On August 21, 2026, I set up a small DigitalOcean server running Debian and named it Pinebox, after Pine, the University of Washington's old text-mode mail program, which I have used since 1993. The first thing I installed was Alpine, Pine's modern descendant, along with tmux and automatic security updates. Then I turned on the firewall. That was the whole plan: a quiet machine I could SSH into from any of my ThinkPads and read my Gmail in a text terminal.
For a few weeks it stayed that kind of place. On September 2 I imported my address book. On September 9 I set up S/MIME certificates for Alpine and curated a newsrc for reading Usenet. On September 12 I installed WordGrinder and Joe, two text-mode word processors, and the 1999 release of WordPerfect 8 for Linux, and made a ~/text folder for writing. A folder of poems followed at the end of the month. Pinebox was a writer's terminal with excellent email.
September 12 is also when I first talked to an AI on it, through a small chat script that logged every conversation. On September 29 I made a small repository of shell commands so every ThinkPad would reach Pinebox the same way. On September 30 everything changed: I installed git, the GitHub command line, and Claude Code, and that afternoon Claude and I made the first commit of Blackbox, the secretary that now runs my days. My own notes from that night include a to-do to bump the server to 1 GB of memory. It was already outgrowing its first size.
October is when the work moved in. Blackbox connected to Todoist, my Google calendar and inbox, and Upwork's new MCP server, with timers that renew its sign-ins twice a day, close my day at 11:45 PM, and push an encrypted backup every night. On October 4 I added a ~/projects folder, and Hill Mole moved in that day, followed by my firm's site on the 5th, my consulting site on the 6th, and my podcast's site on the 8th. On October 14 Claude set up Google's Lighthouse there to measure them all, and this weblog joined them tonight. On October 15 Node.js went in so OpenAI's Codex could join Claude Code, and the same day the server got a Google Places API key for local search work. Each new job came with its own requirements, and every one of them landed on a machine sized for reading email.
By tonight the numbers had caught up with the work. The server had one processor that sat mostly idle, 967 MB of memory with only 343 MB free, more than 400 MB already pushed into swap, and a disk 79 percent full. One Claude Code session alone was using 438 MB. Memory was the bottleneck, and two AI sessions at once meant everything slowed to a crawl. So I took a snapshot, powered it off, and resized it to two processors, 4 GB of memory, and an 80 GB disk, for about $24 a month. It came back with 3.2 GB free, no swap in use, the disk a quarter full, and every timer, backup, and sign-in intact.
Alpine is still there. When Blackbox drafts an email, it hands the draft to Alpine, and the message goes out only when I press Ctrl+X. The machine I set up to read email in a terminal still sends my email that way, with an AI secretary, two coding agents, and five websites living around it.
Update, October 16, 2026, 9:43 PM: Chris confirmed he has used Pine since 1993, so that detail is back in. Claude had cut an earlier version of the line because it had no source.