diff --git a/deployment/win-x86/Dockerfile b/deployment/win-x86/Dockerfile
new file mode 100644
index 000000000..91a575b3e
--- /dev/null
+++ b/deployment/win-x86/Dockerfile
@@ -0,0 +1,37 @@
+FROM debian:10
+# Docker build arguments
+ARG SOURCE_DIR=/jellyfin
+ARG PLATFORM_DIR=/jellyfin/deployment/win-x86
+ARG ARTIFACT_DIR=/dist
+ARG SDK_VERSION=2.2
+# Docker run environment
+ENV SOURCE_DIR=/jellyfin
+ENV ARTIFACT_DIR=/dist
+ENV DEB_BUILD_OPTIONS=noddebs
+ENV ARCH=amd64
+
+# Prepare Debian build environment
+RUN apt-get update \
+ && apt-get install -y apt-transport-https debhelper gnupg wget devscripts mmv libc6-dev libcurl4-openssl-dev libfontconfig1-dev libfreetype6-dev libssl-dev libssl1.1 liblttng-ust0 zip
+
+# Install dotnet repository
+# https://dotnet.microsoft.com/download/linux-package-manager/debian9/sdk-current
+RUN wget https://download.visualstudio.microsoft.com/download/pr/228832ea-805f-45ab-8c88-fa36165701b9/16ce29a06031eeb09058dee94d6f5330/dotnet-sdk-2.2.401-linux-x64.tar.gz -O dotnet-sdk.tar.gz \
+ && mkdir -p dotnet-sdk \
+ && tar -xzf dotnet-sdk.tar.gz -C dotnet-sdk \
+ && ln -s $( pwd )/dotnet-sdk/dotnet /usr/bin/dotnet
+
+# Install yarn package manager
+RUN wget -q -O- https://dl.yarnpkg.com/debian/pubkey.gpg | apt-key add - \
+ && echo "deb https://dl.yarnpkg.com/debian/ stable main" | tee /etc/apt/sources.list.d/yarn.list \
+ && apt update \
+ && apt install -y yarn
+
+# Link to docker-build script
+RUN ln -sf ${PLATFORM_DIR}/docker-build.sh /docker-build.sh
+
+VOLUME ${ARTIFACT_DIR}/
+
+COPY . ${SOURCE_DIR}/
+
+ENTRYPOINT ["/docker-build.sh"]
diff --git a/deployment/win-x86/build.sh b/deployment/win-x86/build.sh
deleted file mode 100755
index 610db356a..000000000
--- a/deployment/win-x86/build.sh
+++ /dev/null
@@ -1,7 +0,0 @@
-#!/usr/bin/env bash
-
-source ../common.build.sh
-
-VERSION=`get_version ../..`
-
-build_jellyfin ../../Jellyfin.Server Release win-x86 `pwd`/dist/jellyfin_${VERSION}
diff --git a/deployment/win-x86/clean.sh b/deployment/win-x86/clean.sh
index 3df2d7796..8b78c5e4b 100755
--- a/deployment/win-x86/clean.sh
+++ b/deployment/win-x86/clean.sh
@@ -1,7 +1,27 @@
 #!/usr/bin/env bash
 
-source ../common.build.sh
+keep_artifacts="${1}"
 
-VERSION=`get_version ../..`
+WORKDIR="$( pwd )"
 
