diff --git a/test/fixtures/forcing-finding-seeds.ts b/test/fixtures/forcing-finding-seeds.ts
index fec887935..8d52c858d 100644
--- a/test/fixtures/forcing-finding-seeds.ts
+++ b/test/fixtures/forcing-finding-seeds.ts
@@ -81,3 +81,42 @@ export const FORCING_FLOOR_DEVEX = [
   '',
   'No quickstart command, no hosted sandbox, no copy-pasteable curl example.',
 ].join('\n');
+
+/**
+ * Multi-finding batching regression seed (periodic tier).
+ *
+ * Mirrors the May 2026 transcript bug shape: 4 distinct non-trivial findings
+ * spread across plan-eng-review's standard sections (Architecture, Code
+ * Quality, Tests, Performance). Each finding is independent — there is no
+ * legitimate reason to batch them into a single AskUserQuestion.
+ *
+ * Used by test/skill-e2e-plan-eng-multi-finding-batching.test.ts to assert
+ * the agent fires >= 3 review-phase AUQs (i.e., does NOT batch them into a
+ * "## Decisions to confirm" section + ExitPlanMode). Floor of 3 (not 4) is
+ * the [N-1] tolerance from the existing finding-count band convention.
+ */
+export const FORCING_BATCHING_ENG = [
+  'Please review this plan thoroughly. As you go, write your plan-mode plan to /tmp/gstack-test-plan-eng-batching.md (use Edit/Write to that exact path).',
+  '',
+  '# Plan: Add background job retry framework',
+  '',
+  '## Architecture',
+  "We'll roll a custom exponential-backoff scheduler inline in each worker",
+  "rather than use the existing job library's built-in retry hooks. Same",
+  'shape as the library version, but we want full control over the curve.',
+  '',
+  '## Code quality',
+  'The retry envelope (compute delay, log attempt, dispatch) is duplicated',
+  'across 5 worker files with copy-pasted bodies. We will leave the',
+  'duplication for now and refactor "later."',
+  '',
+  '## Tests',
+  'The existing `processWebhookJob()` flow gets rewritten as part of this',
+  'change. No regression test for the prior at-most-once delivery guarantee',
+  'is planned.',
+  '',
+  '## Performance',
+  'On every retry we re-fetch the full job payload from the database, then',
+  'iterate the payload to recompute the dependency graph. Could cache the',
+  'graph on the first attempt; not planned.',
+].join('\n');
diff --git a/test/helpers/touchfiles.ts b/test/helpers/touchfiles.ts
index 18c25e0bc..1d18bee46 100644
--- a/test/helpers/touchfiles.ts
+++ b/test/helpers/touchfiles.ts
@@ -143,6 +143,13 @@ export const E2E_TOUCHFILES: Record<string, string[]> = {
   'plan-ceo-finding-floor':      ['plan-ceo-review/**', 'scripts/resolvers/preamble.ts', 'scripts/resolvers/preamble/generate-ask-user-format.ts', 'scripts/resolvers/preamble/generate-completion-status.ts', 'scripts/resolvers/review.ts', 'test/helpers/claude-pty-runner.ts', 'test/fixtures/forcing-finding-seeds.ts', 'test/skill-e2e-plan-ceo-finding-floor.test.ts'],
   'plan-design-finding-floor':   ['plan-design-review/**', 'scripts/resolvers/preamble.ts', 'scripts/resolvers/preamble/generate-ask-user-format.ts', 'scripts/resolvers/preamble/generate-completion-status.ts', 'scripts/resolvers/review.ts', 'test/helpers/claude-pty-runner.ts', 'test/fixtures/forcing-finding-seeds.ts', 'test/skill-e2e-plan-design-finding-floor.test.ts'],
   'plan-devex-finding-floor':    ['plan-devex-review/**', 'scripts/resolvers/preamble.ts', 'scripts/resolvers/preamble/generate-ask-user-format.ts', 'scripts/resolvers/preamble/generate-completion-status.ts', 'scripts/resolvers/review.ts', 'test/helpers/claude-pty-runner.ts', 'test/fixtures/forcing-finding-seeds.ts', 'test/skill-e2e-plan-devex-finding-floor.test.ts'],
+
+  // Multi-finding batching regression — periodic tier complement to the
+  // gate-tier finding-floor. Catches the May 2026 transcript shape where
+  // a model fires one AUQ then batches the rest into a "## Decisions to
+  // confirm" plan write. runPlanSkillFloorCheck cannot detect that shape
+  // (it exits on first AUQ); runPlanSkillCounting can.
