diff --git a/.github/workflows/build_and_test_workflow.yml b/.github/workflows/build_and_test_workflow.yml
index fbf9d4ba5490..b84bc77e3545 100644
--- a/.github/workflows/build_and_test_workflow.yml
+++ b/.github/workflows/build_and_test_workflow.yml
@@ -75,6 +75,10 @@ jobs:
     runs-on: windows-latest
     name: Build and Verify on Windows
     steps:
+      - name: Configure git's autocrlf
+        run: |
+          git config --global core.autocrlf false
+
       - name: Checkout code
         uses: actions/checkout@v2
 
@@ -129,6 +133,12 @@ jobs:
       - name: Checkout code
         uses: actions/checkout@v2
 
+      - name: Setup JDK
+        uses: actions/setup-java@v3
+        with:
+          java-version: '11'
+          distribution: 'adopt'
+
       - name: Setup Node
         uses: actions/setup-node@v2
         with:
@@ -140,9 +150,8 @@ 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
@@ -168,6 +177,10 @@ jobs:
     steps:
       - run: echo Running functional tests for ciGroup${{ matrix.group }}
 
+      - name: Configure git's autocrlf
+        run: |
+          git config --global core.autocrlf false
+
       - name: Checkout code
         uses: actions/checkout@v2
 
@@ -188,9 +201,8 @@ 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
@@ -270,7 +282,7 @@ jobs:
     name: Build min release artifacts on Windows
     defaults:
       run:
-        working-directory: ./artifacts
+        working-directory: artifacts
     strategy:
       matrix:
         include:
@@ -279,15 +291,19 @@ jobs:
             suffix: windows-x64
             script: build-platform --windows --skip-os-packages
     steps:
+      - name: Configure git's autocrlf
+        run: |
+          git config --global core.autocrlf false
+
       - name: Checkout code
         uses: actions/checkout@v2
         with:
-          path: ./artifacts
+          path: artifacts
 
       - name: Setup Node
         uses: actions/setup-node@v2
         with:
-          node-version-file: './artifacts/.nvmrc'
+          node-version-file: 'artifacts/.nvmrc'
           registry-url: 'https://registry.npmjs.org'
 
       - name: Setup Yarn
@@ -313,7 +329,7 @@ jobs:
         if: success()
         with:
           name: ${{ matrix.suffix }}-${{ env.VERSION }}
-          path: ./artifacts/target/${{ env.ARTIFACT_BUILD_NAME }}
+          path: artifacts/target/${{ env.ARTIFACT_BUILD_NAME }}
           retention-days: 1
 
   bwc-tests:
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/scripts/upgrade_chromedriver.js b/scripts/upgrade_chromedriver.js
new file mode 100644
index 000000000000..f42aae924440
--- /dev/null
+++ b/scripts/upgrade_chromedriver.js
@@ -0,0 +1,123 @@
+/*
+ * 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}/${cmd}`)
+      )
+    );
+}
+
+let versionCheckOutput;
+versionCheckCommands.some((cmd) => {
+  try {
+    console.log(cmd);
+    versionCheckOutput = execSync(cmd, { encoding: 'utf8' })?.trim?.();
+    return true;
+  } catch (e) {
+    console.log('Failed to get version using', cmd);
+    console.log(e);
+  }
+});
+
+// Versions 90+
+const majorVersion = versionCheckOutput?.match?.(/(?:^|\s)(9\d|\d{3})\./)?.[1];
+
+if (majorVersion) {
+  if (process.argv.includes('--install')) {
+    console.log(`Installing chromedriver@^${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.`);
+}