diff --git a/.github/workflows/cypress-workflow.yml b/.github/workflows/cypress-workflow.yml
index 1b5a3c34f..aad6ab0af 100644
--- a/.github/workflows/cypress-workflow.yml
+++ b/.github/workflows/cypress-workflow.yml
@@ -15,8 +15,10 @@ jobs:
     name: Run Cypress E2E tests
     strategy:
       matrix:
-        os: [ubuntu-latest]
+        os: [ubuntu-latest, windows-latest]
         include:
+          - os: windows-latest
+            cypress_cache_folder: ~/AppData/Local/Cypress/Cache
           - os: ubuntu-latest
             cypress_cache_folder: ~/.cache/Cypress
     runs-on: ${{ matrix.os }}
@@ -32,6 +34,10 @@ jobs:
           # TODO: Parse this from security analytics plugin (https://github.com/opensearch-project/security-analytics/issues/170)
           java-version: 11
 
+      - name: Enable longer filenames
+        if: ${{ matrix.os == 'windows-latest' }}
+        run: git config --system core.longpaths true
+
       - name: Checkout security analytics
         uses: actions/checkout@v2
         with:
@@ -87,7 +93,14 @@ jobs:
           yarn start --no-base-path --no-watch &
         shell: bash
 
-      - name: Sleep until OSD server starts
+      # Window is slow so wait longer
+      - name: Sleep until OSD server starts - windows
+        if: ${{ matrix.os == 'windows-latest' }}
+        run: Start-Sleep -s 400
+        shell: powershell
+
+      - name: Sleep until OSD server starts - non-windows
+        if: ${{ matrix.os != 'windows-latest' }}
         run: sleep 300
         shell: bash