diff --git a/.travis.yml b/.travis.yml
index ca70b59c2..74f6705cb 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -2,42 +2,51 @@ language: bash
 services: docker
 
 env:
-  - VERSION=3.6 VARIANT=
-  - VERSION=3.6 VARIANT=slim
-  - VERSION=3.6 VARIANT=alpine
-  - VERSION=3.6 VARIANT=alpine3.6
   - VERSION=3.6 VARIANT=stretch
-  - VERSION=3.5 VARIANT=
-  - VERSION=3.5 VARIANT=slim
-  - VERSION=3.5 VARIANT=alpine
-  - VERSION=3.4 VARIANT=
-  - VERSION=3.4 VARIANT=slim
-  - VERSION=3.4 VARIANT=alpine
+  - VERSION=3.6 VARIANT=jessie
+  - VERSION=3.6 VARIANT=jessie/slim
+  - VERSION=3.6 VARIANT=alpine3.6
+  - VERSION=3.6 VARIANT=alpine3.4
+  - VERSION=3.5 VARIANT=jessie
+  - VERSION=3.5 VARIANT=jessie/slim
+  - VERSION=3.5 VARIANT=alpine3.4
+  - VERSION=3.4 VARIANT=jessie
+  - VERSION=3.4 VARIANT=jessie/slim
   - VERSION=3.4 VARIANT=wheezy
-  - VERSION=3.3 VARIANT=
-  - VERSION=3.3 VARIANT=slim
-  - VERSION=3.3 VARIANT=alpine
+  - VERSION=3.4 VARIANT=alpine3.4
+  - VERSION=3.3 VARIANT=jessie
+  - VERSION=3.3 VARIANT=jessie/slim
   - VERSION=3.3 VARIANT=wheezy
-  - VERSION=2.7 VARIANT=
-  - VERSION=2.7 VARIANT=slim
-  - VERSION=2.7 VARIANT=alpine
-  - VERSION=2.7 VARIANT=alpine3.6
+  - VERSION=3.3 VARIANT=alpine3.4
   - VERSION=2.7 VARIANT=stretch
+  - VERSION=2.7 VARIANT=jessie
+  - VERSION=2.7 VARIANT=jessie/slim
   - VERSION=2.7 VARIANT=wheezy
+  - VERSION=2.7 VARIANT=alpine3.6
+  - VERSION=2.7 VARIANT=alpine3.4
 
 install:
   - git clone https://github.com/docker-library/official-images.git ~/official-images
 
 before_script:
   - env | sort
-  - cd "$VERSION"
-  - image="$(awk '$1 == "FROM" { print $2; exit }' onbuild/Dockerfile)${VARIANT:+-$VARIANT}"
+  - cd "$VERSION/$VARIANT"
+  - slash='/'; image="python:${VERSION}-${VARIANT//$slash/-}"
 
 script:
-  - travis_retry docker build -t "$image" "${VARIANT:-.}"
-  - ~/official-images/test/run.sh "$image"
-# the "onbuild" variant has to happen with the base variant because it's FROM it
-  - true && [ "$VARIANT" ] || travis_retry docker build -t "${image}-onbuild" onbuild
+  - |
+    (
+      set -Eeuo pipefail
+      set -x
+      travis_retry docker build -t "$image" .
+      ~/official-images/test/run.sh "$image"
+      if [ -d onbuild ]; then
+        onbuildFrom="$(awk 'toupper($1) == "FROM" { print $2; exit }' onbuild/Dockerfile)"
+        docker tag "$image" "$onbuildFrom"
+        docker build -t "$image-onbuild" onbuild
+        ~/official-images/test/run.sh "$image-onbuild"
+      fi
+    )
 