-clean_jellyfin ../.. Release `pwd`/dist/jellyfin_${VERSION}
+package_temporary_dir="${WORKDIR}/pkg-dist-tmp"
+output_dir="${WORKDIR}/pkg-dist"
+current_user="$( whoami )"
+image_name="jellyfin-windows-x86-build"
+
+rm -rf "${package_temporary_dir}" &>/dev/null \
+  || sudo rm -rf "${package_temporary_dir}" &>/dev/null
+
+rm -rf "${output_dir}" &>/dev/null \
+  || sudo rm -rf "${output_dir}" &>/dev/null
+
+if [[ ${keep_artifacts} == 'n' ]]; then
+    docker_sudo=""
+    if [[ ! -z $(id -Gn | grep -q 'docker') ]] \
+      && [[ ! ${EUID:-1000} -eq 0 ]] \
+      && [[ ! ${USER} == "root" ]] \
+      && [[ ! -z $( echo "${OSTYPE}" | grep -q "darwin" ) ]]; then
+        docker_sudo=sudo
+    fi
+    ${docker_sudo} docker image rm ${image_name} --force
+fi
diff --git a/deployment/win-x86/dependencies.txt b/deployment/win-x86/dependencies.txt
index 3d25d1bdf..bdb967096 100644
--- a/deployment/win-x86/dependencies.txt
+++ b/deployment/win-x86/dependencies.txt
@@ -1 +1 @@
-dotnet
+docker
diff --git a/deployment/win-x86/docker-build.sh b/deployment/win-x86/docker-build.sh
new file mode 100755
index 000000000..fced38eab
--- /dev/null
+++ b/deployment/win-x86/docker-build.sh
@@ -0,0 +1,60 @@
+#!/bin/bash
+
+# Builds the ZIP archive inside the Docker container
+
+set -o errexit
+set -o xtrace
+
+# Version variables
+NSSM_VERSION="nssm-2.24-101-g897c7ad"
+NSSM_URL="https://nssm.cc/ci/${NSSM_VERSION}.zip"
+FFMPEG_VERSION="ffmpeg-4.0.2-win32-static"
+FFMPEG_URL="https://ffmpeg.zeranoe.com/builds/win32/static/${FFMPEG_VERSION}.zip"
+
+# Move to source directory
+pushd ${SOURCE_DIR}
+
+# Clone down and build Web frontend
+web_build_dir="$( mktemp -d )"
+web_target="${SOURCE_DIR}/MediaBrowser.WebDashboard/jellyfin-web"
+git clone https://github.com/jellyfin/jellyfin-web.git ${web_build_dir}/
+pushd ${web_build_dir}
+if [[ -n ${web_branch} ]]; then
+    checkout -b origin/${web_branch}
+fi
+yarn install
+yarn build
+mkdir -p ${web_target}
+mv dist/* ${web_target}/
+popd
+
+# Get version
+version="$( grep "version:" ./build.yaml | sed -E 's/version: "([0-9\.]+.*)"/\1/' )"
+
+# Build binary
+dotnet publish --configuration Release --self-contained --runtime win-x86 --output /dist/jellyfin_${version}/ "-p:GenerateDocumentationFile=false;DebugSymbols=false;DebugType=none;UseAppHost=true"
+
+# Prepare addins
+addin_build_dir="$( mktemp -d )"
+wget ${NSSM_URL} -O ${addin_build_dir}/nssm.zip
+wget ${FFMPEG_URL} -O ${addin_build_dir}/ffmpeg.zip
+unzip ${addin_build_dir}/nssm.zip -d ${addin_build_dir}
+cp ${addin_build_dir}/${NSSM_VERSION}/win64/nssm.exe /dist/jellyfin_${version}/nssm.exe
+unzip ${addin_build_dir}/ffmpeg.zip -d ${addin_build_dir}
+cp ${addin_build_dir}/${FFMPEG_VERSION}/bin/ffmpeg.exe /dist/jellyfin_${version}/ffmpeg.exe
+cp ${addin_build_dir}/${FFMPEG_VERSION}/bin/ffprobe.exe /dist/jellyfin_${version}/ffprobe.exe
+
+# Prepare scripts
+cp ${SOURCE_DIR}/deployment/windows/legacy/install-jellyfin.ps1 /dist/jellyfin_${version}/install-jellyfin.ps1
+cp ${SOURCE_DIR}/deployment/windows/legacy/install.bat /dist/jellyfin_${version}/install.bat
+
+# Create zip package
+pushd /dist
+zip /jellyfin_${version}.portable.zip jellyfin_${version}
+popd
+rm -rf /dist/jellyfin_${version}
+
+# Move the artifacts out
+mkdir -p ${ARTIFACT_DIR}/
+mv /jellyfin[-_]*.zip ${ARTIFACT_DIR}/
+chown -Rc $(stat -c %u:%g ${ARTIFACT_DIR}) ${ARTIFACT_DIR}
diff --git a/deployment/win-x86/package.sh b/deployment/win-x86/package.sh
index a3d9fe2a8..65e7e2928 100755
--- a/deployment/win-x86/package.sh
+++ b/deployment/win-x86/package.sh
@@ -1,45 +1,34 @@
 #!/usr/bin/env bash
-package_win32() (
-    local NSSM_VERSION="nssm-2.24-101-g897c7ad"
-    local NSSM_URL="https://nssm.cc/ci/${NSSM_VERSION}.zip"
-    local FFMPEG_VERSION="ffmpeg-4.0.2-win32-static"
-    local FFMPEG_URL="https://ffmpeg.zeranoe.com/builds/win32/static/${FFMPEG_VERSION}.zip"
-    local ROOT=${1-$DEFAULT_ROOT}
-    local OUTPUT_DIR=${2-$DEFAULT_OUTPUT_DIR}
-    local PKG_DIR=${3-$DEFAULT_PKG_DIR}
-    local ARCHIVE_CMD="zip -r"
-    # Package portable build result
-    if [ -d ${OUTPUT_DIR} ]; then      
-        echo -e "${CYAN}Packaging build in '${OUTPUT_DIR}' for `basename "${OUTPUT_DIR}"` to '${PKG_DIR}' with root '${ROOT}'.${NC}"
-        local TEMP_DIR="$(mktemp -d)" 
-        wget ${NSSM_URL} -O ${TEMP_DIR}/nssm.zip
-        wget ${FFMPEG_URL} -O ${TEMP_DIR}/ffmpeg.zip
-        unzip ${TEMP_DIR}/nssm.zip -d $TEMP_DIR
-        cp ${TEMP_DIR}/${NSSM_VERSION}/win32/nssm.exe ${OUTPUT_DIR}/nssm.exe
-        unzip ${TEMP_DIR}/ffmpeg.zip -d $TEMP_DIR
-        cp ${TEMP_DIR}/${FFMPEG_VERSION}/bin/ffmpeg.exe ${OUTPUT_DIR}/ffmpeg.exe
-        cp ${TEMP_DIR}/${FFMPEG_VERSION}/bin/ffprobe.exe ${OUTPUT_DIR}/ffprobe.exe
-        rm -r ${TEMP_DIR}
-        cp ${ROOT}/deployment/windows/legacy/install-jellyfin.ps1 ${OUTPUT_DIR}/install-jellyfin.ps1
-        cp ${ROOT}/deployment/windows/legacy/install.bat ${OUTPUT_DIR}/install.bat
-        mkdir -p ${PKG_DIR}
-        pushd ${OUTPUT_DIR} 
-        ${ARCHIVE_CMD} ${ROOT}/${PKG_DIR}/`basename "${OUTPUT_DIR}"`.zip .
-        popd
-        local EXIT_CODE=$?
-        if [ $EXIT_CODE -eq 0 ]; then
-            echo -e "${GREEN}[DONE] Packaging build in '${OUTPUT_DIR}' for `basename "${OUTPUT_DIR}"` to '${PKG_DIR}' with root '${ROOT}' complete.${NC}"
-        else
-            echo -e "${RED}[FAIL] Packaging build in '${OUTPUT_DIR}' for `basename "${OUTPUT_DIR}"` to '${PKG_DIR}' with root '${ROOT}' FAILED.${NC}"
-        fi       
-    else
-        echo -e "${RED}[FAIL] Build artifacts do not exist for ${OUTPUT_DIR}. Run build.sh first.${NC}"
-    fi
-)
-source ../common.build.sh
 
