diff --git a/.github/workflows/joining-tweet.yaml b/.github/workflows/joining-tweet.yaml
deleted file mode 100644
index eb8d73b8..00000000
--- a/.github/workflows/joining-tweet.yaml
+++ /dev/null
@@ -1,38 +0,0 @@
-name: Joining Tweet
-
-on:
-    schedule:
-        - cron: "20 16 * * 6" # Every Saturday at 4:20 PM UTC (i.e., 09:50 PM IST)
-    workflow_dispatch:
-
-jobs:
-    send-joining-tweet:
-        runs-on: ubuntu-latest
-        steps:
-            - name: Checkout repository
-              uses: actions/checkout@v2
-              with:
-                  persist-credentials: false
-
-            - name: Set environment variable
-              run: |
-                  sudo apt-get update
-                  sudo apt-get install nodejs
-                  catchup_number=$(node util/get-next-catchup-number.js)
-                  echo "CATCHUP_NUMBER=${catchup_number}" >> ${GITHUB_ENV}
-
-            - name: Send joining Tweet
-              uses: Eomm/why-don-t-you-tweet@v1
-              with:
-                  tweet-message: |
-                      Going live in 10 mins!
-
-                      Join us for the ${{ env.CATCHUP_NUMBER }} #OTCCatchUp, an informal open-to-all Tech discussion.
-
-                      Join in at any time! 👇
-                      https://catchup.ourtech.community/attend
-              env:
-                  TWITTER_CONSUMER_API_KEY: ${{ secrets.TWITTER_API_KEY }}
-                  TWITTER_CONSUMER_API_SECRET: ${{ secrets.TWITTER_API_KEY_SECRET }}
-                  TWITTER_ACCESS_TOKEN: ${{ secrets.TWITTER_ACCESS_TOKEN }}
-                  TWITTER_ACCESS_TOKEN_SECRET: ${{ secrets.TWITTER_ACCESS_TOKEN_SECRET }}
diff --git a/.github/workflows/reminder-tweet.yaml b/.github/workflows/reminder-tweet.yaml
deleted file mode 100644
index bfced24f..00000000
--- a/.github/workflows/reminder-tweet.yaml
+++ /dev/null
@@ -1,49 +0,0 @@
-name: Reminder Tweet
-
-on:
-    schedule:
-        - cron: "30 11 * * 6" # Every Saturday at 11:30 AM UTC (i.e., 5 PM IST)
-    workflow_dispatch:
-
-jobs:
-    send-reminder-tweet:
-        runs-on: ubuntu-latest
-        steps:
-            - name: Checkout repository
-              uses: actions/checkout@v2
-              with:
-                  persist-credentials: false
-
-            - name: Set environment variables
-              run: |
-                  sudo apt-get update
-                  sudo apt-get install nodejs
-
-                  upcoming_catchup_number=$(node util/get-next-catchup-number.js)
-                  echo "UPCOMING_CATCHUP_NUMBER=${upcoming_catchup_number}" >> ${GITHUB_ENV}
-
-                  prev_catchup_number=$(node util/get-latest-catchup-number.js)
-                  echo "PREV_CATCHUP_NUMBER=${prev_catchup_number}" >> ${GITHUB_ENV}
-
-                  catchup_date=$(date +"%b %d")
-                  echo "CATCHUP_DATE=${catchup_date}" >> ${GITHUB_ENV}
-
-            - name: Send reminder Tweet
-              uses: Eomm/why-don-t-you-tweet@v1
-              with:
-                  tweet-message: |
-                      Reminder! 🚨
-
-                      The ${{ env.UPCOMING_CATCHUP_NUMBER }} OTC CatchUp session will be held today (${{ env.CATCHUP_DATE }}) from 10:30 PM IST.
-
-                      Join us for an informal open-to-all Tech discussion!
-
-                      Previous session details 👇
-                      https://catchup.ourtech.community/summary/${{ env.PREV_CATCHUP_NUMBER }}
-
-                      #OTC #OTCCatchUp #Community #Tech
-              env:
-                  TWITTER_CONSUMER_API_KEY: ${{ secrets.TWITTER_API_KEY }}
-                  TWITTER_CONSUMER_API_SECRET: ${{ secrets.TWITTER_API_KEY_SECRET }}
-                  TWITTER_ACCESS_TOKEN: ${{ secrets.TWITTER_ACCESS_TOKEN }}
-                  TWITTER_ACCESS_TOKEN_SECRET: ${{ secrets.TWITTER_ACCESS_TOKEN_SECRET }}
diff --git a/.github/workflows/send-messages.yaml b/.github/workflows/send-messages.yaml
new file mode 100644
index 00000000..ee7bcd06
--- /dev/null
+++ b/.github/workflows/send-messages.yaml
@@ -0,0 +1,129 @@
+name: Reminder Tweet
+
+on:
+    schedule:
+        # Schedule job 10 minutes before time to account for delays
+        # Every Saturday at 11:20 AM UTC (05:00 PM IST - 10 min)
+        - cron: "20 11 * * SAT"
+        # Every Saturday at 04:30 PM UTC (10:10 PM IST - 10 min)
+        - cron: "30 16 * * SAT"
+    workflow_dispatch:
+        inputs:
+            message-template:
+                type: choice
+                required: true
+                default: automatic
+                options:
+                    - automatic
+                    - reminder
+                    - joining
+                description: |
+                    Which message template to use.
