diff --git a/2.7/alpine3.6/Dockerfile b/2.7/alpine3.6/Dockerfile
index fae7a13e4..609cb9c56 100644
--- a/2.7/alpine3.6/Dockerfile
+++ b/2.7/alpine3.6/Dockerfile
@@ -17,7 +17,7 @@ ENV PYTHON_VERSION 2.7.13
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
 		gnupg \
-		openssl \
+		libressl \
 		tar \
 		xz \
 	\
@@ -41,8 +41,8 @@ RUN set -ex \
 		linux-headers \
 		make \
 		ncurses-dev \
-		openssl \
-		openssl-dev \
+		libressl \
+		libressl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
@@ -85,7 +85,7 @@ ENV PYTHON_PIP_VERSION 9.0.1
 
 RUN set -ex; \
 	\
-	apk add --no-cache --virtual .fetch-deps openssl; \
+	apk add --no-cache --virtual .fetch-deps libressl; \
 	\
 	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
 	\
diff --git a/3.6/alpine3.6/Dockerfile b/3.6/alpine3.6/Dockerfile
index f0e479e67..4238d889b 100644
--- a/3.6/alpine3.6/Dockerfile
+++ b/3.6/alpine3.6/Dockerfile
@@ -23,7 +23,7 @@ ENV PYTHON_VERSION 3.6.1
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
 		gnupg \
-		openssl \
+		libressl \
 		tar \
 		xz \
 	\
@@ -47,8 +47,8 @@ RUN set -ex \
 		linux-headers \
 		make \
 		ncurses-dev \
-		openssl \
-		openssl-dev \
+		libressl \
+		libressl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
@@ -100,7 +100,7 @@ ENV PYTHON_PIP_VERSION 9.0.1
 
 RUN set -ex; \
 	\
-	apk add --no-cache --virtual .fetch-deps openssl; \
+	apk add --no-cache --virtual .fetch-deps libressl; \
 	\
 	wget -O get-pip.py 'https://bootstrap.pypa.io/get-pip.py'; \
 	\
diff --git a/update.sh b/update.sh
index aad5668d3..9a225deac 100755
--- a/update.sh
+++ b/update.sh
@@ -116,6 +116,7 @@ for version in "${versions[@]}"; do
 		cp "$version/alpine/Dockerfile" "$version/alpine3.6/Dockerfile"
 		sed -ri \
 			-e 's/(alpine):3.4/\1:3.6/g' \
+			-e 's/openssl/libressl/g' \
 			"$version/alpine3.6/Dockerfile"
 	fi
 	for variant in wheezy alpine3.6 alpine slim ''; do