diff --git a/.buildkite/pipeline.yml b/.buildkite/pipeline.yml
index aa4e398c..d6630385 100644
--- a/.buildkite/pipeline.yml
+++ b/.buildkite/pipeline.yml
@@ -30,8 +30,38 @@ steps:
           tar -xzf dist.tar.gz
           echo "--- :docker: Starting wp-env"
           make wp-env-start
-          echo "--- :performing_arts: Running E2E tests"
-          make test-e2e
+          WP_CONTAINER=$(docker ps -qf "publish=8888" | head -1)
+          echo "--- :performing_arts: Running E2E tests in Playwright container"
+          E2E_EXIT=0
+          docker run --rm \
+            --userns=host \
+            --network host \
+            -v "$(pwd):/work" \
+            -w /work \
+            -e CI=true \
+            mcr.microsoft.com/playwright:v1.58.2-noble \
+            bash -c "npm ci && npx playwright install chromium && npx playwright test" \
+            || E2E_EXIT=$?
+          echo "--- :broom: Fixing ownership of root-owned files"
+          docker run --rm \
+            --userns=host \
+            -v "$(pwd):/work" \
+            -w /work \
+            mcr.microsoft.com/playwright:v1.58.2-noble \
+            chown -R "$(id -u):$(id -g)" /work
+          echo "--- :wordpress: WordPress debug log"
+          if [ -n "$WP_CONTAINER" ]; then
+            docker exec "$WP_CONTAINER" cat /var/www/html/wp-content/debug.log 2>/dev/null || echo "(no debug.log found)"
+            echo "--- :file_folder: Uploads directory permissions"
+            docker exec "$WP_CONTAINER" ls -la /var/www/html/wp-content/uploads/ 2>/dev/null || echo "(no uploads directory)"
+            echo "--- :whale: WordPress container status"
+            docker inspect --format='{{.State.Status}}' "$WP_CONTAINER" 2>/dev/null || echo "(container gone)"
+          else
+            echo "(WordPress container not found before tests)"
+          fi
+          exit $E2E_EXIT
+      agents:
+          queue: default
       plugins: *plugins
 
     - label: ':android: Publish Android Library'
diff --git a/bin/wp-env-setup.sh b/bin/wp-env-setup.sh
index f7464810..4eaf3945 100755
--- a/bin/wp-env-setup.sh
+++ b/bin/wp-env-setup.sh
@@ -65,7 +65,31 @@ done
 # ---------------------------------------------------------------------------
 
 echo "Flushing rewrite rules..."
-npm run --silent wp-env run cli -- wp rewrite structure '/%postname%/' --hard 2>/dev/null
+npm run --silent wp-env run cli -- wp rewrite structure '/%postname%/' 2>/dev/null
+
+echo "Writing .htaccess for pretty permalinks..."
+WP_CONTAINER=$(docker ps -qf "publish=8888" | head -1)
+if [ -z "$WP_CONTAINER" ]; then
+    echo "Error: Could not find WordPress container on port 8888."
+    echo "Running containers:"
+    docker ps --format "{{.ID}} {{.Image}} {{.Ports}} {{.Names}}"
+    exit 1
+fi
+echo "Found WordPress container: $WP_CONTAINER"
+docker exec -u 0 "$WP_CONTAINER" sh -c 'cat > /var/www/html/.htaccess << "HTACCESS"
+# BEGIN WordPress
+<IfModule mod_rewrite.c>
+RewriteEngine On
+RewriteRule .* - [E=HTTP_AUTHORIZATION:%{HTTP:Authorization}]
+RewriteBase /
+RewriteRule ^index\.php$ - [L]
+RewriteCond %{REQUEST_FILENAME} !-f
+RewriteCond %{REQUEST_FILENAME} !-d
+RewriteRule . /index.php [L]
+</IfModule>
+# END WordPress
+HTACCESS
+'
 
 # ---------------------------------------------------------------------------
 # Enable Jetpack blocks module
diff --git a/e2e/image-upload.spec.js b/e2e/image-upload.spec.js
index 8e1c4635..18c5a43b 100644
--- a/e2e/image-upload.spec.js
+++ b/e2e/image-upload.spec.js
@@ -13,6 +13,59 @@ const TEST_IMAGE = path.resolve( import.meta.dirname, 'assets/test-image.png' );
 
 test.describe( 'Image Upload', () => {
 	test( 'should upload an image via the Image block', async ( { page } ) => {
+		// Log all network requests to wp-env for debugging upload issues in CI.
+		page.on( 'request', ( request ) => {
+			const url = request.url();
+			if ( url.includes( 'localhost:8888' ) ) {
+				// eslint-disable-next-line no-console
+				console.log(
+					`[REQ] ${ request.method() } ${ url } headers=${ JSON.stringify(
+						Object.fromEntries(
+							Object.entries( request.headers() ).filter(
+								( [ k ] ) =>
+									[
+										'content-type',
+										'authorization',
+										'origin',
+									].includes( k )
+							)
+						)
+					) }`
+				);
+			}
+		} );
+		page.on( 'response', ( response ) => {
+			const url = response.url();
+			if ( url.includes( 'localhost:8888' ) ) {
+				// eslint-disable-next-line no-console
+				console.log(
+					`[RES] ${ response.status() } ${ url } headers=${ JSON.stringify(
+						Object.fromEntries(
+							Object.entries( response.headers() ).filter(
+								( [ k ] ) =>
+									[
+										'access-control-allow-origin',
+										'access-control-allow-headers',
+										'access-control-allow-methods',
+									].includes( k )
+							)
+						)
+					) }`
+				);
+			}
+		} );
+		page.on( 'requestfailed', ( request ) => {
+			const url = request.url();
+			if ( url.includes( 'localhost:8888' ) ) {
+				// eslint-disable-next-line no-console
+				console.log(
+					`[FAIL] ${ request.method() } ${ url } failure=${
+						request.failure()?.errorText
+					}`
+				);
+			}
+		} );
+
 		const editor = new EditorPage( page );
 		await editor.setup();