diff --git a/.travis.yml b/.travis.yml
index 560c2a270..a730c572b 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -4,36 +4,34 @@ services: docker
 env:
   - VERSION=3.7 VARIANT=stretch
   - VERSION=3.7 VARIANT=stretch/slim
+  - VERSION=3.7 VARIANT=alpine3.9
   - VERSION=3.7 VARIANT=alpine3.8
-  - VERSION=3.7 VARIANT=alpine3.7
   - VERSION=3.6 VARIANT=stretch
   - VERSION=3.6 VARIANT=stretch/slim
   - VERSION=3.6 VARIANT=jessie
   - VERSION=3.6 VARIANT=jessie/slim
+  - VERSION=3.6 VARIANT=alpine3.9
   - VERSION=3.6 VARIANT=alpine3.8
-  - VERSION=3.6 VARIANT=alpine3.7
-  - VERSION=3.6 VARIANT=alpine3.6
   - VERSION=3.5 VARIANT=stretch
   - VERSION=3.5 VARIANT=stretch/slim
   - VERSION=3.5 VARIANT=jessie
   - VERSION=3.5 VARIANT=jessie/slim
+  - VERSION=3.5 VARIANT=alpine3.9
   - VERSION=3.5 VARIANT=alpine3.8
-  - VERSION=3.5 VARIANT=alpine3.7
   - VERSION=3.4 VARIANT=stretch
   - VERSION=3.4 VARIANT=stretch/slim
   - VERSION=3.4 VARIANT=jessie
   - VERSION=3.4 VARIANT=jessie/slim
   - VERSION=3.4 VARIANT=wheezy
+  - VERSION=3.4 VARIANT=alpine3.9
   - VERSION=3.4 VARIANT=alpine3.8
-  - VERSION=3.4 VARIANT=alpine3.7
   - VERSION=2.7 VARIANT=stretch
   - VERSION=2.7 VARIANT=stretch/slim
   - VERSION=2.7 VARIANT=jessie
   - VERSION=2.7 VARIANT=jessie/slim
   - VERSION=2.7 VARIANT=wheezy
+  - VERSION=2.7 VARIANT=alpine3.9
   - VERSION=2.7 VARIANT=alpine3.8
-  - VERSION=2.7 VARIANT=alpine3.7
-  - VERSION=2.7 VARIANT=alpine3.6
 
