }}"
 
-      # The Workers serve these to tabs still running this build after later deploys. Both Workers read the same bucket,
-      # so only one matrix leg uploads.
+      - name: Download storybook docs artifact
+        continue-on-error: true
+        # v7
+        uses: actions/download-artifact@37930b1c2abaa49bbe596cd826c3c89aef350131
+        with:
+          name: storybook-docs-artifact
+          path: ./dist/docs
+
+      - name: Install Cloudflare Worker dependencies
+        working-directory: web/cloudflare-worker
+        run: npm ci
+
+      - name: Deploy to Cloudflare Workers
+        working-directory: web/cloudflare-worker
+        run: npx wrangler deploy --env test-staging
+        env:
+          CLOUDFLARE_API_TOKEN: ${{ secrets.CLOUDFLARE_WORKERS_DEPLOY_TOKEN }}
+          CLOUDFLARE_ACCOUNT_ID: ${{ secrets.CLOUDFLARE_ACCOUNT_ID }}
+          WRANGLER_SEND_METRICS: false
+
+      - name: Verify deploy
+        run: |
+          APP_VERSION=$(jq -r .version < package.json)
+          ./.github/scripts/verifyDeploy.sh "$HOST" "$APP_VERSION"
+        env:
+          HOST: https://test-staging.new.expensify.com
+
+  webDeployStagingWorker:
+    name: Deploy Web to the staging Cloudflare Worker
+    # After webDeploy, so the S3 copy of this build is in place before the Worker's version check.
+    needs: [prep, webBuild, buildStorybook, webDeploy]
+    if: ${{ always() && needs.webBuild.result == 'success' && needs.prep.outputs.DEPLOY_ENV == 'staging' }}
+    runs-on: blacksmith-2vcpu-ubuntu-2404
+    steps:
+      - name: Checkout
+        uses: useblacksmith/checkout@0647fdbab2614a5eb86d2971070e325060d91056 # v1.7.0
+        with:
+          ref: ${{ needs.prep.outputs.DEPLOY_SHA }}
+
+      - name: Setup Node
+        # v6.1.0
+        uses: actions/setup-node@395ad3262231945c25e8478fd5baf05154b1d79f
+        with:
+          node-version-file: '.nvmrc'
+          cache: npm
+          cache-dependency-path: web/cloudflare-worker/package-lock.json
+
+      - name: Download web build artifact
+        # v7
+        uses: actions/download-artifact@37930b1c2abaa49bbe596cd826c3c89aef350131
+        with:
+          name: web-build-tar-gz-artifact
+          path: ./
+
+      - name: Extract web build
+        run: tar -xzf "${{ needs.webBuild.outputs.TAR_FILENAME }}"
+
+      # The Workers serve these to tabs still running this build after later deploys.
       - name: Upload web build to the previous builds bucket
-        if: ${{ matrix.environment == 'staging' }}
         continue-on-error: true
         run: |
           if [[ -z "$AWS_ACCESS_KEY_ID" ]]; then
@@ -848,17 +900,18 @@ jobs:
 
       - name: Deploy to Cloudflare Workers
         working-directory: web/cloudflare-worker
-        run: npx wrangler deploy --env "${{ matrix.environment }}"
+        run: npx wrangler deploy --env staging
         env:
           CLOUDFLARE_API_TOKEN: ${{ secrets.CLOUDFLARE_WORKERS_DEPLOY_TOKEN }}
           CLOUDFLARE_ACCOUNT_ID: ${{ secrets.CLOUDFLARE_ACCOUNT_ID }}
           WRANGLER_SEND_METRICS: false
 
       - name: Verify deploy
-        if: ${{ matrix.environment == 'test-staging' }}
         run: |
           APP_VERSION=$(jq -r .version < package.json)
-          ./.github/scripts/verifyDeploy.sh https://test-staging.new.expensify.com "$APP_VERSION"
+          ./.github/scripts/verifyDeploy.sh "$HOST" "$APP_VERSION"
+        env:
+          HOST: ${{ vars.WEB_STAGING_HOST }}
 