 after_script:
   - docker images
diff --git a/2.7/alpine/Dockerfile b/2.7/alpine3.4/Dockerfile
similarity index 100%
rename from 2.7/alpine/Dockerfile
rename to 2.7/alpine3.4/Dockerfile
diff --git a/2.7/Dockerfile b/2.7/jessie/Dockerfile
similarity index 100%
rename from 2.7/Dockerfile
rename to 2.7/jessie/Dockerfile
diff --git a/2.7/onbuild/Dockerfile b/2.7/jessie/onbuild/Dockerfile
similarity index 100%
rename from 2.7/onbuild/Dockerfile
rename to 2.7/jessie/onbuild/Dockerfile
diff --git a/2.7/slim/Dockerfile b/2.7/jessie/slim/Dockerfile
similarity index 100%
rename from 2.7/slim/Dockerfile
rename to 2.7/jessie/slim/Dockerfile
diff --git a/3.3/alpine/Dockerfile b/3.3/alpine3.4/Dockerfile
similarity index 100%
rename from 3.3/alpine/Dockerfile
rename to 3.3/alpine3.4/Dockerfile
diff --git a/3.3/Dockerfile b/3.3/jessie/Dockerfile
similarity index 100%
rename from 3.3/Dockerfile
rename to 3.3/jessie/Dockerfile
diff --git a/3.3/onbuild/Dockerfile b/3.3/jessie/onbuild/Dockerfile
similarity index 100%
rename from 3.3/onbuild/Dockerfile
rename to 3.3/jessie/onbuild/Dockerfile
diff --git a/3.3/slim/Dockerfile b/3.3/jessie/slim/Dockerfile
similarity index 100%
rename from 3.3/slim/Dockerfile
rename to 3.3/jessie/slim/Dockerfile
diff --git a/3.4/alpine/Dockerfile b/3.4/alpine3.4/Dockerfile
similarity index 100%
rename from 3.4/alpine/Dockerfile
rename to 3.4/alpine3.4/Dockerfile
diff --git a/3.4/Dockerfile b/3.4/jessie/Dockerfile
similarity index 100%
rename from 3.4/Dockerfile
rename to 3.4/jessie/Dockerfile
diff --git a/3.4/onbuild/Dockerfile b/3.4/jessie/onbuild/Dockerfile
similarity index 100%
rename from 3.4/onbuild/Dockerfile
rename to 3.4/jessie/onbuild/Dockerfile
diff --git a/3.4/slim/Dockerfile b/3.4/jessie/slim/Dockerfile
similarity index 100%
rename from 3.4/slim/Dockerfile
rename to 3.4/jessie/slim/Dockerfile
diff --git a/3.5/alpine/Dockerfile b/3.5/alpine3.4/Dockerfile
similarity index 100%
rename from 3.5/alpine/Dockerfile
rename to 3.5/alpine3.4/Dockerfile
diff --git a/3.5/Dockerfile b/3.5/jessie/Dockerfile
similarity index 100%
rename from 3.5/Dockerfile
rename to 3.5/jessie/Dockerfile
diff --git a/3.5/onbuild/Dockerfile b/3.5/jessie/onbuild/Dockerfile
similarity index 100%
rename from 3.5/onbuild/Dockerfile
rename to 3.5/jessie/onbuild/Dockerfile
diff --git a/3.5/slim/Dockerfile b/3.5/jessie/slim/Dockerfile
similarity index 100%
rename from 3.5/slim/Dockerfile
rename to 3.5/jessie/slim/Dockerfile
diff --git a/3.6/alpine/Dockerfile b/3.6/alpine3.4/Dockerfile
similarity index 100%
rename from 3.6/alpine/Dockerfile
rename to 3.6/alpine3.4/Dockerfile
diff --git a/3.6/Dockerfile b/3.6/jessie/Dockerfile
similarity index 100%
rename from 3.6/Dockerfile
rename to 3.6/jessie/Dockerfile
diff --git a/3.6/onbuild/Dockerfile b/3.6/jessie/onbuild/Dockerfile
similarity index 100%
rename from 3.6/onbuild/Dockerfile
rename to 3.6/jessie/onbuild/Dockerfile
diff --git a/3.6/slim/Dockerfile b/3.6/jessie/slim/Dockerfile
similarity index 100%
rename from 3.6/slim/Dockerfile
rename to 3.6/jessie/slim/Dockerfile
diff --git a/Dockerfile-alpine.template b/Dockerfile-alpine.template
index 091049c95..4c8d7e2c9 100644
--- a/Dockerfile-alpine.template
+++ b/Dockerfile-alpine.template
@@ -1,4 +1,4 @@
-FROM alpine:3.4
+FROM alpine:%%PLACEHOLDER%%
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
@@ -17,7 +17,7 @@ ENV PYTHON_VERSION %%PLACEHOLDER%%
 RUN set -ex \
 	&& apk add --no-cache --virtual .fetch-deps \
 		gnupg \
-		openssl \
+		libressl \
 		tar \
 		xz \
 	\
@@ -43,8 +43,8 @@ RUN set -ex \
 		linux-headers \
 		make \
 		ncurses-dev \
-		openssl \
-		openssl-dev \
+		libressl \
+		libressl-dev \
 		pax-utils \
 		readline-dev \
 		sqlite-dev \
@@ -98,7 +98,7 @@ ENV PYTHON_PIP_VERSION %%PLACEHOLDER%%
 
