diff --git a/.envrc b/.envrc
index 75b29ed44ada29..2a6c34a1bf3b44 100644
--- a/.envrc
+++ b/.envrc
@@ -3,18 +3,13 @@
 # initialization (e.g. activating the venv) or giving recommendations on how to reach the desired state.
 # It also sets useful environment variables.
 # If you'd like to override or set any custom environment variables, this .envrc will read a .env file at the end.
-
 set -e
-HERE="$(
+SENTRY_ROOT="$(
     cd "$(dirname "${BASH_SOURCE[0]}")"
     pwd -P
 )"
 
-bold="$(tput bold)"
-red="$(tput setaf 1)"
-green="$(tput setaf 2)"
-yellow="$(tput setaf 3)"
-reset="$(tput sgr0)"
+source "${SENTRY_ROOT}/scripts/lib.sh"
 
 # XXX: we can't trap bash EXIT, because it'll override direnv's finalizing routines.
 #      consequently, using "exit" anywhere will skip this notice from showing.
@@ -58,10 +53,6 @@ report_to_sentry() {
     rm "$_SENTRY_LOG_FILE"
 }
 
-require() {
-    command -v "$1" >/dev/null 2>&1
-}
-
 debug() {
     if [ "${SENTRY_DIRENV_DEBUG}" ]; then
         echo -e "${@}"
@@ -86,6 +77,27 @@ die() {
     return 1
 }
 
+prompt_python_venv_creation() {
+    echo -e "${yellow}You are missing a Python virtualenv and we ${bold}need${reset}${yellow} to run a bootstrapping script (it can take a few minutes)"
+    info "About to create ${venv_name}..."
+    echo -e "\nContinue (y/N)?"
+    read -r resp
+    case "$resp" in
+    y | Y) echo "Okay, let's do this." ;;
+    *)
+        die "Aborted!"
+        ;;
+    esac
+}
+
+show_commands_info() {
+    echo -e "\n${red}Run the following commands to bring your environment up-to-date:"
+    for cmd in "${commands_to_run[@]}"; do
+        warn "    ${red}$cmd"
+    done
+    echo ""
+}
+
 ### Environment ###
 
 commands_to_run=()
@@ -111,9 +123,9 @@ export SENTRY_UI_HOT_RELOAD=1
 
 ### You can override the exported variables with a .env file
 # All exports should happen before here unless they're safeguarded (see devenv error reporting below)
-if [ -f "${HERE}/.env" ]; then
-    debug "Loading variables from ${HERE}/.env"
-    dotenv "${HERE}/.env"
+if [ -f "${SENTRY_ROOT}/.env" ]; then
+    info "Loading variables from ${SENTRY_ROOT}/.env"
+    dotenv "${SENTRY_ROOT}/.env"
 fi
 
 ## Notify of reporting to Sentry
@@ -156,15 +168,7 @@ make setup-git-config
 venv_name=".venv"
 
 if [ ! -f "${venv_name}/bin/activate" ]; then
-    warn "You are missing a Python virtualenv and we ${bold}need${reset} to run a bootstrapping script (it can take a few minutes)"
-    echo -e "\nContinue (y/N)?"
-    read -r resp
-    case "$resp" in
-    y | Y) echo "Okay, let's do this." ;;
-    *)
-        die "Aborted!"
-        ;;
-    esac
+    prompt_python_venv_creation
     # This is time consuming but it has to be done
     source ./scripts/bootstrap-py3-venv
 fi
@@ -181,7 +185,7 @@ source "${venv_name}/bin/activate"
 unset PS1
 
 debug "Ensuring proper virtualenv..."
-"${HERE}/scripts/ensure-venv.sh"
+"${SENTRY_ROOT}/scripts/ensure-venv.sh"
 
 if ! require sentry; then
     warn "Your virtualenv is activated, but sentry doesn't seem to be installed."
@@ -216,11 +220,7 @@ PATH_add node_modules/.bin
 
