diff --git a/.dependabot/config.yml b/.dependabot/config.yml
index 8f7a4d5e1..501804a21 100644
--- a/.dependabot/config.yml
+++ b/.dependabot/config.yml
@@ -4,7 +4,7 @@ version: 1
 
 update_configs:
   - package_manager: "docker"
-    directory: "/release/preview/alpine/dependabot"
+    directory: "/release/preview/alpine39/dependabot"
     update_schedule: "daily"
 
   - package_manager: "docker"
@@ -16,7 +16,7 @@ update_configs:
     update_schedule: "daily"
 
   - package_manager: "docker"
-    directory: "/release/preview/fedora28/dependabot"
+    directory: "/release/preview/fedora/dependabot"
     update_schedule: "daily"
 
   - package_manager: "docker"
diff --git a/build.ps1 b/build.ps1
index 13610a28e..4b901c8d4 100644
--- a/build.ps1
+++ b/build.ps1
@@ -441,11 +441,11 @@ End {
     if($GenerateTagsYaml.IsPresent)
     {
         Write-Output "repos:"
-        foreach($repo in $tagGroups.Keys)
+        foreach($repo in $tagGroups.Keys | Sort-Object)
         {
             Write-Output "  - repoName: $repo"
             Write-Output "    tagGroups:"
-            foreach($tag in $tagGroups.$repo)
+            foreach($tag in $tagGroups.$repo | Sort-Object -Property dockerfile)
             {
                 Write-Output "    - tags: [$($tag.Tags -join ', ')]"
                 Write-Output "      osVersion: $($tag.osVersion)"
diff --git a/release/preview/alpine/docker/Dockerfile b/release/preview/alpine38/docker/Dockerfile
similarity index 100%
rename from release/preview/alpine/docker/Dockerfile
rename to release/preview/alpine38/docker/Dockerfile
diff --git a/release/preview/alpine/getLatestTag.ps1 b/release/preview/alpine38/getLatestTag.ps1
similarity index 72%
rename from release/preview/alpine/getLatestTag.ps1
rename to release/preview/alpine38/getLatestTag.ps1
index 16be03136..bc836c038 100644
--- a/release/preview/alpine/getLatestTag.ps1
+++ b/release/preview/alpine38/getLatestTag.ps1
@@ -1,9 +1,9 @@
 # Copyright (c) Microsoft Corporation. All rights reserved.
 # Licensed under the MIT License.
 
-# return objects representing the tags we need to base the xenial image on
+# return objects representing the tags we need to base the Alpine image on
 
-# The versions of xenial we care about
+# The versions of Alpine we care about, for this dockerfile
 $shortTags = @('3.8')
 
 $parent = Join-Path -Path $PSScriptRoot -ChildPath '..'
@@ -11,4 +11,4 @@ $repoRoot = Join-Path -path (Join-Path -Path $parent -ChildPath '..') -ChildPath
 $modulePath = Join-Path -Path $repoRoot -ChildPath 'tools\getDockerTags'
 Import-Module $modulePath
 
-Get-DockerTags -ShortTags $shortTags -Image "alpine" -FullTagFilter '^3.8$' -OnlyShortTags
+Get-DockerTags -ShortTags $shortTags -Image "alpine" -FullTagFilter '^3.\d$' -OnlyShortTags
diff --git a/release/preview/alpine/meta.json b/release/preview/alpine38/meta.json
similarity index 100%
rename from release/preview/alpine/meta.json
rename to release/preview/alpine38/meta.json
diff --git a/release/preview/alpine/test-deps/docker/Dockerfile b/release/preview/alpine38/test-deps/docker/Dockerfile
similarity index 100%
rename from release/preview/alpine/test-deps/docker/Dockerfile
rename to release/preview/alpine38/test-deps/docker/Dockerfile
diff --git a/release/preview/alpine/test-deps/meta.json b/release/preview/alpine38/test-deps/meta.json
similarity index 100%
rename from release/preview/alpine/test-deps/meta.json
rename to release/preview/alpine38/test-deps/meta.json
diff --git a/release/preview/alpine/dependabot/Dockerfile b/release/preview/alpine39/dependabot/Dockerfile
similarity index 88%
rename from release/preview/alpine/dependabot/Dockerfile
rename to release/preview/alpine39/dependabot/Dockerfile
index 5ef7a1e2e..cf026e7c3 100644
--- a/release/preview/alpine/dependabot/Dockerfile
+++ b/release/preview/alpine39/dependabot/Dockerfile
@@ -3,4 +3,4 @@
 
