diff --git a/crates/goose-cli/src/cli.rs b/crates/goose-cli/src/cli.rs
index 0ac0c4feb..7360827dd 100644
--- a/crates/goose-cli/src/cli.rs
+++ b/crates/goose-cli/src/cli.rs
@@ -1480,6 +1480,9 @@ async fn handle_serve_command(args: ServeCommandArgs) -> Result<()> {
         })
         .collect::<Result<Vec<_>>>()?;
     let secret_key = env_secret.unwrap_or_else(generate_serve_secret_key);
+    if let Err(error) = server.start_scheduler().await {
+        warn!("Scheduler failed to start; scheduled jobs will not run until a client connects: {error}");
+    }
     let router = create_router(
         server,
         secret_key,
diff --git a/crates/goose/src/acp/server_factory.rs b/crates/goose/src/acp/server_factory.rs
index 752400b12..cb89febfd 100644
--- a/crates/goose/src/acp/server_factory.rs
+++ b/crates/goose/src/acp/server_factory.rs
@@ -32,6 +32,13 @@ impl AcpServer {
         }
     }
 
+    /// Start the scheduler now instead of on first client connect, so a
+    /// headless `goose serve` runs scheduled jobs; on failure `create_agent`
+    /// retries. No-op when the scheduler is disabled.
+    pub async fn start_scheduler(&self) -> Result<()> {
+        self.scheduler().await.map(|_| ())
+    }
+
     async fn scheduler(&self) -> Result<Option<Arc<dyn SchedulerTrait>>> {
         if !self.config.enable_scheduler {
             return Ok(None);
@@ -57,6 +64,10 @@ impl AcpServer {
         let config = crate::config::Config::global();
         let disable_session_naming = config.get_goose_disable_session_naming().unwrap_or(false);
         let scheduler = self.scheduler().await?;
+        if let Some(scheduler) = &scheduler {
+            // Listing syncs from storage, registering jobs persisted by other processes.
+            scheduler.list_scheduled_jobs().await;
+        }
 
         let provider_factory: AcpProviderFactory =
             Arc::new(move |provider_name, extensions, working_dir| {
@@ -123,4 +134,32 @@ mod tests {
 
         assert!(server.scheduler().await.unwrap().is_some());
     }
+
+    #[tokio::test]
+    async fn start_scheduler_initializes_before_any_client_connects() {
+        let root = tempfile::tempdir().unwrap();
+        let server = server(root.path().to_path_buf(), true);
+
+        assert!(!server.scheduler.initialized());
+        server.start_scheduler().await.unwrap();
+        assert!(server.scheduler.initialized());
+    }
+
+    #[tokio::test]
+    async fn start_scheduler_is_idempotent() {
+        let root = tempfile::tempdir().unwrap();
+        let server = server(root.path().to_path_buf(), true);
+
+        server.start_scheduler().await.unwrap();
+        server.start_scheduler().await.unwrap();
+    }
+
+    #[tokio::test]
+    async fn start_scheduler_does_not_construct_one_when_disabled() {
+        let root = tempfile::tempdir().unwrap();
+        let server = server(root.path().to_path_buf(), false);
+
+        server.start_scheduler().await.unwrap();
+        assert!(!server.scheduler.initialized());
+    }
 }