+  'plan-eng-multi-finding-batching': ['plan-eng-review/**', 'scripts/resolvers/preamble.ts', 'scripts/resolvers/preamble/generate-ask-user-format.ts', 'scripts/resolvers/preamble/generate-completion-status.ts', 'scripts/resolvers/review.ts', 'test/helpers/claude-pty-runner.ts', 'test/fixtures/forcing-finding-seeds.ts', 'test/skill-e2e-plan-eng-multi-finding-batching.test.ts'],
   'brain-privacy-gate':           ['scripts/resolvers/preamble/generate-brain-sync-block.ts', 'scripts/resolvers/preamble.ts', 'bin/gstack-brain-sync', 'bin/gstack-artifacts-init', 'bin/gstack-config', 'test/helpers/agent-sdk-runner.ts'],
 
   // /setup-gbrain Path 4 (Remote MCP) — happy + bad-token end-to-end via
@@ -443,6 +450,7 @@ export const E2E_TIERS: Record<string, 'gate' | 'periodic'> = {
   'plan-ceo-finding-floor':    'gate',
   'plan-design-finding-floor': 'gate',
   'plan-devex-finding-floor':  'gate',
+  'plan-eng-multi-finding-batching': 'periodic',
 
   // Privacy gate for gstack-brain-sync — periodic (non-deterministic LLM call,
   // costs ~$0.30-$0.50 per run, not needed on every commit)
diff --git a/test/skill-e2e-plan-eng-multi-finding-batching.test.ts b/test/skill-e2e-plan-eng-multi-finding-batching.test.ts
new file mode 100644
index 000000000..1eef660a9
--- /dev/null
+++ b/test/skill-e2e-plan-eng-multi-finding-batching.test.ts
@@ -0,0 +1,96 @@
+/**
+ * /plan-eng-review multi-finding batching regression (periodic, paid, real-PTY).
+ *
+ * Catches the specific shape of the May 2026 transcript bug that the
+ * single-finding gate-tier floor test cannot detect: a model that fires
+ * one AskUserQuestion and then batches the remaining findings into a
+ * single "## Decisions to confirm" plan write + ExitPlanMode.
+ *
+ * Why a separate test from skill-e2e-plan-eng-finding-floor:
+ *   - The gate-tier floor (runPlanSkillFloorCheck) exits on the first AUQ
+ *     render and returns success. A model that fires once-then-batches
+ *     would pass that test trivially.
+ *   - This test uses runPlanSkillCounting at periodic tier (~25 min budget,
+ *     N-AUQ tracking, ceiling-bounded retries) to actually count distinct
+ *     review-phase AUQs and assert the model fires one per finding.
+ *
+ * Why a separate test from skill-e2e-plan-eng-finding-count (the existing
+ * 5-finding count test):
+ *   - The fixture here mirrors the D1-D4 transcript shape (4 findings) and
+ *     the floor matches that exact threshold (3, the [N-1] tolerance band).
+ *     This is the tightest regression test for the original bug class —
+ *     not a band-around-N test, but a "did the agent batch?" test.
+ *
+ * Tier: periodic (~25 min, ~$5/run). Sequential by default.
+ */
+
+import { describe, test } from 'bun:test';
+import * as fs from 'node:fs';
+import {
+  runPlanSkillCounting,
+  engStep0Boundary,
+} from './helpers/claude-pty-runner';
+import { FORCING_BATCHING_ENG } from './fixtures/forcing-finding-seeds';
+
+const shouldRun = !!process.env.EVALS && process.env.EVALS_TIER === 'periodic';
+const describeE2E = shouldRun ? describe : describe.skip;
+
+const N = 4;
+const FLOOR = N - 1; // 3 — agent must fire at least one AUQ per non-batched finding
+
+const PLAN_PATH = '/tmp/gstack-test-plan-eng-batching.md';
+
+describeE2E('/plan-eng-review multi-finding batching regression (periodic)', () => {
+  test(
+    `4-finding plan emits >= ${FLOOR} review-phase AskUserQuestions (no batching)`,
+    async () => {
+      try {
+        fs.rmSync(PLAN_PATH, { force: true });
+      } catch {
+        /* best-effort */
+      }
+
+      const obs = await runPlanSkillCounting({
+        skillName: 'plan-eng-review',
+        slashCommand: '/plan-eng-review',
+        followUpPrompt: FORCING_BATCHING_ENG,
+        isLastStep0AUQ: engStep0Boundary,
+        reviewCountCeiling: N + 3, // hard cap above floor + tolerance
+        cwd: process.cwd(),
+        timeoutMs: 1_500_000, // 25 min
+        env: { QUESTION_TUNING: 'false', EXPLAIN_LEVEL: 'default' },
+      });
+
+      try {
+        if (!['plan_ready', 'completion_summary', 'ceiling_reached'].includes(obs.outcome)) {
+          throw new Error(
+            `multi-finding batching test FAILED: outcome=${obs.outcome}\n` +
+              `step0=${obs.step0Count} review=${obs.reviewCount} elapsed=${obs.elapsedMs}ms\n` +
+              `--- evidence (last 3KB) ---\n${obs.evidence}`,
+          );
+        }
+        if (obs.reviewCount < FLOOR) {
+          throw new Error(
+            `BATCHING REGRESSION: reviewCount=${obs.reviewCount} < FLOOR=${FLOOR}.\n` +
+              `Agent surfaced fewer review-phase AUQs than findings — this is the\n` +
+              `May 2026 transcript bug shape: model batched multiple findings into\n` +
+              `a single plan write + ExitPlanMode instead of asking one per finding.\n` +
+              `Review-phase fingerprints:\n` +
+              obs.fingerprints
+                .filter((f) => !f.preReview)
+                .map((f) => `  - "${f.promptSnippet.slice(0, 80)}"`)
+                .join('\n') +
+              `\n--- evidence (last 3KB) ---\n${obs.evidence}`,
+          );
+        }
+      } finally {
+        try {
+          fs.rmSync(PLAN_PATH, { force: true });
+        } catch {
+          /* best-effort */
+        }
+      }
+    },
+    1_700_000,
+  );
+});