 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/Dockerfile-debian.template b/Dockerfile-debian.template
index 4fe2f6bd0..6799174e5 100644
--- a/Dockerfile-debian.template
+++ b/Dockerfile-debian.template
@@ -1,4 +1,4 @@
-FROM buildpack-deps:jessie
+FROM buildpack-deps:%%PLACEHOLDER%%
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
diff --git a/Dockerfile-slim.template b/Dockerfile-slim.template
index 643300733..638baeaad 100644
--- a/Dockerfile-slim.template
+++ b/Dockerfile-slim.template
@@ -1,4 +1,4 @@
-FROM debian:jessie
+FROM debian:%%PLACEHOLDER%%
 
 # ensure local python is preferred over distribution python
 ENV PATH /usr/local/bin:$PATH
diff --git a/generate-stackbrew-library.sh b/generate-stackbrew-library.sh
index bc3d5e111..4e8f2c532 100755
--- a/generate-stackbrew-library.sh
+++ b/generate-stackbrew-library.sh
@@ -1,5 +1,5 @@
-#!/bin/bash
-set -eu
+#!/usr/bin/env bash
+set -Eeuo pipefail
 
 declare -A aliases=(
 	[3.6-rc]='rc'
@@ -7,12 +7,32 @@ declare -A aliases=(
 	[2.7]='2'
 )
 
+defaultDebianSuite='stretch'
+declare -A debianSuites=(
+	[2.7]='jessie'
+	[3.3]='jessie'
+	[3.4]='jessie'
+	[3.5]='jessie'
+	[3.6]='jessie'
+)
+defaultAlpineVersion='3.6'
+declare -A alpineVersions=(
+	[2.7]='3.4'
+	[3.3]='3.4'
+	[3.4]='3.4'
+	[3.5]='3.4'
+	[3.6]='3.4'
+)
+
 self="$(basename "$BASH_SOURCE")"
 cd "$(dirname "$(readlink -f "$BASH_SOURCE")")"
 
 versions=( */ )
 versions=( "${versions[@]%/}" )
 
+# sort version numbers with highest first
+IFS=$'\n'; versions=( $(echo "${versions[*]}" | sort -rV) ); unset IFS
+
 # get the most recent commit which modified any of "$@"
 fileCommit() {
 	git log -1 --format='format:%H' HEAD -- "$@"
@@ -39,7 +59,7 @@ getArches() {
 	local repo="$1"; shift
 	local officialImagesUrl='https://github.com/docker-library/official-images/raw/master/library/'
 
-	eval "declare -A -g parentRepoToArches=( $(
+	eval "declare -g -A parentRepoToArches=( $(
 		find -name 'Dockerfile' -exec awk '
 				toupper($1) == "FROM" && $2 !~ /^('"$repo"'|scratch|microsoft\/[^:]+)(:|$)/ {
 					print "'"$officialImagesUrl"'" $2
@@ -67,29 +87,12 @@ join() {
 }
 