+                    if set to `automatic`, resolves to:
+                      `joining`, if time is after 10pm on Saturday (IST)
+                      `reminder`, otherwise
+
+jobs:
+    send-messages:
+        runs-on: ubuntu-latest
+        steps:
+            - name: Checkout repository
+              uses: actions/checkout@v2
+              with:
+                  persist-credentials: false
+
+            - name: Set environment variables
+              run: |
+                  upcoming_catchup_number=$(node util/get-next-catchup-number.js)
+                  echo "UPCOMING_CATCHUP_NUMBER=${upcoming_catchup_number}" >> ${GITHUB_ENV}
+
+                  prev_catchup_number=$(node util/get-latest-catchup-number.js)
+                  echo "PREV_CATCHUP_NUMBER=${prev_catchup_number}" >> ${GITHUB_ENV}
+
+                  catchup_date=$(date +"%b %d")
+                  echo "CATCHUP_DATE=${catchup_date}" >> ${GITHUB_ENV}
+
+                  message_template=${{ inputs.message-template }}
+                  if [ "${message_template}" = "automatic" ]; then
+                      message_template=$(node util/get-current-message-template.js)
+                  fi
+                  echo "MESSAGE_TEMPLATE=${message_template}" >> ${GITHUB_ENV}
+
+            # Reminder messages
+            - name: Wait until 17:00 IST
+              if: ${{ env.MESSAGE_TEMPLATE }} == 'reminder'
+              run: sleep $(node util\get-seconds-until-ist-time.js 17:00)
+
+            - name: Send reminder Telegram message
+              if: ${{ env.MESSAGE_TEMPLATE }} == 'reminder'
+              run: |
+                  export TELEGRAM_MESSAGE="Reminder! 🚨
+
+                  The ${{ env.UPCOMING_CATCHUP_NUMBER }} OTC CatchUp session will be held today (${{ env.CATCHUP_DATE }}) from 10:30 PM IST.
+
+                  Join us for an informal open-to-all Tech discussion!
+
+                  Joining link 👇
+                  https://catchup.ourtech.community/attend
+
+                  Previous session details 👇
+                  https://catchup.ourtech.community/summary/${{ env.PREV_CATCHUP_NUMBER }}"
+
+                  BOT_TOKEN=${{ secrets.TELEGRAM_BOT_TOKEN }} node util/post-telegram-message.js
+
+            - name: Send reminder Tweet
+              if: ${{ env.MESSAGE_TEMPLATE }} == 'reminder'
+              uses: Eomm/why-don-t-you-tweet@v1
+              with:
+                  tweet-message: |
+                      Reminder! 🚨
+
+                      The ${{ env.UPCOMING_CATCHUP_NUMBER }} OTC CatchUp session will be held today (${{ env.CATCHUP_DATE }}) from 10:30 PM IST.
+
+                      Join us for an informal open-to-all Tech discussion!
+
+                      Previous session details 👇
+                      https://catchup.ourtech.community/summary/${{ env.PREV_CATCHUP_NUMBER }}
+
+                      #OTC #OTCCatchUp #Community #Tech
+              env:
+                  TWITTER_CONSUMER_API_KEY: ${{ secrets.TWITTER_API_KEY }}
+                  TWITTER_CONSUMER_API_SECRET: ${{ secrets.TWITTER_API_KEY_SECRET }}
+                  TWITTER_ACCESS_TOKEN: ${{ secrets.TWITTER_ACCESS_TOKEN }}
+                  TWITTER_ACCESS_TOKEN_SECRET: ${{ secrets.TWITTER_ACCESS_TOKEN_SECRET }}
+
+            # Joining messages
+            - name: Wait until 22:10 IST
+              if: ${{ env.MESSAGE_TEMPLATE }} == 'joining'
+              run: sleep $(node util/get-seconds-until-ist-time.js 22:10)
+
+            - name: Send joining Telegram message
+              if: ${{ env.MESSAGE_TEMPLATE }} == 'joining'
+              run: |
+                  export TELEGRAM_MESSAGE="<b>${{ env.UPCOMING_CATCHUP_NUMBER }} OTC CatchUp</b>
+
+                  An informal open-to-all Tech discussion!
+
+                  We start at 10:30 PM IST.
