diff --git a/.travis.yml b/.travis.yml
index 5c94bc40cf..50a719b4cb 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -4,6 +4,7 @@ services: docker
 env:
   - VERSION=2.6-rc VARIANT=stretch
   - VERSION=2.6-rc VARIANT=stretch/slim
+  - VERSION=2.6-rc VARIANT=alpine3.8
   - VERSION=2.6-rc VARIANT=alpine3.7
   - VERSION=2.5 VARIANT=stretch
   - VERSION=2.5 VARIANT=stretch/slim
@@ -18,6 +19,7 @@ env:
   - VERSION=2.3 VARIANT=stretch/slim
   - VERSION=2.3 VARIANT=jessie
   - VERSION=2.3 VARIANT=jessie/slim
+  - VERSION=2.3 VARIANT=alpine3.8
   - VERSION=2.3 VARIANT=alpine3.7
 
 install:
diff --git a/2.3/alpine3.8/Dockerfile b/2.3/alpine3.8/Dockerfile
new file mode 100644
index 0000000000..187b7914e8
--- /dev/null
+++ b/2.3/alpine3.8/Dockerfile
@@ -0,0 +1,111 @@
+FROM alpine:3.8
+
+# skip installing gem documentation
+RUN mkdir -p /usr/local/etc \
+	&& { \
+		echo 'install: --no-document'; \
+		echo 'update: --no-document'; \
+	} >> /usr/local/etc/gemrc
+
+ENV RUBY_MAJOR 2.3
+ENV RUBY_VERSION 2.3.7
+ENV RUBY_DOWNLOAD_SHA256 c61f8f2b9d3ffff5567e186421fa191f0d5e7c2b189b426bb84498825d548edb
+ENV RUBYGEMS_VERSION 2.7.7
+ENV BUNDLER_VERSION 1.16.4
+
+# some of ruby's build scripts are written in ruby
+#   we purge system ruby later to make sure our final image uses what we just built
+# readline-dev vs libedit-dev: https://bugs.ruby-lang.org/issues/11869 and https://github.com/docker-library/ruby/issues/75
+RUN set -ex \
+	\
+	&& apk add --no-cache --virtual .ruby-builddeps \
+		autoconf \
+		bison \
+		bzip2 \
+		bzip2-dev \
+		ca-certificates \
+		coreutils \
+		dpkg-dev dpkg \
+		gcc \
+		gdbm-dev \
+		glib-dev \
+		libc-dev \
+		libffi-dev \
+		libressl \
+		libressl-dev \
+		libxml2-dev \
+		libxslt-dev \
+		linux-headers \
+		make \
+		ncurses-dev \
+		procps \
+		readline-dev \
+		ruby \
+		tar \
+		xz \
+		yaml-dev \
+		zlib-dev \
+	\
+	&& wget -O ruby.tar.xz "https://cache.ruby-lang.org/pub/ruby/${RUBY_MAJOR%-rc}/ruby-$RUBY_VERSION.tar.xz" \
+	&& echo "$RUBY_DOWNLOAD_SHA256 *ruby.tar.xz" | sha256sum -c - \
+	\
+	&& mkdir -p /usr/src/ruby \
+	&& tar -xJf ruby.tar.xz -C /usr/src/ruby --strip-components=1 \
+	&& rm ruby.tar.xz \
+	\
+	&& cd /usr/src/ruby \
+	\
+# hack in "ENABLE_PATH_CHECK" disabling to suppress:
+#   warning: Insecure world writable dir
+	&& { \
+		echo '#define ENABLE_PATH_CHECK 0'; \
+		echo; \
+		cat file.c; \
+	} > file.c.new \
+	&& mv file.c.new file.c \
+	\
+	&& autoconf \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+# the configure script does not detect isnan/isinf as macros
+	&& export ac_cv_func_isnan=yes ac_cv_func_isinf=yes \
+	&& ./configure \
+		--build="$gnuArch" \
+		--disable-install-doc \
+		--enable-shared \
+	&& make -j "$(nproc)" \
+	&& make install \
+	\
+	&& runDeps="$( \
+		scanelf --needed --nobanner --format '%n#p' --recursive /usr/local \
+			| tr ',' '\n' \
+			| sort -u \
+			| awk 'system("[ -e /usr/local/lib/" $1 " ]") == 0 { next } { print "so:" $1 }' \
+	)" \
