diff --git a/CHANGELOG.md b/CHANGELOG.md
index 13056320aee..3d0f4fe7a8e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -25,6 +25,7 @@ Docs: https://docs.openclaw.ai
 - Docker/GCP onboarding: reduce first-build OOM risk by capping Node heap during `pnpm install`, reuse existing gateway token during `docker-setup.sh` reruns so `.env` stays aligned with config, auto-bootstrap Control UI allowed origins for non-loopback Docker binds, and add GCP docs guidance for tokenized dashboard links + pairing recovery commands. (#26253) Thanks @pandego.
 - Pairing/Multi-account isolation: keep non-default account pairing allowlists and pending requests strictly account-scoped, while default account continues to use channel-scoped pairing allowlist storage. Thanks @gumadeiras.
 - Security/Config includes: harden `$include` file loading with verified-open reads, reject hardlinked include aliases, and enforce include file-size guardrails so config include resolution remains bounded to trusted in-root files. This ships in the next npm release (`2026.2.26`). Thanks @zpbrent for reporting.
+- Cron/CLI: add `--session` for session-key routing and rename target selection to `--session-target` for `openclaw cron add/edit`, including `--clear-session` on edit for unsetting the key. (#27167) thanks @Matt-Hulme.
 
 ## 2026.2.25
 
diff --git a/docs/automation/cron-jobs.md b/docs/automation/cron-jobs.md
index 8d140192607..7abe6df8638 100644
--- a/docs/automation/cron-jobs.md
+++ b/docs/automation/cron-jobs.md
@@ -38,7 +38,7 @@ Create a one-shot reminder, verify it exists, and run it immediately:
 openclaw cron add \
   --name "Reminder" \
   --at "2026-02-01T16:00:00Z" \
-  --session main \
+  --session-target main \
   --system-event "Reminder: check the cron docs draft" \
   --wake now \
   --delete-after-run
@@ -55,7 +55,7 @@ openclaw cron add \
   --name "Morning brief" \
   --cron "0 7 * * *" \
   --tz "America/Los_Angeles" \
-  --session isolated \
+  --session-target isolated \
   --message "Summarize overnight updates." \
   --announce \
   --channel slack \
@@ -479,7 +479,7 @@ One-shot reminder (UTC ISO, auto-delete after success):
 openclaw cron add \
   --name "Send reminder" \
   --at "2026-01-12T18:00:00Z" \
-  --session main \
+  --session-target main \
   --system-event "Reminder: submit expense report." \
   --wake now \
   --delete-after-run
@@ -491,7 +491,7 @@ One-shot reminder (main session, wake immediately):
 openclaw cron add \
   --name "Calendar check" \
   --at "20m" \
-  --session main \
+  --session-target main \
   --system-event "Next heartbeat: check calendar." \
   --wake now
 ```
@@ -503,7 +503,7 @@ openclaw cron add \
   --name "Morning status" \
   --cron "0 7 * * *" \
   --tz "America/Los_Angeles" \
-  --session isolated \
+  --session-target isolated \
   --message "Summarize inbox + calendar for today." \
   --announce \
   --channel whatsapp \
@@ -518,7 +518,7 @@ openclaw cron add \
   --cron "0 * * * * *" \
   --tz "UTC" \
   --stagger 30s \
-  --session isolated \
+  --session-target isolated \
   --message "Run minute watcher checks." \
   --announce
 ```
@@ -530,7 +530,7 @@ openclaw cron add \
   --name "Nightly summary (topic)" \
   --cron "0 22 * * *" \
   --tz "America/Los_Angeles" \
-  --session isolated \
+  --session-target isolated \
   --message "Summarize today; send to the nightly topic." \
   --announce \
   --channel telegram \
@@ -544,7 +544,7 @@ openclaw cron add \
   --name "Deep analysis" \
   --cron "0 6 * * 1" \
   --tz "America/Los_Angeles" \
-  --session isolated \
+  --session-target isolated \
   --message "Weekly deep analysis of project progress." \
   --model "opus" \
   --thinking high \
@@ -557,7 +557,7 @@ Agent selection (multi-agent setups):
 
 ```bash
 # Pin a job to agent "ops" (falls back to default if that agent is missing)
-openclaw cron add --name "Ops sweep" --cron "0 6 * * *" --session isolated --message "Check ops queue" --agent ops
+openclaw cron add --name "Ops sweep" --cron "0 6 * * *" --session-target isolated --message "Check ops queue" --agent ops
 
 # Switch or clear the agent on an existing job
 openclaw cron edit <jobId> --agent ops
diff --git a/docs/automation/cron-vs-heartbeat.md b/docs/automation/cron-vs-heartbeat.md
index 9676d960d23..3124b72b1b1 100644
--- a/docs/automation/cron-vs-heartbeat.md
+++ b/docs/automation/cron-vs-heartbeat.md
@@ -106,7 +106,7 @@ openclaw cron add \
   --name "Morning briefing" \
   --cron "0 7 * * *" \
   --tz "America/New_York" \
-  --session isolated \
+  --session-target isolated \
   --message "Generate today's briefing: weather, calendar, top emails, news summary." \
   --model opus \
   --announce \
@@ -122,7 +122,7 @@ This runs at exactly 7:00 AM New York time, uses Opus for quality, and announces
 openclaw cron add \
   --name "Meeting reminder" \
   --at "20m" \
-  --session main \
+  --session-target main \
   --system-event "Reminder: standup meeting starts in 10 minutes." \
   --wake now \
   --delete-after-run
@@ -178,13 +178,13 @@ The most efficient setup uses **both**:
 
