diff --git a/.github/workflows/insiders.yml b/.github/workflows/insiders.yml
index 36e50002e242..77b7fa3c9091 100644
--- a/.github/workflows/insiders.yml
+++ b/.github/workflows/insiders.yml
@@ -120,6 +120,19 @@ jobs:
     name: Tests
     # The value of runs-on is the OS of the current job (specified in the strategy matrix below) instead of being hardcoded.
     runs-on: ${{ matrix.os }}
+    env:
+      # Something in Node 12.16.0 breaks the TS debug adapter, and ubuntu-latest bundles Node 12.16.1.
+      # We can remove this when we switch over to the python-based DA in https://github.com/microsoft/vscode-python/issues/7136.
+      # See https://github.com/microsoft/ptvsd/issues/2068
+      # At this point pinning is only needed for consistency. We no longer have TS debug adapter.
+      NODE_VERSION: 12.15.0
+      # Force a path with spaces and to test extension works in these scenarios
+      # Unicode characters are causing 2.7 failures so skip that for now.
+      special-working-directory: './path with spaces'
+      special-working-directory-relative: 'path with spaces'
+    defaults:
+      run:
+        working-directory: ${{env.special-working-directory}}
     if: github.repository == 'microsoft/vscode-python'
     strategy:
       fail-fast: false
@@ -130,15 +143,11 @@ jobs:
         # Run the tests on the oldest and most recent versions of Python.
         python: [2.7, 3.8]
         test-suite: [ts-unit, python-unit, venv, single-workspace, multi-workspace, debugger, functional]
-    env:
-      # Something in Node 12.16.0 breaks the TS debug adapter, and ubuntu-latest bundles Node 12.16.1.
-      # We can remove this when we switch over to the python-based DA in https://github.com/microsoft/vscode-python/issues/7136.
-      # See https://github.com/microsoft/ptvsd/issues/2068
-      # At this point pinning is only needed for consistency. We no longer have TS debug adapter.
-      NODE_VERSION: 12.15.0
     steps:
       - name: Checkout
         uses: actions/checkout@v2
+        with:
+          path: ${{env.special-working-directory-relative}}
 
       - name: Cache pip files
         uses: actions/cache@v2
@@ -157,7 +166,7 @@ jobs:
         id: out-cache
         uses: actions/cache@v2
         with:
-          path: ./out
+          path: ${{env.special-working-directory}}/out
           key: ${{runner.os}}-${{env.CACHE_OUT_DIRECTORY}}-${{hashFiles('src/**')}}
 
       - name: Install dependencies (npm ci)
@@ -315,6 +324,7 @@ jobs:
         uses: GabrielBB/xvfb-action@v1.4
         with:
           run: npm run testSingleWorkspace
+          working-directory: ${{env.special-working-directory}}
         if: matrix.test-suite == 'venv'
 
       - name: Run single-workspace tests
@@ -323,6 +333,7 @@ jobs:
         uses: GabrielBB/xvfb-action@v1.4
         with:
           run: npm run testSingleWorkspace
+          working-directory: ${{env.special-working-directory}}
         if: matrix.test-suite == 'single-workspace'
 
       - name: Run multi-workspace tests
@@ -331,6 +342,7 @@ jobs:
         uses: GabrielBB/xvfb-action@v1.4
         with:
           run: npm run testMultiWorkspace
+          working-directory: ${{env.special-working-directory}}
         if: matrix.test-suite == 'multi-workspace'
 
       - name: Run debugger tests
@@ -339,6 +351,7 @@ jobs:
         uses: GabrielBB/xvfb-action@v1.4
         with:
           run: npm run testDebugger
+          working-directory: ${{env.special-working-directory}}
         if: matrix.test-suite == 'debugger'
 
       - name: Run functional tests