Sidekick Desk — Communication skill for Claude Code

Sidekick

A pixel-art octopus that floats on your Windows desktop and manages your day. You do the deep work in your Claude Code chats; Sidekick keeps the plan, helps you shape prompts and choose a direction, and pings you with a speech bubble when something needs you. Click it and it unfolds into a small chat.

Work in progress. Built in small phases; see the commit history.

What it does today

• The octopus floats above your windows; clicks pass through everywhere except the octopus itself.
• Drag it anywhere (it remembers the spot), click to open the chat, right-click for the menu (open chat, tasks folder, quit).
• Greets you with the date at start, reads your profile and today's tasks, and asks for the plan.
• When an answer lands while the chat is closed, it shows up as a speech bubble; click the bubble to open the chat.
• Every bubble about your chats is also kept as a card in the Sidekick chat, and the manager is told about them with your next message, so you can ask it "what happened?". Click a card to jump to that chat: Sidekick focuses the VS Code window it was opened in and opens its tab (reopening it if closed).
• Keeps tasks.md current as you talk ("add…", "done with…", "move to backlog").
• Writes prompts for your other chats as code blocks with a one-click copy button.
• Watches your Claude Code and Codex (OpenAI) chats, in VS Code or the terminal, several per project if you like: a green bubble when one finishes, a yellow one when a Claude chat needs your permission. Labels read "PROJECT · tab title".
• Codex is followed read-only through its session files (~/.codex/sessions), with no change to its config. Its file edits are recorded for the file guard, so a Claude chat is stopped before touching a file Codex just edited; Codex itself has no pre-edit hook, so its own clashes are reported after the fact.
• Stoppers: a reminder when a chat has waited for you 10 minutes (writing in that chat cancels it), and a purple bubble when a chat's con