diff --git a/charts/lobu/templates/deployment.yaml b/charts/lobu/templates/deployment.yaml
index 314386cff..d18437dea 100644
--- a/charts/lobu/templates/deployment.yaml
+++ b/charts/lobu/templates/deployment.yaml
@@ -94,9 +94,14 @@ spec:
             - secretRef:
                 name: {{ $secretName }}
           {{- end }}
+          # Readiness probes the DB too (/health/ready does SELECT 1).
+          # Failing readiness pulls the pod out of the Service endpoint set
+          # without restarting it — right semantic for a transient DB blip.
+          # Liveness stays on /health (process-up only) so a pooler hiccup
+          # doesn't trigger CrashLoopBackOff.
           readinessProbe:
             httpGet:
-              path: /health
+              path: /health/ready
               port: http
             initialDelaySeconds: {{ .Values.healthCheck.readinessProbe.initialDelaySeconds }}
             periodSeconds: {{ .Values.healthCheck.readinessProbe.periodSeconds }}
diff --git a/packages/server/src/index.ts b/packages/server/src/index.ts
index 77e006ac1..3b6d37270 100644
--- a/packages/server/src/index.ts
+++ b/packages/server/src/index.ts
@@ -387,7 +387,9 @@ app.use('/*', async (c, next) => {
 });
 
 /**
- * Health check endpoint
+ * Liveness probe — process is up. Cheap, dependency-free; failing this
+ * signals "restart the pod." Don't add DB or downstream checks here, or a
+ * transient pooler hiccup will cause a CrashLoop.
  */
 app.get('/health', (c) => {
   return c.json({
@@ -398,6 +400,24 @@ app.get('/health', (c) => {
   });
 });
 
+/**
+ * Readiness probe — process is up AND can talk to the database. Failing
+ * this drops the pod from the Service's endpoint set without restarting
+ * it, which is the right semantic for transient DB unavailability.
+ */
+app.get('/health/ready', async (c) => {
+  try {
+    const sql = getDb();
+    await sql`SELECT 1`;
+    return c.json({ status: 'ok', service: 'lobu-api' });
+  } catch (error) {
+    return c.json(
+      { status: 'unready', service: 'lobu-api', error: errorMessage(error) },
+      503
+    );
+  }
+});
+
 /**
  * Scheduler health check endpoint
  * Returns detailed metrics about the feed scheduling system
diff --git a/packages/server/src/server.ts b/packages/server/src/server.ts
index 8cbf7c68e..92291e314 100644
--- a/packages/server/src/server.ts
+++ b/packages/server/src/server.ts
@@ -28,7 +28,7 @@ import path from 'node:path';
 import { fileURLToPath } from 'node:url';
 import { getRequestListener } from '@hono/node-server';
 import { Hono } from 'hono';
-import { closeDbSingleton, probeListenNotify } from './db/client';
+import { closeDbSingleton, getDb, probeListenNotify } from './db/client';
 import { mountViteDev } from './dev-vite';
 import type { Env } from './index';
 import { app as mainApp } from './index';
@@ -43,6 +43,7 @@ import { assertExternalDepsResolvable } from '../../connector-worker/src/runtime
 import { isSentryReported, markSentryReported } from './sentry';
 import { getEnvFromProcess } from './utils/env';
 import logger from './utils/logger';
+import { assertSchemaUpToDate } from './utils/schema-version-check';
 import { initWorkspaceProvider } from './workspace';
 
 // Create a wrapper app that injects environment into each request
@@ -145,6 +146,19 @@ async function main() {
   }
   process.env.DATABASE_URL = databaseUrl;
 
+  // Refuse to boot if the image expects a migration the database hasn't
+  // applied. Skippable via SKIP_SCHEMA_VERSION_CHECK=1 for emergency
+  // forward-flight (e.g. rolling back to an older image whose migrations
+  // dir is a strict prefix of what's already applied). See
+  // utils/schema-version-check.ts for the 2026-05-16 incident this guards.
