diff --git a/cli/src/connection.rs b/cli/src/connection.rs
index f4231649d..62fb0bc15 100644
--- a/cli/src/connection.rs
+++ b/cli/src/connection.rs
@@ -477,9 +477,11 @@ fn connect(session: &str) -> Result<Connection, String> {
 }
 
 pub fn send_command(cmd: Value, session: &str) -> Result<Response, String> {
-    // Retry logic for transient errors (EAGAIN/EWOULDBLOCK/connection issues)
-    const MAX_RETRIES: u32 = 5;
-    const RETRY_DELAY_MS: u64 = 200;
+    // Retry logic for transient errors (EAGAIN/EWOULDBLOCK/connection issues).
+    // Use generous retries to handle slow or resource-constrained environments
+    // (e.g. VMs) where the daemon may be slow to start or respond.
+    const MAX_RETRIES: u32 = 8;
+    const RETRY_DELAY_MS: u64 = 500;
 
     let mut last_error = String::new();
 
@@ -543,6 +545,9 @@ fn send_command_once(cmd: &Value, session: &str) -> Result<Response, String> {
     stream
         .write_all(json_str.as_bytes())
         .map_err(|e| format!("Failed to send: {}", e))?;
+    stream
+        .flush()
+        .map_err(|e| format!("Failed to send: {}", e))?;
 
     let mut reader = BufReader::new(stream);
     let mut response_line = String::new();
diff --git a/cli/src/native/daemon.rs b/cli/src/native/daemon.rs
index 8b1c8506a..50f3465f2 100644
--- a/cli/src/native/daemon.rs
+++ b/cli/src/native/daemon.rs
@@ -360,6 +360,7 @@ async fn handle_connection<S>(
                         let mut resp = serde_json::to_string(&err).unwrap_or_default();
                         resp.push('\n');
                         let _ = writer.write_all(resp.as_bytes()).await;
+                        let _ = writer.flush().await;
                         continue;
                     }
                 };
@@ -380,6 +381,9 @@ async fn handle_connection<S>(
                 if writer.write_all(resp.as_bytes()).await.is_err() {
                     break;
                 }
+                if writer.flush().await.is_err() {
+                    break;
+                }
 
                 if is_close {
                     if let Some(ref path) = stream_file_cleanup {