diff --git a/docs/api-reference.md b/docs/api-reference.md
index 47c22e0b..810c321d 100644
--- a/docs/api-reference.md
+++ b/docs/api-reference.md
@@ -87,6 +87,85 @@ the HTTP status.
 
 Adding a new error code is non-breaking; removing or renaming one is a major change.
 
+## Cron jobs
+
+Saved jobs and their launch history are separate from the legacy `/api/scheduled`
+duration-bounded loops. Use `/api/v1/cron/...` in external clients; `/api/cron/...`
+is the unversioned alias. These routes use the response envelope above; the table
+lists the value inside `data` on success.
+
+| Method | Path | Request body | Response `data` |
+| --- | --- | --- | --- |
+| GET | `/api/v1/cron/jobs` | None | `CronJob[]` |
+| POST | `/api/v1/cron/jobs` | Full job definition below | `{ job: CronJob }` |
+| GET | `/api/v1/cron/jobs/:id` | None | `CronJob` |
+| PUT | `/api/v1/cron/jobs/:id` | Partial job definition | `{ job: CronJob }` |
+| DELETE | `/api/v1/cron/jobs/:id` | None | `{}` |
+| PUT | `/api/v1/cron/jobs/:id/enabled` | `{ enabled: boolean }` | `{ job: CronJob }` |
+| POST | `/api/v1/cron/jobs/:id/run` | None | `{ run: CronJobRun, activeAgents: number }` |
+| GET | `/api/v1/cron/jobs/:id/runs` | None | `CronJobRun[]` |
+| GET | `/api/v1/cron/runs` | None | `CronJobRun[]` |
+
+### Job request fields
+
+The create body requires `name`, `agentType`, `workingDir`, `promptMode`,
+`inputMode`, `scheduleType`, `enabled`, and `concurrencyPolicy`. Additional fields
+are required according to the selected prompt and schedule:
+
+| Field | Type / validation |
+| --- | --- |
+| `name` | String, 1–200 characters |
+| `agentType` | A supported session mode (including `shell`) |
+| `workingDir` | Existing, allowed working-directory path |
+| `launchCommand` | Optional single-line string, at most 2000 characters; for shell jobs |
+| `promptMode` | `inline_text` or `prompt_file_path` |
+| `promptText` | Required for `inline_text`; nonempty single-line string, at most 100000 characters |
+| `promptFilePath` | Required for `prompt_file_path`; regular file confined to `workingDir`, at most 1 MiB, read when the job fires |
+| `inputMode` | `paste` or `typed` |
+| `scheduleType` | `once`, `interval`, `daily`, or `weekly` |
+| `runAt` | Required for `once`; positive integer Unix timestamp in milliseconds |
+| `intervalMinutes` | Required for `interval`; integer from 1 to 525600 |
+| `dailyTime` | Required for `daily`; `HH:MM` in server-local time |
+| `weeklyDays` | Required for `weekly`; 1–7 weekday integers, 0 (Sunday) through 6 (Saturday) |
+| `weeklyTime` | Required for `weekly`; `HH:MM` in server-local time |
+| `enabled` | Boolean |
+| `concurrencyPolicy` | `warn_only` or `skip_if_same_agent_running`; scheduled runs only |
+| `autoClosePreviousSession` | Optional boolean, default `true`; ignored for `once` |
+| `notes` | Optional string, at most 2000 characters |
+
+`PUT /jobs/:id` accepts any subset of these fields, then validates the merged job.
+When changing `promptMode` or `scheduleType`, supply the fields the new mode needs.
+`Run Now` works even when the job is disabled, bypasses the scheduled concurrency
+policy, and does not change the schedule. `activeAgents` counts live sessions of
+the same agent type, excluding sessions created by this job.
+
+### Job and run response fields
+
+`CronJob` contains the request fields plus server-maintained `id`, optional
+`owner` (multi-user mode), `createdAt`, `updatedAt`, `lastRunAt`, `nextRunAt`,
+`lastStatus`, `lastDueKey`, and optional `completedOnce`. Times are Unix
+milliseconds; `lastRunAt`, `nextRunAt`, `lastStatus`, and `lastDueKey` can be `null`.
+
+`CronJobRun` contains `id`, `cronJobId`, nullable `sessionId` and `sessionName`,
+`startedAt`, nullable `finishedAt`, `status`, optional `errorMessage`,
+`triggerType` (`scheduled` or `manual_run_now`), and nullable `createdSessionUrl`.
+Run times are also Unix milliseconds. Status is one of `created`,
+`session_started`, `prompt_sent`, `failed`, or `skipped`.
+
+Prompt delivery continues asynchronously after session launch, so `Run Now` can
+return `session_started` before the prompt is sent. Read run history for the later
+status. `finishedAt` refers to the launch/prompt-delivery attempt, **not completion
+of the agent's task**; `prompt_sent` does not prove that the task succeeded.
+
+In multi-user mode, list/history endpoints filter to accessible jobs. An unknown
+or inaccessible job returns `NOT_FOUND`. Job creation and updates can return
+`FORBIDDEN` for a working directory outside the owner's workspace or a shell /
+launch-command job without the required privilege grant. Invalid definitions or
+working directories return `INVALID_INPUT`; launch/delivery failures are recorded
+on the run, so inspect its `status` and `errorMessage` even after an HTTP success.
+
+See [Cron Jobs](wiki/Cron-Jobs.md) for the UI, scheduling, and prompt-file rules.
+
 ## Long-polling (agent wait)
 