+  if (process.env.SKIP_SCHEMA_VERSION_CHECK !== '1') {
+    const migrationsDir =
+      process.env.LOBU_MIGRATIONS_DIR?.trim() || path.join(PACKAGE_REPO_ROOT, 'db', 'migrations');
+    await assertSchemaUpToDate(getDb(), { migrationsDir });
+  } else {
+    logger.warn('[schema-check] SKIP_SCHEMA_VERSION_CHECK=1 — skipping boot-time assertion');
+  }
+
   // Verify LISTEN/NOTIFY actually delivers. This is a *detector*, not a gate:
   // the runs-queue has a 200ms SKIP-LOCKED poll fallback that keeps the queue
   // correct even when LISTEN is silently dropped (transaction-mode pgbouncer,
diff --git a/packages/server/src/utils/__tests__/schema-version-check.test.ts b/packages/server/src/utils/__tests__/schema-version-check.test.ts
new file mode 100644
index 000000000..f33f58c07
--- /dev/null
+++ b/packages/server/src/utils/__tests__/schema-version-check.test.ts
@@ -0,0 +1,137 @@
+import { mkdtempSync, rmSync, writeFileSync } from 'node:fs';
+import { tmpdir } from 'node:os';
+import path from 'node:path';
+import type { Sql } from 'postgres';
+import { afterEach, beforeEach, describe, expect, it } from 'vitest';
+import type { DbClient } from '../../db/client';
+import {
+  assertSchemaUpToDate,
+  compareSchemaVersions,
+  readExpectedSchemaVersion,
+} from '../schema-version-check';
+
+/**
+ * Build a stub DbClient that always returns the given `applied` version when
+ * a tagged-template query runs. Just enough surface to satisfy the call site
+ * in `assertSchemaUpToDate`.
+ */
+function makeStubDb(applied: string | null): DbClient {
+  const fn = ((_strings: TemplateStringsArray, ..._values: unknown[]) => {
+    return Object.assign(Promise.resolve([{ version: applied }]), { count: 1 });
+  }) as unknown as Sql;
+  return fn as unknown as DbClient;
+}
+
+describe('readExpectedSchemaVersion', () => {
+  let dir: string;
+
+  beforeEach(() => {
+    dir = mkdtempSync(path.join(tmpdir(), 'schema-check-'));
+  });
+
+  afterEach(() => {
+    rmSync(dir, { recursive: true, force: true });
+  });
+
+  it('returns the highest version prefix from migration filenames', () => {
+    writeFileSync(path.join(dir, '20260512000000_first.sql'), '');
+    writeFileSync(path.join(dir, '20260515150000_geo_enrichment.sql'), '');
+    writeFileSync(path.join(dir, '20260516200000_events_search_tsv.sql'), '');
+    expect(readExpectedSchemaVersion(dir)).toBe('20260516200000');
+  });
+
+  it('ignores non-migration files (no dbmate-style prefix)', () => {
+    writeFileSync(path.join(dir, '20260512000000_real.sql'), '');
+    writeFileSync(path.join(dir, 'README.md'), '');
+    writeFileSync(path.join(dir, 'rollback.sql'), '');
+    expect(readExpectedSchemaVersion(dir)).toBe('20260512000000');
+  });
+
+  it('returns null for an unreadable directory (treat as "no expectation")', () => {
+    expect(readExpectedSchemaVersion(path.join(dir, 'does-not-exist'))).toBeNull();
+  });
+
+  it('returns null for an empty directory', () => {
+    expect(readExpectedSchemaVersion(dir)).toBeNull();
+  });
+});
+
+describe('compareSchemaVersions', () => {
+  it('returns ok when applied >= expected', () => {
+    expect(compareSchemaVersions('20260516200000', '20260516200000')).toEqual({
+      kind: 'ok',
+      expected: '20260516200000',
+      applied: '20260516200000',
+    });
+    expect(compareSchemaVersions('20260516200000', '20260517000000')).toMatchObject({
+      kind: 'ok',
+    });
+  });
+
+  it('returns mismatch when applied is behind expected', () => {
+    expect(compareSchemaVersions('20260516200000', '20260516120000')).toEqual({
+      kind: 'mismatch',
+      expected: '20260516200000',
+      applied: '20260516120000',
+    });
+  });
+
+  it('returns mismatch when no version is applied yet', () => {
+    expect(compareSchemaVersions('20260516200000', null)).toEqual({
+      kind: 'mismatch',
+      expected: '20260516200000',
+      applied: null,
+    });
+  });
+
+  it('returns ok when expected is null (dev fallback / no migrations on disk)', () => {
+    expect(compareSchemaVersions(null, null)).toMatchObject({ kind: 'ok' });
