diff --git a/src/Dockerfile b/src/Dockerfile
index 81f88d9cf..fdc4b7239 100644
--- a/src/Dockerfile
+++ b/src/Dockerfile
@@ -65,7 +65,18 @@ RUN cd /etc/.pihole && \
     install -T -m 0755 ./advanced/Templates/pihole-FTL-prestart.sh /opt/pihole/pihole-FTL-prestart.sh && \
     install -T -m 0755 ./advanced/Templates/pihole-FTL-poststop.sh /opt/pihole/pihole-FTL-poststop.sh && \
     addgroup -S pihole && adduser -S pihole -G pihole && \
-    echo "${PIHOLE_DOCKER_TAG}" > /pihole.docker.tag
+    echo "${PIHOLE_DOCKER_TAG}" > /pihole.docker.tag && \
+    # sed a new function into the `pihole` script just above the `helpFunc()` function for later use.
+    sed -i $'s/helpFunc() {/unsupportedFunc() {\\\n  echo "Function not supported in Docker images"\\\n  exit 0\\\n}\\\n\\\nhelpFunc() {/g' /usr/local/bin/pihole && \
+    # Replace a few of the `pihole` options with calls to `unsupportedFunc`:
+    # pihole -up / pihole updatePihole
+    sed -i $'s/)\s*updatePiholeFunc/) unsupportedFunc/g' /usr/local/bin/pihole && \
+    # pihole uninstall
+    sed -i $'s/)\s*uninstallFunc/) unsupportedFunc/g' /usr/local/bin/pihole && \
+    # pihole -r / pihole reconfigure
+    sed -i $'s/)\s*reconfigurePiholeFunc/) unsupportedFunc/g' /usr/local/bin/pihole && \
+    # pihole checkout
+    sed -i $'s/)\s*piholeCheckoutFunc/) unsupportedFunc/g' /usr/local/bin/pihole
 
 COPY --chmod=0755 bash_functions.sh /usr/bin/bash_functions.sh
 COPY --chmod=0755 start.sh /usr/bin/start.sh
diff --git a/test/tests/test_general.py b/test/tests/test_general.py
index a0f539831..36cbee253 100644
--- a/test/tests/test_general.py
+++ b/test/tests/test_general.py
@@ -28,3 +28,17 @@ def test_pihole_ftl_clean_shutdown(docker):
     )
     assert "INFO: Shutting down... // exit code 0 // jmpret 0" in func.stdout
     assert "INFO: ########## FTL terminated after" in func.stdout
+
+
+# Ensure the unsupportedFunc monkeypatch is working
+@pytest.mark.parametrize("test_args", ['-e "PH_VERBOSE=1"'])
+def test_unsupported_monkeypatch(docker):
+    output = "Function not supported in Docker images"
+    checkout = docker.run("pihole checkout core dev")
+    update = docker.run("pihole -up")
+    uninstall = docker.run("pihole uninstall")
+    reconfigure = docker.run("pihole reconfigure")
+    assert output in checkout.stdout
+    assert output in update.stdout
+    assert output in uninstall.stdout
+    assert output in reconfigure.stdout