diff --git a/nix/dev-shell.nix b/nix/dev-shell.nix
index be0ec784e..a7cb3fb6f 100644
--- a/nix/dev-shell.nix
+++ b/nix/dev-shell.nix
@@ -1,153 +1,155 @@
 { mkShell
 , stdenv
 , lib
 , amqp-cpp
 , awscli2
 , arcanist
 , aws-sdk-cpp
 , better-prompt
 , boost
 , bundler
 , c-ares_cmake-config
 , cmake
 , cmake-format
 , cocoapods
 , corrosion
 , darwin
 , double-conversion
 , folly
 , fmt
 , glog
 , grpc
 , gtest
 , libiconv
 , libuv
 , localstack
 , mariadb
 , mariadb-up
 , nodejs-16_x-openssl_1_1
 , olm
 , openjdk11
 , openssl
 , pkg-config
 , protobuf_3_15_cmake
 , python3
 , rabbitmq-server
 , redis
 , redis-up
 , rustup
 , shellcheck
 , sqlite
 , terraform
 , watchman
 , rustfmt
 , yarn
 }:
 
 mkShell {
 
   # programs which are meant to be executed should go here
   nativeBuildInputs = [
     # generic development or tools
     arcanist
     awscli2
     shellcheck
     terraform
 
     # android
     openjdk11
 
     # node development
     mariadb
     nodejs-16_x-openssl_1_1
     yarn
     watchman # react native
     python3
     redis
 
     # native dependencies
     # C/CXX toolchains are already brought in with mkShell
     # Identity Service
     rustfmt
     rustup
 
     # Tunnelbroker + CMake
     amqp-cpp
     c-ares_cmake-config
     cmake
     cmake-format # linting
     libuv
     # Localstack is currently broken by partial update
     # See https://github.com/NixOS/nixpkgs/pull/197572
     #localstack
     pkg-config
     protobuf_3_15_cmake
     grpc
     rabbitmq-server # runtime service
   ] ++ lib.optionals stdenv.isDarwin [
     cocoapods # needed for ios
     bundler
   ];
 
   # include any libraries buildInputs
   buildInputs = [
     # protobuf exposes both a library and a command
     # thus should appear in both inputs
     protobuf_3_15_cmake
     aws-sdk-cpp # tunnelbroker
     corrosion # tunnelbroker
     double-conversion # tunnelbroker
     glog # tunnelbroker
     gtest # testing services
     folly # cpp tools
     fmt # needed for folly
     boost # needed for folly
     olm # needed for CryptoTools
     sqlite # needed for sqlite_orm
     openssl # needed for grpc
   ] ++ lib.optionals stdenv.isDarwin (with darwin.apple_sdk.frameworks; [
     CoreFoundation
     CoreServices
     Security
     libiconv  # identity service
   ]);
 
   JAVA_HOME = openjdk11.passthru.home;
 
   # shell commands to be ran upon entering shell
   shellHook = ''
     PRJ_ROOT=$(git rev-parse --show-toplevel)
 
     # Set development environment variable defaults
     source "${../scripts/source_development_defaults.sh}"
 
     # Cache development path for some use cases such as XCode
     "$PRJ_ROOT/scripts/save_path.sh"
 
   ''
   # Darwin condition can be removed once linux services are supported
   + lib.optionalString stdenv.isDarwin ''
     # Start MariaDB development services
     "${mariadb-up}"/bin/mariadb-up &
     mariadb_pid=$!
 
     "${redis-up}"/bin/redis-up &
     redis_pid=$!
 
     wait "$mariadb_pid" "$redis_pid"
 
     ${../scripts}/install_homebrew_macos.sh
+
+    ${../scripts}/prompt_direnv_macos.sh
   '' + ''
 
     # Render default configuration for keyserver
     $PRJ_ROOT/scripts/create_url_facts.sh
 
     # Ensure rustup tooling is installed
     $PRJ_ROOT/scripts/ensure_rustup_setup.sh
 
     # Provide decent bash prompt
     source "${better-prompt}/bin/better-prompt"
 
     echo "Welcome to Comm dev environment! :)"
   '';
 }
diff --git a/scripts/prompt_direnv_macos.sh b/scripts/prompt_direnv_macos.sh
new file mode 100755
index 000000000..ec2a2ee1a
--- /dev/null
+++ b/scripts/prompt_direnv_macos.sh
@@ -0,0 +1,79 @@
+#!/usr/bin/env bash
+
+set -euo pipefail
+
+COMM_CACHE="${XDG_CACHE_HOME:-$HOME/Library/Caches}/app.comm"
+mkdir -p "$COMM_CACHE"
+COMM_DIRENV="$COMM_CACHE/install-direnv"
+
+if command -v direnv >/dev/null || [[ -s "$COMM_DIRENV" ]]; then
+  # Already using direnv or anwsered no previously. Exit immediately.
+  exit 0
+fi
+
+# Currently, this script only works on macOS as it assumes homebrew usage
+if ! [[ "$OSTYPE" == 'darwin'* ]]; then
+  echo "This script is only meant to be ran on macOS" >&2
+  exit 1
+fi
+
+# Check if in an interactive shell
+# `test -t` tests if a file descriptor is open, 0 being stdin
+# Normally, a non-interactive shell will not have 0 FD bound
+# However, Buildkite still has 0 FD bound, so check if PS1 is empty
+if [[ ! -t 0 ]] || [[ -z "$PS1" ]]; then
+  exit 0
+fi
+
+if [[ ! -e "${COMM_DIRENV}" ]]; then
+  echo "Direnv is a tool which will automatically setup the development environment upon entering the comm/ directory."
+  read -r \
+    -p "Would you like to install direnv? [y/N]" \
+    response
+  case "$response" in
+    [yY][eE][sS]|[yY])
+      echo "1" > "${COMM_DIRENV}"
+      ;;
+    *)
+      touch "${COMM_DIRENV}"
+      exit 1
+      ;;
+  esac
+fi
+
+brew install direnv
+
+# A more recent version of bash is required for nix-direnv to work correctly
+# Default version on macOS is bash 3.2. Output taken from '/bin/bash --version'
+# shellcheck disable=SC2076
+if [[ "$(bash --version)" =~ "GNU bash, version 3.2" ]]; then
+  brew install bash
+fi
+
+# Install the hook for a given shell in the related file.
+install_direnv_hook() {
+  local shell="$1"
+  local source_file="$2"
+
+  # Skip hook installation of shells which don't exist
+  if ! command -v "$shell" >/dev/null; then
+    return 0
+  fi
+
+  # If the file already mentions direnv, then hook is likely already installed
+  if [[ ! -e "$source_file" ]] \
+      || ! grep "direnv" "$source_file" >/dev/null; then
+    # shellcheck disable=SC2016
+    echo "eval \"\$(direnv hook $shell)\"" >> "$source_file"
+  fi
+
+}
+
+# ~/.zshenv would be preferred location to install the hook, however, it
+# gets sourced before ~/.zprofile for login shells; and since
+# Homebrew asks you to install its hook in ~/.zprofile, we need to
+# follow the same convention.
+install_direnv_hook zsh ~/.zprofile
+install_direnv_hook zsh ~/.zshrc
+install_direnv_hook bash ~/.bash_profile
+install_direnv_hook bash ~/.bashrc