 # These are commands that can take a significant amount of time
 if [ ${#commands_to_run[@]} -ne 0 ]; then
-    echo -e "\n${red}Run the following commands to bring your environment up-to-date:"
-    for cmd in "${commands_to_run[@]}"; do
-        warn "    ${red}$cmd"
-    done
-    echo ""
+    show_commands_info
 fi
 
 if [ "${log_level}" != "info" ]; then
diff --git a/.github/actions/setup-python/action.yml b/.github/actions/setup-python/action.yml
index 24837ef5650d66..abd0e2f9789766 100644
--- a/.github/actions/setup-python/action.yml
+++ b/.github/actions/setup-python/action.yml
@@ -16,7 +16,7 @@ inputs:
     description: 'pip cache version in order to bust cache'
     required: false
   python-version:
-    description: "python version to install"
+    description: 'python version to install'
     required: false
 
 outputs:
@@ -38,7 +38,7 @@ runs:
       shell: bash
       run: |
         if [ "${{ inputs.python-version }}" == "" ]; then
-          echo "::set-output name=python-version::$(cat .python-version)"
+          echo "::set-output name=python-version::$(SENTRY_NO_VENV_CHECK=1 ./scripts/do.sh get-pyenv-version)"
         else
           echo "::set-output name=python-version::${{ inputs.python-version }}"
         fi
diff --git a/.github/workflows/development-environment.yml b/.github/workflows/development-environment.yml
index 8e8c2dc58ce13c..00fb6bd36fdb31 100644
--- a/.github/workflows/development-environment.yml
+++ b/.github/workflows/development-environment.yml
@@ -2,13 +2,13 @@ name: dev env
 on:
   pull_request:
     paths:
-    - 'Makefile'
-    - '.github/workflows/development-environment.yml'
-    - '.envrc'
-    - 'Brewfile'
-    - 'scripts/*'
-    - 'src/sentry/runner/commands/devserver.py'
-    - 'src/sentry/runner/commands/devservices.py'
+      - 'Makefile'
+      - '.github/workflows/development-environment.yml'
+      - '.envrc'
+      - 'Brewfile'
+      - 'scripts/*'
+      - 'src/sentry/runner/commands/devserver.py'
+      - 'src/sentry/runner/commands/devservices.py'
 
 jobs:
   dev-environment:
@@ -20,7 +20,7 @@ jobs:
         # macosx-11.0 is Big Sur, however, it takes long for jobs to get started
         # Using Ubuntu 18 until I figure out this error:
         # -> ImportError: libffi.so.6: cannot open shared object file: No such file or directory
-        os: [ macos-11.0, ubuntu-18.04 ]
+        os: [macos-11.0, ubuntu-18.04]
       fail-fast: false
     env:
       PIP_DISABLE_PIP_VERSION_CHECK: on
@@ -36,7 +36,7 @@ jobs:
         # Sometimes, brew needs to be updated before brew bundle would work
         # After installing Docker (via homebrew) we need to make sure that it is properly initialized on Mac
         run: |
-          brew update -q && brew bundle -q
+          brew update && brew bundle -q
           # This code is mentioned in our dev docs. Only remove if you adjust the docs as well
           SENTRY_NO_VENV_CHECK=1 ./scripts/do.sh init-docker
 
@@ -44,7 +44,7 @@ jobs:
       - name: Set environment variables & others
         id: info
         run: |
-          echo "::set-output name=python-version::$(cat .python-version)"
+          echo "::set-output name=python-version::$(SENTRY_NO_VENV_CHECK=1 ./scripts/do.sh get-pyenv-version)"
           echo "::set-output name=pip-cache-dir::$(pip3 cache dir)"
           echo "::set-output name=pip-version::$(pip -V | awk -F ' ' '{print $2}')"
           echo "::set-output name=yarn-cache-dir::$(yarn cache dir)"
diff --git a/.github/workflows/python-deps.yml b/.github/workflows/python-deps.yml
index 9ccbb822c948dd..654d9b8a3c7a28 100644
--- a/.github/workflows/python-deps.yml
+++ b/.github/workflows/python-deps.yml
@@ -2,8 +2,8 @@ name: python deps
 on:
   pull_request:
     paths:
-    - '.github/workflows/python-deps.yml'
-    - 'requirements*'
+      - '.github/workflows/python-deps.yml'
+      - 'requirements*'
 