 ```bash
 # Daily morning briefing at 7am
-openclaw cron add --name "Morning brief" --cron "0 7 * * *" --session isolated --message "..." --announce
+openclaw cron add --name "Morning brief" --cron "0 7 * * *" --session-target isolated --message "..." --announce
 
 # Weekly project review on Mondays at 9am
-openclaw cron add --name "Weekly review" --cron "0 9 * * 1" --session isolated --message "..." --model opus
+openclaw cron add --name "Weekly review" --cron "0 9 * * 1" --session-target isolated --message "..." --model opus
 
 # One-shot reminder
-openclaw cron add --name "Call back" --at "2h" --session main --system-event "Call back the client" --wake now
+openclaw cron add --name "Call back" --at "2h" --session-target main --system-event "Call back the client" --wake now
 ```
 
 ## Lobster: Deterministic workflows with approvals
@@ -229,7 +229,7 @@ Both heartbeat and cron can interact with the main session, but differently:
 
 ### When to use main session cron
 
-Use `--session main` with `--system-event` when you want:
+Use `--session-target main` with `--system-event` when you want:
 
 - The reminder/event to appear in main session context
 - The agent to handle it during the next heartbeat with full context
@@ -239,14 +239,14 @@ Use `--session main` with `--system-event` when you want:
 openclaw cron add \
   --name "Check project" \
   --every "4h" \
-  --session main \
+  --session-target main \
   --system-event "Time for a project health check" \
   --wake now
 ```
 
 ### When to use isolated cron
 
-Use `--session isolated` when you want:
+Use `--session-target isolated` when you want:
 
 - A clean slate without prior context
 - Different model or thinking settings
@@ -257,7 +257,7 @@ Use `--session isolated` when you want:
 openclaw cron add \
   --name "Deep analysis" \
   --cron "0 6 * * 0" \
-  --session isolated \
+  --session-target isolated \
   --message "Weekly codebase analysis..." \
   --model opus \
   --thinking high \
diff --git a/src/cli/cron-cli.test.ts b/src/cli/cron-cli.test.ts
index 940fbdad075..4085f1bf62a 100644
--- a/src/cli/cron-cli.test.ts
+++ b/src/cli/cron-cli.test.ts
@@ -42,6 +42,7 @@ type CronUpdatePatch = {
     schedule?: { kind?: string; expr?: string; tz?: string; staggerMs?: number };
     payload?: { message?: string; model?: string; thinking?: string };
     delivery?: { mode?: string; channel?: string; to?: string; bestEffort?: boolean };
+    sessionKey?: unknown;
   };
 };
 
@@ -51,6 +52,7 @@ type CronAddParams = {
   delivery?: { mode?: string };
   deleteAfterRun?: boolean;
   agentId?: string;
+  sessionKey?: string;
   sessionTarget?: string;
 };
 
@@ -153,7 +155,7 @@ describe("cron cli", () => {
       "Daily",
       "--cron",
       "* * * * *",
-      "--session",
+      "--session-target",
       "isolated",
       "--message",
       "hello",
@@ -180,7 +182,7 @@ describe("cron cli", () => {
       "Daily",
       "--cron",
       "* * * * *",
-      "--session",
+      "--session-target",
       "isolated",
       "--message",
       "hello",
@@ -192,7 +194,7 @@ describe("cron cli", () => {
     expect(params?.delivery?.mode).toBe("announce");
   });
 
-  it("infers sessionTarget from payload when --session is omitted", async () => {
+  it("infers sessionTarget from payload when --session-target is omitted", async () => {
     await runCronCommand([
       "cron",
       "add",
@@ -234,7 +236,7 @@ describe("cron cli", () => {
       "Keep me",
       "--at",
       "20m",
-      "--session",
+      "--session-target",
       "main",
       "--system-event",
       "hello",
@@ -262,7 +264,7 @@ describe("cron cli", () => {
       "Agent pinned",
       "--cron",
       "* * * * *",
-      "--session",
+      "--session-target",
       "isolated",
       "--message",
       "hi",
@@ -275,6 +277,27 @@ describe("cron cli", () => {
     expect(params?.agentId).toBe("ops");
   });
 