+    expect(compareSchemaVersions(null, '20260516200000')).toMatchObject({ kind: 'ok' });
+  });
+});
+
+describe('assertSchemaUpToDate', () => {
+  let dir: string;
+  const originalNodeEnv = process.env.NODE_ENV;
+
+  beforeEach(() => {
+    dir = mkdtempSync(path.join(tmpdir(), 'schema-check-'));
+  });
+
+  afterEach(() => {
+    rmSync(dir, { recursive: true, force: true });
+    process.env.NODE_ENV = originalNodeEnv;
+  });
+
+  it('throws in production when the migrations directory is missing (fail closed)', async () => {
+    process.env.NODE_ENV = 'production';
+    const missingDir = path.join(dir, 'does-not-exist');
+    await expect(
+      assertSchemaUpToDate(makeStubDb('20260516200000'), { migrationsDir: missingDir })
+    ).rejects.toThrow(/missing db\/migrations/i);
+  });
+
+  it('passes in development when the migrations directory is missing (fail open for dev)', async () => {
+    process.env.NODE_ENV = 'development';
+    const missingDir = path.join(dir, 'does-not-exist');
+    await expect(
+      assertSchemaUpToDate(makeStubDb(null), { migrationsDir: missingDir })
+    ).resolves.toBeUndefined();
+  });
+
+  it('throws when the database is behind the migrations directory', async () => {
+    process.env.NODE_ENV = 'production';
+    writeFileSync(path.join(dir, '20260516200000_events_search_tsv.sql'), '');
+    await expect(
+      assertSchemaUpToDate(makeStubDb('20260515120000'), { migrationsDir: dir })
+    ).rejects.toThrow(/database is behind/i);
+  });
+
+  it('passes when the database is at the expected version', async () => {
+    process.env.NODE_ENV = 'production';
+    writeFileSync(path.join(dir, '20260516200000_events_search_tsv.sql'), '');
+    await expect(
+      assertSchemaUpToDate(makeStubDb('20260516200000'), { migrationsDir: dir })
+    ).resolves.toBeUndefined();
+  });
+});
diff --git a/packages/server/src/utils/logger.ts b/packages/server/src/utils/logger.ts
index 9f8f1ba0d..a0d070c04 100644
--- a/packages/server/src/utils/logger.ts
+++ b/packages/server/src/utils/logger.ts
@@ -25,6 +25,14 @@ const getLogLevel = (): pino.Level => {
 /**
  * Create a Pino logger instance
  */
+// pino's default error serializer only fires for the `err` key, so
+// `logger.error({ error }, '...')` silently logs `error: {}` (Error's own
+// fields are non-enumerable). Register the same serializer on the `error`
+// key too so either spelling produces a real stack/message. Found during
+// the 2026-05-16 prod outage where every queue failure logged `error: {}`
+// and hid `column "events.search_tsv" does not exist`.
+const errSerializer = pino.stdSerializers.err;
+
 const logger = pino({
   level: getLogLevel(),
   browser: {
@@ -35,6 +43,10 @@ const logger = pino({
       return { level: label };
     },
   },
+  serializers: {
+    err: errSerializer,
+    error: errSerializer,
+  },
 });
 
 export default logger;
diff --git a/packages/server/src/utils/schema-version-check.ts b/packages/server/src/utils/schema-version-check.ts
new file mode 100644
index 000000000..a810e7968
--- /dev/null
+++ b/packages/server/src/utils/schema-version-check.ts
@@ -0,0 +1,137 @@
+/**
+ * Boot-time schema-version assertion.
+ *
+ * Compares the highest migration version present in `db/migrations/` (what
+ * this image expects to run against) with the highest version recorded in
+ * the database's `schema_migrations` table. If the database is behind,
+ * throws — the server boot path catches it, logs, and exits non-zero so the
+ * pod fails readiness and Kubernetes refuses to route traffic.
+ *
+ * Why: on 2026-05-16 the pre-upgrade migration Job for
+ * `20260516200000_events_search_tsv.sql` timed out at 60s (table rewrite on
+ * a 1.15M-row events table under ACCESS EXCLUSIVE > statement_timeout). The
+ * Job exited non-zero, but the app Deployment rolled forward anyway with an
+ * image that queried the new view's `search_tsv` column. Every request
+ * through the affected paths threw; the pod OOM'd and CrashLoopBackOff'd.
+ * A boot-time gate would have refused to start that image and kept the
+ * previous version serving traffic.