 for version in "${versions[@]}"; do
-	commit="$(dirCommit "$version")"
-
-	parent="$(awk 'toupper($1) == "FROM" { print $2 }' "$version/Dockerfile")"
-	arches="${parentRepoToArches[$parent]}"
-
-	fullVersion="$(git show "$commit":"$version/Dockerfile" | awk '$1 == "ENV" && $2 == "PYTHON_VERSION" { print $3; exit }')"
-
-	versionAliases=(
-		$fullVersion
-		$version
-		${aliases[$version]:-}
-	)
-
-	echo
-	cat <<-EOE
-		Tags: $(join ', ' "${versionAliases[@]}")
-		Architectures: $(join ', ' $arches)
-		GitCommit: $commit
-		Directory: $version
-	EOE
+	debianSuite="${debianSuites[$version]:-$defaultDebianSuite}"
+	alpineVersion="${alpineVersions[$version]:-$defaultAlpineVersion}"
 
 	for v in \
-		slim alpine alpine3.6 wheezy onbuild \
+		{stretch,jessie,wheezy}{,/slim,/onbuild} \
+		alpine{3.6,3.4} \
 		windows/windowsservercore windows/nanoserver \
 	; do
 		dir="$version/$v"
@@ -99,14 +102,34 @@ for version in "${versions[@]}"; do
 
 		commit="$(dirCommit "$dir")"
 
+		versionDockerfile="$dir/Dockerfile"
+		if [ "$variant" = 'onbuild' ]; then
+			versionDockerfile="$(dirname "$dir")/Dockerfile"
+		fi
+		fullVersion="$(git show "$commit":"$versionDockerfile" | awk '$1 == "ENV" && $2 == "PYTHON_VERSION" { print $3; exit }')"
+
+		versionAliases=(
+			$fullVersion
+			$version
+			${aliases[$version]:-}
+		)
+
 		variantAliases=( "${versionAliases[@]/%/-$variant}" )
+		if [ "$variant" = "$debianSuite" ]; then
+			variantAliases+=( "${versionAliases[@]}" )
+		elif [ "$variant" = "alpine${alpineVersion}" ]; then
+			variantAliases+=( "${versionAliases[@]/%/-alpine}" )
+		fi
 		variantAliases=( "${variantAliases[@]//latest-/}" )
 
 		case "$v" in
 			windows/*) variantArches='windows-amd64' ;;
-			onbuild)   variantArches="$arches" ;;
+			*/onbuild)
+				variantParent="$(awk 'toupper($1) == "FROM" { print $2 }' "$(dirname "$dir")/Dockerfile")"
+				variantArches="${parentRepoToArches[$variantParent]}"
+				;;
 			*)
-				variantParent="$(awk 'toupper($1) == "FROM" { print $2 }' "$version/$v/Dockerfile")"
+				variantParent="$(awk 'toupper($1) == "FROM" { print $2 }' "$dir/Dockerfile")"
 				variantArches="${parentRepoToArches[$variantParent]}"
 				;;
 		esac
@@ -118,6 +141,6 @@ for version in "${versions[@]}"; do
 			GitCommit: $commit
 			Directory: $dir
 		EOE
-		[ "$variant" = "$v" ] || echo "Constraints: $variant"
+		[[ "$v" == windows/* ]] && echo "Constraints: $variant"
 	done
 done
diff --git a/update.sh b/update.sh
index d7ffeac3a..21363f324 100755
--- a/update.sh
+++ b/update.sh
@@ -1,4 +1,4 @@
-#!/bin/bash
+#!/usr/bin/env bash
 set -Eeuo pipefail
 shopt -s nullglob
 
@@ -80,64 +80,56 @@ for version in "${versions[@]}"; do
 			echo
 		} >&2
 		exit 1
-	else
-		if [[ "$version" != 2.* ]]; then
-			for variant in \
-				debian \
-				alpine \
-				slim \
-				onbuild \
-				windows/windowsservercore \
-			; do
-				if [ "$variant" = 'debian' ]; then
-					dir="$version"
-				else
-					dir="$version/$variant"
-					variant="$(basename "$variant")"
-				fi
-				[ -d "$dir" ] || continue
-				template="Dockerfile-$variant.template"
-				{ generated_warning; cat "$template"; } > "$dir/Dockerfile"
-			done
-		fi
-		(
-			set -x
-			sed -ri \
-				-e 's/^(ENV GPG_KEY) .*/\1 '"${gpgKeys[$rcVersion]}"'/' \
-				-e 's/^(ENV PYTHON_VERSION) .*/\1 '"$fullVersion"'/' \
-				-e 's/^(ENV PYTHON_RELEASE) .*/\1 '"${fullVersion%%[a-z]*}"'/' \
-				-e 's/^(ENV PYTHON_PIP_VERSION) .*/\1 '"$pipVersion"'/' \
-				-e 's/^(FROM python):.*/\1:'"$version"'/' \
-				"$version"/{,*/,*/*/}Dockerfile
-		)
 	fi
-	for variant in wheezy stretch alpine3.6 alpine slim ''; do
-		[ -d "$version/$variant" ] || continue
 
