Batch-convert a folder of Word and PDF files to Markdown

7 August 2026 · Milldown team · All posts

One file is a drag-and-drop. Three hundred files — a documentation export, a decade of meeting minutes, a knowledge base leaving SharePoint — need automation. Here are the four ways Milldown does folder-scale conversion, from zero-setup to fully scripted, all running locally on your Mac.

1. Drop the whole folder

The simplest batch is no batch at all: drop a folder onto Milldown and it converts everything inside, recursively, producing a mirrored tree of .md files that preserves your directory structure. Mixed contents are fine — Word, PDF, PowerPoint, Excel, EPUB, and scanned documents each go through the right converter, with OCR applied on-device where needed.

2. Watch folders: conversion as infrastructure

Point Milldown at a folder and every document that lands there is converted automatically into a Markdown/ subfolder. This turns conversion into plumbing: set a watch on your scanner’s output folder, a shared drop folder, or wherever your browser downloads reports, and the Markdown just appears. Watch folders persist across app restarts (they’re stored as security-scoped bookmarks, so they survive macOS sandbox rules) and outputs land in their own subfolder precisely so they never get re-converted in a loop.

3. The CLI, for scripts and repeatability

Install the command-line tool from the app menu (Install Command-Line Tool) and you get full option parity in scripts:

# one file
milldown report.pdf -o report.md

# a whole tree, mirrored
milldown ./contracts -o ./contracts-md

Because it’s the same local engine, a CI job or a cron script gets identical output to the app — useful when conversion is a step in a larger pipeline, like preparing a corpus for RAG.

4. Shortcuts and the URL scheme

Milldown registers a milldown://convert URL scheme, which makes it scriptable from Apple Shortcuts, Alfred, Raycast, or anything that can open a URL. A two-step Shortcut — receive files, open milldown://convert — puts “Convert to Markdown” in the Share sheet everywhere on your Mac. There’s also the zero-automation path: right-click any file in Finder → Services → Convert to Markdown.

Picking the right mode

Situation	Use
One-off migration of an archive	Drop the folder
Documents arrive continuously	Watch folder
Part of a scripted pipeline	CLI
Ad-hoc, from anywhere in macOS	Services menu or Shortcuts