 jobs:
   # This workflow makes sure that Python dependencies install correctly for
@@ -14,8 +14,8 @@ jobs:
     timeout-minutes: 20
     strategy:
       matrix:
-        os: [ macos-11.0, ubuntu-20.04 ]
-        python-version: [ 3.6.13, 3.8.10 ]
+        os: [macos-11.0, ubuntu-20.04]
+        python-version: [3.6.13, 3.8.11]
       fail-fast: false
     env:
       PIP_DISABLE_PIP_VERSION_CHECK: on
@@ -27,25 +27,16 @@ jobs:
       - uses: actions/checkout@v2
 
       - name: Install prerequisites
+        # Sometimes, brew needs to be updated before brew bundle would work
         run: |
-          HOMEBREW_NO_AUTO_UPDATE=1 brew bundle --no-upgrade
+          brew update && brew bundle -q
 
-      # Until GH composite actions can use `uses`, we need to setup python here
-      - uses: actions/setup-python@v2
+      - name: Setup python
+        id: setup-python
+        uses: ./.github/actions/setup-python
         with:
-          python-version: ${{ matrix.python-version }}
-
-      - name: Setup pip
-        uses: ./.github/actions/setup-pip
-        id: pip
-
-      - name: Cache
-        uses: actions/cache@v2
-        with:
-          path: |
-            ${{ steps.pip.outputs.pip-cache-dir }}
-          key: |
-            python-deps-${{ matrix.os }}-py${{ matrix.python-version }}-${{ hashFiles('requirements-*.txt') }}
+          # XXX: We need to pass this python-deps-${{ matrix.os }}-py${{ matrix.python-version }}-${{ hashFiles('requirements-*.txt') }}
+          cache-files-hash: ${{ hashFiles('requirements-*.txt') }}
 
       - name: Install dependencies
         run: |
diff --git a/.python-version b/.python-version
deleted file mode 100644
index 3609cf77078c22..00000000000000
--- a/.python-version
+++ /dev/null
@@ -1 +0,0 @@
-3.6.13
diff --git a/requirements-base.txt b/requirements-base.txt
index 485ef639a2f235..8013198faa7322 100644
--- a/requirements-base.txt
+++ b/requirements-base.txt
@@ -20,6 +20,9 @@ google-cloud-core==1.5.0
 googleapis-common-protos==1.52.0
 google-cloud-pubsub==2.2.0
 google-cloud-storage==1.35.0
+# Only necessary to prevent installing the latest version
+# https://github.com/googleapis/python-crc32c/issues/83
+google-crc32c==1.1.2; python_version == '3.8'
 jsonschema==3.2.0
 lxml==4.6.3
 maxminddb==2.0.3
diff --git a/scripts/bootstrap-py3-venv b/scripts/bootstrap-py3-venv
index f62ca0ea3f0ace..3b8f583e12fd5b 100644
--- a/scripts/bootstrap-py3-venv
+++ b/scripts/bootstrap-py3-venv
@@ -11,6 +11,11 @@
 # trap "echo 'bootstrap FAILED.' && trap - ERR && return" ERR
 
 # So just going to sprinkle returns everywhere.
+SCRIPTS_DIR="$(
+    cd "$(dirname "${BASH_SOURCE[0]}")"
+    pwd -P
+)"
+source "${SCRIPTS_DIR}/lib.sh"
 
 command -v pyenv >/dev/null || {
     echo "You need to install pyenv. https://develop.sentry.dev/environment/#python"
@@ -24,7 +29,10 @@ command -v direnv >/dev/null || {
 
 gitroot="$(git rev-parse --show-toplevel)"
 cd "$gitroot"
-export venv_name="${PWD}/.venv"
+# This executes very quickly if the Python versions are already installed
+make setup-pyenv
+export PYENV_VERSION=$(SENTRY_NO_VENV_CHECK=1 ./scripts/do.sh get-pyenv-version)
+venv_name="${PWD}/.venv"
 
 if [[ -f "${venv_name}/bin/activate" ]]; then
     prompt_text="You have an existing virtualenv. This script will OVERWRITE it. Continue (y/N)?"
@@ -40,9 +48,7 @@ fi
 deactivate 2>/dev/null || true
 rm -rf "$venv_name"
 