+ */
+
+import { readdirSync } from 'node:fs';
+import type { DbClient } from '../db/client';
+import logger from './logger';
+
+const MIGRATION_FILENAME_RE = /^(\d+)_[^/]+\.sql$/;
+
+/**
+ * Find the largest version prefix (e.g. `20260516200000`) across files in
+ * `migrationsDir`. Returns null if the directory is empty / unreadable —
+ * that case is treated as "no expectation" rather than failing closed, so a
+ * dev environment without migrations checked out doesn't deadlock boot.
+ */
+export function readExpectedSchemaVersion(migrationsDir: string): string | null {
+  let entries: string[];
+  try {
+    entries = readdirSync(migrationsDir);
+  } catch (err) {
+    logger.warn(
+      { err, migrationsDir },
+      '[schema-check] migrations directory not readable — skipping schema-version assertion'
+    );
+    return null;
+  }
+
+  let max: string | null = null;
+  for (const name of entries) {
+    const match = MIGRATION_FILENAME_RE.exec(name);
+    if (!match) continue;
+    const version = match[1];
+    if (max === null || version > max) max = version;
+  }
+  return max;
+}
+
+/**
+ * Query the highest applied version from the database. Returns null if the
+ * `schema_migrations` table is empty (fresh install) — the caller decides
+ * whether that's expected.
+ */
+export async function readAppliedSchemaVersion(sql: DbClient): Promise<string | null> {
+  const rows = (await sql`SELECT MAX(version) AS version FROM public.schema_migrations`) as Array<{
+    version: string | null;
+  }>;
+  return rows[0]?.version ?? null;
+}
+
+export interface SchemaVersionMismatch {
+  kind: 'mismatch';
+  expected: string;
+  applied: string | null;
+}
+
+export interface SchemaVersionOk {
+  kind: 'ok';
+  expected: string | null;
+  applied: string | null;
+}
+
+/**
+ * Compare expected (from disk) vs applied (from DB). Returns a discriminated
+ * union the caller can branch on, instead of throwing — keeps tests cheap.
+ */
+export function compareSchemaVersions(
+  expected: string | null,
+  applied: string | null
+): SchemaVersionOk | SchemaVersionMismatch {
+  if (expected === null) return { kind: 'ok', expected, applied };
+  if (applied !== null && applied >= expected) {
+    return { kind: 'ok', expected, applied };
+  }
+  return { kind: 'mismatch', expected, applied };
+}
+
+/**
+ * Boot-time assertion: throws if the database is behind the image's
+ * migrations directory. Call once during server startup, before opening the
+ * HTTP listener.
+ *
+ * Fails closed in production: if `migrationsDir` can't be listed (bad path,
+ * missing copy in the image, wrong volume mount), `NODE_ENV=production`
+ * treats that as a deployment defect and throws. In dev a missing/empty
+ * directory degrades to a warning — so `bun run dev` from a worktree that
+ * doesn't have `db/` checked out still boots.
+ */
+export async function assertSchemaUpToDate(
+  sql: DbClient,
+  options: { migrationsDir: string }
+): Promise<void> {
+  const expected = readExpectedSchemaVersion(options.migrationsDir);
+
+  if (expected === null && process.env.NODE_ENV === 'production') {
+    const msg =
+      `[schema-check] migrations directory ${options.migrationsDir} is empty or unreadable in a ` +
+      `production build — the image is missing db/migrations. Refusing to start.`;
+    logger.error({ migrationsDir: options.migrationsDir }, msg);
+    throw new Error(msg);
+  }
+
+  const applied = await readAppliedSchemaVersion(sql);
+  const result = compareSchemaVersions(expected, applied);
+
+  if (result.kind === 'mismatch') {
+    const msg =
+      `[schema-check] database is behind the image. Expected migration ${result.expected} ` +
+      `to be applied, but the highest applied version is ${result.applied ?? '(none)'}. ` +
+      `Run \`dbmate up\` against this database before rolling out this image.`;
+    logger.error(
+      { expected: result.expected, applied: result.applied, migrationsDir: options.migrationsDir },
+      msg
+    );
+    throw new Error(msg);
+  }
+
+  logger.info(
+    { expected: result.expected, applied: result.applied },
+    '[schema-check] schema version up to date'
+  );
+}
diff --git a/packages/web b/packages/web
index 4516312cf..c390103ed 160000
--- a/packages/web
+++ b/packages/web
@@ -1 +1 @@
-Subproject commit 4516312cf933313e693a2093da4ffb024740cbc5
+Subproject commit c390103ed009f00f91fb5547a811235c914dd3d8