diff --git a/src/helpers/scheduleDelayed.ts b/src/helpers/scheduleDelayed.ts
new file mode 100644
index 00000000..789bd7d1
--- /dev/null
+++ b/src/helpers/scheduleDelayed.ts
@@ -0,0 +1,48 @@
+/** SetTimeout delays above this overflow a signed 32-bit integer and fire immediately. */
+const MAX_TIMEOUT_DELAY_MS = 2 ** 31 - 1;
+
+type ArmTimer = (callback: () => void, delayMs: number) => ReturnType<typeof setTimeout>;
+
+const armNativeTimer: ArmTimer = (callback, delayMs) => setTimeout(callback, delayMs);
+
+export type ScheduledTask = {
+  /** Stops the task. Works across chunk boundaries, unlike a raw timer handle. */
+  cancel: () => void;
+};
+
+export function scheduleDelayed(
+  delayMs: number,
+  task: () => void,
+  armTimer: ArmTimer = armNativeTimer,
+): ScheduledTask {
+  let handle: ReturnType<typeof setTimeout> | undefined;
+  let cancelled = false;
+
+  const arm = (remainingMs: number) => {
+    const chunkMs = Math.min(remainingMs, MAX_TIMEOUT_DELAY_MS);
+    handle = armTimer(() => {
+      if (cancelled) {
+        return;
+      }
+
+      const restMs = remainingMs - chunkMs;
+      if (restMs > 0) {
+        arm(restMs);
+        return;
+      }
+
+      task();
+    }, chunkMs);
+  };
+
+  arm(delayMs);
+
+  return {
+    cancel: () => {
+      cancelled = true;
+      if (handle !== undefined) {
+        clearTimeout(handle);
+      }
+    },
+  };
+}
diff --git a/src/index.tsx b/src/index.tsx
index 995934f2..3fcff561 100644
--- a/src/index.tsx
+++ b/src/index.tsx
@@ -8,6 +8,7 @@ import db from "./db/db";
 import { Jobs } from "./db/types";
 import { AUTO_DELETE_EVERY_N_HOURS, WEBROOT } from "./helpers/env";
 import "./helpers/printVersions";
+import { scheduleDelayed, ScheduledTask } from "./helpers/scheduleDelayed";
 import { chooseConverter } from "./pages/chooseConverter";
 import { convert } from "./pages/convert";
 import { deleteFile } from "./pages/deleteFile";
@@ -75,12 +76,15 @@ app.listen(process.env.PORT || 3000);
 
 console.log(`🦊 Elysia is running at http://${app.server?.hostname}:${app.server?.port}${WEBROOT}`);
 
-let clearJobsTimer: ReturnType<typeof setTimeout> | undefined;
+const MILLISECONDS_PER_HOUR = 60 * 60 * 1000;
+const autoDeleteIntervalMs = AUTO_DELETE_EVERY_N_HOURS * MILLISECONDS_PER_HOUR;
+let clearJobsTimer: ScheduledTask;
+
 const clearJobs = () => {
   const jobs = db
     .query("SELECT * FROM jobs WHERE date_created < ?")
     .as(Jobs)
-    .all(new Date(Date.now() - AUTO_DELETE_EVERY_N_HOURS * 60 * 60 * 1000).toISOString());
+    .all(new Date(Date.now() - autoDeleteIntervalMs).toISOString());
 
   for (const job of jobs) {
     // delete the directories
@@ -97,7 +101,7 @@ const clearJobs = () => {
     db.query("DELETE FROM jobs WHERE id = ?").run(job.id);
   }
 
-  clearJobsTimer = setTimeout(clearJobs, AUTO_DELETE_EVERY_N_HOURS * 60 * 60 * 1000);
+  clearJobsTimer = scheduleDelayed(autoDeleteIntervalMs, clearJobs);
 };
 
