diff --git a/package-lock.json b/package-lock.json
index d7025d81..bf7dd727 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -22,6 +22,7 @@
         "nodemailer": "^6.5.0",
         "notifme-sdk": "^1.10.0",
         "prettier": "^2.2.1",
+        "rrule": "^2.8.1",
         "shelljs": "^0.8.4",
         "tcp-ping": "^0.1.1",
         "ws": "^7.4.6"
@@ -11955,6 +11956,14 @@
         "url": "https://github.com/sponsors/isaacs"
       }
     },
+    "node_modules/rrule": {
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/rrule/-/rrule-2.8.1.tgz",
+      "integrity": "sha512-hM3dHSBMeaJ0Ktp7W38BJZ7O1zOgaFEsn41PDk+yHoEtfLV+PoJt9E9xAlZiWgf/iqEqionN0ebHFZIDAp+iGw==",
+      "dependencies": {
+        "tslib": "^2.4.0"
+      }
+    },
     "node_modules/rsvp": {
       "version": "4.8.5",
       "resolved": "https://registry.npmjs.org/rsvp/-/rsvp-4.8.5.tgz",
@@ -23461,6 +23470,14 @@
         "glob": "^7.1.3"
       }
     },
+    "rrule": {
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/rrule/-/rrule-2.8.1.tgz",
+      "integrity": "sha512-hM3dHSBMeaJ0Ktp7W38BJZ7O1zOgaFEsn41PDk+yHoEtfLV+PoJt9E9xAlZiWgf/iqEqionN0ebHFZIDAp+iGw==",
+      "requires": {
+        "tslib": "^2.4.0"
+      }
+    },
     "rsvp": {
       "version": "4.8.5",
       "resolved": "https://registry.npmjs.org/rsvp/-/rsvp-4.8.5.tgz",
diff --git a/package.json b/package.json
index 00960807..ed5ced35 100644
--- a/package.json
+++ b/package.json
@@ -57,6 +57,7 @@
     "nodemailer": "^6.5.0",
     "notifme-sdk": "^1.10.0",
     "prettier": "^2.2.1",
+    "rrule": "^2.8.1",
     "shelljs": "^0.8.4",
     "tcp-ping": "^0.1.1",
     "ws": "^7.4.6"
diff --git a/src/update.ts b/src/update.ts
index a72dc7f7..3ed9e725 100644
--- a/src/update.ts
+++ b/src/update.ts
@@ -2,6 +2,7 @@ import dns from "dns";
 import { isIP, isIPv6 } from "net";
 import slugify from "@sindresorhus/slugify";
 import dayjs from "dayjs";
+import utc from "dayjs/plugin/utc";
 import { mkdirp, readFile, writeFile } from "fs-extra";
 import { load } from "js-yaml";
 import { join } from "path";
@@ -17,6 +18,10 @@ import { curl } from "./helpers/request";
 import { getOwnerRepo, getSecret } from "./helpers/secrets";
 import { SiteHistory } from "./interfaces";
 import { generateSummary } from "./summary";
+import {  rrulestr } from 'rrule';
+import { Octokit } from "@octokit/rest";
+
+dayjs.extend(utc);
 
 const delay = (ms: number) => new Promise((resolve) => setTimeout(resolve, ms));
 
@@ -41,6 +46,45 @@ function getHumanReadableTimeDifference(startTime: Date): string {
   return result.join(", ");
 }
 
