diff --git a/docker/Dockerfile b/docker/Dockerfile
index ffadc3c9..d4283f56 100644
--- a/docker/Dockerfile
+++ b/docker/Dockerfile
@@ -55,6 +55,10 @@ RUN mkdir -pv "${DEFAULT_WORKSPACE}" && \
       g++ \
       make \
       libffi-dev
+    && \
+    # Ensure we did not delete pip, which is needed for yt-dlp updates
+    python3 -m pip --help
+
 
 ###############################################################################
 # CONTAINER CONFIGS
diff --git a/docker/Dockerfile.gui b/docker/Dockerfile.gui
index 98f1b3cc..4cd4def5 100644
--- a/docker/Dockerfile.gui
+++ b/docker/Dockerfile.gui
@@ -78,7 +78,9 @@ RUN mkdir -p /config && \
       python3-venv && \
     apt-get autoremove -y && \
     apt-get purge -y --auto-remove && \
-    rm -rf /var/lib/apt/lists/*
+    rm -rf /var/lib/apt/lists/* && \
+    # Ensure we did not delete pip, which is needed for yt-dlp updates
+    python3 -m pip --help
 
 ###############################################################################
 # CONTAINER CONFIGS
diff --git a/docker/Dockerfile.ubuntu b/docker/Dockerfile.ubuntu
index e6c432f0..174902d9 100644
--- a/docker/Dockerfile.ubuntu
+++ b/docker/Dockerfile.ubuntu
@@ -81,7 +81,9 @@ RUN mkdir -pv "${DEFAULT_WORKSPACE}" && \
       python3-venv && \
     apt-get autoremove -y && \
     apt-get purge -y --auto-remove && \
-    rm -rf /var/lib/apt/lists/*
+    rm -rf /var/lib/apt/lists/* && \
+    # Ensure we did not delete pip, which is needed for yt-dlp updates
+    python3 -m pip --help
 
 ###############################################################################
 # CONTAINER CONFIGS