 Three calls block until something happens instead of answering immediately. They
diff --git a/docs/wiki/Cron-Jobs.md b/docs/wiki/Cron-Jobs.md
index 699c89ee..c71c03c4 100644
--- a/docs/wiki/Cron-Jobs.md
+++ b/docs/wiki/Cron-Jobs.md
@@ -4,8 +4,8 @@ Saved, named jobs that start a session and send it a prompt on a schedule. Cron
 sessions: *every weekday at 03:00, open a Claude session in `~/proj` and tell it to update
 dependencies and open a PR.*
 
-The ⏰ **Cron** header button is opt-in. Turn it on in
-**App Settings → Header & Panels**.
+The ⏰ **Cron** button in the bottom toolbar is opt-in. Turn it on under
+**App Settings → Header & Panels → Scheduling**.
 
 ## Creating a job
 
@@ -96,11 +96,16 @@ The skip policy has the details you would want it to have:
 
 Every fire is recorded per job, with a status:
 
-| Status    | Meaning                                                              |
-| --------- | -------------------------------------------------------------------- |
-| `created` | The run started and a session was created.                            |
-| `skipped` | The concurrency policy blocked it. Not counted as a run.              |
-| `failed`  | The prompt could not be resolved, or the working directory was gone.  |
+| Status            | Meaning                                                           |
+| ----------------- | ----------------------------------------------------------------- |
+| `created`         | The run record was created; the session has not started yet.       |
+| `session_started` | The session started; prompt delivery is still pending.             |
+| `prompt_sent`     | The prompt was sent to the session.                                |
+| `skipped`         | The concurrency policy blocked it. Not counted as a run.           |
+| `failed`          | Prompt resolution, session launch, or prompt delivery failed.      |
+
+History records whether the session started and the prompt was delivered, **not whether
+the agent's task succeeded**. `prompt_sent` is not a task-completion signal.
 
 The schedule is advanced **before** the session launches, so a slow start cannot cause the
 same job to re-trigger.
diff --git a/docs/wiki/HTTP-API.md b/docs/wiki/HTTP-API.md
index 7cd94f11..b4fb3cae 100644
--- a/docs/wiki/HTTP-API.md
+++ b/docs/wiki/HTTP-API.md
@@ -92,6 +92,32 @@ Roughly 235 handlers across 26 route modules. By domain:
 
 Each route module documents its own endpoints in its file header.
 