-# XXX: You'll also need to temporarily pyenv local "$SENTRY_PYTHON_VERSION"
-#      and then revert changes to the .python-version after bootstrap finishes.
-if [[ -z "$SENTRY_PYTHON_VERSION" ]] && ! [[ "$(python3 -V 2>&1)" = "Python $(grep "3.6" .python-version)" ]]; then
+if [[ -z "$SENTRY_PYTHON_VERSION" ]] && ! query-valid-python-version; then
     echo "Your python3 version isn't as expected. Please run: make setup-pyenv"
     return 1
 fi
@@ -50,7 +56,7 @@ fi
 python3 -m pip install -U pip           || { echo "bootstrap failed!"; return 1; }
 python3 -m venv "${venv_name}"          || { echo "bootstrap failed!"; return 1; }
 source "${venv_name}/bin/activate"      || { echo "bootstrap failed!"; return 1; }
-python3 -m pip install -U pip           || { echo "bootstrap failed!"; return 1; }
+python3 -m pip install -U pip wheel     || { echo "bootstrap failed!"; return 1; }
 make setup-git                          || { echo "bootstrap failed!"; return 1; }
 make install-py-dev                     || { echo "bootstrap failed!"; return 1; }
 deactivate                              || { echo "bootstrap failed!"; return 1; }
diff --git a/scripts/do.sh b/scripts/do.sh
index 734aa045b1dcac..9a2f20c744b0fb 100755
--- a/scripts/do.sh
+++ b/scripts/do.sh
@@ -2,8 +2,10 @@
 # This script is an interface to any of the methods of lib.sh
 # Call this script as "do.sh method_from_lib" to execute any function from that library
 set -eu
-
-HERE="$(cd "$(dirname "${BASH_SOURCE[0]}")"; pwd -P)"
+HERE="$(
+    cd "$(dirname "${BASH_SOURCE[0]}")"
+    pwd -P
+)"
 # shellcheck disable=SC1090
 source "${HERE}/lib.sh"
 
diff --git a/scripts/ensure-venv.sh b/scripts/ensure-venv.sh
index 92e33c392e5c67..8a0800eb9c19ba 100755
--- a/scripts/ensure-venv.sh
+++ b/scripts/ensure-venv.sh
@@ -1,4 +1,10 @@
 #!/bin/bash
+HERE="$(
+    cd "$(dirname "${BASH_SOURCE[0]}")" || exit
+    pwd -P
+)"
+# shellcheck disable=SC1090
+source "${HERE}/lib.sh"
 
 # optionally opt out of virtualenv creation
 # WARNING: this will be removed (most likely renamed) soon!
@@ -6,11 +12,6 @@ if [[ "$SENTRY_NO_VIRTUALENV_CREATION" == "1" ]]; then
     exit 0
 fi
 
-red="$(tput setaf 1)"
-yellow="$(tput setaf 3)"
-bold="$(tput bold)"
-reset="$(tput sgr0)"
-
 venv_name=".venv"
 
