diff --git a/core/Dockerfile b/core/Dockerfile
index 9ccd2cd..65a13e0 100644
--- a/core/Dockerfile
+++ b/core/Dockerfile
@@ -13,8 +13,8 @@ RUN --mount=type=cache,target=/root/.cache \
   # Mailman html to plaintext conversion uses lynx.
   # psutil needs linux-headers to compile on musl c library.
     && apk add --no-cache bash su-exec postgresql-client mysql-client curl python3 py3-pip linux-headers py-cryptography mariadb-connector-c lynx tzdata \
-    && python3 -m pip install -U pip setuptools wheel \
-        && python3 -m pip install psycopg2 \
+    && python3 -m pip install --break-system-packages -U pip setuptools wheel \
+        && python3 -m pip install --break-system-packages psycopg2 \
                    gunicorn==19.9.0 \
                    pymysql \
                    -r /tmp/requirements.txt \
diff --git a/core/Dockerfile.dev b/core/Dockerfile.dev
index 1814afd..7064e34 100644
--- a/core/Dockerfile.dev
+++ b/core/Dockerfile.dev
@@ -14,8 +14,8 @@ RUN --mount=type=cache,target=/root/.cache \
    	    postgresql-dev git libffi-dev g++ \
     && apk add --no-cache bash su-exec postgresql-client mysql-client \
         curl python3 py3-pip linux-headers py-cryptography mariadb-connector-c tzdata \
-    && python3 -m pip install -U psycopg2 pymysql setuptools wheel \
-    && python3 -m pip install \
+    && python3 -m pip install -U --break-system-packages psycopg2 pymysql setuptools wheel \
+    && python3 -m pip install --break-system-packages \
         git+https://gitlab.com/mailman/mailman \
         git+https://gitlab.com/mailman/mailman-hyperkitty \
         gunicorn==19.9.0 \
diff --git a/postorius/Dockerfile b/postorius/Dockerfile
index 7e329f6..b668805 100644
--- a/postorius/Dockerfile
+++ b/postorius/Dockerfile
@@ -1,5 +1,5 @@
 # syntax = docker/dockerfile:1.3
-FROM alpine:3.18.4
+FROM alpine:3.19.0
 
 # Install packages and dependencies for postorius and hyperkitty Add user for
 # executing apps, change ownership for uwsgi+django files and set execution
@@ -11,8 +11,8 @@ RUN --mount=type=cache,target=/root/.cache \
 	&& apk add --no-cache --virtual .mailman-rundeps bash sassc tzdata \
 		postgresql-client mysql-client py3-mysqlclient curl mailcap gettext \
 		python3 py3-pip libffi libuuid pcre-dev py-cryptography \
-	&& python3 -m pip install -U 'Django<4.2' pip setuptools wheel \
-	&& python3 -m pip install postorius==1.3.7 \
+	&& python3 -m pip install --break-system-packages -U 'Django<4.2' pip setuptools wheel \
+	&& python3 -m pip install --break-system-packages postorius==1.3.7 \
         uwsgi \
 		'psycopg2<2.9' \
 		dj-database-url \
diff --git a/postorius/Dockerfile.dev b/postorius/Dockerfile.dev
index 1613acd..0321c6c 100644
--- a/postorius/Dockerfile.dev
+++ b/postorius/Dockerfile.dev
@@ -1,5 +1,5 @@
 # syntax = docker/dockerfile:1.3
-FROM alpine:3.18.4
+FROM alpine:3.19.0
 
