diff --git a/.travis.yml b/.travis.yml
index ce2782d84..2b5ebb15e 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -4,21 +4,22 @@ services: docker
 env:
   - VERSION=2.7-rc VARIANT=stretch
   - VERSION=2.7-rc VARIANT=stretch/slim
+  - VERSION=2.7-rc VARIANT=alpine3.10
   - VERSION=2.7-rc VARIANT=alpine3.9
   - VERSION=2.6 VARIANT=stretch
   - VERSION=2.6 VARIANT=stretch/slim
+  - VERSION=2.6 VARIANT=alpine3.10
   - VERSION=2.6 VARIANT=alpine3.9
-  - VERSION=2.6 VARIANT=alpine3.8
   - VERSION=2.5 VARIANT=stretch
   - VERSION=2.5 VARIANT=stretch/slim
+  - VERSION=2.5 VARIANT=alpine3.10
   - VERSION=2.5 VARIANT=alpine3.9
-  - VERSION=2.5 VARIANT=alpine3.8
   - VERSION=2.4 VARIANT=stretch
   - VERSION=2.4 VARIANT=stretch/slim
   - VERSION=2.4 VARIANT=jessie
   - VERSION=2.4 VARIANT=jessie/slim
+  - VERSION=2.4 VARIANT=alpine3.10
   - VERSION=2.4 VARIANT=alpine3.9
-  - VERSION=2.4 VARIANT=alpine3.8
 
 install:
   - git clone --depth 1 https://github.com/docker-library/official-images.git ~/official-images
diff --git a/2.4/alpine3.8/Dockerfile b/2.4/alpine3.10/Dockerfile
similarity index 98%
rename from 2.4/alpine3.8/Dockerfile
rename to 2.4/alpine3.10/Dockerfile
index 5eb236529..b182eb5d6 100644
--- a/2.4/alpine3.8/Dockerfile
+++ b/2.4/alpine3.10/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.10
 
 RUN apk add --no-cache \
 		gmp-dev
@@ -38,8 +38,8 @@ RUN set -ex \
 		linux-headers \
 		make \
 		ncurses-dev \
-		libressl \
-		libressl-dev \
+		openssl \
+		openssl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.5/alpine3.8/Dockerfile b/2.5/alpine3.10/Dockerfile
similarity index 98%
rename from 2.5/alpine3.8/Dockerfile
rename to 2.5/alpine3.10/Dockerfile
index 5b36deb8d..efa5ddbaa 100644
--- a/2.5/alpine3.8/Dockerfile
+++ b/2.5/alpine3.10/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.10
 
 RUN apk add --no-cache \
 		gmp-dev
@@ -38,8 +38,8 @@ RUN set -ex \
 		linux-headers \
 		make \
 		ncurses-dev \
-		libressl \
-		libressl-dev \
+		openssl \
+		openssl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.6/alpine3.8/Dockerfile b/2.6/alpine3.10/Dockerfile
similarity index 98%
rename from 2.6/alpine3.8/Dockerfile
rename to 2.6/alpine3.10/Dockerfile
index 0fe771b34..2611f102e 100644
--- a/2.6/alpine3.8/Dockerfile
+++ b/2.6/alpine3.10/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.8
+FROM alpine:3.10
 
