diff --git a/nix/dev-shell.nix b/nix/dev-shell.nix
--- a/nix/dev-shell.nix
+++ b/nix/dev-shell.nix
@@ -137,6 +137,8 @@
     wait "$mariadb_pid" "$redis_pid"
 
     ${../scripts}/install_homebrew_macos.sh
+
+    ${../scripts}/prompt_direnv_macos.sh
   '' + ''
 
     # Render default configuration for keyserver
diff --git a/scripts/prompt_direnv_macos.sh b/scripts/prompt_direnv_macos.sh
new file mode 100755
--- /dev/null
+++ b/scripts/prompt_direnv_macos.sh
@@ -0,0 +1,80 @@
+#!/usr/bin/env bash
+
+set -euo pipefail
+set -x
+
+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 "$PS1" ]]; then
+  return 0
+fi
+
+if [[ ! -e "${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