diff --git a/crates/openshell-bootstrap/src/lib.rs b/crates/openshell-bootstrap/src/lib.rs
index 9098fd4a..93898675 100644
--- a/crates/openshell-bootstrap/src/lib.rs
+++ b/crates/openshell-bootstrap/src/lib.rs
@@ -48,10 +48,10 @@ pub use crate::docker::{
     DockerPreflight, ExistingGatewayInfo, check_docker_available, create_ssh_docker_client,
 };
 pub use crate::metadata::{
-    GatewayMetadata, clear_active_gateway, extract_host_from_ssh_destination, get_gateway_metadata,
-    list_gateways, load_active_gateway, load_gateway_metadata, load_last_sandbox,
-    remove_gateway_metadata, resolve_ssh_hostname, save_active_gateway, save_last_sandbox,
-    store_gateway_metadata,
+    GatewayMetadata, clear_active_gateway, clear_last_sandbox_if_matches,
+    extract_host_from_ssh_destination, get_gateway_metadata, list_gateways, load_active_gateway,
+    load_gateway_metadata, load_last_sandbox, remove_gateway_metadata, resolve_ssh_hostname,
+    save_active_gateway, save_last_sandbox, store_gateway_metadata,
 };
 
 /// Options for remote SSH deployment.
diff --git a/crates/openshell-bootstrap/src/metadata.rs b/crates/openshell-bootstrap/src/metadata.rs
index bd49ba8c..15f79c08 100644
--- a/crates/openshell-bootstrap/src/metadata.rs
+++ b/crates/openshell-bootstrap/src/metadata.rs
@@ -271,6 +271,20 @@ pub fn load_last_sandbox(gateway: &str) -> Option<String> {
     if name.is_empty() { None } else { Some(name) }
 }
 
+/// Clear the last-used sandbox record for a gateway if it matches the given name.
+///
+/// This should be called after a sandbox is deleted so that subsequent commands
+/// don't try to connect to a sandbox that no longer exists.
+pub fn clear_last_sandbox_if_matches(gateway: &str, sandbox: &str) {
+    if let Some(current) = load_last_sandbox(gateway) {
+        if current == sandbox {
+            if let Ok(path) = last_sandbox_path(gateway) {
+                let _ = std::fs::remove_file(path);
+            }
+        }
+    }
+}
+
 /// List all gateways that have stored metadata.
 ///
 /// Scans `$XDG_CONFIG_HOME/openshell/gateways/` for subdirectories containing
diff --git a/crates/openshell-cli/src/main.rs b/crates/openshell-cli/src/main.rs
index 3799b392..5de31c79 100644
--- a/crates/openshell-cli/src/main.rs
+++ b/crates/openshell-cli/src/main.rs
@@ -2268,7 +2268,7 @@ async fn main() -> Result<()> {
                             run::sandbox_list(endpoint, limit, offset, ids, names, &tls).await?;
                         }
                         SandboxCommands::Delete { names, all } => {
-                            run::sandbox_delete(endpoint, &names, all, &tls).await?;
+                            run::sandbox_delete(endpoint, &names, all, &tls, &ctx.name).await?;
                         }
                         SandboxCommands::Connect { name, editor } => {
                             let name = resolve_sandbox_name(name, &ctx.name)?;
diff --git a/crates/openshell-cli/src/run.rs b/crates/openshell-cli/src/run.rs
index a4331ee5..e32eec2a 100644
--- a/crates/openshell-cli/src/run.rs
+++ b/crates/openshell-cli/src/run.rs
@@ -16,10 +16,10 @@ use hyper_util::{client::legacy::Client, rt::TokioExecutor};
 use indicatif::{MultiProgress, ProgressBar, ProgressStyle};
 use miette::{IntoDiagnostic, Result, WrapErr, miette};
 use openshell_bootstrap::{
-    DeployOptions, GatewayMetadata, RemoteOptions, clear_active_gateway, container_name,
-    extract_host_from_ssh_destination, get_gateway_metadata, list_gateways, load_active_gateway,
-    remove_gateway_metadata, resolve_ssh_hostname, save_active_gateway, save_last_sandbox,
-    store_gateway_metadata,
+    DeployOptions, GatewayMetadata, RemoteOptions, clear_active_gateway,
+    clear_last_sandbox_if_matches, container_name, extract_host_from_ssh_destination,
+    get_gateway_metadata, list_gateways, load_active_gateway, remove_gateway_metadata,
+    resolve_ssh_hostname, save_active_gateway, save_last_sandbox, store_gateway_metadata,
 };
 use openshell_core::proto::{
     ApproveAllDraftChunksRequest, ApproveDraftChunkRequest, ClearDraftChunksRequest,
@@ -1904,13 +1904,14 @@ async fn finalize_sandbox_create_session(
     persist: bool,
     session_result: Result<()>,
     tls: &TlsOptions,
+    gateway: &str,
 ) -> Result<()> {
     if persist {
         return session_result;
     }
 
     let names = [sandbox_name.to_string()];
-    if let Err(err) = sandbox_delete(server, &names, false, tls).await {
+    if let Err(err) = sandbox_delete(server, &names, false, tls, gateway).await {
         if session_result.is_ok() {
             return Err(err);
         }
@@ -2380,6 +2381,7 @@ pub async fn sandbox_create(
                     persist,
                     connect_result,
                     &effective_tls,
+                    gateway_name,
                 )
                 .await;
             }
@@ -2415,6 +2417,7 @@ pub async fn sandbox_create(
                 persist,
                 exec_result,
                 &effective_tls,
+                gateway_name,
             )
             .await
         }
@@ -2824,6 +2827,7 @@ pub async fn sandbox_delete(
     names: &[String],
     all: bool,
     tls: &TlsOptions,
+    gateway: &str,
 ) -> Result<()> {
     let mut client = grpc_client(server, tls).await?;
 
@@ -2864,6 +2868,7 @@ pub async fn sandbox_delete(
 
         let deleted = response.into_inner().deleted;
         if deleted {
+            clear_last_sandbox_if_matches(gateway, name);
             println!("{} Deleted sandbox {name}", "✓".green().bold());
         } else {
             println!("{} Sandbox {name} not found", "!".yellow());