+  it("sends session key on cron add", async () => {
+    await runCronCommand([
+      "cron",
+      "add",
+      "--name",
+      "Session pinned",
+      "--cron",
+      "* * * * *",
+      "--session-target",
+      "isolated",
+      "--message",
+      "hi",
+      "--session",
+      " agent:project-lead:calculator ",
+    ]);
+
+    const addCall = callGatewayFromCli.mock.calls.find((call) => call[0] === "cron.add");
+    const params = addCall?.[2] as { sessionKey?: string };
+    expect(params?.sessionKey).toBe("agent:project-lead:calculator");
+  });
+
   it.each([
     {
       label: "omits empty model and thinking",
@@ -305,6 +328,28 @@ describe("cron cli", () => {
     expect(clearPatch?.patch?.agentId).toBeNull();
   });
 
+  it("sets and clears session key on cron edit", async () => {
+    await runCronCommand(["cron", "edit", "job-1", "--session", " agent:project-lead:dashboard "]);
+
+    const setPatch = getGatewayCallParams<{ patch?: { sessionKey?: unknown } }>("cron.update");
+    expect(setPatch?.patch?.sessionKey).toBe("agent:project-lead:dashboard");
+
+    await runCronCommand(["cron", "edit", "job-2", "--clear-session"]);
+    const clearPatch = getGatewayCallParams<{ patch?: { sessionKey?: unknown } }>("cron.update");
+    expect(clearPatch?.patch?.sessionKey).toBeNull();
+  });
+
+  it("rejects --session with --clear-session on cron edit", async () => {
+    await expectCronCommandExit([
+      "cron",
+      "edit",
+      "job-1",
+      "--session",
+      "agent:project-lead:dashboard",
+      "--clear-session",
+    ]);
+  });
+
   it("allows model/thinking updates without --message", async () => {
     await runCronCommand(["cron", "edit", "job-1", "--model", "opus", "--thinking", "low"]);
 
@@ -418,7 +463,7 @@ describe("cron cli", () => {
       "0 * * * *",
       "--stagger",
       "45s",
-      "--session",
+      "--session-target",
       "main",
       "--system-event",
       "tick",
@@ -434,7 +479,7 @@ describe("cron cli", () => {
       "--cron",
       "0 * * * *",
       "--exact",
-      "--session",
+      "--session-target",
       "main",
       "--system-event",
       "tick",
@@ -454,7 +499,7 @@ describe("cron cli", () => {
       "--stagger",
       "1m",
       "--exact",
-      "--session",
+      "--session-target",
       "main",
       "--system-event",
       "tick",
@@ -471,7 +516,7 @@ describe("cron cli", () => {
       "10m",
       "--stagger",
       "30s",
-      "--session",
+      "--session-target",
       "main",
       "--system-event",
       "tick",
diff --git a/src/cli/cron-cli/register.cron-add.ts b/src/cli/cron-cli/register.cron-add.ts
index 8d44c77778f..415875c8ba9 100644
--- a/src/cli/cron-cli/register.cron-add.ts
+++ b/src/cli/cron-cli/register.cron-add.ts
@@ -70,8 +70,8 @@ export function registerCronAddCommand(cron: Command) {
       .option("--delete-after-run", "Delete one-shot job after it succeeds", false)
       .option("--keep-after-run", "Keep one-shot job after it succeeds", false)
       .option("--agent <id>", "Agent id for this job")
-      .option("--session <target>", "Session target (main|isolated)")
-      .option("--session-key <key>", "Session key for job routing (e.g. agent:my-agent:my-session)")
+      .option("--session-target <target>", "Session target (main|isolated)")
+      .option("--session <key>", "Session key for job routing (e.g. agent:my-agent:my-session)")
       .option("--wake <mode>", "Wake mode (now|next-heartbeat)", "now")
       .option("--at <when>", "Run once at time (ISO) or +duration (e.g. 20m)")
       .option("--every <duration>", "Run every duration (e.g. 10m, 1h)")
@@ -195,13 +195,14 @@ export function registerCronAddCommand(cron: Command) {
             typeof cmd?.getOptionValueSource === "function"
               ? (name: string) => cmd.getOptionValueSource(name)
               : () => undefined;
-          const sessionSource = optionSource("session");
-          const sessionTargetRaw = typeof opts.session === "string" ? opts.session.trim() : "";
+          const sessionSource = optionSource("sessionTarget");
+          const sessionTargetRaw =
+            typeof opts.sessionTarget === "string" ? opts.sessionTarget.trim() : "";
           const inferredSessionTarget = payload.kind === "agentTurn" ? "isolated" : "main";
           const sessionTarget =
             sessionSource === "cli" ? sessionTargetRaw || "" : inferredSessionTarget;
           if (sessionTarget !== "main" && sessionTarget !== "isolated") {
-            throw new Error("--session must be main or isolated");
+            throw new Error("--session-target must be main or isolated");
           }
 
