diff --git a/crosslink/src/main.rs b/crosslink/src/main.rs
index 153c69f4..86f8c91e 100644
--- a/crosslink/src/main.rs
+++ b/crosslink/src/main.rs
@@ -1600,7 +1600,12 @@ enum KickoffCommands {
         /// Path to a design document (markdown) with structured requirements
         #[arg(long, value_name = "PATH")]
         doc: Option<PathBuf>,
-        /// Pass --dangerously-skip-permissions to the claude CLI (for sandboxed agents)
+        /// Per-invocation: pass --dangerously-skip-permissions to claude CLI.
+        ///
+        /// One-shot override that bypasses ALL Claude permission prompts for
+        /// this launch. Persistent policy lives in the worktree's
+        /// .claude/settings.json (allowedTools / permissions blocks); reach
+        /// for that instead of this flag for repeatable configuration.
         #[arg(long)]
         skip_permissions: bool,
     },
@@ -1720,7 +1725,11 @@ enum KickoffCommands {
         /// Print the prompt without launching
         #[arg(long = "dry-run")]
         dry_run: bool,
-        /// Pass --dangerously-skip-permissions to the claude CLI
+        /// Per-invocation: pass --dangerously-skip-permissions to claude CLI.
+        ///
+        /// One-shot override that bypasses ALL Claude permission prompts.
+        /// Persistent policy lives in the worktree's .claude/settings.json
+        /// (allowedTools / permissions blocks).
         #[arg(long)]
         skip_permissions: bool,
     },
diff --git a/docs_src/guides/container-agents.qmd b/docs_src/guides/container-agents.qmd
index 2c338a3e..739a4086 100644
--- a/docs_src/guides/container-agents.qmd
+++ b/docs_src/guides/container-agents.qmd
@@ -152,6 +152,8 @@ The same crosslink hooks that enforce policy in local sessions also run inside c
 
 This means you can use `--dangerously-skip-permissions` for the Claude Code CLI inside the container (to avoid interactive trust prompts) while still maintaining policy enforcement through hooks.
 
+That CLI flag is a **per-invocation override**, not a configuration. Persistent agent permissions are set in the worktree's `.claude/settings.json` -- specifically the `allowedTools` array and Claude Code's `permissions` block -- which crosslink writes via `init` and preserves across `init --force` merges. If you find yourself passing `--skip-permissions` to every container kickoff, the right move is to add the relevant tool patterns to `allowedTools` instead, so the agent runs unattended for that surface while every other tool still prompts. See [Configuring agent permissions](kickoff.qmd#configuring-agent-permissions) in the kickoff guide for the full contrast.
+
 &nbsp;
 
 ---
diff --git a/docs_src/guides/kickoff.qmd b/docs_src/guides/kickoff.qmd
index 91cc68d4..bf23feff 100644
--- a/docs_src/guides/kickoff.qmd
+++ b/docs_src/guides/kickoff.qmd
@@ -226,6 +226,17 @@ The background agent operates under the same crosslink hook enforcement as inter
 
 &nbsp;
 
+### Configuring agent permissions
+
+Agent permissions live in the **agent config file** -- `.claude/settings.json` in the worktree, written by `crosslink init` from crosslink's template. They are *not* configured through any `crosslink config` key. There are two levers, and they answer different questions:
+
+- **Persistent policy (`.claude/settings.json`)** -- the `allowedTools` array (and Claude Code's `permissions.allow` / `permissions.deny` blocks) decide which tools the agent may run without prompting on *every* run. Edit this file to teach a repo "agents may always run `npm test`" or "agents may never run `curl`". Crosslink's `init` merges its defaults with whatever the file already contains, so hand-edits are preserved across `init --force`.
+- **Per-invocation override (`--skip-permissions`)** -- the `crosslink kickoff run --skip-permissions` flag passes `--dangerously-skip-permissions` to the Claude CLI for that single launch, bypassing *all* prompts. It is a one-shot dial, not a setting. Reach for it when you have decided the surrounding environment (sandbox, container, isolated worktree, hook policy) makes the agent's blast radius acceptable. Do not reach for it as a substitute for configuring `allowedTools`.
+
+If you find yourself passing `--skip-permissions` on every kickoff, that's a signal to add the relevant tool patterns to `allowedTools` in `.claude/settings.json` instead -- agents will then run unattended for the allowed surface without giving up the prompt for everything else. See [Claude Code's settings reference](https://docs.claude.com/en/docs/claude-code/settings) for the full schema of `allowedTools` and `permissions`.
+
+&nbsp;
+
 ---
 
 ## Managing kickoffs