 install:
   - git clone https://github.com/docker-library/official-images.git ~/official-images
diff --git a/2.7/alpine3.6/Dockerfile b/2.7/alpine3.6/Dockerfile
deleted file mode 100644
index 46f34f0fa..000000000
--- a/2.7/alpine3.6/Dockerfile
+++ /dev/null
@@ -1,123 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM alpine:3.6
-
-# ensure local python is preferred over distribution python
-ENV PATH /usr/local/bin:$PATH
-
-# http://bugs.python.org/issue19846
-# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
-ENV LANG C.UTF-8
-# https://github.com/docker-library/python/issues/147
-ENV PYTHONIOENCODING UTF-8
-
-# install ca-certificates so that HTTPS works consistently
-# other runtime dependencies for Python are installed later
-RUN apk add --no-cache ca-certificates
-
-ENV GPG_KEY C01E1CAD5EA2C4F0B8E3571504C367C218ADD4FF
-ENV PYTHON_VERSION 2.7.15
-
-RUN set -ex \
-	&& apk add --no-cache --virtual .fetch-deps \
-		gnupg \
-		libressl \
-		tar \
-		xz \
-	\
-	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
-	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
-	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
-	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
-	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
-	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
-	&& mkdir -p /usr/src/python \
-	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
-	&& rm python.tar.xz \
-	\
-	&& apk add --no-cache --virtual .build-deps  \
-		bzip2-dev \
-		coreutils \
-		dpkg-dev dpkg \
-		expat-dev \
-		findutils \
-		gcc \
-		gdbm-dev \
-		libc-dev \
-		libffi-dev \
-		libressl \
-		libressl-dev \
-		linux-headers \
-		make \
-		ncurses-dev \
-		pax-utils \
-		readline-dev \
-		sqlite-dev \
-		tcl-dev \
-		tk \
-		tk-dev \
-		zlib-dev \
-# add build deps before removing fetch deps in case there's overlap
-	&& apk del .fetch-deps \
-	\
-	&& cd /usr/src/python \
-	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
-	&& ./configure \
-		--build="$gnuArch" \
-		--enable-shared \
-		--enable-unicode=ucs4 \
-		--with-system-expat \
-		--with-system-ffi \
-	&& make -j "$(nproc)" \
-# set thread stack size to 1MB so we don't segfault before we hit sys.getrecursionlimit()
-# https://github.com/alpinelinux/aports/commit/2026e1259422d4e0cf92391ca2d3844356c649d0
-		EXTRA_CFLAGS="-DTHREAD_STACK_SIZE=0x100000" \
-	&& make install \
-	\
-	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec scanelf --needed --nobanner --format '%n#p' '{}' ';' \
-		| tr ',' '\n' \
-		| sort -u \
-		| awk 'system("[ -e /usr/local/lib/" $1 " ]") == 0 { next } { print "so:" $1 }' \
-		| xargs -rt apk add --no-cache --virtual .python-rundeps \
-	&& apk del .build-deps \
-	\
-	&& find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
-		\) -exec rm -rf '{}' + \
-	&& rm -rf /usr/src/python \
-	\
-	&& python2 --version
-
-# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 19.0.1
-
-RUN set -ex; \
-	\
-	apk add --no-cache --virtual .fetch-deps libressl; trap 'apk del .fetch-deps' EXIT; \
-	\
-	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
-	\
-	python get-pip.py \
-		--disable-pip-version-check \
-		--no-cache-dir \
-		"pip==$PYTHON_PIP_VERSION" \
-	; \
-	pip --version; \
-	\
-	find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
-		\) -exec rm -rf '{}' +; \
-	rm -f get-pip.py
-
-CMD ["python2"]
diff --git a/2.7/alpine3.8/Dockerfile b/2.7/alpine3.8/Dockerfile
index 6ac97f254..4a8b2239c 100644
--- a/2.7/alpine3.8/Dockerfile
+++ b/2.7/alpine3.8/Dockerfile
@@ -50,11 +50,11 @@ RUN set -ex \
 		libc-dev \
 		libffi-dev \
 		libnsl-dev \
-		libressl-dev \
 		libtirpc-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/2.7/alpine3.7/Dockerfile b/2.7/alpine3.9/Dockerfile
similarity index 99%
rename from 2.7/alpine3.7/Dockerfile
rename to 2.7/alpine3.9/Dockerfile
index 0a5b17b5f..fa76b9573 100644
--- a/2.7/alpine3.7/Dockerfile
+++ b/2.7/alpine3.9/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.7
+FROM alpine:3.9
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -50,11 +50,11 @@ RUN set -ex \
 		libc-dev \
 		libffi-dev \
 		libnsl-dev \
-		libressl-dev \
 		libtirpc-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/3.4/alpine3.8/Dockerfile b/3.4/alpine3.8/Dockerfile
index ce260a54d..cb1e184b8 100644
--- a/3.4/alpine3.8/Dockerfile
+++ b/3.4/alpine3.8/Dockerfile
@@ -47,10 +47,10 @@ RUN set -ex \
 		gdbm-dev \
 		libc-dev \
 		libffi-dev \
-		libressl-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/3.4/alpine3.7/Dockerfile b/3.4/alpine3.9/Dockerfile
similarity index 99%
rename from 3.4/alpine3.7/Dockerfile
rename to 3.4/alpine3.9/Dockerfile
index e8ca6853f..710b2bb84 100644
--- a/3.4/alpine3.7/Dockerfile
+++ b/3.4/alpine3.9/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.7
+FROM alpine:3.9
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -47,10 +47,10 @@ RUN set -ex \
 		gdbm-dev \
 		libc-dev \
 		libffi-dev \
-		libressl-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/3.5/alpine3.8/Dockerfile b/3.5/alpine3.8/Dockerfile
index 2ab76a31e..b3fe35970 100644
--- a/3.5/alpine3.8/Dockerfile
+++ b/3.5/alpine3.8/Dockerfile
@@ -47,10 +47,10 @@ RUN set -ex \
 		gdbm-dev \
 		libc-dev \
 		libffi-dev \
-		openssl-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/3.5/alpine3.7/Dockerfile b/3.5/alpine3.9/Dockerfile
similarity index 99%
rename from 3.5/alpine3.7/Dockerfile
rename to 3.5/alpine3.9/Dockerfile
index 99f6a0976..f8d9f56a6 100644
--- a/3.5/alpine3.7/Dockerfile
