diff --git a/.github/workflows/build_pex.yml b/.github/workflows/build_pex.yml
index f7b84a5a524..e0b57257cec 100644
--- a/.github/workflows/build_pex.yml
+++ b/.github/workflows/build_pex.yml
@@ -14,15 +14,13 @@ on:
 jobs:
   build_pex:
     name: Build PEX
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-latest
+    container:
+      image: python:3.6-buster
     outputs:
       pex-file-name: ${{ steps.get-pex-filename.outputs.pex-file-name }}
     steps:
     - uses: actions/checkout@v4
-    - name: Set up Python 3.6
-      uses: actions/setup-python@v5
-      with:
-        python-version: 3.6
     - uses: actions/cache@v4
       with:
         path: ~/.cache/pip
diff --git a/.github/workflows/build_whl.yml b/.github/workflows/build_whl.yml
index be1b76fc4ad..f62ccc9e462 100644
--- a/.github/workflows/build_whl.yml
+++ b/.github/workflows/build_whl.yml
@@ -13,27 +13,27 @@ on:
 jobs:
   build_whl:
     name: Build WHL
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-latest
+    container:
+      image: python:3.6-buster
     outputs:
       whl-file-name: ${{ steps.get-whl-filename.outputs.whl-file-name }}
       tar-file-name: ${{ steps.get-tar-filename.outputs.tar-file-name }}
     steps:
+    - name: Install Ubuntu dependencies
+      run: |
+        apt-get -y -qq update
+        apt-get install -y gettext sudo sqlite3 binutils-aarch64-linux-gnu binutils-arm-linux-gnueabihf git-lfs
     - uses: actions/checkout@v4
       with:
         fetch-depth: 0
         lfs: true
-    - name: Install Ubuntu dependencies
-      run: |
-        sudo apt-get -y -qq update
-        sudo apt-get install -y gettext sudo sqlite3 binutils-aarch64-linux-gnu binutils-arm-linux-gnueabihf
-    - name: Set up Python 3.6
-      uses: actions/setup-python@v5
-      with:
-        python-version: 3.6
     - name: Use Node.js
       uses: actions/setup-node@v4
       with:
         node-version: '18.x'
+    - name: Install Yarn
+      run: npm install -g yarn@1
     - name: Get yarn cache directory path
       id: yarn-cache-dir-path
       run: echo "dir=$(yarn cache dir)" >> $GITHUB_OUTPUT
diff --git a/.github/workflows/c_extensions.yml b/.github/workflows/c_extensions.yml
deleted file mode 100644
index 1534f3a690b..00000000000
--- a/.github/workflows/c_extensions.yml
+++ /dev/null
@@ -1,100 +0,0 @@
-name: Static dependencies with and without C extensions
-
-on:
-  push:
-    branches:
-    - develop
-    - 'release-v**'
-  pull_request:
-    branches:
-    - develop
-    - 'release-v**'
-
-jobs:
-  pre_job:
-    name: Path match check
-    runs-on: ubuntu-latest
-    # Map a step output to a job output
-    outputs:
-      should_skip: ${{ steps.skip_check.outputs.should_skip }}
-    steps:
-      - id: skip_check
-        uses: fkirc/skip-duplicate-actions@master
-        with:
-          github_token: ${{ github.token }}
-          paths: '["**.py", "requirements/base.txt", "requirements/build.txt"]'
-  c_ext:
-    name: C Extensions
-    needs: pre_job
-    if: ${{ needs.pre_job.outputs.should_skip != 'true' }}
-    runs-on: ubuntu-20.04
-    steps:
-    - uses: actions/checkout@v4
-    - uses: actions/setup-python@v5
-      with:
-        python-version: 3.6
-    - name: pip cache
-      uses: actions/cache@v4