+	&& apk add --virtual .ruby-rundeps $runDeps \
+		bzip2 \
+		ca-certificates \
+		libffi-dev \
+		procps \
+		yaml-dev \
+		zlib-dev \
+	&& apk del .ruby-builddeps \
+	&& cd / \
+	&& rm -r /usr/src/ruby \
+	\
+	&& gem update --system "$RUBYGEMS_VERSION" \
+	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& rm -r /root/.gem/
+
+# install things globally, for great justice
+# and don't create ".bundle" in all our apps
+ENV GEM_HOME /usr/local/bundle
+ENV BUNDLE_PATH="$GEM_HOME" \
+	BUNDLE_SILENCE_ROOT_WARNING=1 \
+	BUNDLE_APP_CONFIG="$GEM_HOME"
+# path recommendation: https://github.com/bundler/bundler/pull/6469#issuecomment-383235438
+ENV PATH $GEM_HOME/bin:$BUNDLE_PATH/gems/bin:$PATH
+# adjust permissions of a few directories for running "gem install" as an arbitrary user
+RUN mkdir -p "$GEM_HOME" && chmod 777 "$GEM_HOME"
+# (BUNDLE_PATH = GEM_HOME, no need to mkdir/chown both)
+
+CMD [ "irb" ]
diff --git a/2.6-rc/alpine3.8/Dockerfile b/2.6-rc/alpine3.8/Dockerfile
new file mode 100644
index 0000000000..de382a1464
--- /dev/null
+++ b/2.6-rc/alpine3.8/Dockerfile
@@ -0,0 +1,111 @@
+FROM alpine:3.8
+
+# skip installing gem documentation
+RUN mkdir -p /usr/local/etc \
+	&& { \
+		echo 'install: --no-document'; \
+		echo 'update: --no-document'; \
+	} >> /usr/local/etc/gemrc
+
+ENV RUBY_MAJOR 2.6-rc
+ENV RUBY_VERSION 2.6.0-preview2
+ENV RUBY_DOWNLOAD_SHA256 00ddfb5e33dee24469dd0b203597f7ecee66522ebb496f620f5815372ea2d3ec
+ENV RUBYGEMS_VERSION 2.7.7
+ENV BUNDLER_VERSION 1.16.4
+
+# some of ruby's build scripts are written in ruby
+#   we purge system ruby later to make sure our final image uses what we just built
+# readline-dev vs libedit-dev: https://bugs.ruby-lang.org/issues/11869 and https://github.com/docker-library/ruby/issues/75
+RUN set -ex \
+	\
+	&& apk add --no-cache --virtual .ruby-builddeps \
+		autoconf \
+		bison \
+		bzip2 \
+		bzip2-dev \
+		ca-certificates \
+		coreutils \
+		dpkg-dev dpkg \
+		gcc \
+		gdbm-dev \
+		glib-dev \
+		libc-dev \
+		libffi-dev \
+		libressl \
+		libressl-dev \
+		libxml2-dev \
+		libxslt-dev \
+		linux-headers \
+		make \
+		ncurses-dev \
+		procps \
+		readline-dev \
+		ruby \
+		tar \
+		xz \
+		yaml-dev \
+		zlib-dev \
+	\
+	&& wget -O ruby.tar.xz "https://cache.ruby-lang.org/pub/ruby/${RUBY_MAJOR%-rc}/ruby-$RUBY_VERSION.tar.xz" \
+	&& echo "$RUBY_DOWNLOAD_SHA256 *ruby.tar.xz" | sha256sum -c - \
+	\
+	&& mkdir -p /usr/src/ruby \
+	&& tar -xJf ruby.tar.xz -C /usr/src/ruby --strip-components=1 \
+	&& rm ruby.tar.xz \
+	\
+	&& cd /usr/src/ruby \
+	\
+# hack in "ENABLE_PATH_CHECK" disabling to suppress:
+#   warning: Insecure world writable dir
+	&& { \
+		echo '#define ENABLE_PATH_CHECK 0'; \
+		echo; \
+		cat file.c; \
+	} > file.c.new \
+	&& mv file.c.new file.c \
+	\
+	&& autoconf \
+	&& gnuArch="$(dpkg-architecture --query DEB_BUILD_GNU_TYPE)" \
+# the configure script does not detect isnan/isinf as macros
+	&& export ac_cv_func_isnan=yes ac_cv_func_isinf=yes \
+	&& ./configure \