+## Cron jobs
+
+Saved scheduled jobs are distinct from the legacy `/api/scheduled` loops. Their
+versioned endpoints are:
+
+| Method | Path | Purpose |
+| --- | --- | --- |
+| GET | `/api/v1/cron/jobs` | List jobs |
+| POST | `/api/v1/cron/jobs` | Create a job |
+| GET | `/api/v1/cron/jobs/:id` | Read a job |
+| PUT | `/api/v1/cron/jobs/:id` | Update a job (partial body) |
+| DELETE | `/api/v1/cron/jobs/:id` | Delete a job |
+| PUT | `/api/v1/cron/jobs/:id/enabled` | Enable/disable with `{ enabled: boolean }` |
+| POST | `/api/v1/cron/jobs/:id/run` | Run now, without changing the schedule |
+| GET | `/api/v1/cron/jobs/:id/runs` | Read a job's run history |
+| GET | `/api/v1/cron/runs` | Read all accessible run history |
+
+Responses use the envelope above: job lists/history have arrays in `data`, a
+single-job GET has the job itself, create/update/enable have `{ job }`, delete has
+`{}`, and Run Now has `{ run, activeAgents }`. Prompt delivery is asynchronous;
+`session_started` and `prompt_sent` describe launch/delivery, not task success.
+
+The [cron API reference](https://github.com/Ark0N/Codeman/blob/master/docs/api-reference.md#cron-jobs)
+lists all request and response fields, validation, and ownership restrictions.
+[Creating a job](Cron-Jobs) covers the UI and schedule semantics.
+
 ## Long-polling instead of polling
 
 Three calls block until something happens, so an agent driving Codeman from a shell can wait
diff --git a/test/cron-docs.test.ts b/test/cron-docs.test.ts
new file mode 100644
index 00000000..8c154805
--- /dev/null
+++ b/test/cron-docs.test.ts
@@ -0,0 +1,43 @@
+import { readFileSync } from 'node:fs';
+import { describe, expect, it } from 'vitest';
+import { CronJobSchema } from '../src/web/schemas.js';
+
+const read = (path: string) => readFileSync(new URL(`../${path}`, import.meta.url), 'utf8');
+const reference = read('docs/api-reference.md');
+const wiki = read('docs/wiki/HTTP-API.md');
+const guide = read('docs/wiki/Cron-Jobs.md');
+
+const cronSection = (text: string) => text.split('## Cron jobs\n')[1]?.split('\n## ')[0] ?? '';
+
+describe('cron documentation', () => {
+  it('documents every cron route in both API references', () => {
+    const routes = [...read('src/web/routes/cron-routes.ts').matchAll(/app\.(get|post|put|delete)\('([^']+)'/g)];
+    expect(routes).toHaveLength(9);
+    for (const [, method, path] of routes) {
+      const row = `| ${method.toUpperCase()} | \`${path.replace('/api/', '/api/v1/')}\` |`;
+      expect(cronSection(reference)).toContain(row);
+      expect(cronSection(wiki)).toContain(row);
+    }
+  });
+
+  it('documents every accepted job field and validates the guide example', () => {
+    for (const field of Object.keys(CronJobSchema.shape)) {
+      expect(cronSection(reference)).toContain(`| \`${field}\` |`);
+    }
+    const example = guide.match(/-d '(\{[\s\S]*?\})'/)?.[1];
+    expect(example).toBeDefined();
+    expect(CronJobSchema.safeParse(JSON.parse(example!)).success).toBe(true);
+  });
+
+  it('documents all run statuses without treating prompt delivery as task success', () => {
+    const statusType = read('src/types/cron.ts').match(/export type CronJobRunStatus = ([^;]+);/)?.[1];
+    expect(statusType).toBeDefined();
+    for (const [, status] of statusType!.matchAll(/'([^']+)'/g)) {
+      expect(guide).toContain(`| \`${status}\``);
+      expect(cronSection(reference)).toContain(`\`${status}\``);
+    }
+    expect(guide).toContain("not whether\nthe agent's task succeeded");
+    expect(guide).toContain('bottom toolbar');
+    expect(guide).toContain('App Settings → Header & Panels → Scheduling');
+  });
+});