           if (opts.deleteAfterRun && opts.keepAfterRun) {
@@ -218,7 +219,7 @@ export function registerCronAddCommand(cron: Command) {
             (opts.announce || typeof opts.deliver === "boolean") &&
             (sessionTarget !== "isolated" || payload.kind !== "agentTurn")
           ) {
-            throw new Error("--announce/--no-deliver require --session isolated.");
+            throw new Error("--announce/--no-deliver require --session-target isolated.");
           }
 
           const deliveryMode =
@@ -242,8 +243,8 @@ export function registerCronAddCommand(cron: Command) {
               : undefined;
 
           const sessionKey =
-            typeof opts.sessionKey === "string" && opts.sessionKey.trim()
-              ? opts.sessionKey.trim()
+            typeof opts.session === "string" && opts.session.trim()
+              ? opts.session.trim()
               : undefined;
 
           const params = {
diff --git a/src/cli/cron-cli/register.cron-edit.ts b/src/cli/cron-cli/register.cron-edit.ts
index 9bc9916a06d..6c45110e428 100644
--- a/src/cli/cron-cli/register.cron-edit.ts
+++ b/src/cli/cron-cli/register.cron-edit.ts
@@ -34,11 +34,11 @@ export function registerCronEditCommand(cron: Command) {
       .option("--disable", "Disable job", false)
       .option("--delete-after-run", "Delete one-shot job after it succeeds", false)
       .option("--keep-after-run", "Keep one-shot job after it succeeds", false)
-      .option("--session <target>", "Session target (main|isolated)")
+      .option("--session-target <target>", "Session target (main|isolated)")
       .option("--agent <id>", "Set agent id")
       .option("--clear-agent", "Unset agent and use default", false)
-      .option("--session-key <key>", "Set session key for job routing")
-      .option("--clear-session-key", "Unset session key", false)
+      .option("--session <key>", "Set session key for job routing")
+      .option("--clear-session", "Unset session key", false)
       .option("--wake <mode>", "Wake mode (now|next-heartbeat)")
       .option("--at <when>", "Set one-shot time (ISO) or duration like 20m")
       .option("--every <duration>", "Set interval duration like 10m")
@@ -63,14 +63,14 @@ export function registerCronEditCommand(cron: Command) {
       .option("--no-best-effort-deliver", "Fail job when delivery fails")
       .action(async (id, opts) => {
         try {
-          if (opts.session === "main" && opts.message) {
+          if (opts.sessionTarget === "main" && opts.message) {
             throw new Error(
-              "Main jobs cannot use --message; use --system-event or --session isolated.",
+              "Main jobs cannot use --message; use --system-event or --session-target isolated.",
             );
           }
-          if (opts.session === "isolated" && opts.systemEvent) {
+          if (opts.sessionTarget === "isolated" && opts.systemEvent) {
             throw new Error(
-              "Isolated jobs cannot use --system-event; use --message or --session main.",
+              "Isolated jobs cannot use --system-event; use --message or --session-target main.",
             );
           }
           if (opts.announce && typeof opts.deliver === "boolean") {
@@ -120,8 +120,8 @@ export function registerCronEditCommand(cron: Command) {
           if (opts.keepAfterRun) {
             patch.deleteAfterRun = false;
           }
-          if (typeof opts.session === "string") {
-            patch.sessionTarget = opts.session;
+          if (typeof opts.sessionTarget === "string") {
+            patch.sessionTarget = opts.sessionTarget;
           }
           if (typeof opts.wake === "string") {
             patch.wakeMode = opts.wake;
@@ -135,13 +135,13 @@ export function registerCronEditCommand(cron: Command) {
           if (opts.clearAgent) {
             patch.agentId = null;
           }
-          if (opts.sessionKey && opts.clearSessionKey) {
-            throw new Error("Use --session-key or --clear-session-key, not both");
+          if (opts.session && opts.clearSession) {
+            throw new Error("Use --session or --clear-session, not both");
           }
-          if (typeof opts.sessionKey === "string" && opts.sessionKey.trim()) {
-            patch.sessionKey = opts.sessionKey.trim();
+          if (typeof opts.session === "string" && opts.session.trim()) {
+            patch.sessionKey = opts.session.trim();
           }
-          if (opts.clearSessionKey) {
+          if (opts.clearSession) {
             patch.sessionKey = null;
           }