+++ b/3.5/alpine3.9/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.7
+FROM alpine:3.9
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -47,10 +47,10 @@ RUN set -ex \
 		gdbm-dev \
 		libc-dev \
 		libffi-dev \
-		libressl-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/3.6/alpine3.6/Dockerfile b/3.6/alpine3.6/Dockerfile
deleted file mode 100644
index 14a6a3900..000000000
--- a/3.6/alpine3.6/Dockerfile
+++ /dev/null
@@ -1,130 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM alpine:3.6
-
-# ensure local python is preferred over distribution python
-ENV PATH /usr/local/bin:$PATH
-
-# http://bugs.python.org/issue19846
-# > At the moment, setting "LANG=C" on a Linux system *fundamentally breaks Python 3*, and that's not OK.
-ENV LANG C.UTF-8
-
-# install ca-certificates so that HTTPS works consistently
-# other runtime dependencies for Python are installed later
-RUN apk add --no-cache ca-certificates
-
-ENV GPG_KEY 0D96DF4D4110E5C43FBFB17F2D347EA6AA65421D
-ENV PYTHON_VERSION 3.6.8
-
-RUN set -ex \
-	&& apk add --no-cache --virtual .fetch-deps \
-		gnupg \
-		libressl \
-		tar \
-		xz \
-	\
-	&& wget -O python.tar.xz "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz" \
-	&& wget -O python.tar.xz.asc "https://www.python.org/ftp/python/${PYTHON_VERSION%%[a-z]*}/Python-$PYTHON_VERSION.tar.xz.asc" \
-	&& export GNUPGHOME="$(mktemp -d)" \
-	&& gpg --batch --keyserver ha.pool.sks-keyservers.net --recv-keys "$GPG_KEY" \
-	&& gpg --batch --verify python.tar.xz.asc python.tar.xz \
-	&& { command -v gpgconf > /dev/null && gpgconf --kill all || :; } \
-	&& rm -rf "$GNUPGHOME" python.tar.xz.asc \
-	&& mkdir -p /usr/src/python \
-	&& tar -xJC /usr/src/python --strip-components=1 -f python.tar.xz \
-	&& rm python.tar.xz \
-	\
-	&& apk add --no-cache --virtual .build-deps  \
-		bzip2-dev \
-		coreutils \
-		dpkg-dev dpkg \
-		expat-dev \
-		findutils \
-		gcc \
-		gdbm-dev \
-		libc-dev \
-		libffi-dev \
-		libressl \
-		libressl-dev \
-		linux-headers \
-		make \
-		ncurses-dev \
-		pax-utils \
-		readline-dev \
-		sqlite-dev \
-		tcl-dev \
-		tk \
-		tk-dev \
-		xz-dev \
-		zlib-dev \
-# add build deps before removing fetch deps in case there's overlap
-	&& apk del .fetch-deps \
-	\
-	&& cd /usr/src/python \
-	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
-	&& ./configure \
-		--build="$gnuArch" \
-		--enable-loadable-sqlite-extensions \
-		--enable-shared \
-		--with-system-expat \
-		--with-system-ffi \
-		--without-ensurepip \
-	&& make -j "$(nproc)" \
-# set thread stack size to 1MB so we don't segfault before we hit sys.getrecursionlimit()
-# https://github.com/alpinelinux/aports/commit/2026e1259422d4e0cf92391ca2d3844356c649d0
-		EXTRA_CFLAGS="-DTHREAD_STACK_SIZE=0x100000" \
-	&& make install \
-	\
-	&& find /usr/local -type f -executable -not \( -name '*tkinter*' \) -exec scanelf --needed --nobanner --format '%n#p' '{}' ';' \
-		| tr ',' '\n' \
-		| sort -u \
-		| awk 'system("[ -e /usr/local/lib/" $1 " ]") == 0 { next } { print "so:" $1 }' \
-		| xargs -rt apk add --no-cache --virtual .python-rundeps \
-	&& apk del .build-deps \
-	\
-	&& find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
-		\) -exec rm -rf '{}' + \
-	&& rm -rf /usr/src/python \
-	\
-	&& python3 --version
-
-# make some useful symlinks that are expected to exist
-RUN cd /usr/local/bin \
-	&& ln -s idle3 idle \
-	&& ln -s pydoc3 pydoc \
-	&& ln -s python3 python \
-	&& ln -s python3-config python-config
-
-# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 19.0.1
-
-RUN set -ex; \
-	\
-	apk add --no-cache --virtual .fetch-deps libressl; trap 'apk del .fetch-deps' EXIT; \
-	\
-	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
-	\
-	python get-pip.py \
-		--disable-pip-version-check \
-		--no-cache-dir \
-		"pip==$PYTHON_PIP_VERSION" \
-	; \
-	pip --version; \
-	\
-	find /usr/local -depth \
-		\( \
-			\( -type d -a \( -name test -o -name tests \) \) \
-			-o \
-			\( -type f -a \( -name '*.pyc' -o -name '*.pyo' \) \) \
-		\) -exec rm -rf '{}' +; \
-	rm -f get-pip.py
-
-CMD ["python3"]
diff --git a/3.6/alpine3.8/Dockerfile b/3.6/alpine3.8/Dockerfile
index 4d9bdb5bf..48cd91d86 100644
--- a/3.6/alpine3.8/Dockerfile
+++ b/3.6/alpine3.8/Dockerfile
@@ -48,11 +48,11 @@ RUN set -ex \
 		libc-dev \
 		libffi-dev \
 		libnsl-dev \
-		libressl-dev \
 		libtirpc-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/3.6/alpine3.7/Dockerfile b/3.6/alpine3.9/Dockerfile
similarity index 99%
rename from 3.6/alpine3.7/Dockerfile
rename to 3.6/alpine3.9/Dockerfile
index 03eadf000..7a16e75a4 100644
--- a/3.6/alpine3.7/Dockerfile
+++ b/3.6/alpine3.9/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.7
+FROM alpine:3.9
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -48,11 +48,11 @@ RUN set -ex \
 		libc-dev \
 		libffi-dev \
 		libnsl-dev \
-		libressl-dev \
 		libtirpc-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/3.7/alpine3.8/Dockerfile b/3.7/alpine3.8/Dockerfile
index a631c7405..a9c7c7202 100644
--- a/3.7/alpine3.8/Dockerfile
+++ b/3.7/alpine3.8/Dockerfile
@@ -48,11 +48,11 @@ RUN set -ex \
 		libc-dev \
 		libffi-dev \
 		libnsl-dev \
-		libressl-dev \
 		libtirpc-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/3.7/alpine3.7/Dockerfile b/3.7/alpine3.9/Dockerfile
similarity index 99%
rename from 3.7/alpine3.7/Dockerfile
rename to 3.7/alpine3.9/Dockerfile
index 46b982a87..de3f400a9 100644
--- a/3.7/alpine3.7/Dockerfile
+++ b/3.7/alpine3.9/Dockerfile
@@ -4,7 +4,7 @@
 # PLEASE DO NOT EDIT IT DIRECTLY.
 #
 