-      with:
-        path: ~/.cache/pip
-        key: ${{ runner.os }}-pip-ext-${{ hashFiles('requirements/*.txt') }}
-        restore-keys: |
-          ${{ runner.os }}-pip-ext
-    - name: Install dependencies
-      run: |
-        python -m pip install --upgrade pip
-        pip install -r requirements/base.txt
-        pip install -r requirements/build.txt
-        pip install -r requirements/test.txt
-    - name: Check C extensions build and run
-      run: |
-        # Ensure that for this Python version, we can actually compile ALL files
-        # in the kolibri directory
-        python -m compileall -q kolibri -x py2only
-        # Until we have staged builds, we will be running this in each and every
-        # environment even though builds should be done in Py 3.6
-        make staticdeps
-        make staticdeps-cext
-        pip install .
-        # Start and stop kolibri
-        kolibri start --port=8081
-        kolibri stop
-        # Run just tests in test/
-        py.test --color=no test/
-  no_c_ext:
-    name: No C Extensions
-    needs: pre_job
-    if: ${{ needs.pre_job.outputs.should_skip != 'true' }}
-    runs-on: ubuntu-20.04
-    steps:
-    - uses: actions/checkout@v4
-    - uses: actions/setup-python@v5
-      with:
-        python-version: 3.6
-    - name: pip cache
-      uses: actions/cache@v4
-      with:
-        path: ~/.cache/pip
-        key: ${{ runner.os }}-pip-no-ext-${{ hashFiles('requirements/*.txt') }}
-        restore-keys: |
-          ${{ runner.os }}-pip-no-ext
-    - name: Install dependencies
-      run: |
-        python -m pip install --upgrade pip
-        pip install -r requirements/base.txt
-        pip install -r requirements/build.txt
-        pip install -r requirements/test.txt
-    - name: Check No C extensions build and run
-      run: |
-        # Ensure that for this Python version, we can actually compile ALL files
-        # in the kolibri directory
-        python -m compileall -q kolibri -x py2only
-        # Until we have staged builds, we will be running this in each and every
-        # environment even though builds should be done in Py 3.6
-        make staticdeps
-        pip install .
-        # Start and stop kolibri
-        kolibri start --port=8081
-        kolibri stop
-        # Run just tests in test/
-        py.test --color=no test/
diff --git a/.github/workflows/morango_integration.yml b/.github/workflows/morango_integration.yml
index c49eb6faf1e..2a4d4f2a910 100644
--- a/.github/workflows/morango_integration.yml
+++ b/.github/workflows/morango_integration.yml
@@ -22,15 +22,15 @@ jobs:
           github_token: ${{ github.token }}
           paths: '["requirements/base.txt", ".github/workflows/morango_integration.yml"]'
   morango_integration_tests_sqlite:
-    name: Morango Integration Tests
+    name: Morango Integration Tests for currently supported Python versions
     needs: pre_job
     if: needs.pre_job.outputs.should_skip != 'true'
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-latest
     env:
       INTEGRATION_TEST: 'true'
     strategy:
       matrix:
-        python-version: [3.6, 3.7, 3.8, 3.9, '3.10', '3.11', '3.12']
+        python-version: [3.9, '3.10', '3.11', '3.12']
 
