diff --git a/.github/workflows/smoke-test-release.yml b/.github/workflows/smoke-test-release.yml
new file mode 100644
index 00000000000..83e0f287ac2
--- /dev/null
+++ b/.github/workflows/smoke-test-release.yml
@@ -0,0 +1,46 @@
+name: Smoke test release
+on:
+  release:
+    types: [published]
+jobs:
+  login-run:
+    name: Daily smoke test on release.
+    runs-on: ubuntu-18.04
+    steps:
+
+      - name: Create dirs.
+        run: |
+              mkdir -p code/woocommerce
+              mkdir -p package/woocommerce
+              mkdir -p tmp/woocommerce
+              mkdir -p node_modules
+
+      - name: Checkout code.
+        uses: actions/checkout@v2
+        with:
+          ref: trunk
+
+      - name: Install prerequisites.
+        run: |
+          npm install
+          composer install --no-dev
+          npm run build:assets
+          npm install jest
+          
+      - name: Run smoke test.
+        env:
+          SMOKE_TEST_URL: ${{ secrets.RELEASE_TEST_URL }}
+          SMOKE_TEST_ADMIN_USER: ${{ secrets.RELEASE_TEST_ADMIN_USER }}
+          SMOKE_TEST_ADMIN_PASSWORD: ${{ secrets.RELEASE_TEST_ADMIN_PASSWORD }}
+          SMOKE_TEST_ADMIN_USER_EMAIL: ${{ secrets.RELEASE_TEST_ADMIN_USER_EMAIL }}
+          SMOKE_TEST_CUSTOMER_USER: ${{ secrets.RELEASE_TEST_CUSTOMER_USER }}
+          SMOKE_TEST_CUSTOMER_PASSWORD: ${{ secrets.RELEASE_TEST_CUSTOMER_PASSWORD }}
+          WC_E2E_SCREENSHOTS: 1
+          E2E_RETEST: 1
+          E2E_SLACK_TOKEN: ${{ secrets.SMOKE_TEST_SLACK_TOKEN }}
+          E2E_SLACK_CHANNEL: ${{ secrets.SMOKE_TEST_SLACK_CHANNEL }}
+          TEST_RELEASE: 1
+          UPDATE_WC: 1
+        run: |
+          npx wc-e2e test:e2e ./tests/e2e/specs/smoke-tests/update-woocommerce.js
+          npx wc-e2e test:e2e
diff --git a/tests/e2e/env/CHANGELOG.md b/tests/e2e/env/CHANGELOG.md
index e57468d8e24..430535092db 100644
--- a/tests/e2e/env/CHANGELOG.md
+++ b/tests/e2e/env/CHANGELOG.md
@@ -6,6 +6,7 @@
 - Added plugin zip utility functions:
   - `checkNestedZip( zipFilePath, savePath )` checks a plugin zip file for any nested zip files. If one is found, it is extracted. Returns the path where the zip file is located.
   - `downloadZip( fileUrl, downloadPath )` downloads a plugin zip file from a remote location to the provided path.
+- Added `getLatestReleaseZipUrl( owner, repository, getPrerelease, perPage )` util function to get the latest release zip from a GitHub repository
 
 # 0.2.2
 
diff --git a/tests/e2e/env/README.md b/tests/e2e/env/README.md
index c3b38dd3bd2..6420d746d5e 100644
--- a/tests/e2e/env/README.md
+++ b/tests/e2e/env/README.md
@@ -196,6 +196,14 @@ The above method also makes use of the following utility methods which can also
 - `checkNestedZip( zipFilePath, savePath )` used to check a plugin zip file for any nested zip files. If one is found, it is extracted. Returns the path where the zip file is located.
 - `downloadZip( fileUrl, downloadPath )` can be used to directly download a plugin zip file from a remote location to the provided path.
 
+### Get the latest released zip URL
+
+If you would like to get the latest release zip URL, which can be used in the methods mentioned above, you can use the following helper function to do so:
+
+`getLatestReleaseZipUrl( owner, repository, getPrerelease, perPage )`
+
+This will return a string with the latest release URL. Optionally, you can use the `getPrerelease` boolean flag, which defaults to false, on whether or not to get a prerelease instead. The `perPage` flag can be used to return more results when getting the list of releases. The default value is 3.
+
 ## Additional information
 
 Refer to [`tests/e2e/core-tests`](https://github.com/woocommerce/woocommerce/tree/trunk/tests/e2e/core-tests) for some test examples, and [`tests/e2e`](https://github.com/woocommerce/woocommerce/tree/trunk/tests/e2e) for general information on e2e tests.
diff --git a/tests/e2e/env/utils/get-plugin-zip.js b/tests/e2e/env/utils/get-plugin-zip.js
index edd9f404be9..856478719db 100644
--- a/tests/e2e/env/utils/get-plugin-zip.js
+++ b/tests/e2e/env/utils/get-plugin-zip.js
@@ -29,6 +29,52 @@ const getRemotePluginZip = async ( fileUrl ) => {
 	return filePath;
 };
 