 # Dummy docker image to trigger dependabot PRs
 
-FROM alpine:3.8
+FROM alpine:3.10.0
diff --git a/release/preview/alpine39/docker/Dockerfile b/release/preview/alpine39/docker/Dockerfile
new file mode 100644
index 000000000..4c2a5b4e3
--- /dev/null
+++ b/release/preview/alpine39/docker/Dockerfile
@@ -0,0 +1,109 @@
+# Copyright (c) Microsoft Corporation. All rights reserved.
+# Licensed under the MIT License.
+
+# Docker image file that describes an Alpine3.x image with PowerShell installed from .tar.gz file(s)
+
+# Define arg(s) needed for the From statement
+ARG fromTag=3.9
+ARG imageRepo=alpine
+
+FROM ${imageRepo}:${fromTag} AS installer-env
+
+# Define Args for the needed to add the package
+ARG PS_VERSION=6.2.0-preview.3
+ARG PS_PACKAGE=powershell-${PS_VERSION}-linux-alpine-x64.tar.gz
+ARG PS_PACKAGE_URL=https://github.com/PowerShell/PowerShell/releases/download/v${PS_VERSION}/${PS_PACKAGE}
+ARG PS_INSTALL_VERSION=7-preview
+
+# Download the Linux tar.gz and save it
+ADD ${PS_PACKAGE_URL} /tmp/linux.tar.gz
+
+# define the folder we will be installing PowerShell to
+ENV PS_INSTALL_FOLDER=/opt/microsoft/powershell/$PS_INSTALL_VERSION
+
+# Create the install folder
+RUN mkdir -p ${PS_INSTALL_FOLDER}
+
+# Unzip the Linux tar.gz
+RUN tar zxf /tmp/linux.tar.gz -C ${PS_INSTALL_FOLDER}
+
+# Start a new stage so we lose all the tar.gz layers from the final image
+FROM ${imageRepo}:${fromTag}
+
+# Copy only the files we need from the previous stage
+COPY --from=installer-env ["/opt/microsoft/powershell", "/opt/microsoft/powershell"]
+
+# Define Args and Env needed to create links
+ARG PS_INSTALL_VERSION=7-preview
+ENV PS_INSTALL_FOLDER=/opt/microsoft/powershell/$PS_INSTALL_VERSION \
+    \
+    # Define ENVs for Localization/Globalization
+    DOTNET_SYSTEM_GLOBALIZATION_INVARIANT=false \
+    LC_ALL=en_US.UTF-8 \
+    LANG=en_US.UTF-8 \
+    # set a fixed location for the Module analysis cache
+    PSModuleAnalysisCachePath=/var/cache/microsoft/powershell/PSModuleAnalysisCache/ModuleAnalysisCache
+
+# Install dotnet dependencies and ca-certificates
+RUN apk add --no-cache \
+    ca-certificates \
+    less \
+    \
+    # PSReadline/console dependencies
+    ncurses-terminfo-base \
+    \
+    # .NET Core dependencies
+    krb5-libs \
+    libgcc \
+    libintl \
+    libssl1.1 \
+    libstdc++ \
+    tzdata \
+    userspace-rcu \
+    zlib \
+    icu-libs \
+    && apk -X https://dl-cdn.alpinelinux.org/alpine/edge/main add --no-cache \
+    lttng-ust \
+    \
+    # Create the pwsh symbolic link that points to powershell
+    && ln -s ${PS_INSTALL_FOLDER}/pwsh /usr/bin/pwsh \
+    \
+    # Create the pwsh-preview symbolic link that points to powershell
+    && ln -s ${PS_INSTALL_FOLDER}/pwsh /usr/bin/pwsh-preview \
+    # Give all user execute permissions and remove write permissions for others
+    && chmod a+x,o-w ${PS_INSTALL_FOLDER}/pwsh \
+    # intialize powershell module cache
+    && pwsh \
+        -NoLogo \
+        -NoProfile \
+        -Command " \
+          \$ErrorActionPreference = 'Stop' ; \
+          \$ProgressPreference = 'SilentlyContinue' ; \
+          while(!(Test-Path -Path \$env:PSModuleAnalysisCachePath)) {  \
+            Write-Host "'Waiting for $env:PSModuleAnalysisCachePath'" ; \
+            Start-Sleep -Seconds 6 ; \
+          }"
+
+# Define args needed only for the labels
+ARG PS_VERSION=6.2.0-preview.2
+ARG IMAGE_NAME=mcr.microsoft.com/powershell:preview-alpine-3.8
+ARG VCS_REF="none"
+
+# Add label last as it's just metadata and uses a lot of parameters
+LABEL maintainer="PowerShell Team <powershellteam@hotmail.com>" \
