diff --git a/core/Dockerfile b/core/Dockerfile
index aaadfa2..04148ca 100644
--- a/core/Dockerfile
+++ b/core/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.12
 
 MAINTAINER Abhilash Raj
 
@@ -10,7 +10,7 @@ RUN apk update \
 	&& apk add --virtual build-deps gcc python3-dev musl-dev postgresql-dev \
 	   libffi-dev \
   # psutil needs linux-headers to compile on musl c library.
-	&& apk add --no-cache bash su-exec postgresql-client mysql-client curl python3 py3-setuptools linux-headers \
+	&& apk add --no-cache bash su-exec postgresql-client mysql-client curl python3 py3-pip linux-headers \
 	&& python3 -m pip install -U pip setuptools wheel \
         && python3 -m pip install psycopg2 \
                    gunicorn==19.9.0 \
diff --git a/core/Dockerfile.dev b/core/Dockerfile.dev
index 6e2ff35..8ea5cc3 100644
--- a/core/Dockerfile.dev
+++ b/core/Dockerfile.dev
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.12
 
 MAINTAINER Abhilash Raj
 
@@ -15,7 +15,7 @@ ARG MM3_HK_REF
 RUN apk update \
 	&& apk add --no-cache --virtual build-deps gcc python3-dev musl-dev \
    	    postgresql-dev git libffi-dev  \
-    && apk add --no-cache bash su-exec postgresql-client mysql-client curl python3 py3-setuptools linux-headers \
+    && apk add --no-cache bash su-exec postgresql-client mysql-client curl python3 py3-pip linux-headers \
     && python3 -m pip install -U psycopg2 pymysql setuptools wheel \
     && python3 -m pip install \
         git+https://gitlab.com/mailman/mailman@${CORE_REF} \
diff --git a/postorius/Dockerfile b/postorius/Dockerfile
index ed63ef1..a91cdc9 100644
--- a/postorius/Dockerfile
+++ b/postorius/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.12
 
 MAINTAINER Abhilash Raj
 
@@ -14,8 +14,8 @@ RUN set -ex \
 	&& apk add --no-cache --virtual .build-deps gcc libc-dev linux-headers \
 		postgresql-dev mariadb-dev python3-dev libffi-dev gettext \
 	&& apk add --no-cache --virtual .mailman-rundeps bash sassc \
-		postgresql-client mysql-client py-mysqldb curl mailcap \
-		python3 py3-setuptools libffi \
+		postgresql-client mysql-client py3-mysqlclient curl mailcap \
+		python3 py3-pip libffi \
 	&& python3 -m pip install -U 'Django<3.0' pip wheel setuptools \
 	&& python3 -m pip install postorius==1.3.3 \
 		uwsgi \
diff --git a/postorius/Dockerfile.dev b/postorius/Dockerfile.dev
index 4e89cd1..24b8ca3 100644
--- a/postorius/Dockerfile.dev
+++ b/postorius/Dockerfile.dev
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.12
 
 MAINTAINER Abhilash Raj
 
@@ -16,8 +16,8 @@ RUN set -ex \
 	&& apk add --no-cache --virtual .build-deps gcc libc-dev linux-headers \
 		postgresql-dev mariadb-dev python3-dev libffi-dev git \
 	&& apk add --no-cache --virtual .mailman-rundeps bash sassc \
-		postgresql-client mysql-client py-mysqldb curl mailcap \
-		python3 py3-setuptools libffi gettext \
+		postgresql-client mysql-client py3-mysqlclient curl mailcap \
+		python3 py3-pip libffi gettext \
 	&& python3 -m pip install -U 'Django<3.0' pip setuptools wheel \
 	&& python3 -m pip install git+https://gitlab.com/mailman/postorius@${POSTORIUS_REF} \
 		uwsgi \
diff --git a/web/Dockerfile b/web/Dockerfile
index 6298cb1..10a7f52 100644
--- a/web/Dockerfile
+++ b/web/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.12
 
 MAINTAINER Abhilash Raj
 
@@ -14,8 +14,8 @@ RUN set -ex \
 	&& apk add --no-cache --virtual .build-deps gcc libc-dev linux-headers \
 		postgresql-dev mariadb-dev python3-dev libffi-dev openldap-dev \
 	&& apk add --no-cache --virtual .mailman-rundeps bash sassc \
-	   postgresql-client mysql-client py-mysqldb curl mailcap gettext \
-	   python3 py3-setuptools xapian-core xapian-bindings-python3 libffi \
+	   postgresql-client mysql-client py3-mysqlclient curl mailcap gettext \
+	   python3 py3-pip xapian-core xapian-bindings-python3 libffi \
 	&& python3 -m pip install -U 'Django<3.0' pip setuptools wheel \
 	&& pip install mailmanclient==3.3.1 \
 		postorius==1.3.3 \
diff --git a/web/Dockerfile.dev b/web/Dockerfile.dev
index 4839f40..da18d49 100644
--- a/web/Dockerfile.dev
+++ b/web/Dockerfile.dev
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.12
 
 MAINTAINER Abhilash Raj
 
@@ -19,7 +19,7 @@ RUN set -ex \
     && apk add --no-cache --virtual .build-deps gcc libc-dev linux-headers git \
         postgresql-dev mariadb-dev python3-dev libffi-dev openldap-dev \
     && apk add --no-cache --virtual .mailman-rundeps bash sassc \
-      python3 py3-setuptools postgresql-client mysql-client py-mysqldb\
+      python3 py3-pip postgresql-client mysql-client py3-mysqlclient \
         curl mailcap xapian-core xapian-bindings-python3 libffi gettext \
     && python3 -m pip install -U pip setuptools wheel \
     && python3 -m pip install -U \