-FROM alpine:3.7
+FROM alpine:3.9
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -48,11 +48,11 @@ RUN set -ex \
 		libc-dev \
 		libffi-dev \
 		libnsl-dev \
-		openssl-dev \
 		libtirpc-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
diff --git a/Dockerfile-alpine.template b/Dockerfile-alpine.template
index 9f2a84eb6..35d25ab06 100644
--- a/Dockerfile-alpine.template
+++ b/Dockerfile-alpine.template
@@ -17,7 +17,6 @@ ENV PYTHON_VERSION %%PLACEHOLDER%%
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
 		gnupg \
-		libressl \
 		tar \
 		xz \
 	\
@@ -43,12 +42,11 @@ RUN set -ex \
 		libc-dev \
 		libffi-dev \
 		libnsl-dev \
-		libressl \
-		libressl-dev \
 		libtirpc-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
@@ -104,8 +102,6 @@ RUN cd /usr/local/bin \
 ENV PYTHON_PIP_VERSION %%PLACEHOLDER%%
 
 RUN set -ex; \
-	\
-	apk add --no-cache --virtual .fetch-deps libressl; trap 'apk del .fetch-deps' EXIT; \
 	\
 	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
 	\
diff --git a/Dockerfile-caveman-alpine.template b/Dockerfile-caveman-alpine.template
index 475255d87..8af172f5e 100644
--- a/Dockerfile-caveman-alpine.template
+++ b/Dockerfile-caveman-alpine.template
@@ -19,7 +19,6 @@ ENV PYTHON_VERSION %%PLACEHOLDER%%
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
 		gnupg \
-		libressl \
 		tar \
 		xz \
 	\
@@ -45,12 +44,11 @@ RUN set -ex \
 		libc-dev \
 		libffi-dev \
 		libnsl-dev \
-		libressl \
-		libressl-dev \
 		libtirpc-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
@@ -96,8 +94,6 @@ RUN set -ex \
 ENV PYTHON_PIP_VERSION %%PLACEHOLDER%%
 
