diff --git a/.changes/next-release/feature-Python-48862.json b/.changes/next-release/feature-Python-48862.json
new file mode 100644
index 000000000000..54b71a3dd84b
--- /dev/null
+++ b/.changes/next-release/feature-Python-48862.json
@@ -0,0 +1,5 @@
+{
+  "type": "feature",
+  "category": "Python",
+  "description": "Upgrade embedded Python version from Python 3.8 to Python 3.9. All standalone artifacts now run on Python 3.9.11."
+}
diff --git a/exe/assets/THIRD_PARTY_LICENSES b/exe/assets/THIRD_PARTY_LICENSES
index de2e2b0713d6..d6680435d0de 100644
--- a/exe/assets/THIRD_PARTY_LICENSES
+++ b/exe/assets/THIRD_PARTY_LICENSES
@@ -1263,7 +1263,7 @@ LICENSE ISSUES
 
 ------
 
-** Python 3.8.8; version 3.8.8 -- https://github.com/python/cpython/tree/v3.8.8
+** Python 3.9.11; version 3.9.11 -- https://github.com/python/cpython/tree/v3.9.11
 Copyright © 2001-2020 Python Software Foundation. All rights reserved.
 
 PYTHON SOFTWARE FOUNDATION LICENSE VERSION 2
diff --git a/exe/tests/install.bats b/exe/tests/install.bats
index 33f5e26b7a4d..71d340582659 100644
--- a/exe/tests/install.bats
+++ b/exe/tests/install.bats
@@ -42,7 +42,7 @@ create_exes() {
 }
 
 aws_version_output() {
-  echo "aws-cli/$1 Python/3.8.8 Darwin/17.7.0 botocore/1.12.48"
+  echo "aws-cli/$1 Python/3.9.11 Darwin/17.7.0 botocore/1.12.48"
 }
 
 run_install() {
diff --git a/scripts/install_deps.py b/scripts/install_deps.py
index baf7fc37f0cf..ee76c6e8c97a 100644
--- a/scripts/install_deps.py
+++ b/scripts/install_deps.py
@@ -3,7 +3,7 @@
 from utils import cd, bin_path, run, virtualenv_enabled
 
 INSTALL_ARGS = "--no-build-isolation --no-cache-dir --no-index "
-PINNED_PIP_VERSION = '20.0.2'
+PINNED_PIP_VERSION = '22.0.4'
 SETUP_DEPS = ("setuptools-", "setuptools_scm", "wheel")
 
 
diff --git a/tox.ini b/tox.ini
index 485762af80da..d5ed1f7bd4c2 100644
--- a/tox.ini
+++ b/tox.ini
@@ -10,7 +10,7 @@ commands =
 
 
 [testenv:exe]
-basepython = python3.8
+basepython = python3.9
 install_command =
     python -m pip install --no-build-isolation {opts} {packages}
 deps =
@@ -20,7 +20,7 @@ commands =
 
 
 [testenv:macpkg]
-basepython = python3.8
+basepython = python3.9
 install_command =
     python -m pip install --no-build-isolation  {opts} {packages}
 deps =
@@ -30,7 +30,7 @@ commands =
 
 
 [testenv:test-exe]
-basepython = python3.8
+basepython = python3.9
 install_command =
     python -m pip install --no-build-isolation  {opts} {packages}
 deps =
@@ -41,6 +41,6 @@ commands =
 
 
 [testenv:sign-exe]
-basepython = python3.8
+basepython = python3.9
 commands =
     {envpython} {toxinidir}/scripts/installers/sign-exe {posargs}