+
+                  Join in at any time! 👇
+                  https://catchup.ourtech.community/attend"
+
+                  BOT_TOKEN=${{ secrets.TELEGRAM_BOT_TOKEN }} node util/post-telegram-message.js
+
+            - name: Send joining Tweet
+              if: ${{ env.MESSAGE_TEMPLATE }} == 'joining'
+              uses: Eomm/why-don-t-you-tweet@v1
+              with:
+                  tweet-message: |
+                      Going live in 30 mins!
+
+                      Join us for the ${{ env.UPCOMING_CATCHUP_NUMBER }} #OTCCatchUp, an informal open-to-all Tech discussion.
+
+                      Join in at any time! 👇
+                      https://catchup.ourtech.community/attend
+              env:
+                  TWITTER_CONSUMER_API_KEY: ${{ secrets.TWITTER_API_KEY }}
+                  TWITTER_CONSUMER_API_SECRET: ${{ secrets.TWITTER_API_KEY_SECRET }}
+                  TWITTER_ACCESS_TOKEN: ${{ secrets.TWITTER_ACCESS_TOKEN }}
+                  TWITTER_ACCESS_TOKEN_SECRET: ${{ secrets.TWITTER_ACCESS_TOKEN_SECRET }}
diff --git a/.github/workflows/tg-joining-msg.yaml b/.github/workflows/tg-joining-msg.yaml
deleted file mode 100644
index d80e5945..00000000
--- a/.github/workflows/tg-joining-msg.yaml
+++ /dev/null
@@ -1,38 +0,0 @@
-name: Telegram joining message
-
-on:
-    schedule:
-        - cron: "30 16 * * 6" # Every Saturday at 4:30 PM UTC (i.e., 10:00 PM IST)
-    workflow_dispatch:
-
-jobs:
-    send-joining-msg:
-        runs-on: ubuntu-latest
-        steps:
-            - name: Checkout repository
-              uses: actions/checkout@v2
-              with:
-                  persist-credentials: false
-
-            - name: Set environment variable
-              run: |
-                  sudo apt-get update
-                  sudo apt-get install nodejs
-                  catchup_number=$(node util/get-next-catchup-number.js)
-                  echo "CATCHUP_NUMBER=${catchup_number}" >> ${GITHUB_ENV}
-
-            - name: Send joining message on OTC's Telegram group
-              uses: appleboy/telegram-action@master
-              with:
-                  to: ${{ secrets.TELEGRAM_CHAT_ID }}
-                  token: ${{ secrets.TELEGRAM_BOT_TOKEN }}
-                  format: markdown
-                  message: |
-                      **${{ env.CATCHUP_NUMBER }} OTC CatchUp**
-
-                      An informal open-to-all Tech discussion!
-
-                      We start at 10:30 PM IST.
-
-                      Join in at any time! 👇
-                      https://catchup.ourtech.community/attend
diff --git a/.github/workflows/tg-reminder-msg.yaml b/.github/workflows/tg-reminder-msg.yaml
deleted file mode 100644
index 9eaa0155..00000000
--- a/.github/workflows/tg-reminder-msg.yaml
+++ /dev/null
@@ -1,49 +0,0 @@
-name: Telegram reminder message
-
-on:
-    schedule:
-        - cron: "30 11 * * 6" # Every Saturday at 11:30 AM UTC (i.e., 5 PM IST)
-    workflow_dispatch:
-
-jobs:
-    send-reminder-message:
-        runs-on: ubuntu-latest
-        steps:
-            - name: Checkout repository
-              uses: actions/checkout@v2
-              with:
-                  persist-credentials: false
-
-            - name: Set environment variables
-              run: |
-                  sudo apt-get update
-                  sudo apt-get install nodejs
-
-                  upcoming_catchup_number=$(node util/get-next-catchup-number.js)
-                  echo "UPCOMING_CATCHUP_NUMBER=${upcoming_catchup_number}" >> ${GITHUB_ENV}
-
-                  prev_catchup_number=$(node util/get-latest-catchup-number.js)
-                  echo "PREV_CATCHUP_NUMBER=${prev_catchup_number}" >> ${GITHUB_ENV}
-
-                  catchup_date=$(date +"%b %d")
-                  echo "CATCHUP_DATE=${catchup_date}" >> ${GITHUB_ENV}
-
-            - name: Send reminder message on OTC's Telegram group
-              uses: appleboy/telegram-action@master
-              with:
-                  to: ${{ secrets.TELEGRAM_CHAT_ID }}
-                  token: ${{ secrets.TELEGRAM_BOT_TOKEN }}
-                  format: markdown
-                  disable_web_page_preview: true
-                  message: |
-                      Reminder! 🚨
-
-                      The ${{ env.UPCOMING_CATCHUP_NUMBER }} OTC CatchUp session will be held today (${{ env.CATCHUP_DATE }}) from 10:30 PM IST.
