diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index d34cc11918..3249d91c60 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -109,6 +109,14 @@ jobs:
       env:
         DISABLE_INSPECT_FUSE: on
         SIGN_MACOS_SCRIPT: noop.sh
+    - name: Upload installer size
+      if: ${{ github.repository == 'signalapp/Signal-Desktop-Private' && github.ref == 'refs/heads/main' }}
+      run: |
+        node ts/scripts/dd-installer-size.js macos-arm64
+        node ts/scripts/dd-installer-size.js macos-x64
+        node ts/scripts/dd-installer-size.js macos-universal
+      env:
+        DD_API_KEY: ${{ secrets.DATADOG_API_KEY }}
     - name: Rebuild native modules for x64
       run: npm run electron:install-app-deps
     - run: npm run test-release
@@ -169,6 +177,12 @@ jobs:
       env:
         DISABLE_INSPECT_FUSE: on
 
+    - name: Upload installer size
+      if: ${{ github.repository == 'signalapp/Signal-Desktop-Private' && github.ref == 'refs/heads/main' }}
+      run: node ts/scripts/dd-installer-size.js linux
+      env:
+        DD_API_KEY: ${{ secrets.DATADOG_API_KEY }}
+
     - run: xvfb-run --auto-servernum npm run test-node
     - run: xvfb-run --auto-servernum npm run test-electron
       timeout-minutes: 5
@@ -247,6 +261,12 @@ jobs:
       env:
         DISABLE_INSPECT_FUSE: on
 
+    - name: Upload installer size
+      if: ${{ github.repository == 'signalapp/Signal-Desktop-Private' && github.ref == 'refs/heads/main' }}
+      run: node ts/scripts/dd-installer-size.js windows
+      env:
+        DD_API_KEY: ${{ secrets.DATADOG_API_KEY }}
+
     - run: npm run test-electron
       env:
         ARTIFACTS_DIR: artifacts/windows
diff --git a/ts/scripts/dd-installer-size.ts b/ts/scripts/dd-installer-size.ts
new file mode 100644
index 0000000000..91731b915d
--- /dev/null
+++ b/ts/scripts/dd-installer-size.ts
@@ -0,0 +1,100 @@
+// Copyright 2024 Signal Messenger, LLC
+// SPDX-License-Identifier: AGPL-3.0-only
+
+import { stat } from 'node:fs/promises';
+import { join } from 'node:path';
+
+import { name as NAME, version as VERSION } from '../../package.json';
+
+const SUPPORT_CONFIG = new Set([
+  'linux',
+  'windows',
+  'macos-arm64',
+  'macos-x64',
+  'macos-universal',
+]);
+
+const RELEASE_DIR = join(__dirname, '..', '..', 'release');
+
+async function main(): Promise<void> {
+  const config = process.argv[2];
+  if (!SUPPORT_CONFIG.has(config)) {
+    throw new Error(`Invalid argument: ${config}`);
+  }
+
+  const { DD_API_KEY } = process.env;
+  if (DD_API_KEY == null) {
+    throw new Error('Missing DD_API_KEY env variable');
+  }
+
+  let fileName: string;
+  let platform: string;
+  let arch: string;
+  if (config === 'linux') {
+    fileName = `${NAME}_${VERSION}_amd64.deb`;
+    platform = 'linux';
+    arch = 'x64';
+  } else if (config === 'windows') {
+    fileName = `${NAME}-win-${VERSION}.exe`;
+    platform = 'windows';
+    arch = 'x64';
+  } else if (config === 'macos-arm64') {
+    fileName = `${NAME}-mac-arm64-${VERSION}.dmg`;
+    platform = 'macos';
+    arch = 'arm64';
+  } else if (config === 'macos-x64') {
+    fileName = `${NAME}-mac-x64-${VERSION}.dmg`;
+    platform = 'macos';
+    arch = 'x64';
+  } else if (config === 'macos-universal') {
+    fileName = `${NAME}-mac-universal-${VERSION}.dmg`;
+    platform = 'macos';
+    arch = 'universal';
+  } else {
+    throw new Error(`Unsupported config: ${config}`);
+  }
+
+  const filePath = join(RELEASE_DIR, fileName);
+  const { size } = await stat(filePath);
+
+  const res = await fetch('https://api.datadoghq.com/api/v2/series', {
+    method: 'POST',
+    headers: {
+      'content-type': 'application/json',
+      'DD-API-KEY': DD_API_KEY,
+    },
+    body: JSON.stringify({
+      series: [
+        {
+          metric: 'desktop.ci.installerSize',
+          type: 0,
+          points: [
+            {
+              timestamp: Math.floor(Date.now() / 1000),
+              value: size,
+            },
+          ],
+          tags: [
+            `hash:${process.env.GITHUB_SHA ?? ''}`,
+            `platform:${platform}`,
+            `arch:${arch}`,
+          ],
+        },
+      ],
+    }),
+  });
+
+  if (!res.ok) {
+    throw new Error(
+      `Failed to submit metrics, status: ${res.status}, ` +
+        `body: ${await res.text()}`
+    );
+  }
+
+  console.log(`Submitted: ${size}`);
+}
+
+main().catch(err => {
+  console.error('Failed', err);
+  process.exit(1);
+});