     steps:
       - name: Checkout repository
@@ -53,6 +53,34 @@ jobs:
       - name: Test with tox
         run: tox -e py${{ matrix.python-version }} -- kolibri/core/auth/test/test_morango_integration.py
 
+  morango_integration_tests_sqlite_eol_python:
+    name: Morango Integration Tests for EOL Python versions
+    needs: pre_job
+    if: needs.pre_job.outputs.should_skip != 'true'
+    runs-on: ubuntu-latest
+    env:
+      INTEGRATION_TEST: 'true'
+    strategy:
+      matrix:
+        python-version: [3.6, 3.7, 3.8]
+    container:
+      image: python:${{ matrix.python-version }}-buster
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v4
+
+      - name: Install tox
+        run: |
+          python -m pip install --upgrade pip
+          pip install "tox<4"
+      - name: tox env cache
+        uses: actions/cache@v4
+        with:
+          path: ${{ github.workspace }}/.tox/py${{ matrix.python-version }}
+          key: ${{ runner.os }}-tox-py${{ matrix.python-version }}-${{ hashFiles('requirements/*.txt') }}
+      - name: Test with tox
+        run: tox -e py${{ matrix.python-version }} -- kolibri/core/auth/test/test_morango_integration.py
+
 
   morango_integration_tests_postgres:
     name: Morango Integration Tests with PostgreSQL
diff --git a/.github/workflows/pr_build_kolibri.yml b/.github/workflows/pr_build_kolibri.yml
index 1e9cbdb256f..019a513dcf2 100644
--- a/.github/workflows/pr_build_kolibri.yml
+++ b/.github/workflows/pr_build_kolibri.yml
@@ -66,3 +66,47 @@ jobs:
     with:
       deb-file-name: ${{ needs.deb.outputs.deb-file-name }}
       ref: v1.0.0
+  test_whl_file:
+    name: Test WHL file
+    needs: whl
+    strategy:
+      matrix:
+        python-version: [3.9, '3.10', '3.11', '3.12']
+        cext: [true, false]
+    runs-on: ubuntu-latest
+    steps:
+      - name: Install Python
+        uses: actions/setup-python@v5
+        with:
+          python-version: ${{ matrix.python-version }}
+      - uses: actions/download-artifact@v4
+        with:
+          name: ${{ needs.whl.outputs.whl-file-name }}
+          path: dist
+      - name: Install WHL file
+        run: pip install dist/${{ needs.whl.outputs.whl-file-name }}
+      - name: Smoke test WHL file
+        env:
+          KOLIBRI_NO_C_EXTENSIONS: ${{ matrix.cext == false && '1' || '' }}
+        run: kolibri configure setup
+  test_whl_file_eol_python:
+    name: Test WHL file with EOL Python versions
+    needs: whl
+    strategy:
+      matrix:
+        python-version: [3.6, 3.7, 3.8]
+        cext: [true, false]
+    runs-on: ubuntu-latest
+    container:
+      image: python:${{ matrix.python-version }}-buster
+    steps:
+      - uses: actions/download-artifact@v4
+        with:
+          name: ${{ needs.whl.outputs.whl-file-name }}
+          path: dist
+      - name: Install WHL file
+        run: pip install dist/${{ needs.whl.outputs.whl-file-name }}
+      - name: Smoke test WHL file
+        env:
+          KOLIBRI_NO_C_EXTENSIONS: ${{ matrix.cext == false && '1' || '' }}
+        run: kolibri configure setup
diff --git a/.github/workflows/pypi_upload.yml b/.github/workflows/pypi_upload.yml
index 3ef0687ee84..d6386f15eb6 100644
--- a/.github/workflows/pypi_upload.yml
+++ b/.github/workflows/pypi_upload.yml
@@ -25,7 +25,7 @@ on:
 
 jobs:
   deploy:
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-latest
     steps:
     - uses: actions/checkout@v4
     - name: Set up Python
diff --git a/.github/workflows/tox.yml b/.github/workflows/tox.yml
index e5223672819..dfc8c700344 100644
--- a/.github/workflows/tox.yml
+++ b/.github/workflows/tox.yml
@@ -24,13 +24,13 @@ jobs:
           github_token: ${{ github.token }}
           paths: '["**.py", "requirements/*.txt", ".github/workflows/tox.yml", "tox.ini"]'
   unit_test:
-    name: Python unit tests
+    name: Python unit tests for currently supported Python versions
     needs: pre_job
-    runs-on: ubuntu-20.04
+    runs-on: ubuntu-latest
     strategy:
       max-parallel: 5
       matrix:
-        python-version: [3.6, 3.7, 3.8, 3.9, '3.10', '3.11', '3.12']
+        python-version: [3.9, '3.10', '3.11', '3.12']
 
