diff --git a/src/cli/cron-cli/register.cron-add.ts b/src/cli/cron-cli/register.cron-add.ts
index 2388b00a388..8d44c77778f 100644
--- a/src/cli/cron-cli/register.cron-add.ts
+++ b/src/cli/cron-cli/register.cron-add.ts
@@ -71,6 +71,7 @@ export function registerCronAddCommand(cron: Command) {
       .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("--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)")
@@ -240,12 +241,18 @@ export function registerCronAddCommand(cron: Command) {
               ? opts.description.trim()
               : undefined;
 
+          const sessionKey =
+            typeof opts.sessionKey === "string" && opts.sessionKey.trim()
+              ? opts.sessionKey.trim()
+              : undefined;
+
           const params = {
             name,
             description,
             enabled: !opts.disabled,
             deleteAfterRun: opts.deleteAfterRun ? true : opts.keepAfterRun ? false : undefined,
             agentId,
+            sessionKey,
             schedule,
             sessionTarget,
             wakeMode,
diff --git a/src/cli/cron-cli/register.cron-edit.ts b/src/cli/cron-cli/register.cron-edit.ts
index f1e6c74d77f..9bc9916a06d 100644
--- a/src/cli/cron-cli/register.cron-edit.ts
+++ b/src/cli/cron-cli/register.cron-edit.ts
@@ -37,6 +37,8 @@ export function registerCronEditCommand(cron: Command) {
       .option("--session <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("--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")
@@ -133,6 +135,15 @@ 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 (typeof opts.sessionKey === "string" && opts.sessionKey.trim()) {
+            patch.sessionKey = opts.sessionKey.trim();
+          }
+          if (opts.clearSessionKey) {
+            patch.sessionKey = null;
+          }
 
           const scheduleChosen = [opts.at, opts.every, opts.cron].filter(Boolean).length;
           if (scheduleChosen > 1) {