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 +1,59 @@
+#!/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
+
+
+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
+# shellcheck disable=SC2076
+if [[ "$(bash --version)" =~ "GNU bash, version 3.2" ]]; then
+  brew install bash
+fi
+
+# ~/.zshenv would be preferred location to install the hook, however, it
+# gets sourced before ~/.zprofile for login shells; and since
+# Homebrew asks you to install its hook in ~/.zprofile, we need to
+# follow the same convention.
+if [[ ! -e ~/.zprofile ]] \
+    || ! grep 'direnv hook zsh' ~/.zprofile >/dev/null; then
+  # shellcheck disable=SC2016
+  echo 'eval "$(direnv hook zsh)"' >> ~/.zprofile
+fi
+
+echo ""
+echo "Please open a new terminal window for direnv effects to apply" >&2
+echo ""
+echo "If you would prefer to use direnv with a shell other than zsh, please follow the instructions at https://direnv.net/docs/hook.html"
+echo ""