diff --git a/enterprise/Dockerfile b/enterprise/Dockerfile
index e4f0997f75..62725957f3 100644
--- a/enterprise/Dockerfile
+++ b/enterprise/Dockerfile
@@ -24,9 +24,9 @@ RUN apt-get update && \
     rm -rf /var/lib/apt/lists/*
 
 # Install Python packages with security fixes
-RUN pip install alembic psycopg2-binary cloud-sql-python-connector pg8000 gspread stripe python-keycloak asyncpg sqlalchemy[asyncio] resend tenacity slack-sdk ddtrace "posthog>=6.0.0" "limits==5.2.0" coredis prometheus-client shap scikit-learn pandas numpy google-cloud-recaptcha-enterprise && \
+RUN /app/.venv/bin/pip install alembic psycopg2-binary cloud-sql-python-connector pg8000 gspread stripe python-keycloak asyncpg sqlalchemy[asyncio] resend tenacity slack-sdk ddtrace "posthog>=6.0.0" "limits==5.2.0" coredis prometheus-client shap scikit-learn pandas numpy google-cloud-recaptcha-enterprise && \
     # Update packages with known CVE fixes
-    pip install --upgrade \
+    /app/.venv/bin/pip install --upgrade \
         "mcp>=1.10.0" \
         "pillow>=11.3.0"