 ARG POSTORIUS_REF
 ARG DJ_MM3_REF
@@ -15,8 +15,8 @@ RUN --mount=type=cache,target=/root/.cache \
 	&& apk add --no-cache --virtual .mailman-rundeps bash sassc tzdata \
 		postgresql-client mysql-client py3-mysqlclient curl mailcap \
 		python3 py3-pip libffi gettext py-cryptography \
-    && python3 -m pip install -U pip setuptools wheel \
-    && python3 -m pip install -U \
+    && python3 -m pip install --break-system-packages -U pip setuptools wheel \
+    && python3 -m pip install --break-system-packages -U \
         git+https://gitlab.com/mailman/mailmanclient \
         git+https://gitlab.com/mailman/postorius \
 		uwsgi \
@@ -25,8 +25,8 @@ RUN --mount=type=cache,target=/root/.cache \
 		mysqlclient \
 		typing \
 		django-utils-six \
-    && python3 -m pip install -U 'Django<3.2' \
-    && python3 -m pip install -U \
+    && python3 -m pip install --break-system-packages -U 'Django<3.2' \
+    && python3 -m pip install --break-system-packages -U \
        git+https://gitlab.com/mailman/django-mailman3 \
 	&& apk del .build-deps \
 	&& addgroup -S mailman \
diff --git a/postorius/mailman-web/urls.py b/postorius/mailman-web/urls.py
index 6a9bbaf..3e3c312 100644
--- a/postorius/mailman-web/urls.py
+++ b/postorius/mailman-web/urls.py
@@ -18,16 +18,16 @@
 
 from django.conf.urls import include
 from django.contrib import admin
-from django.urls import path, reverse_lazy
+from django.urls import re_path, reverse_lazy
 from django.views.generic import RedirectView
 
 urlpatterns = [
-    path(r'^$', RedirectView.as_view(
+    re_path(r'^$', RedirectView.as_view(
         url=reverse_lazy('list_index'),
         permanent=True)),
-    path(r'postorius/', include('postorius.urls')),
-    path(r'', include('django_mailman3.urls')),
-    path(r'accounts/', include('allauth.urls')),
+    re_path(r'postorius/', include('postorius.urls')),
+    re_path(r'', include('django_mailman3.urls')),
+    re_path(r'accounts/', include('allauth.urls')),
     # Django admin
-    path(r'^admin/', admin.site.urls),
+    re_path(r'^admin/', admin.site.urls),
 ]
diff --git a/web/Dockerfile b/web/Dockerfile
index 704cc71..e6956b8 100644
--- a/web/Dockerfile
+++ b/web/Dockerfile
@@ -14,8 +14,8 @@ RUN --mount=type=cache,target=/root/.cache \
 	&& apk add --no-cache --virtual .mailman-rundeps bash sassc tzdata \
 	   postgresql-client mysql-client py3-mysqlclient curl mailcap gettext \
 	   python3 py3-pip xapian-core xapian-bindings-python3 libffi pcre-dev py-cryptography \
-	&& python3 -m pip install -U 'Django<4.2' pip setuptools wheel \
-	&& pip install -r /tmp/requirements.txt \
+	&& python3 -m pip install --break-system-packages -U 'Django<4.2' pip setuptools wheel \
+	&& pip install --break-system-packages -r /tmp/requirements.txt \
 		whoosh \
 		uwsgi \
 		psycopg2 \
diff --git a/web/Dockerfile.dev b/web/Dockerfile.dev
index 285025c..a875b02 100644
--- a/web/Dockerfile.dev
+++ b/web/Dockerfile.dev
@@ -16,8 +16,8 @@ RUN --mount=type=cache,target=/root/.cache \
     && apk add --no-cache --virtual .mailman-rundeps bash sassc pcre-dev tzdata \
         python3 py3-pip postgresql-client mysql-client py3-mysqlclient \
         curl mailcap xapian-core xapian-bindings-python3 libffi gettext py-cryptography \
-    && python3 -m pip install -U pip setuptools wheel \
-    && python3 -m pip install -U \
+    && python3 -m pip install --break-system-packages -U pip setuptools wheel \
+    && python3 -m pip install --break-system-packages -U \
         git+https://gitlab.com/mailman/mailmanclient \
         git+https://gitlab.com/mailman/postorius \
         git+https://gitlab.com/mailman/hyperkitty \
@@ -32,8 +32,8 @@ RUN --mount=type=cache,target=/root/.cache \
 	tzdata \
         diskcache \
         django-utils-six \
-    && python3 -m pip install -U 'Django<4.2' \
-    && python3 -m pip install -U \
+    && python3 -m pip install --break-system-packages -U 'Django<4.2' \
+    && python3 -m pip install --break-system-packages -U \
        git+https://gitlab.com/mailman/django-mailman3 \
     && apk del .build-deps \
     && addgroup -S mailman \