 if (AUTO_DELETE_EVERY_N_HOURS > 0) {
@@ -109,7 +113,7 @@ const handleShutdown = async () => {
   if (isShuttingDown) return;
   isShuttingDown = true;
   if (clearJobsTimer) {
-    clearTimeout(clearJobsTimer);
+    clearJobsTimer.cancel();
   }
   try {
     await app.stop(true);
diff --git a/tests/helpers/scheduleDelayed.test.ts b/tests/helpers/scheduleDelayed.test.ts
new file mode 100644
index 00000000..2a2c532a
--- /dev/null
+++ b/tests/helpers/scheduleDelayed.test.ts
@@ -0,0 +1,144 @@
+import { expect, test } from "bun:test";
+
+import { scheduleDelayed } from "../../src/helpers/scheduleDelayed";
+
+/** Largest delay setTimeout accepts before a 32-bit overflow. */
+const MAX_TIMEOUT_DELAY_MS = 2 ** 31 - 1;
+/** Delay reported in the TimeoutOverflowWarning: 30 days in milliseconds. */
+const THIRTY_DAYS_MS = 30 * 24 * 60 * 60 * 1000;
+
+type ArmedTimer = {
+  delayMs: number;
+  fire: () => void;
+};
+
+function captureTimers(): {
+  armed: ArmedTimer[];
+  armTimer: (callback: () => void, delayMs: number) => ReturnType<typeof setTimeout>;
+} {
+  const armed: ArmedTimer[] = [];
+  const armTimer = (callback: () => void, delayMs: number) => {
+    armed.push({ delayMs, fire: callback });
+    return 0 as unknown as ReturnType<typeof setTimeout>;
+  };
+  return { armed, armTimer };
+}
+
+test("runs a one day delay as a single timer", () => {
+  const { armed, armTimer } = captureTimers();
+  let runs = 0;
+  const oneDayMs = 24 * 60 * 60 * 1000;
+
+  scheduleDelayed(
+    oneDayMs,
+    () => {
+      runs += 1;
+    },
+    armTimer,
+  );
+
+  expect(armed).toHaveLength(1);
+  const timer = armed.shift();
+  expect(timer?.delayMs).toBe(oneDayMs);
+  expect(runs).toBe(0);
+
+  timer?.fire();
+  expect(runs).toBe(1);
+  expect(armed).toHaveLength(0);
+});
+
+test("runs a 30 day delay in timer-sized chunks that add up to 30 days", () => {
+  expect(THIRTY_DAYS_MS).toBe(2_592_000_000);
+
+  const { armed, armTimer } = captureTimers();
+  let runs = 0;
+  scheduleDelayed(
+    THIRTY_DAYS_MS,
+    () => {
+      runs += 1;
+    },
+    armTimer,
+  );
+
+  let elapsedMs = 0;
+  let chunks = 0;
+  while (runs === 0) {
+    chunks += 1;
+    expect(chunks).toBeLessThanOrEqual(3);
+
+    const next = armed.shift();
+    if (!next) {
+      throw new Error("timer chain ended before the task ran");
+    }
+
+    expect(next.delayMs).toBeGreaterThan(0);
+    expect(next.delayMs).toBeLessThanOrEqual(MAX_TIMEOUT_DELAY_MS);
+    elapsedMs += next.delayMs;
+    next.fire();
+  }
+
+  expect(runs).toBe(1);
+  expect(elapsedMs).toBe(THIRTY_DAYS_MS);
+  expect(armed).toHaveLength(0);
+});
+
+test("cancelling before the first chunk fires prevents the task", () => {
+  const { armed, armTimer } = captureTimers();
+  let runs = 0;
+  const scheduled = scheduleDelayed(
+    THIRTY_DAYS_MS,
+    () => {
+      runs += 1;
+    },
+    armTimer,
+  );
+
+  scheduled.cancel();
+  armed.shift()?.fire();
+  expect(runs).toBe(0);
+  expect(armed).toHaveLength(0);
+});
+
+test("cancelling after a chunk fired still stops the remaining chain", () => {
+  const { armed, armTimer } = captureTimers();
+  let runs = 0;
+  const scheduled = scheduleDelayed(
+    THIRTY_DAYS_MS,
+    () => {
+      runs += 1;
+    },
+    armTimer,
+  );
+
+  armed.shift()?.fire();
+  expect(armed).toHaveLength(1);
+  expect(runs).toBe(0);
+
+  scheduled.cancel();
+  armed.shift()?.fire();
+  expect(runs).toBe(0);
+  expect(armed).toHaveLength(0);
+});
+
+test("does not emit a timeout overflow warning for a 30 day delay", async () => {
+  const warnings: string[] = [];
+  const onWarning = (warning: Error) => {
+    warnings.push(warning.message);
+  };
+  process.on("warning", onWarning);
+
+  let ran = false;
+  const scheduled = scheduleDelayed(THIRTY_DAYS_MS, () => {
+    ran = true;
+  });
+
+  try {
+    await new Promise((resolve) => setTimeout(resolve, 40));
+    expect(ran).toBe(false);
+    expect(warnings.join("\n")).not.toContain("TimeoutOverflowWarning");
+    expect(warnings.join("\n")).not.toContain("2592000000");
+  } finally {
+    scheduled.cancel();
+    process.off("warning", onWarning);
+  }
+});