   buildStorybook:
     name: Build storybook docs
@@ -907,6 +960,7 @@ jobs:
         iosSubmit,
         webBuild,
         webDeploy,
+        webDeployStagingWorker,
         victoryChartRendererBuild,
       ]
     steps:
@@ -922,7 +976,7 @@ jobs:
     name: Post a Slack message when the deploy is cancelled manually
     runs-on: blacksmith-2vcpu-ubuntu-2404
     if: ${{ cancelled() }}
-    needs: [androidBuild, androidUploadGooglePlay, androidSubmit, iosBuild, iosUploadTestflight, iosSubmit, webBuild, webDeploy]
+    needs: [androidBuild, androidUploadGooglePlay, androidSubmit, iosBuild, iosUploadTestflight, iosSubmit, webBuild, webDeploy, webDeployStagingWorker]
     steps:
       - name: Check whether a newer deploy run exists
         id: check
@@ -961,7 +1015,7 @@ jobs:
       ANDROID_RESULT: ${{ steps.platformResults.outputs.ANDROID_RESULT }}
       IOS_RESULT: ${{ steps.platformResults.outputs.IOS_RESULT }}
       WEB_RESULT: ${{ steps.platformResults.outputs.WEB_RESULT }}
-    needs: [androidBuild, androidUploadGooglePlay, androidSubmit, iosBuild, iosUploadTestflight, iosSubmit, webBuild, webDeploy, victoryChartRendererBuild]
+    needs: [androidBuild, androidUploadGooglePlay, androidSubmit, iosBuild, iosUploadTestflight, iosSubmit, webBuild, webDeploy, webDeployStagingWorker, victoryChartRendererBuild]
     if: ${{ always() }}
     steps:
       # Determine effective result for each platform
@@ -996,9 +1050,11 @@ jobs:
             echo "IOS_RESULT=${{ needs.iosUploadTestflight.result }}" >> "$GITHUB_OUTPUT"
           fi
 
-          # Web: propagate build failure even when deploy is skipped
+          # Web: propagate build failure even when deploy is skipped. Staging is only deployed once its Worker is too.
           if [ "${{ needs.webBuild.result }}" == "failure" ]; then
             echo "WEB_RESULT=failure" >> "$GITHUB_OUTPUT"
+          elif [ "${{ env.DEPLOY_ENV }}" == "staging" ] && [ "${{ needs.webDeployStagingWorker.result }}" != "success" ]; then
+            echo "WEB_RESULT=${{ needs.webDeployStagingWorker.result }}" >> "$GITHUB_OUTPUT"
           else
             echo "WEB_RESULT=${{ needs.webDeploy.result }}" >> "$GITHUB_OUTPUT"
           fi
diff --git a/web/cloudflare-worker/README.md b/web/cloudflare-worker/README.md
index e57f421bdae3..bcdb5556a404 100644
--- a/web/cloudflare-worker/README.md
+++ b/web/cloudflare-worker/README.md
@@ -111,7 +111,9 @@ The script diffs status, caching and security headers for a fixed set of paths.
 | `staging` | `staging-new-expensify-assets` | None until switchover, then `staging.new.expensify.com/*` (managed in Cloudflare, not in `wrangler.jsonc`) | Staging |
 | `production` | `new-expensify-assets` | None until switchover, then `new.expensify.com/*` | Production |
 
-Every staging deploy also deploys the same build to the `test-staging` and `staging` Workers (the `webDeployCloudflareWorkers` job in `.github/workflows/deploy.yml`). It uses `CLOUDFLARE_WORKERS_DEPLOY_TOKEN`, which can only edit those two Workers. That token can't read zones, so routes aren't in `wrangler.jsonc`: wrangler would try to sync them and fail. A failure there does not fail the staging deploy.
+Every staging deploy also deploys the same build to the `staging` Worker (the `webDeployStagingWorker` job in `.github/workflows/deploy.yml`) and the `test-staging` Worker (`webDeployTestStaging`). Both use `CLOUDFLARE_WORKERS_DEPLOY_TOKEN`, which can only edit those two Workers. That token can't read zones, so routes aren't in `wrangler.jsonc`: wrangler would try to sync them and fail.
+
+The `staging` deploy runs after the S3 upload and is required: if it fails, or `staging.new.expensify.com/version.json` doesn't report the new version, the staging deploy fails. The `test-staging` deploy is a trial, so its failures don't affect the staging deploy.
 
 `test-staging` serves a staging build on a hostname nobody else uses. `staging` serves nothing until `staging.new.expensify.com/*` is pointed at its Worker in Cloudflare.