 die() {
@@ -21,33 +22,31 @@ EOF
 }
 
 if [[ -n "$VIRTUAL_ENV" ]]; then
-    minor=$(python -c "import sys; print(sys.version_info[1])")
-    # If .venv is less than Python 3.6 fail
-    [[ "$minor" -lt 6 ]] &&
-        die "Remove $VIRTUAL_ENV and try again since the Python version installed should be at least 3.6."
-    # If .venv is created with Python greater than 3.6 you might encounter problems and we want to ask you to downgrade
-    # unless you explicitely set an environment variable
-    if [[ "$minor" -gt 6 ]]; then
-        if [[ -n "$SENTRY_PYTHON_VERSION" ]]; then
-            cat <<EOF
+    # The developer is inside a virtualenv *and* has set a SENTRY_PYTHON_VERSION
+    # Let's assume that they know what they're doing
+    if [[ -n "$SENTRY_PYTHON_VERSION" ]]; then
+        cat <<EOF
 ${yellow}${bold}
-You have explicitly set a non-recommended Python version (${SENTRY_PYTHON_VERSION}). You're on your own.
+You have explicitly set a non-recommended Python version ($(python -V | awk '{print $2}')). You're on your own.
 ${reset}
 EOF
-        else
-            cat <<EOF
-${red}${bold}
-ERROR! You are running a virtualenv with a Python version different than 3.6
-We recommend you start with a fresh virtualenv or to set the variable SENTRY_PYTHON_VERSION
-to the Python version you want to use (e.g. 3.7).
-${reset}
+        exit 0
+    fi
+
+    # Let's make sure they know that they're not using a different version by mistake
+
+    if ! query-valid-python-version; then
+        cat <<EOF
+    ${yellow}${bold}
+    WARNING! You are running a virtualenv with a Python version ($(which python))
+    different than 3.6.13 or 3.8.11. We recommend you start with a fresh virtualenv OR"
+    use SENTRY_PYTHON_VERSION to by-pass this check.
+    ${reset}
 EOF
-            exit 1
-        fi
     fi
 else
     if [[ ! -f "${venv_name}/bin/activate" ]]; then
-        die "You don't seem to have a virtualenv. Please create one by running: python3.6 -m venv ${venv_name}"
+        die "You don't seem to have a virtualenv. Please create one by running: source ./scripts/bootstrap-py3-venv"
     fi
     die "You have a virtualenv, but it doesn't seem to be activated. Please run: source ${venv_name}/bin/activate"
 fi
diff --git a/scripts/lib.sh b/scripts/lib.sh
index 41b2299fd83f88..c6c45e56270735 100755
--- a/scripts/lib.sh
+++ b/scripts/lib.sh
@@ -1,6 +1,16 @@
 #!/bin/bash
 # Module containing code shared across various shell scripts
 # Execute functions from this module via the script do.sh
+# shellcheck disable=SC2034 # Unused variables
+
+# This block is a safe-guard since in CI calling tput will fail and abort scripts
+if [ -z "${CI+x}" ]; then
+    bold="$(tput bold)"
+    red="$(tput setaf 1)"
+    green="$(tput setaf 2)"
+    yellow="$(tput setaf 3)"
+    reset="$(tput sgr0)"
+fi
 
 # NOTE: This file is sourced in CI across different repos (e.g. snuba),
 # so renaming this file or any functions can break CI!
@@ -23,13 +33,35 @@ query-mac() {
     [[ $(uname -s) = 'Darwin' ]]
 }
 
-query_big_sur() {
+query-big-sur() {
     if require sw_vers && sw_vers -productVersion | grep -E "11\." >/dev/null; then
         return 0
     fi
     return 1
 }
 
+query-apple-m1() {
+    query-mac && [[ $(uname -m) = 'arm64' ]]
+}
+
+get-pyenv-version() {
+    local PYENV_VERSION
+    PYENV_VERSION=3.6.13
+    if query-apple-m1; then
+        PYENV_VERSION=3.8.11
+    fi
+    echo "${PYENV_VERSION}"
+}
+
+query-valid-python-version() {
+    python_version=$(python3 -V 2>&1 | awk '{print $2}')
+    if [ "${python_version}" == 3.6.13 ] || [ "${python_version}" == 3.8.11 ]; then
+        return 0
+    else
+        return 1
+    fi
+}
+
 sudo-askpass() {
     if [ -z "${sudo-askpass-x}" ]; then
         sudo --askpass "$@"
diff --git a/scripts/pyenv_setup.sh b/scripts/pyenv_setup.sh
index db8975d39a7091..7743fd7e0ad983 100755
--- a/scripts/pyenv_setup.sh
+++ b/scripts/pyenv_setup.sh
@@ -3,15 +3,20 @@
 #
 # Assumptions:
 # - This script assumes you're calling from the top directory of the repository
+#
+# shellcheck disable=SC2155 # Declare and assign separately to avoid masking return values.
+
 set -eu
 