+/**
+ * Get the latest release zip for a plugin from a GiHub repository.
+ *
+ * @param {string} owner The owner of the plugin repository.
+ * @param {string} repository The repository name.
+ * @param {boolean} getPrerelease Flag on whether to get a prelease or not.
+ * @param {number} perPage Limit of entries returned from the latest releases list, defaults to 3.
+ * @returns {Promise<string>}} Returns the URL for the release zip file.
+ */
+const getLatestReleaseZipUrl = async ( owner, repository, getPrerelease = false, perPage = 3 ) => {
+	let requesturl;
+
+	if ( getPrerelease ) {
+		requesturl = `https://api.github.com/repos/${owner}/${repository}/releases?per_page=${perPage}`;
+	} else {
+		requesturl = `https://api.github.com/repos/${owner}/${repository}/releases/latest`;
+	}
+
+	const options = {
+		url: requesturl,
+		method: 'GET',
+		json: true,
+		headers: {'user-agent': 'node.js'}
+	};
+
+	// Wrap in a promise to make the request async
+	return new Promise( function( resolve, reject ) {
+		request.get(options, function( err, resp, body ) {
+			if ( err ) {
+				reject( err );
+			} else {
+				if ( getPrerelease ) {
+					// Loop until we find the first pre-release, then return it.
+					body.forEach(release => {
+						if ( release.prerelease ) {
+							resolve( release.zipball_url );
+						}
+					});
+				} else {
+					resolve( body.zipball_url );
+				}
+			}
+		})
+	});
+}
+
 /**
  * Check the zip file for any nested zips. If one is found, extract it.
  *
@@ -80,6 +126,7 @@ const downloadZip = async ( fileUrl, downloadPath ) => {
 
 module.exports = {
 	getRemotePluginZip,
+	getLatestReleaseZipUrl,
 	checkNestedZip,
 	downloadZip,
 };
diff --git a/tests/e2e/env/utils/index.js b/tests/e2e/env/utils/index.js
index 6df8984caf7..3a3e220c88c 100644
--- a/tests/e2e/env/utils/index.js
+++ b/tests/e2e/env/utils/index.js
@@ -1,7 +1,7 @@
 const getAppRoot = require( './app-root' );
 const { getAppName, getAppBase } = require( './app-name' );
 const { getTestConfig, getAdminConfig } = require( './test-config' );
-const { getRemotePluginZip } = require('./get-plugin-zip');
+const { getRemotePluginZip, getLatestReleaseZipUrl } = require('./get-plugin-zip');
 const takeScreenshotFor = require( './take-screenshot' );
 const updateReadyPageStatus = require('./update-ready-page');
 const consoleUtils = require( './filter-console' );
@@ -13,6 +13,7 @@ module.exports = {
 	getTestConfig,
 	getAdminConfig,
 	getRemotePluginZip,
+	getLatestReleaseZipUrl,
 	takeScreenshotFor,
 	updateReadyPageStatus,
 	...consoleUtils,
diff --git a/tests/e2e/specs/smoke-tests/update-woocommerce.js b/tests/e2e/specs/smoke-tests/update-woocommerce.js
index 8b1d2380a15..a6c2794b884 100644
--- a/tests/e2e/specs/smoke-tests/update-woocommerce.js
+++ b/tests/e2e/specs/smoke-tests/update-woocommerce.js
@@ -3,7 +3,7 @@
  */
 const { merchant, utils } = require( '@woocommerce/e2e-utils' );
 
-const { getRemotePluginZip } = require( '@woocommerce/e2e-environment' );
+const { getRemotePluginZip, getLatestReleaseZipUrl } = require( '@woocommerce/e2e-environment' );
 
 /**
  * External dependencies
@@ -13,16 +13,23 @@ const {
 	beforeAll,
 } = require( '@jest/globals' );
 
-const { UPDATE_WC } = process.env;
+const { UPDATE_WC, TEST_RELEASE } = process.env;
 
-const nightlyZip = 'https://github.com/woocommerce/woocommerce/releases/download/nightly/woocommerce-trunk-nightly.zip';
+let zipUrl;
 const pluginName = 'WooCommerce';
 
 let pluginPath;
 
 utils.describeIf( UPDATE_WC )( 'WooCommerce plugin can be uploaded and activated', () => {
 	beforeAll( async () => {
-		pluginPath = await getRemotePluginZip( nightlyZip );
+
+		if ( TEST_RELEASE ) {
+			zipUrl = await getLatestReleaseZipUrl('woocommerce', 'woocommerce');
+		} else {
+			zipUrl = 'https://github.com/woocommerce/woocommerce/releases/download/nightly/woocommerce-trunk-nightly.zip';
+		}
+
+		pluginPath = await getRemotePluginZip( zipUrl );
 		await merchant.login();
 	});