diff --git a/common/dataset-updater.js b/common/dataset-updater.js
index 03b5e25f..91bb37d3 100644
--- a/common/dataset-updater.js
+++ b/common/dataset-updater.js
@@ -341,6 +341,18 @@ export const rowsMissingACheck = async (rows, { pattern, now = new Date() }) =>
     return stale;
 };
 
+/**
+ * Sentry Crons settings for a run updating `rowCount` datasets in turn: its
+ * longest legitimate run is every row at its timeout, plus a margin, so a
+ * healthy run is never marked failed. Exported for tests.
+ */
+export const monitorConfigFor = (pattern, rowCount, timezone) => ({
+    schedule: { type: 'crontab', value: pattern },
+    timezone,
+    checkinMargin: 60,
+    maxRuntime: Math.ceil((rowCount * UPDATE_TIMEOUT_MS) / 60000) + 10,
+});
+
 let scheduler = null;
 
 /**
@@ -360,7 +372,7 @@ export const startDatasetScheduler = (rows) => {
     scheduler = new Cron(pattern, { protect: true, unref: true }, () => withCronMonitor(
         'dataset-update',
         () => updateDatasets(scheduled),
-        { schedule: { type: 'crontab', value: pattern }, timezone, checkinMargin: 60, maxRuntime: 60 },
+        monitorConfigFor(pattern, scheduled.length, timezone),
     ).catch((error) => logger.error({ err: error }, 'dataset update run failed')));
     const next = scheduler.nextRun()?.toLocaleString('en-US', { hour12: false });
     logger.info(`🗓️  Dataset auto update: ${scheduled.map((row) => row.id).join(', ')} at cron ${pattern} (next ${next})`);
diff --git a/tests/dataset-updater.test.js b/tests/dataset-updater.test.js
index f7b5a97f..1c1bf1c3 100644
--- a/tests/dataset-updater.test.js
+++ b/tests/dataset-updater.test.js
@@ -15,7 +15,7 @@ import lockfile from 'proper-lockfile';
 import {
     STATE_FILE, LOCK_FILE, updateDataset, bootstrapDataset, readState, isPresent,
     isAutoUpdateEnabled, startDatasetScheduler, DEFAULT_UPDATE_CRON, rowsMissingACheck, watchDatasets,
-    updateDatasets, downloadToFile,
+    updateDatasets, downloadToFile, monitorConfigFor,
 } from '../common/dataset-updater.js';
 import logger from '../common/logger.js';
 import { setUpstreamUserAgent } from '../common/fetch-with-timeout.js';
@@ -302,6 +302,16 @@ describe('startDatasetScheduler', () => {
     });
 });
 
+describe('monitorConfigFor', () => {
+    it('allows every scheduled row its full timeout, plus a margin', () => {
+        const config = monitorConfigFor('30 4 * * *', 4, 'Asia/Singapore');
+        assert.equal(config.maxRuntime, 4 * 30 + 10);
+        assert.deepEqual(config.schedule, { type: 'crontab', value: '30 4 * * *' });
+        assert.equal(config.timezone, 'Asia/Singapore');
+        assert.equal(monitorConfigFor('30 4 * * *', 1).maxRuntime, 40);
+    });
+});
+
 describe('rowsMissingACheck', () => {
     const at = (day, hour, minute) => new Date(2026, 9, day, hour, minute); // local time, like the cron
     const pattern = '30 4 * * *';