     steps:
     - uses: actions/checkout@v4
@@ -53,6 +53,32 @@ jobs:
     - name: Test with tox
       if: ${{ needs.pre_job.outputs.should_skip != 'true' }}
       run: tox -e py${{ matrix.python-version }}
+  unit_test_eol_python:
+    name: Python unit tests for EOL Python versions
+    needs: pre_job
+    runs-on: ubuntu-latest
+    strategy:
+      max-parallel: 5
+      matrix:
+        python-version: [3.6, 3.7, 3.8]
+    container:
+      image: python:${{ matrix.python-version }}-buster
+    steps:
+    - uses: actions/checkout@v4
+    - name: Install tox
+      if: ${{ needs.pre_job.outputs.should_skip != 'true' }}
+      run: |
+        python -m pip install --upgrade pip
+        pip install "tox<4"
+    - name: tox env cache
+      if: ${{ needs.pre_job.outputs.should_skip != 'true' }}
+      uses: actions/cache@v4
+      with:
+        path: ${{ github.workspace }}/.tox/py${{ matrix.python-version }}
+        key: ${{ runner.os }}-tox-py${{ matrix.python-version }}-${{ hashFiles('requirements/*.txt') }}
+    - name: Test with tox
+      if: ${{ needs.pre_job.outputs.should_skip != 'true' }}
+      run: tox -e py${{ matrix.python-version }}
   postgres:
     name: Python postgres unit tests
     needs: pre_job
diff --git a/kolibri/utils/env.py b/kolibri/utils/env.py
index 154080db30b..e117220a977 100644
--- a/kolibri/utils/env.py
+++ b/kolibri/utils/env.py
@@ -28,6 +28,9 @@ def settings_module():
     "KOLIBRI_APK_VERSION_NAME": {
         "description": "Version name for the Kolibri APK (Android Installer)",
     },
+    "KOLIBRI_NO_C_EXTENSIONS": {
+        "description": "Disable C extensions.",
+    },
     "LISTEN_PID": {
         "description": """
             The PID of the process to listen for signals from -
@@ -136,6 +139,7 @@ def set_env():
     from the distributed version in case it exists before importing anything
     else.
     """
+
     monkey_patch_markdown()
     monkey_patch_distutils()
 
@@ -143,8 +147,9 @@ def set_env():
 
     sys.path = [os.path.realpath(os.path.dirname(kolibri_dist.__file__))] + sys.path
 
-    # Add path for c extensions to sys.path
-    prepend_cext_path(os.path.realpath(os.path.dirname(kolibri_dist.__file__)))
+    if not os.environ.get("KOLIBRI_NO_C_EXTENSIONS", False):
+        # Add path for c extensions to sys.path
+        prepend_cext_path(os.path.realpath(os.path.dirname(kolibri_dist.__file__)))
 
     # Set default env
     for key, value in ENVIRONMENT_VARIABLES.items():
diff --git a/kolibri/utils/tests/test_sanity_check.py b/kolibri/utils/tests/test_sanity_check.py
index d2aa72e8a08..b288d814e22 100644
--- a/kolibri/utils/tests/test_sanity_check.py
+++ b/kolibri/utils/tests/test_sanity_check.py
@@ -15,7 +15,9 @@
 class SanityCheckTestCase(TestCase):
     @patch("kolibri.utils.sanity_checks.logging.error")
     @override_option(
-        "Paths", "CONTENT_DIR", "Z:\\NOTREAL" if sys.platform == "win32" else "/dir_dne"
+        "Paths",
+        "CONTENT_DIR",
+        "Z:\\NOTREAL" if sys.platform == "win32" else "/proc/self/mem/impossible",
     )
     def test_content_dir_dne(self, logging_mock):
         with self.assertRaises(SystemExit):