-
-                      Join us for an informal open-to-all Tech discussion!
-
-                      Joining link 👇
-                      https://catchup.ourtech.community/attend
-
-                      Previous session details 👇
-                      https://catchup.ourtech.community/summary/${{ env.PREV_CATCHUP_NUMBER }}
diff --git a/util/get-current-message-template.js b/util/get-current-message-template.js
new file mode 100644
index 00000000..a71e58b0
--- /dev/null
+++ b/util/get-current-message-template.js
@@ -0,0 +1,19 @@
+function getCurrentMessageTemplate(date = new Date()) {
+	let istDate = new Date(
+		date.toLocaleString("en-US", {
+			timeZone: "Asia/Kolkata"
+		})
+	);
+
+	// if time is after 10pm on saturday return joining,
+	// else return reminder
+	// 6 is Saturday
+	if (istDate.getDay() === 6 && istDate.getHours() >= 22) return "joining";
+	else return "reminder";
+}
+
+module.exports = {
+	getCurrentMessageTemplate
+};
+
+if (require.main) console.log(getCurrentMessageTemplate());
diff --git a/util/get-seconds-until-ist-time.js b/util/get-seconds-until-ist-time.js
new file mode 100644
index 00000000..f2a89fd6
--- /dev/null
+++ b/util/get-seconds-until-ist-time.js
@@ -0,0 +1,18 @@
+const time = process.argv[2];
+const [hours, minutes] = time.split(":");
+if (!time || !hours || !minutes) {
+	console.error(`invalid timestamp: ${time}`);
+	process.exit(1);
+}
+
+let now = new Date(
+	new Date().toLocaleString("en-US", {
+		timeZone: "Asia/Kolkata"
+	})
+);
+
+let date = new Date(now);
+
+let seconds = Math.floor((date.getTime() - now.getTime()) / 1000);
+if (seconds < 0) seconds = 0;
+console.log(seconds);
diff --git a/util/post-telegram-message.js b/util/post-telegram-message.js
new file mode 100644
index 00000000..a3e3b8f7
--- /dev/null
+++ b/util/post-telegram-message.js
@@ -0,0 +1,93 @@
+const https = require("https");
+
+async function fetch(url, options = {}) {
+	return new Promise((resolve, reject) => {
+		let req = https.request(url, options, (res) => {
+			let data = [];
+			res.on("data", (d) => data.push(d));
+			res.on("end", (e) => {
+				let rawData = Buffer.concat(data).toString();
+				resolve({
+					headers: res.headers,
+					status: res.statusCode,
+					text: async () => rawData,
+					json: async () => JSON.parse(rawData)
+				});
+			});
+		});
+
+		req.on("error", reject);
+
+		if (options.body && options.method != "GET" && options.method != "HEAD")
+			req.write(options.body);
+
+		req.end();
+	});
+}
+
+let BOT_TOKEN;
+
+const BASE_URL = "https://api.telegram.org";
+async function sendApiRequestRaw(method, body = {}) {
+	let url = `${BASE_URL}/bot${BOT_TOKEN}/${method}`;
+	return fetch(url, {
+		method: "POST",
+		headers: {
+			"content-type": "application/json"
+		},
+		body: JSON.stringify(body)
+	});
+}
+
+async function sendApiRequest(method, body) {
+	return sendApiRequestRaw(method, body).then((e) => e.json());
+}
+
+async function sendMessageToChat(chat_id, text) {
+	return sendApiRequest("sendMessage", {
+		chat_id,
+		text,
+		parse_mode: "html",
+		disable_web_page_preview: true
+	});
+}
+
+async function sendAndPinMessageToChat(chat_id, text) {
+	let { message_id } = await sendMessageToChat(text);
+	return sendApiRequest("pinChatMessage", {
+		chat_id,
+		message_id
+	});
+}
+
+async function main() {
+	BOT_TOKEN = process.env.BOT_TOKEN;
+	if (typeof BOT_TOKEN !== "string") {
+		console.error("missing value for env variable: BOT_TOKEN");
+		return 1;
+	}
+
+	let chat_id = process.env.TELEGRAM_CHAT_ID;
+	if (typeof chat_id !== "string") {
+		console.error("missing value for env variable: TELEGRAM_CHAT_ID");
+		return 1;
+	}
+
+	let message = process.env.TELEGRAM_MESSAGE;
+	if (typeof message !== "string") {
+		console.error("missing value for env variable: TELEGRAM_MESSAGE");
+		return 1;
+	}
+
+	await sendAndPinMessageToChat(chat_id, message);
+}
+
+if (require.main)
+	main()
+		.then((exitCode) => {
+			if (typeof exitCode == "number") process.exit(exitCode);
+		})
+		.catch((e) => {
+			console.error(e);
+			process.exit(2);
+		});