diff --git a/packages/node/src/cron/common.ts b/packages/node/src/cron/common.ts
new file mode 100644
index 000000000000..c710d154fdd5
--- /dev/null
+++ b/packages/node/src/cron/common.ts
@@ -0,0 +1,50 @@
+const replacements: [string, string][] = [
+  ['january', '1'],
+  ['february', '2'],
+  ['march', '3'],
+  ['april', '4'],
+  ['may', '5'],
+  ['june', '6'],
+  ['july', '7'],
+  ['august', '8'],
+  ['september', '9'],
+  ['october', '10'],
+  ['november', '11'],
+  ['december', '12'],
+  ['jan', '1'],
+  ['feb', '2'],
+  ['mar', '3'],
+  ['apr', '4'],
+  ['may', '5'],
+  ['jun', '6'],
+  ['jul', '7'],
+  ['aug', '8'],
+  ['sep', '9'],
+  ['oct', '10'],
+  ['nov', '11'],
+  ['dec', '12'],
+  ['sunday', '0'],
+  ['monday', '1'],
+  ['tuesday', '2'],
+  ['wednesday', '3'],
+  ['thursday', '4'],
+  ['friday', '5'],
+  ['saturday', '6'],
+  ['sun', '0'],
+  ['mon', '1'],
+  ['tue', '2'],
+  ['wed', '3'],
+  ['thu', '4'],
+  ['fri', '5'],
+  ['sat', '6'],
+];
+
+/**
+ * Replaces names in cron expressions
+ */
+export function replaceCronNames(cronExpression: string): string {
+  return replacements.reduce(
+    (acc, [name, replacement]) => acc.replace(new RegExp(name, 'gi'), replacement),
+    cronExpression,
+  );
+}
diff --git a/packages/node/src/cron/cron.ts b/packages/node/src/cron/cron.ts
new file mode 100644
index 000000000000..a8b42ec0fed7
--- /dev/null
+++ b/packages/node/src/cron/cron.ts
@@ -0,0 +1,115 @@
+import { withMonitor } from '@sentry/core';
+import { replaceCronNames } from './common';
+
+export type CronJobParams = {
+  cronTime: string | Date;
+  onTick: (context: unknown, onComplete?: unknown) => void | Promise<void>;
+  onComplete?: () => void | Promise<void>;
+  start?: boolean | null;
+  context?: unknown;
+  runOnInit?: boolean | null;
+  utcOffset?: number;
+  timeZone?: string;
+  unrefTimeout?: boolean | null;
+};
+
+export type CronJob = {
+  //
+};
+
+export type CronJobConstructor = {
+  from: (param: CronJobParams) => CronJob;
+
+  new (
+    cronTime: CronJobParams['cronTime'],
+    onTick: CronJobParams['onTick'],
+    onComplete?: CronJobParams['onComplete'],
+    start?: CronJobParams['start'],
+    timeZone?: CronJobParams['timeZone'],
+    context?: CronJobParams['context'],
+    runOnInit?: CronJobParams['runOnInit'],
+    utcOffset?: CronJobParams['utcOffset'],
+    unrefTimeout?: CronJobParams['unrefTimeout'],
+  ): CronJob;
+};
+
+const ERROR_TEXT = 'Automatic instrumentation of CronJob only supports crontab string';
+
+/**
+ * Instruments the `cron` library to send a check-in event to Sentry for each job execution.