+    readme.md="https://github.com/PowerShell/PowerShell/blob/master/docker/README.md" \
+    description="This Dockerfile will install the latest release of PowerShell." \
+    org.label-schema.usage="https://github.com/PowerShell/PowerShell/tree/master/docker#run-the-docker-image-you-built" \
+    org.label-schema.url="https://github.com/PowerShell/PowerShell/blob/master/docker/README.md" \
+    org.label-schema.vcs-url="https://github.com/PowerShell/PowerShell-Docker" \
+    org.label-schema.name="powershell" \
+    org.label-schema.vendor="PowerShell" \
+    org.label-schema.vcs-ref=${VCS_REF} \
+    org.label-schema.version=${PS_VERSION} \
+    org.label-schema.schema-version="1.0" \
+    org.label-schema.docker.cmd="docker run ${IMAGE_NAME} pwsh -c '$psversiontable'" \
+    org.label-schema.docker.cmd.devel="docker run ${IMAGE_NAME}" \
+    org.label-schema.docker.cmd.test="docker run ${IMAGE_NAME} pwsh -c Invoke-Pester" \
+    org.label-schema.docker.cmd.help="docker run ${IMAGE_NAME} pwsh -c Get-Help"
+
+CMD [ "pwsh" ]
diff --git a/release/preview/alpine39/getLatestTag.ps1 b/release/preview/alpine39/getLatestTag.ps1
new file mode 100644
index 000000000..bab6f5f80
--- /dev/null
+++ b/release/preview/alpine39/getLatestTag.ps1
@@ -0,0 +1,14 @@
+# Copyright (c) Microsoft Corporation. All rights reserved.
+# Licensed under the MIT License.
+
+# return objects representing the tags we need to base the Alpine image on
+
+# The versions of Alpine we care about, for this dockerfile
+$shortTags = @('3.9','3.10')
+
+$parent = Join-Path -Path $PSScriptRoot -ChildPath '..'
+$repoRoot = Join-Path -path (Join-Path -Path $parent -ChildPath '..') -ChildPath '..'
+$modulePath = Join-Path -Path $repoRoot -ChildPath 'tools\getDockerTags'
+Import-Module $modulePath
+
+Get-DockerTags -ShortTags $shortTags -Image "alpine" -FullTagFilter '^3.\d\d?$' -OnlyShortTags
diff --git a/release/preview/alpine39/meta.json b/release/preview/alpine39/meta.json
new file mode 100644
index 000000000..85f6c8894
--- /dev/null
+++ b/release/preview/alpine39/meta.json
@@ -0,0 +1,15 @@
+{
+    "IsLinux" : true,
+    "UseLinuxVersion": false,
+    "PackageFormat": "powershell-${PS_VERSION}-linux-alpine-x64.tar.gz",
+    "osVersion": "Alpine",
+    "tagTemplates": [
+        "#psversion#-alpine-#tag#",
+        "preview-alpine-#shorttag#"
+    ],
+    "SkipGssNtlmSspTests": true,
+    "SubImage": "test-deps",
+    "TestProperties": {
+        "size": 165
+    }
+}
diff --git a/release/preview/alpine39/test-deps/docker/Dockerfile b/release/preview/alpine39/test-deps/docker/Dockerfile
new file mode 100644
index 000000000..f7bb8a2d4
--- /dev/null
+++ b/release/preview/alpine39/test-deps/docker/Dockerfile
@@ -0,0 +1,57 @@
+# Docker image file that describes an Alpine image with PowerShell and test dependencies
+
+ARG BaseImage=mcr.microsoft.com/powershell:alpine-3.9
+
+FROM node:10.15.3-alpine as node
+
+# Do nothing, just added to borrow the already built node files.
+
+FROM ${BaseImage}
+
+ENV NODE_VERSION 10.15.3
+ENV YARN_VERSION=1.13.0
+ENV NVM_DIR="/root/.nvm"
+
+# workaround for Alpine to run in Azure DevOps
+ENV NODE_NO_WARNINGS=1
+
+# Copy node and yarn into image
+COPY --from=node /usr/local/bin/node /usr/local/bin/node
+COPY --from=node /opt/yarn-v${YARN_VERSION} /opt/yarn-v${YARN_VERSION}
+
+RUN apk add --no-cache --virtual .pipeline-deps readline linux-pam \
+    && apk add \
+        bash \
+        sudo \
+        shadow \
+        openssl \
+        curl \
+    && apk del .pipeline-deps \
+    && ln -s /opt/yarn-v$YARN_VERSION/bin/yarn /usr/local/bin/yarn \