 HERE="$(
   cd "$(dirname "${BASH_SOURCE[0]}")"
   pwd -P
 )"
-# shellcheck disable=SC1090
 source "${HERE}/lib.sh"
 
+# We can use PYENV_VERSION to define different Python versions, otherwise, determine load default values
+[ -z ${PYENV_VERSION+x} ] && export PYENV_VERSION=$(get-pyenv-version)
+
 get_shell_startup_script() {
   local _startup_script=''
   if [[ -n "$SHELL" ]]; then
@@ -44,7 +49,8 @@ _append_to_startup_script() {
     case "$SHELL" in
     */bash)
       # shellcheck disable=SC2016
-      echo "Visit https://github.com/pyenv/pyenv#installation on how to fully set up your Bash shell.";;
+      echo "Visit https://github.com/pyenv/pyenv#installation on how to fully set up your Bash shell."
+      ;;
     */zsh)
       # shellcheck disable=SC2016
       echo -e '# It is assumed that pyenv is installed via Brew, so this is all we need to do.\n' \
@@ -52,7 +58,7 @@ _append_to_startup_script() {
       ;;
     */fish)
       # shellcheck disable=SC2016
-      echo -e '\n# pyenv init\nstatus is-login; and pyenv init --path | source' >> "${1}"
+      echo -e '\n# pyenv init\nstatus is-login; and pyenv init --path | source' >>"${1}"
       ;;
     esac
 
@@ -78,12 +84,8 @@ append_to_config() {
 
 install_pyenv() {
   if require pyenv; then
-    echo "Installing Python (if missing) via pyenv"
-    local pyenv_version
-    pyenv_version=$(pyenv -v | awk '{print $2}')
-    python_version=$(xargs -n1 <.python-version)
     # NOTE: We're dropping support for older pyenv versions
-    if [[ "$pyenv_version" < 2.0.0 ]]; then
+    if [[ "$(pyenv -v | awk '{print $2}')" < 2.0.0 ]]; then
       echo >&2 "!!! We've dropped support for pyenv v1." \
         "Run the following (this is slow) and try again."
       # brew upgrade does not quite do the right thing
@@ -92,14 +94,16 @@ install_pyenv() {
       exit 1
     fi
 
-    # We need to patch the source code on Big Sur before building Python
-    # We can remove this once we upgrade to newer versions of Python
-    if query_big_sur; then
+    if query-apple-m1; then
+      pyenv install --skip-existing "${PYENV_VERSION}"
+    elif query-big-sur; then
+      # We need to patch the source code on Big Sur before building Python
+      # We can remove this once we upgrade to newer versions of Python
       # cat is used since pyenv would finish to soon when the Python version is already installed
       curl -sSL https://github.com/python/cpython/commit/8ea6353.patch | cat |
-        pyenv install --skip-existing --patch "$python_version"
+        pyenv install --skip-existing --patch "${PYENV_VERSION}"
     else
-      pyenv install --skip-existing "$python_version"
+      pyenv install --skip-existing "${PYENV_VERSION}"
     fi
   else
     echo >&2 "!!! pyenv not found, try running bootstrap script again or run \`brew bundle\` in the sentry repo"
@@ -111,16 +115,14 @@ install_pyenv() {
 setup_pyenv() {
   configure-sentry-cli
   install_pyenv
-  _startup_script=$(get_shell_startup_script)
-  append_to_config "$_startup_script"
+  append_to_config "$(get_shell_startup_script)"
 
   # If the script is called with the "dot space right" approach (. ./scripts/pyenv_setup.sh),
   # the effects of this will be persistent outside of this script
-  echo "Activating pyenv and validating Python version"
   # Sets up PATH for pyenv
   eval "$(pyenv init --path)"
   python_version=$(python -V | sed s/Python\ //g)
-  [[ $python_version == $(cat .python-version) ]] ||
+  [[ $python_version == "${PYENV_VERSION}" ]] ||
     (echo "Wrong Python version: $python_version. Please report in #discuss-dev-tooling" && exit 1)
 }