+ *
+ * ```ts
+ * import * as Sentry from '@sentry/node';
+ * import { CronJob } from 'cron';
+ *
+ * const CronJobWithCheckIn = Sentry.cron.instrumentCron(CronJob, 'my-cron-job');
+ *
+ * // use the constructor
+ * const job = new CronJobWithCheckIn('* * * * *', () => {
+ *  console.log('You will see this message every minute');
+ * });
+ *
+ * // or from
+ * const job = CronJobWithCheckIn.from({ cronTime: '* * * * *', onTick: () => {
+ *   console.log('You will see this message every minute');
+ * });
+ * ```
+ */
+export function instrumentCron<T>(lib: T & CronJobConstructor, monitorSlug: string): T {
+  return new Proxy(lib, {
+    construct(target, args: ConstructorParameters<CronJobConstructor>) {
+      const [cronTime, onTick, onComplete, start, timeZone, ...rest] = args;
+
+      if (typeof cronTime !== 'string') {
+        throw new Error(ERROR_TEXT);
+      }
+
+      const cronString = replaceCronNames(cronTime);
+
+      function monitoredTick(context: unknown, onComplete?: unknown): void | Promise<void> {
+        return withMonitor(
+          monitorSlug,
+          () => {
+            return onTick(context, onComplete);
+          },
+          {
+            schedule: { type: 'crontab', value: cronString },
+            ...(timeZone ? { timeZone } : {}),
+          },
+        );
+      }
+
+      return new target(cronTime, monitoredTick, onComplete, start, timeZone, ...rest);
+    },
+    get(target, prop: keyof CronJobConstructor) {
+      if (prop === 'from') {
+        return (param: CronJobParams) => {
+          const { cronTime, onTick, timeZone } = param;
+
+          if (typeof cronTime !== 'string') {
+            throw new Error(ERROR_TEXT);
+          }
+
+          const cronString = replaceCronNames(cronTime);
+
+          param.onTick = (context: unknown, onComplete?: unknown) => {
+            return withMonitor(
+              monitorSlug,
+              () => {
+                return onTick(context, onComplete);
+              },
+              {
+                schedule: { type: 'crontab', value: cronString },
+                ...(timeZone ? { timeZone } : {}),
+              },
+            );
+          };
+
+          return target.from(param);
+        };
+      } else {
+        return target[prop];
+      }
+    },
+  });
+}
diff --git a/packages/node/src/index.ts b/packages/node/src/index.ts
index 36d2d8beac53..222adc68a4f4 100644
--- a/packages/node/src/index.ts
+++ b/packages/node/src/index.ts
@@ -100,3 +100,10 @@ const INTEGRATIONS = {
 export { INTEGRATIONS as Integrations, Handlers };
 
 export { hapiErrorPlugin } from './integrations/hapi';
+
+import { instrumentCron } from './cron/cron';
+
+/** Methods to instrument cron libraries for Sentry check-ins */
+export const cron = {
+  instrumentCron,
+};
diff --git a/packages/node/test/cron.test.ts b/packages/node/test/cron.test.ts
new file mode 100644
index 000000000000..9d4b082e9c22
--- /dev/null
+++ b/packages/node/test/cron.test.ts
@@ -0,0 +1,81 @@
+import * as SentryCore from '@sentry/core';
+
+import { cron } from '../src';
+import type { CronJob, CronJobParams } from '../src/cron/cron';
+
+describe('cron', () => {
+  let withMonitorSpy: jest.SpyInstance;
+
+  beforeEach(() => {
+    withMonitorSpy = jest.spyOn(SentryCore, 'withMonitor');
+  });
+
+  afterEach(() => {
+    jest.restoreAllMocks();
+  });
+
+  describe('cron', () => {
+    class CronJobMock {
+      constructor(
+        cronTime: CronJobParams['cronTime'],
+        onTick: CronJobParams['onTick'],
+        _onComplete?: CronJobParams['onComplete'],
+        _start?: CronJobParams['start'],
+        _timeZone?: CronJobParams['timeZone'],
+        _context?: CronJobParams['context'],
+        _runOnInit?: CronJobParams['runOnInit'],
+        _utcOffset?: CronJobParams['utcOffset'],
+        _unrefTimeout?: CronJobParams['unrefTimeout'],
+      ) {
+        expect(cronTime).toBe('* * * Jan,Sep Sun');
+        expect(onTick).toBeInstanceOf(Function);
+        setImmediate(() => onTick(undefined, undefined));
+      }
+
+      static from(params: CronJobParams): CronJob {
+        return new CronJobMock(
+          params.cronTime,
+          params.onTick,
+          params.onComplete,
+          params.start,
+          params.timeZone,
+          params.context,
+          params.runOnInit,
+          params.utcOffset,
+          params.unrefTimeout,
+        );
+      }
+    }
+
+    test('new CronJob()', done => {
+      expect.assertions(4);
+
+      const CronJobWithCheckIn = cron.instrumentCron(CronJobMock, 'my-cron-job');
+
+      const _ = new CronJobWithCheckIn('* * * Jan,Sep Sun', () => {
+        expect(withMonitorSpy).toHaveBeenCalledTimes(1);
+        expect(withMonitorSpy).toHaveBeenLastCalledWith('my-cron-job', expect.anything(), {
+          schedule: { type: 'crontab', value: '* * * 1,9 0' },
+        });
+        done();
+      });
+    });
+
+    test('CronJob.from()', done => {
+      expect.assertions(4);
+
+      const CronJobWithCheckIn = cron.instrumentCron(CronJobMock, 'my-cron-job');
+
+      const _ = CronJobWithCheckIn.from({
+        cronTime: '* * * Jan,Sep Sun',
+        onTick: () => {
+          expect(withMonitorSpy).toHaveBeenCalledTimes(1);
+          expect(withMonitorSpy).toHaveBeenLastCalledWith('my-cron-job', expect.anything(), {
+            schedule: { type: 'crontab', value: '* * * 1,9 0' },
+          });
+          done();
+        },
+      });
+    });
+  });
+});