 RUN set -ex; \
-	\
-	apk add --no-cache --virtual .fetch-deps libressl; trap 'apk del .fetch-deps' EXIT; \
 	\
 	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
 	\
diff --git a/generate-stackbrew-library.sh b/generate-stackbrew-library.sh
index dda286792..0b2a9164b 100755
--- a/generate-stackbrew-library.sh
+++ b/generate-stackbrew-library.sh
@@ -8,7 +8,7 @@ declare -A aliases=(
 )
 
 defaultDebianSuite='stretch'
-defaultAlpineVersion='3.8'
+defaultAlpineVersion='3.9'
 
 self="$(basename "$BASH_SOURCE")"
 cd "$(dirname "$(readlink -f "$BASH_SOURCE")")"
@@ -77,7 +77,7 @@ for version in "${versions[@]}"; do
 
 	for v in \
 		{stretch,jessie,wheezy}{,/slim} \
-		alpine{3.8,3.7,3.6} \
+		alpine{3.9,3.8} \
 		windows/windowsservercore-{ltsc2016,1709} \
 		windows/nanoserver-{sac2016,1709} \
 	; do
diff --git a/update.sh b/update.sh
index ec9dfffba..dc26529a7 100755
--- a/update.sh
+++ b/update.sh
@@ -112,7 +112,7 @@ for version in "${versions[@]}"; do
 	echo "$version: $fullVersion"
 
 	for v in \
-		alpine{3.6,3.7,3.8} \
+		alpine{3.8,3.9} \
 		{wheezy,jessie,stretch}{/slim,} \
 		windows/nanoserver-{1709,sac2016} \
 		windows/windowsservercore-{1709,ltsc2016} \
@@ -152,32 +152,30 @@ for version in "${versions[@]}"; do
 			wheezy) sed -ri -e 's/dpkg-architecture --query /dpkg-architecture -q/g' "$dir/Dockerfile" ;;
 		esac
 
-		if [[ "$v" == alpine* ]] && [ "$v" != 'alpine3.6' ]; then
-			# https://github.com/docker-library/python/pull/307
-			# on Alpine 3.6 it's necessary to install libressl to get working HTTPS with wget (and ca-certificates for Python's runtime), but later versions don't require this (support for both is baked into the base)
-			# https://github.com/docker-library/python/issues/324
-			# while Alpine 3.7+ includes CA certs in the base (/etc/ssl/cert.pem) and this is sufficient for working HTTPS in wget and Python, some software (notably, any Golang code) expects CA certs at /etc/ssl/certs/
-			# this means it is still necessary to install ca-certificates in all Alpine images for consistently working HTTPS
-			sed -ri -e '/(libressl|openssl)([ ;]|$)/d' "$dir/Dockerfile"
-
-			# remove any double-empty (or double-empty-continuation) lines the above created
-			uniq "$dir/Dockerfile" > "$dir/Dockerfile.new"
-			mv "$dir/Dockerfile.new" "$dir/Dockerfile"
+		# Alpine < 3.9 used libressl instead of openssl
+		if [ "$v" = 'alpine3.8' ]; then
+			sed -ri -e 's/openssl/libressl/g' "$dir/Dockerfile"
 		fi
 
 		case "$version/$v" in
 			# https://bugs.python.org/issue32598 (Python 3.7.0b1+)
 			# TL;DR: Python 3.7+ uses OpenSSL functionality which LibreSSL 2.6.x in Alpine 3.7 doesn't implement
 			# Python 3.5 on Alpine 3.8 needs OpenSSL too
-			3.7*/alpine3.7 | 3.5*/alpine3.8)
+			3.5*/alpine3.8)
 				sed -ri -e 's/libressl-dev/openssl-dev/g' "$dir/Dockerfile"
 				;;& # (3.5*/alpine* needs to match the next block too)
 
 			# Libraries to build the nis module only available in Alpine 3.7+.
 			# Also require this patch https://bugs.python.org/issue32521 only available in Python 2.7, 3.6+.
-			3.[4-5]*/alpine* | */alpine3.6)
+			3.[4-5]*/alpine*)
 				sed -ri -e '/libnsl-dev/d' -e '/libtirpc-dev/d' "$dir/Dockerfile"
-				;;& # (3.4*/alpine* and 3.5*/alpine* need to match the next block too)
+				;;& # (3.4*/alpine* and 3.5*/alpine* need to match the next blocks too)
+
+			# Alpine 3.9's OpenSSL 1.1.1 is too new for Python 3.4
+			# no OpenSSL 1.0.x package available, so have to switch back to LibreSSL
+			3.4/alpine3.9)
+				sed -ri -e 's/openssl-dev/libressl-dev/g' "$dir/Dockerfile"
+				;;& # (need to match next block too)
 
 			# https://bugs.python.org/issue11063, https://bugs.python.org/issue20519 (Python 3.7.0+)
 			# A new native _uuid module improves uuid import time and avoids using ctypes.