diff --git a/.github/workflows/build_and_test_workflow.yml b/.github/workflows/build_and_test_workflow.yml
index b40c59eb293d..621b5e6033ac 100644
--- a/.github/workflows/build_and_test_workflow.yml
+++ b/.github/workflows/build_and_test_workflow.yml
@@ -152,9 +152,8 @@ jobs:
           npm uninstall -g yarn
           npm i -g yarn@1.22.10
 
-      # image has the latest chrome v99
       - name: Setup chromedriver
-        run: yarn add --dev chromedriver@99.0.0
+        run: node scripts/upgrade_chromedriver.js
 
       - name: Run bootstrap
         run: yarn osd bootstrap
@@ -204,9 +203,8 @@ jobs:
           npm uninstall -g yarn
           npm i -g yarn@1.22.10
 
-      # image has the latest chrome v99
       - name: Setup chromedriver
-        run: yarn add --dev chromedriver@106.0.1
+        run: node scripts/upgrade_chromedriver.js
 
       - name: Run bootstrap
         run: yarn osd bootstrap
diff --git a/.gitignore b/.gitignore
index 01c2aaeaf9ef..3f1759e6665a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -3,6 +3,7 @@
 .ackrc
 /.opensearch
 /.chromium
+/package.json.bak
 .DS_Store
 .node_binaries
 .native_modules
diff --git a/CHANGELOG.md b/CHANGELOG.md
index d7be07729e4d..d71db148d071 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -77,6 +77,8 @@ Inspired from [Keep a Changelog](https://keepachangelog.com/en/1.0.0/)
 - Update backport custom branch name to utilize head template ([#2766](https://github.com/opensearch-project/OpenSearch-Dashboards/pull/2766))
 - Re-enable CI workflows for feature branckes ([#2908](https://github.com/opensearch-project/OpenSearch-Dashboards/pull/2908))
 - Add Windows CI workflows ([#2966](https://github.com/opensearch-project/OpenSearch-Dashboards/pull/2966))
+- Add automatic selection of the appropriate version of chrome driver to run functional tests ([#2990](https://github.com/opensearch-project/OpenSearch-Dashboards/pull/2990))
+
 
 ### 📝 Documentation
 
diff --git a/scripts/upgrade_chromedriver.js b/scripts/upgrade_chromedriver.js
new file mode 100644
index 000000000000..bb5200c30eec
--- /dev/null
+++ b/scripts/upgrade_chromedriver.js
@@ -0,0 +1,122 @@
+/*
+ * Copyright OpenSearch Contributors
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+/**
+ * Upgrades the chromedriver dev-dependency to the one supported by the version of Google Chrome
+ * installed on the machine.
+ *
+ * Usage: node scripts/upgrade_chromedriver.js [--install]
+ */
+
+/* eslint no-restricted-syntax: 0 */
+const { execSync, spawnSync } = require('child_process');
+const { createReadStream, createWriteStream, unlinkSync, renameSync, existsSync } = require('fs');
+const { createInterface } = require('readline');
+
+if (!process.argv.includes(__filename)) {
+  console.error('Usage: node scripts/upgrade_chromedriver.js [--install]');
+  process.exit(1);
+}
+
+const versionCheckCommands = [];
+
+switch (process.platform) {
+  case 'win32':
+    versionCheckCommands.push(
+      'powershell "(Get-Item \\"$Env:Programfiles/Google/Chrome/Application/chrome.exe\\").VersionInfo.FileVersion"'
+    );
+    break;
+
+  case 'darwin':
+    versionCheckCommands.push(
+      '/Applications/Google Chrome.app/Contents/MacOS/Google Chrome --version'
+    );
+    break;
+
+  default:
+    versionCheckCommands.push(
+      ...[
+        '/usr/bin',
+        '/usr/local/bin',
+        '/usr/sbin',
+        '/usr/local/sbin',
+        '/opt/bin',
+        '/usr/bin/X11',
+        '/usr/X11R6/bin',
+      ].flatMap((loc) =>
+        [
+          'google-chrome --version',
+          'google-chrome-stable --version',
+          'chromium --version',
+          'chromium-browser --version',
+        ].map((cmd) => `${loc}/${cmd}`)
+      )
+    );
+}
+
+let versionCheckOutput;
+versionCheckCommands.some((cmd) => {
+  try {
+    console.log(cmd);
+    versionCheckOutput = execSync(cmd, { encoding: 'utf8' })?.trim?.();
+    return true;
+  } catch (e) {
+    console.log('Failed to get version using', cmd);
+  }
+});
+
+// Versions 90+
+const majorVersion = versionCheckOutput?.match?.(/(?:^|\s)(9\d|\d{3})\./)?.[1];
+
+if (majorVersion) {
+  if (process.argv.includes('--install')) {
+    console.log(`Installing chromedriver@^${majorVersion}`);
+
+    spawnSync(`yarn add --dev chromedriver@^${majorVersion}`, {
+      stdio: 'inherit',
+      cwd: process.cwd(),
+      shell: true,
+    });
+  } else {
+    console.log(`Upgrading to chromedriver@^${majorVersion}`);
+
+    let upgraded = false;
+    const writeStream = createWriteStream('package.json.upgrading-chromedriver', { flags: 'w' });
+    const rl = createInterface({
+      input: createReadStream('package.json'),
+      crlfDelay: Infinity,
+    });
+    rl.on('line', (line) => {
+      if (line.includes('"chromedriver": "')) {
+        line = line.replace(
+          /"chromedriver":\s*"[~^]?\d[\d.]*\d"/,
+          `"chromedriver": "^${majorVersion}"`
+        );
+        upgraded = true;
+      }
+      writeStream.write(line + '\n', 'utf8');
+    });
+    rl.on('close', () => {
+      writeStream.end();
+      if (upgraded) {
+        // Remove any previous backups
+        if (existsSync('package.json.bak')) unlinkSync('package.json.bak');
+
+        renameSync('package.json', 'package.json.bak');
+        renameSync('package.json.upgrading-chromedriver', 'package.json');
+
+        console.log(`Backed up package.json and updated chromedriver to ${majorVersion}`);
+      } else {
+        unlinkSync('package.json.upgrading-chromedriver');
+        console.error(
+          `Failed to update chromedriver to ${majorVersion}. Try adding the \`--install\` switch.`
+        );
+      }
+    });
+  }
+} else {
+  console.debug(versionCheckOutput);
+  console.error(`Failed to extract the version of the installed Google Chrome.`);
+}