diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index e76c2915959..c9a845c0320 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -761,31 +761,35 @@ jobs:
     vmImage: 'ubuntu-20.04'
   strategy:
     matrix:
+      # https://wiki.ubuntu.com/Releases
       Xenial:
+        # 16.04
         deb_system: ubuntu
         distro: xenial
-      Trusty:
-        deb_system: ubuntu
-        distro: trusty
       Bionic:
+        # 18.04
         deb_system: ubuntu
         distro: bionic
       Focal:
+        # 20.04
         deb_system: ubuntu
         distro: focal
       Hirsute:
+        # 21.04
         deb_system: ubuntu
         distro: hirsute
-      Jessie:
-        deb_system: debian
-        distro: jessie
+
+      # https://wiki.debian.org/DebianReleases
       Stretch:
+        # 9
         deb_system: debian
         distro: stretch
       Buster:
+        # 10
         deb_system: debian
         distro: buster
       Bullseye:
+        # 11
         deb_system: debian
         distro: bullseye
   steps:
diff --git a/scripts/release/debian/Dockerfile b/scripts/release/debian/Dockerfile
index 6fd8d9d2b20..a3818d8839c 100644
--- a/scripts/release/debian/Dockerfile
+++ b/scripts/release/debian/Dockerfile
@@ -6,7 +6,7 @@ RUN apt-get update
 RUN apt-get install -y libssl-dev libffi-dev python3-dev debhelper zlib1g-dev wget
 
 # Download Python source code
-ARG python_version="3.6.10"
+ARG python_version="3.8.12"
 ENV PYTHON_SRC_DIR=/usr/src/python
 RUN mkdir -p ${PYTHON_SRC_DIR} && \
     wget -qO- https://www.python.org/ftp/python/${python_version}/Python-${python_version}.tgz \
diff --git a/scripts/release/debian/build.sh b/scripts/release/debian/build.sh
index 1c3530afba4..f5a321152e2 100755
--- a/scripts/release/debian/build.sh
+++ b/scripts/release/debian/build.sh
@@ -15,12 +15,13 @@ set -exv
 ls -Rl /mnt/artifacts
 
 WORKDIR=`cd $(dirname $0); cd ../../../; pwd`
-PYTHON_VERSION="3.6.10"
+PYTHON_VERSION="3.8.12"
 SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
 
 # Update APT packages
 apt-get update
-apt-get install -y libssl-dev libffi-dev python3-dev debhelper zlib1g-dev
+# uuid-dev is used to build _uuid module: https://github.com/python/cpython/pull/3796
+apt-get install -y libssl-dev libffi-dev python3-dev debhelper zlib1g-dev uuid-dev
 apt-get install -y wget
 
 # Download Python source code
@@ -33,7 +34,7 @@ $PYTHON_SRC_DIR/*/configure --srcdir $PYTHON_SRC_DIR/* --prefix $WORKDIR/python_
 make
 make install
 
-$WORKDIR/python_env/bin/python3 -m pip install --upgrade pip==21.0.1
+$WORKDIR/python_env/bin/python3 -m pip install --upgrade pip
 
 export PATH=$PATH:$WORKDIR/python_env/bin
 
diff --git a/scripts/release/debian/prepare.sh b/scripts/release/debian/prepare.sh
index c35181a5704..714eef29d1b 100755
--- a/scripts/release/debian/prepare.sh
+++ b/scripts/release/debian/prepare.sh
@@ -78,7 +78,7 @@ Azure CLI
 
 Copyright (c) Microsoft Corporation
 
-All rights reserved. 
+All rights reserved.
 
 MIT License
 
@@ -90,7 +90,7 @@ THE SOFTWARE IS PROVIDED *AS IS*, WITHOUT WARRANTY OF ANY KIND, EXPRESS OR IMPLI
 
 EOM
 
-# TODO: Instead of "_ssl.cpython-36m-x86_64-linux-gnu.so" only, find all .so files with "find debian/azure-cli/opt/az -type f -name '*.so'"
+# TODO: Instead of "_ssl.cpython-38-x86_64-linux-gnu.so" only, find all .so files with "find debian/azure-cli/opt/az -type f -name '*.so'"
 
 cat > $debian_dir/rules << EOM
 #!/usr/bin/make -f
@@ -110,7 +110,7 @@ ${TAB}echo "\043!/usr/bin/env bash\nbin_dir=\140cd \"\044(dirname \"\044BASH_SOU
 ${TAB}chmod 0755 debian/azure-cli/usr/bin/az
 ${TAB}mkdir -p debian/azure-cli/etc/bash_completion.d/
 ${TAB}cat ${completion_script} > debian/azure-cli/etc/bash_completion.d/azure-cli
-${TAB}dpkg-shlibdeps -v --warnings=7 -Tdebian/azure-cli.substvars -dDepends -edebian/azure-cli/opt/az/bin/python3 debian/azure-cli/opt/az/lib/python3.6/lib-dynload/_ssl.cpython-36m-x86_64-linux-gnu.so
+${TAB}dpkg-shlibdeps -v --warnings=7 -Tdebian/azure-cli.substvars -dDepends -edebian/azure-cli/opt/az/bin/python3 debian/azure-cli/opt/az/lib/python3.8/lib-dynload/_ssl.cpython-38-x86_64-linux-gnu.so
 
 
 override_dh_strip:
diff --git a/scripts/release/debian/test_deb_package.py b/scripts/release/debian/test_deb_package.py
index add6309a1cd..c861f648ace 100644
--- a/scripts/release/debian/test_deb_package.py
+++ b/scripts/release/debian/test_deb_package.py
@@ -7,7 +7,7 @@
 import sys
 import subprocess
 
-root_dir = '/opt/az/lib/python3.6/site-packages/azure/cli/command_modules'
+root_dir = '/opt/az/lib/python3.8/site-packages/azure/cli/command_modules'
 mod_list = [mod for mod in sorted(os.listdir(root_dir)) if os.path.isdir(os.path.join(root_dir, mod)) and mod != '__pycache__']
 
 pytest_base_cmd = '/opt/az/bin/python3 -m pytest -x -v --boxed -p no:warnings --log-level=WARN'