+function getDurationMinutes(duration: string): number {
+  const unit = duration.slice(-1).toUpperCase();
+
+  try {
+    if (unit === "M") {
+      return parseInt(duration.slice(0, -1));
+    } else if (unit === "H") {
+      return parseInt(duration.slice(0, -1)) * 60;
+    } else if (unit === "D") {
+      return parseInt(duration.slice(0, -1)) * 60 * 24;
+    } else {
+      return 0;
+    }
+  } catch (error) {
+    console.error("Error parsing duration", duration, error);
+    return 0;
+  }
+}
+
+async function closeMaintenanceIssue(octokit: Octokit, owner: string, repo: string, incidentNumber: number) {
+  await octokit.issues.unlock({
+    owner,
+    repo,
+    issue_number: incidentNumber,
+  });
+  await octokit.issues.update({
+    owner,
+    repo,
+    issue_number: incidentNumber,
+    state: "closed",
+  });
+  await octokit.issues.lock({
+    owner,
+    repo,
+    issue_number: incidentNumber,
+  });
+  console.log("Closed maintenance completed event", incidentNumber);
+}
+
 export const update = async (shouldCommit = false) => {
   if (!(await shouldContinue())) return;
   await mkdirp("history");
@@ -77,38 +121,63 @@ export const update = async (shouldCommit = false) => {
         metadata[i.split(/:(.+)/)[0].trim()] = i.split(/:(.+)/)[1].trim();
       });
     }
-    if (metadata.start && metadata.end) {
-      let expectedDown: string[] = [];
-      let expectedDegraded: string[] = [];
-      if (metadata.expectedDown)
-        expectedDown = metadata.expectedDown
-          .split(",")
-          .map((i) => i.trim())
-          .filter((i) => i.length);
-      if (metadata.expectedDown)
-        expectedDegraded = metadata.expectedDown
-          .split(",")
-          .map((i) => i.trim())
-          .filter((i) => i.length);
 
-      if (dayjs(metadata.end).isBefore(dayjs())) {
-        await octokit.issues.unlock({
-          owner,
-          repo,
-          issue_number: incident.number,
-        });
-        await octokit.issues.update({
-          owner,
-          repo,
-          issue_number: incident.number,
-          state: "closed",
-        });
-        await octokit.issues.lock({
-          owner,
-          repo,
-          issue_number: incident.number,
+    let expectedDown: string[] = [];
+    let expectedDegraded: string[] = [];
+    if (metadata.expectedDown)
+      expectedDown = metadata.expectedDown
+        .split(",")
+        .map((i) => i.trim())
+        .filter((i) => i.length);
+    if (metadata.expectedDegraded)
+      expectedDegraded = metadata.expectedDegraded
+        .split(",")
+        .map((i) => i.trim())
+        .filter((i) => i.length);
+
+    if (metadata.rrule && metadata.duration && metadata.start) {
+      // The DTSTART and UNTIL params in RRules should be in UTC format without colons and dashes
+      if (!metadata.rrule.includes("DTSTART")) {
+        const cleanStartTime = dayjs(metadata.start)
+          .utc()
+          .format()
+          .replaceAll(":", "")
+          .replaceAll("-", "");
+        metadata.rrule += `;DTSTART=${cleanStartTime}`;
+      }
+      if (!metadata.rrule.includes("UNTIL") && metadata.end) {
+        const cleanEndTime = dayjs(metadata.end)
+          .utc()
+          .format()
+          .replaceAll(":", "")
+          .replaceAll("-", "");
+        metadata.rrule += `;UNTIL=${cleanEndTime}`;
+      }
+      const rule = rrulestr(metadata.rrule);
+
+      if (metadata.end && dayjs(metadata.end).isBefore(dayjs())) {
+        await closeMaintenanceIssue(octokit, owner, repo, incident.number);
+      } else {
+        // Get all potentially valid occurrences of this rule (started up to `duration` ago)
+        // Limit to 1000 results to avoid any potential long-running operations
+        const durationMinutes = getDurationMinutes(metadata.duration);
+        const after = dayjs().subtract(durationMinutes, "minutes").toDate();
+        rule.between(after, new Date(), true, (_, i) => i < 1000).forEach((startDate) => {
+            const endDate = dayjs(startDate).add(durationMinutes, "minutes").toDate();
+
+            const start = startDate.toISOString();
+            const end = endDate.toISOString();
+
+            ongoingMaintenanceEvents.push({
+              issueNumber: incident.number,
+              metadata: { start, end, expectedDegraded, expectedDown },
+            });
         });
-        console.log("Closed maintenance completed event", incident.number);
+      }
+
+    } else if (metadata.start && metadata.end) {
+      if (dayjs(metadata.end).isBefore(dayjs())) {
+        await closeMaintenanceIssue(octokit, owner, repo, incident.number);
       } else if (dayjs(metadata.start).isBefore(dayjs())) {
         ongoingMaintenanceEvents.push({
           issueNumber: incident.number,
@@ -519,3 +588,4 @@ generator: Upptime <https://github.com/upptime/upptime>
 };
 
 const wait = (ms: number) => new Promise((resolve) => setTimeout(resolve, ms));
+