diff --git a/crates/openshell-bootstrap/src/lib.rs b/crates/openshell-bootstrap/src/lib.rs
index b6423aae..343653f9 100644
--- a/crates/openshell-bootstrap/src/lib.rs
+++ b/crates/openshell-bootstrap/src/lib.rs
@@ -49,8 +49,9 @@ pub use crate::docker::{
 };
 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,
+    clear_last_sandbox_if_matches, 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,
 };
 
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 84a323b5..6572a286 100644
--- a/crates/openshell-cli/src/main.rs
+++ b/crates/openshell-cli/src/main.rs
@@ -2058,7 +2058,8 @@ 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 37f11fcb..68dc4a68 100644
--- a/crates/openshell-cli/src/run.rs
+++ b/crates/openshell-cli/src/run.rs
@@ -18,7 +18,8 @@ use miette::{IntoDiagnostic, Result, WrapErr};
 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,
+    clear_last_sandbox_if_matches, remove_gateway_metadata, resolve_ssh_hostname,
+    save_active_gateway, save_last_sandbox,
     store_gateway_metadata,
 };
 use openshell_core::proto::{
@@ -2743,6 +2744,7 @@ pub async fn sandbox_delete(
     names: &[String],
     all: bool,
     tls: &TlsOptions,
+    gateway: &str,
 ) -> Result<()> {
     let mut client = grpc_client(server, tls).await?;
 
@@ -2783,6 +2785,7 @@ 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());