-VERSION=`get_version ../..`
+args="${@}"
+declare -a docker_envvars
+for arg in ${args}; do
+    docker_envvars+=("-e ${arg}")
+done
 
-package_win32 ../.. `pwd`/dist/jellyfin_${VERSION}
+WORKDIR="$( pwd )"
 
-#TODO setup and maybe change above code to produce the Windows native zip format.
+package_temporary_dir="${WORKDIR}/pkg-dist-tmp"
+output_dir="${WORKDIR}/pkg-dist"
+current_user="$( whoami )"
+image_name="jellyfin-windows-x86-build"
+
+# Determine if sudo should be used for Docker
+if [[ ! -z $(id -Gn | grep -q 'docker') ]] \
+  && [[ ! ${EUID:-1000} -eq 0 ]] \
+  && [[ ! ${USER} == "root" ]] \
+  && [[ ! -z $( echo "${OSTYPE}" | grep -q "darwin" ) ]]; then
+    docker_sudo="sudo"
+else
+    docker_sudo=""
+fi
+
+# Prepare temporary package dir
+mkdir -p "${package_temporary_dir}"
+# Set up the build environment Docker image
+${docker_sudo} docker build ../.. -t "${image_name}" -f ./Dockerfile
+# Build the DEBs and copy out to ${package_temporary_dir}
+${docker_sudo} docker run --rm -v "${package_temporary_dir}:/dist" "${image_name}" ${docker_envvars}
+# Move the DEBs to the output directory
+mkdir -p "${output_dir}"
+mv "${package_temporary_dir}"/* "${output_dir}"