 RUN apk add --no-cache \
 		gmp-dev
@@ -37,8 +37,8 @@ RUN set -ex \
 		linux-headers \
 		make \
 		ncurses-dev \
-		libressl \
-		libressl-dev \
+		openssl \
+		openssl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.7-rc/alpine3.10/Dockerfile b/2.7-rc/alpine3.10/Dockerfile
new file mode 100644
index 000000000..032dcebf6
--- /dev/null
+++ b/2.7-rc/alpine3.10/Dockerfile
@@ -0,0 +1,118 @@
+FROM alpine:3.10
+
+RUN apk add --no-cache \
+		gmp-dev
+
+# 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 2.7-rc
+ENV RUBY_VERSION 2.7.0-preview1
+ENV RUBY_DOWNLOAD_SHA256 8c546df3345398b3edc9d0ab097846f033783d33762889fd0f3dc8bb465c3354
+
+# 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 \
+		libxml2-dev \
+		libxslt-dev \
+		linux-headers \
+		make \
+		ncurses-dev \
+		openssl \
+		openssl-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 "$RUBY_DOWNLOAD_SHA256 *ruby.tar.xz" | sha256sum -c - \
+	\
+	&& mkdir -p /usr/src/ruby \
+	&& tar -xJf ruby.tar.xz -C /usr/src/ruby --strip-components=1 \
+	&& rm ruby.tar.xz \
+	\
+	&& cd /usr/src/ruby \
+	\
+# https://github.com/docker-library/ruby/issues/196
+# https://bugs.ruby-lang.org/issues/14387#note-13 (patch source)
+# https://bugs.ruby-lang.org/issues/14387#note-16 ("Therefore ncopa's patch looks good for me in general." -- only breaks glibc which doesn't matter here)
+	&& wget -O 'thread-stack-fix.patch' 'https://bugs.ruby-lang.org/attachments/download/7081/0001-thread_pthread.c-make-get_main_stack-portable-on-lin.patch' \
+	&& echo '3ab628a51d92fdf0d2b5835e93564857aea73e0c1de00313864a94a6255cb645 *thread-stack-fix.patch' | sha256sum -c - \
+	&& patch -p1 -i thread-stack-fix.patch \
+	&& rm thread-stack-fix.patch \
+	\
+# hack in "ENABLE_PATH_CHECK" disabling to suppress:
+#   warning: Insecure world writable dir
+	&& { \
+		echo '#define ENABLE_PATH_CHECK 0'; \
+		echo; \
+		cat file.c; \
+	} > file.c.new \
+	&& mv file.c.new file.c \
+	\
+	&& autoconf \
+	&& gnuArch="$(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 --no-network --virtual .ruby-rundeps $runDeps \
+		bzip2 \
+		ca-certificates \
+		libffi-dev \
+		procps \
+		yaml-dev \
+		zlib-dev \
+	&& apk del --no-network .ruby-builddeps \
+	&& cd / \
+	&& rm -r /usr/src/ruby \
+# rough smoke test
+	&& ruby --version && gem --version && bundle --version
+
+# install things globally, for great justice
+# and don't create ".bundle" in all our apps
+ENV GEM_HOME /usr/local/bundle
+ENV BUNDLE_PATH="$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 "$GEM_HOME"
+# (BUNDLE_PATH = GEM_HOME, no need to mkdir/chown both)
+
+CMD [ "irb" ]
diff --git a/update.sh b/update.sh
index 940360589..4298b5ad3 100755
--- a/update.sh
+++ b/update.sh
@@ -71,7 +71,7 @@ for version in "${versions[@]}"; do
 	echo "$version: $fullVersion; $shaVal"
 
 	for v in \
-		alpine{3.7,3.8,3.9} \
+		alpine{3.9,3.10} \
 		{jessie,stretch}{/slim,} \
 	; do
 		dir="$version/$v"
@@ -98,13 +98,6 @@ for version in "${versions[@]}"; do
 			-e 's/^(FROM (debian|buildpack-deps|alpine)):.*/\1:'"$tag"'/' \
 			"$template" > "$dir/Dockerfile"
 
-		case "$variant" in
-			alpine3.8 | alpine3.7)
-				# Alpine 3.9+ uses OpenSSL, but 3.8/3.7 still uses LibreSSL
-				sed -ri -e 's/openssl/libressl/g' "$dir/Dockerfile"
-				;;
-		esac
-
 		if [ -n "${newEnoughRubygems[$rcVersion]:-}" ]; then
 			sed -ri -e '/RUBYGEMS_VERSION/d' "$dir/Dockerfile"
 		fi