+    && ln -s /opt/yarn-v$YARN_VERSION/bin/yarnpkg /usr/local/bin/yarnpkg
+
+# Define args needed only for the labels
+ARG VCS_REF="none"
+ARG IMAGE_NAME=mcr.microsoft.com/powershell/test-deps:alpine-3.8
+ARG PS_VERSION=6.2.0
+
+LABEL maintainer="PowerShell Team <powershellteam@hotmail.com>" \
+      readme.md="https://github.com/PowerShell/PowerShell/blob/master/docker/README.md" \
+      description="This Dockerfile will install the latest release of PowerShell and tools needed for runing CI/CD container jobs." \
+      org.label-schema.usage="https://github.com/PowerShell/PowerShell/tree/master/docker#run-the-docker-image-you-built" \
+      org.label-schema.url="https://github.com/PowerShell/PowerShell/blob/master/docker/README.md" \
+      org.label-schema.vcs-url="https://github.com/PowerShell/PowerShell-Docker" \
+      org.label-schema.name="powershell" \
+      org.label-schema.vendor="PowerShell" \
+      org.label-schema.version=${PS_VERSION} \
+      org.label-schema.schema-version="1.0" \
+      org.label-schema.vcs-ref=${VCS_REF} \
+      org.label-schema.docker.cmd="docker run ${IMAGE_NAME} pwsh -c '$psversiontable'" \
+      org.label-schema.docker.cmd.devel="docker run ${IMAGE_NAME}" \
+      org.label-schema.docker.cmd.test="docker run ${IMAGE_NAME} pwsh -c Invoke-Pester" \
+      org.label-schema.docker.cmd.help="docker run ${IMAGE_NAME} pwsh -c Get-Help" \
+      com.azure.dev.pipelines.agent.handler.node.path="/usr/local/bin/node"
+
+# Use PowerShell as the default shell
+# Use array to avoid Docker prepending /bin/sh -c
+CMD [ "pwsh" ]
diff --git a/release/preview/alpine39/test-deps/meta.json b/release/preview/alpine39/test-deps/meta.json
new file mode 100644
index 000000000..3a5779890
--- /dev/null
+++ b/release/preview/alpine39/test-deps/meta.json
@@ -0,0 +1,16 @@
+{
+    "IsLinux" : true,
+    "UseLinuxVersion": false,
+    "SkipGssNtlmSspTests": true,
+    "osVersion": "Alpine ${fromTag}",
+    "tagTemplates": [
+        "preview-alpine-#shorttag#"
+    ],
+    "OptionalTests": [
+        "test-deps",
+        "test-deps-musl"
+    ],
+    "TestProperties": {
+        "size": 212
+    }
+}
diff --git a/release/preview/fedora/meta.json b/release/preview/fedora/meta.json
index b708d6835..17e89619f 100644
--- a/release/preview/fedora/meta.json
+++ b/release/preview/fedora/meta.json
@@ -2,7 +2,7 @@
     "IsLinux" : true,
     "UseLinuxVersion": false,
     "PackageFormat": "powershell${previewTag}-${PS_VERSION}-1.rhel.7.x86_64.rpm",
-    "osVersion": "Fedora 28",
+    "osVersion": "Fedora",
     "SkipGssNtlmSspTests": false,
     "tagTemplates": [
         "#psversion#-fedora-#tag#",
diff --git a/release/preview/fedora/test-deps/meta.json b/release/preview/fedora/test-deps/meta.json
index 50371938a..e59800f34 100644
--- a/release/preview/fedora/test-deps/meta.json
+++ b/release/preview/fedora/test-deps/meta.json
@@ -1,7 +1,7 @@
 {
     "IsLinux" : true,
     "UseLinuxVersion": false,
-    "osVersion": "Fedora 28",
+    "osVersion": "Fedora ${fromTag}",
     "SkipGssNtlmSspTests": false,
     "tagTemplates": [
         "preview-fedora-#shorttag#"
diff --git a/vsts-ci.yml b/vsts-ci.yml
index c19ca0c29..09de7ef12 100644
--- a/vsts-ci.yml
+++ b/vsts-ci.yml
@@ -57,6 +57,20 @@ jobs:
     name: alpine
     imagename: alpine
     stable: true
+    preview: false
+
+- template: .vsts-ci/phase.yml
+  parameters:
+    name: alpine38
+    imagename: alpine38
+    stable: false
+    preview: true
+
+- template: .vsts-ci/phase.yml
+  parameters:
+    name: alpine39
+    imagename: alpine39
+    stable: false
     preview: true
 
 - template: .vsts-ci/phase.yml