diff --git a/.travis.yml b/.travis.yml
index d927f535f..cb1efe569 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -4,18 +4,18 @@ services: docker
 env:
   - VERSION=2.6 VARIANT=stretch
   - VERSION=2.6 VARIANT=stretch/slim
+  - VERSION=2.6 VARIANT=alpine3.9
   - VERSION=2.6 VARIANT=alpine3.8
-  - VERSION=2.6 VARIANT=alpine3.7
   - VERSION=2.5 VARIANT=stretch
   - VERSION=2.5 VARIANT=stretch/slim
+  - VERSION=2.5 VARIANT=alpine3.9
   - VERSION=2.5 VARIANT=alpine3.8
-  - VERSION=2.5 VARIANT=alpine3.7
   - 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=alpine3.9
   - VERSION=2.4 VARIANT=alpine3.8
-  - VERSION=2.4 VARIANT=alpine3.7
   - VERSION=2.3 VARIANT=stretch
   - VERSION=2.3 VARIANT=stretch/slim
   - VERSION=2.3 VARIANT=jessie
diff --git a/2.3/alpine3.7/Dockerfile b/2.3/alpine3.7/Dockerfile
index 04fd51e76..f4ea5e884 100644
--- a/2.3/alpine3.7/Dockerfile
+++ b/2.3/alpine3.7/Dockerfile
@@ -30,13 +30,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl \
+		libressl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.3/alpine3.8/Dockerfile b/2.3/alpine3.8/Dockerfile
index 202caa1ff..ebf1b7ca0 100644
--- a/2.3/alpine3.8/Dockerfile
+++ b/2.3/alpine3.8/Dockerfile
@@ -30,13 +30,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl \
+		libressl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.4/alpine3.8/Dockerfile b/2.4/alpine3.8/Dockerfile
index b45e328aa..fdba4725d 100644
--- a/2.4/alpine3.8/Dockerfile
+++ b/2.4/alpine3.8/Dockerfile
@@ -30,13 +30,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl \
+		libressl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.4/alpine3.7/Dockerfile b/2.4/alpine3.9/Dockerfile
similarity index 98%
rename from 2.4/alpine3.7/Dockerfile
rename to 2.4/alpine3.9/Dockerfile
index d2fb67ce1..92c39fc29 100644
--- a/2.4/alpine3.7/Dockerfile
+++ b/2.4/alpine3.9/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.7
+FROM alpine:3.9
 
 # skip installing gem documentation
 RUN mkdir -p /usr/local/etc \
@@ -30,13 +30,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl \
+		openssl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.5/alpine3.8/Dockerfile b/2.5/alpine3.8/Dockerfile
index 0ce40e558..152c83197 100644
--- a/2.5/alpine3.8/Dockerfile
+++ b/2.5/alpine3.8/Dockerfile
@@ -30,13 +30,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl \
+		libressl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.5/alpine3.7/Dockerfile b/2.5/alpine3.9/Dockerfile
similarity index 98%
rename from 2.5/alpine3.7/Dockerfile
rename to 2.5/alpine3.9/Dockerfile
index 9a8771d91..283f77b99 100644
--- a/2.5/alpine3.7/Dockerfile
+++ b/2.5/alpine3.9/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.7
+FROM alpine:3.9
 
 # skip installing gem documentation
 RUN mkdir -p /usr/local/etc \
@@ -30,13 +30,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl \
+		openssl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.6/alpine3.8/Dockerfile b/2.6/alpine3.8/Dockerfile
index 2fe3d4dd0..c81f291ff 100644
--- a/2.6/alpine3.8/Dockerfile
+++ b/2.6/alpine3.8/Dockerfile
@@ -29,13 +29,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		libressl \
+		libressl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/2.6/alpine3.7/Dockerfile b/2.6/alpine3.9/Dockerfile
similarity index 98%
rename from 2.6/alpine3.7/Dockerfile
rename to 2.6/alpine3.9/Dockerfile
index a044df661..ab7dfbae8 100644
--- a/2.6/alpine3.7/Dockerfile
+++ b/2.6/alpine3.9/Dockerfile
@@ -1,4 +1,4 @@
-FROM alpine:3.7
+FROM alpine:3.9
 
 # skip installing gem documentation
 RUN mkdir -p /usr/local/etc \
@@ -29,13 +29,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl \
+		openssl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/Dockerfile-alpine.template b/Dockerfile-alpine.template
index 2f891e6d9..5b28ebf81 100644
--- a/Dockerfile-alpine.template
+++ b/Dockerfile-alpine.template
@@ -30,13 +30,13 @@ RUN set -ex \
 		glib-dev \
 		libc-dev \
 		libffi-dev \
-		libressl \
-		libressl-dev \
 		libxml2-dev \
 		libxslt-dev \
 		linux-headers \
 		make \
 		ncurses-dev \
+		openssl \
+		openssl-dev \
 		procps \
 		readline-dev \
 		ruby \
diff --git a/generate-stackbrew-library.sh b/generate-stackbrew-library.sh
index d036d0fbe..d7ab11db7 100755
--- a/generate-stackbrew-library.sh
+++ b/generate-stackbrew-library.sh
@@ -7,9 +7,9 @@ declare -A aliases=(
 )
 
 defaultDebianSuite='stretch'
-defaultAlpineVersion='3.8'
+defaultAlpineVersion='3.9'
 declare -A alpineVersion=(
-	#[2.5]='3.8'
+	[2.3]='3.8'
 )
 
 self="$(basename "$BASH_SOURCE")"
@@ -77,7 +77,7 @@ join() {
 for version in "${versions[@]}"; do
 	for v in \
 		{stretch,jessie}{,/slim} \
-		alpine{3.8,3.7,3.6} \
+		alpine{3.9,3.8,3.7} \
 	; do
 		dir="$version/$v"
 		variant="$(basename "$v")"
diff --git a/update.sh b/update.sh
index 3c404d05a..4cdddfbe3 100755
--- a/update.sh
+++ b/update.sh
@@ -70,7 +70,7 @@ for version in "${versions[@]}"; do
 	echo "$version: $fullVersion; $shaVal"
 
 	for v in \
-		alpine{3.6,3.7,3.8} \
+		alpine{3.7,3.8,3.9} \
 		{jessie,stretch}{/slim,} \
 	; do
 		dir="$version/$v"
@@ -104,6 +104,13 @@ 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 "${newEnoughRubygems[$version]:-}" ]; then
 			sed -ri -e '/RUBYGEMS_VERSION/d' "$dir/Dockerfile"
 		fi