diff --git a/README.md b/README.md
index 19d1252d..9ac8650f 100644
--- a/README.md
+++ b/README.md
@@ -145,6 +145,9 @@ variable (resolution is `$PANOPTICON_*` → `$XDG_*_HOME/panopticon` → the def
   server. Your data under `~/.local/share/panopticon` is left in place.
 - **Check your host:** `panopticon doctor` verifies Python, Docker (and a running daemon), tmux,
   git, and the `claude` CLI, printing a line per check and exiting non-zero if anything is missing.
+- **Stuck?** [`docs/troubleshooting.md`](docs/troubleshooting.md) collects the common first-run
+  failures — auth, missing tokens, a task stuck at `awaiting`, missing services — and where to fix
+  each.
 - **Upgrade:** `pipx upgrade panopticon-app` (or `pip install --upgrade panopticon-app`), then
   `panopticon migrate` to apply any new database migrations.
 - **Uninstall:** `panopticon stop`, then `pipx uninstall panopticon-app`. To remove state too,
diff --git a/docs/overview.md b/docs/overview.md
index 6f8da05b..6f290327 100644
--- a/docs/overview.md
+++ b/docs/overview.md
@@ -138,6 +138,7 @@ This page is the map; these guides are the detail:
 - **[Container auth](auth.md)** — giving each repo's agents their Claude token (and a GitHub token for PRs).
 - **[Image layers](layers.md)** — the composed `base → workflow → repo` image, and adding your own.
 - **[Hooks](hooks.md)** — the per-repo host hook that runs before a container spawns.
+- **[Troubleshooting](troubleshooting.md)** — common first-run failures and where to fix each.
 - **[macOS setup](macos-setup.md)** — the Docker Desktop specifics for running on a Mac.
 - **[Developing](dev.md)** — working *on* panopticon: setup, the check loop, and CI.
 - **[README](../README.md)** — install, quickstart, your first task, and configuration.
diff --git a/docs/troubleshooting.md b/docs/troubleshooting.md
new file mode 100644
index 00000000..627e6f3a
--- /dev/null
+++ b/docs/troubleshooting.md
@@ -0,0 +1,68 @@
+# Troubleshooting — common first-run failures
+
+Quick answers to the problems new installs hit most. Each entry points to the doc that owns
+the detail; start there if the short answer isn't enough. For a fast health check of your host,
+run `panopticon doctor` (see [reading `panopticon doctor`](#how-do-i-read-panopticon-doctor)).
+
+### Quickstart stops at a Claude login, or I don't have a paid account
+
+`claude setup-token` mints the agent's auth token through a browser OAuth flow, which needs a
+**paid Claude subscription or Console login**. If you don't have one, put an `ANTHROPIC_API_KEY`
+in the repo's env-file instead — it overrides the OAuth token and authenticates the same
+containers.
+
+→ [`auth.md`](auth.md#one-time-setup-per-account), and the API-key note in
+[`auth.md`](auth.md#notes).
+
+### My GitHub task can't open a PR, or `gh` fails
+
+The container's `gh` needs a `GH_TOKEN`. Add one to the repo's env-file (the same file that
+holds the Claude token) and respawn the task to pick it up.
+
+→ [`repos.md`](repos.md#secrets-env_file) for the env-file, [`auth.md`](auth.md) for how it's
+injected.
+
+### The workflow I want isn't in the picker
+
+The change-shipping workflows (`github-peer-reviewed`, `github-self-reviewed`,
+`local-git-self-reviewed`) are **opt-in**. `quickstart` enables the one that matches your repo;
+enable any others per repo in the repos form — press `g`, edit the repo, and check the
+workflows you want. `spike` is always available.
+
+→ [`workflows/README.md`](workflows/README.md#how-workflows-are-offered),
+[`repos.md`](repos.md#workflow-visibility).
+
+### A task is stuck at `awaiting`, or the container never reaches `live`
+
+The runner can't finish spawning. Check that the **Docker daemon is running** and the **base
+image is built** (`panopticon doctor` reports the daemon; `make build` builds the base image).
+A spawn step that raised shows as `failed` with a detail string — fix the cause, then respawn
+with `R`.
+
+→ [`container.md`](container.md#when-it-goes-wrong).
+
+### The dashboard and services seem gone (`tmux ls` shows nothing)
+
+They're not on your default tmux server — they live on the dedicated `tmux -L panopticon`
+server. Bring them back with `panopticon start`; if they're already up, `panopticon console`
+re-attaches.
+
+→ [README, Managing your install](../README.md#managing-your-install).
+
+### The agent can't authenticate, or 401s mid-task
+
+The token in the repo's env-file is missing, expired, or revoked. Mint a fresh one — re-run the
+`setup-repo` task (repos form: `g`, highlight the repo, `s`) or overwrite the
+`CLAUDE_CODE_OAUTH_TOKEN` line by hand — then respawn the task with `R` so the container picks
+up the new value. A live task keeps its old token until it respawns.
+
+→ [`auth.md`](auth.md#the-setup-repo-workflow), and the rotate/respawn note in
+[`auth.md`](auth.md#notes).
+
+### How do I read `panopticon doctor`?
+
+It prints one line per prerequisite check — Python, Docker (and a running daemon), tmux, git,
+and the `claude` CLI — marking each pass or fail, and exits non-zero if anything is missing.
+Fix whatever's marked failed and re-run it.
+
+→ [README, Requirements](../README.md#requirements).