-		case "$variant" in
-			alpine3.6)
-				sed -r \
-					-e 's!(alpine):3.4!\1:3.6!g' \
-					-e 's!openssl!libressl!g' \
-					"$version/alpine/Dockerfile" > "$version/$variant/Dockerfile"
-				;;
+	echo "$version: $fullVersion"
 
-			wheezy|stretch)
-				sed -r \
-					-e "s!(buildpack-deps|debian):jessie!\1:${variant}!g" \
-					"$version/Dockerfile" > "$version/$variant/Dockerfile"
-				if [ "$variant" = 'wheezy' ]; then
-					sed -ri -e 's/dpkg-architecture --query /dpkg-architecture -q/g' "$version/$variant/Dockerfile"
-				fi
-				;;
+	for v in \
+		alpine{3.4,3.6} \
+		{wheezy,jessie,stretch}{/slim,/onbuild,} \
+		windows/{windowsservercore,nanoserver} \
+	; do
+		dir="$version/$v"
+		variant="$(basename "$v")"
+
+		[ -d "$dir" ] || continue
+
+		case "$variant" in
+			slim|onbuild|windowsservercore) template="$variant"; tag="$(basename "$(dirname "$dir")")" ;;
+			alpine*) template='alpine'; tag="${variant#alpine}" ;;
+			*) template='debian'; tag="$variant" ;;
 		esac
+		template="Dockerfile-${template}.template"
 
-		travisEnv='\n  - VERSION='"$version VARIANT=$variant$travisEnv"
-	done
-	for winVariant in windowsservercore nanoserver; do
-		if [ -d "$version/windows/$winVariant" ]; then
-			appveyorEnv='\n    - version: '"$version"'\n      variant: '"$winVariant$appveyorEnv"
+		if [[ "$version" == 2.* ]]; then
+			echo "  TODO: vimdiff ${versions[-1]}/$v/Dockerfile $version/$v/Dockerfile"
+		else
+			{ generated_warning; cat "$template"; } > "$dir/Dockerfile"
 		fi
+
+		sed -ri \
+			-e 's/^(ENV GPG_KEY) .*/\1 '"${gpgKeys[$rcVersion]}"'/' \
+			-e 's/^(ENV PYTHON_VERSION) .*/\1 '"$fullVersion"'/' \
+			-e 's/^(ENV PYTHON_RELEASE) .*/\1 '"${fullVersion%%[a-z]*}"'/' \
+			-e 's/^(ENV PYTHON_PIP_VERSION) .*/\1 '"$pipVersion"'/' \
+			-e 's/^(FROM python):.*/\1:'"$version"'/' \
+			-e 's/^(FROM (debian|buildpack-deps|alpine)):.*/\1:'"$tag"'/' \
+			"$dir/Dockerfile"
+
+		case "$variant" in
+			alpine3.4) sed -ri -e 's/libressl/openssl/g' "$dir/Dockerfile" ;;
+			wheezy) sed -ri -e 's/dpkg-architecture --query /dpkg-architecture -q/g' "$dir/Dockerfile" ;;
+		esac
+
+		case "$v" in
+			*/onbuild) ;;
+			windows/*)
+				appveyorEnv='\n    - version: '"$version"'\n      variant: '"$variant$appveyorEnv"
+				;;
+			*)
+				travisEnv='\n  - VERSION='"$version VARIANT=$v$travisEnv"
+				;;
+		esac
 	done
 done