+		--build="$gnuArch" \
+		--disable-install-doc \
+		--enable-shared \
+	&& make -j "$(nproc)" \
+	&& make install \
+	\
+	&& runDeps="$( \
+		scanelf --needed --nobanner --format '%n#p' --recursive /usr/local \
+			| tr ',' '\n' \
+			| sort -u \
+			| awk 'system("[ -e /usr/local/lib/" $1 " ]") == 0 { next } { print "so:" $1 }' \
+	)" \
+	&& apk add --virtual .ruby-rundeps $runDeps \
+		bzip2 \
+		ca-certificates \
+		libffi-dev \
+		procps \
+		yaml-dev \
+		zlib-dev \
+	&& apk del .ruby-builddeps \
+	&& cd / \
+	&& rm -r /usr/src/ruby \
+	\
+	&& gem update --system "$RUBYGEMS_VERSION" \
+	&& gem install bundler --version "$BUNDLER_VERSION" --force \
+	&& rm -r /root/.gem/
+
+# install things globally, for great justice
+# and don't create ".bundle" in all our apps
+ENV GEM_HOME /usr/local/bundle
+ENV BUNDLE_PATH="$GEM_HOME" \
+	BUNDLE_SILENCE_ROOT_WARNING=1 \
+	BUNDLE_APP_CONFIG="$GEM_HOME"
+# path recommendation: https://github.com/bundler/bundler/pull/6469#issuecomment-383235438
+ENV PATH $GEM_HOME/bin:$BUNDLE_PATH/gems/bin:$PATH
+# adjust permissions of a few directories for running "gem install" as an arbitrary user
+RUN mkdir -p "$GEM_HOME" && chmod 777 "$GEM_HOME"
+# (BUNDLE_PATH = GEM_HOME, no need to mkdir/chown both)
+
+CMD [ "irb" ]
diff --git a/generate-stackbrew-library.sh b/generate-stackbrew-library.sh
index a57829f011..ab08a6f37f 100755
--- a/generate-stackbrew-library.sh
+++ b/generate-stackbrew-library.sh
@@ -7,7 +7,13 @@ declare -A aliases=(
 )
 
 defaultDebianSuite='stretch'
-defaultAlpineVersion='3.7'
+defaultAlpineVersion='3.8'
+declare -A alpineVersion=(
+	# "openssl_missing.h:196:22: error: static declaration of 'EVP_PKEY_get0_RSA' follows non-static declaration" (and friends)
+	# https://github.com/docker-library/ruby/issues/228 / https://bugs.ruby-lang.org/issues/14754
+	[2.4]='3.7' # TODO remove this (and add Alpine 3.8) once 2.4.5+ is released
+	[2.5]='3.7' # TODO remove this (and add Alpine 3.8) once 2.5.2+ is released
+)
 
 self="$(basename "$BASH_SOURCE")"
 cd "$(dirname "$(readlink -f "$BASH_SOURCE")")"
@@ -74,7 +80,7 @@ join() {
 for version in "${versions[@]}"; do
 	for v in \
 		{stretch,jessie}{,/slim} \
-		alpine{3.7,3.6} \
+		alpine{3.8,3.7,3.6} \
 	; do
 		dir="$version/$v"
 		variant="$(basename "$v")"
@@ -105,7 +111,7 @@ for version in "${versions[@]}"; do
 			*-"$defaultDebianSuite")
 				variantAliases+=( "${versionAliases[@]/%/-${variant%-$defaultDebianSuite}}" )
 				;;
-			"alpine${defaultAlpineVersion}")
+			"alpine${alpineVersion[$version]:-$defaultAlpineVersion}")
 				variantAliases+=( "${versionAliases[@]/%/-alpine}" )
 				;;
 		esac
diff --git a/update.sh b/update.sh
index a55320b566..0c1222932e 100755
--- a/update.sh
+++ b/update.sh
@@ -66,7 +66,7 @@ for version in "${versions[@]}"; do
 	echo "$version: $fullVersion; rubygems $rubygems, bundler $bundler; $shaVal"
 
 	for v in \
-		alpine{3.6,3.7} \
+		alpine{3.6,3.7,3.8} \
 		{jessie,stretch}{/slim,} \
 	; do
 		dir="$version/$v"