From 762b2b0a5c72f008f8f2a2f5b2882b618a0447f8 Mon Sep 17 00:00:00 2001
From: Craig Jennings <c@cjennings.net>
Date: Wed, 13 May 2026 15:38:41 -0500
Subject: build(deps): install pdftools so every project can edit PDFs

poppler (pdftoppm/pdftotext) plus a dedicated Python venv at ~/.local/venvs/pdftools with pypdf, reportlab, and pillow. Every project session can now stamp checkboxes, dates, and text overlays onto flattened PDFs through that venv, without each project re-wiring the toolchain.

The package name for poppler diverges across distros (poppler-utils on Debian/Ubuntu, poppler on Arch and Homebrew), so the install branch handles each manager inline rather than going through install_pkg. PDFTOOLS_VENV is overridable via env if a machine needs a different path.
---
 Makefile | 21 ++++++++++++++++++++-
 1 file changed, 20 insertions(+), 1 deletion(-)

diff --git a/Makefile b/Makefile
index c0e27be..38d5151 100644
--- a/Makefile
+++ b/Makefile
@@ -14,6 +14,7 @@ OPTIN_HOOKS   := hooks/destructive-bash-confirm.py
 DEFAULT_HOOKS := $(filter-out $(OPTIN_HOOKS),$(HOOKS))
 CLAUDE_CONFIG := $(wildcard .claude/*.json) $(wildcard .claude/.*.json)
 LANGUAGES     := $(notdir $(wildcard languages/*))
+PDFTOOLS_VENV ?= $(HOME)/.local/venvs/pdftools
 
 # LANG is also the standard POSIX locale env var. Make inherits env vars into
 # its variable namespace, so $(LANG) would silently expand to "en_US.UTF-8" (or
@@ -74,7 +75,7 @@ help: ## Show this help
 
 ##@ Dependencies
 
-deps: ## Install required tools (claude, node, jq, fzf, ripgrep, emacs, playwright)
+deps: ## Install required tools (claude, node, jq, fzf, ripgrep, emacs, playwright, pdftools)
 	@echo "Checking dependencies..."
 	@command -v claude >/dev/null 2>&1 && echo "  claude:     installed" || \
 		{ echo "  claude:     installing via npm..."; npm install -g @anthropic-ai/claude-code; }
@@ -99,6 +100,24 @@ deps: ## Install required tools (claude, node, jq, fzf, ripgrep, emacs, playwrig
 		&& uv run --quiet --with textstat python -c "" >/dev/null 2>&1 \
 		&& echo "  textstat:   cached (scripts/readability)" \
 		|| echo "  textstat:   skipped (uv missing or offline)"
+	@# pdftools: poppler (pdftoppm for coordinate-finding) plus a venv with
+	@# pypdf/reportlab/pillow for overlay/stamp edits on flattened PDFs —
+	@# the use case is court forms and the like with no AcroForm fields.
+	@command -v pdftoppm >/dev/null 2>&1 && echo "  poppler:    installed" || { \
+		echo "  poppler:    installing..."; \
+		if command -v brew >/dev/null 2>&1; then brew install poppler; \
+		elif command -v apt-get >/dev/null 2>&1; then sudo apt-get install -y poppler-utils; \
+		elif command -v pacman >/dev/null 2>&1; then sudo pacman -S --noconfirm poppler; \
+		else echo "  poppler:    ERROR — no supported package manager (brew/apt-get/pacman)"; exit 1; \
+		fi; \
+	}
+	@if [ -d "$(PDFTOOLS_VENV)" ]; then \
+		echo "  pdftools:   installed ($(PDFTOOLS_VENV))"; \
+	else \
+		echo "  pdftools:   creating venv + installing pypdf/reportlab/pillow..."; \
+		python3 -m venv "$(PDFTOOLS_VENV)"; \
+		"$(PDFTOOLS_VENV)/bin/pip" install --quiet --upgrade pip pypdf reportlab pillow; \
+	fi
 	@if [ -d "$(CURDIR)/playwright-js" ]; then \
 		if [ -d "$(CURDIR)/playwright-js/node_modules/playwright" ]; then \
 			echo "  playwright (js):  installed (skill node_modules present)"; \
-- 
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