diff --git a/screenpipe-server/Cargo.toml b/screenpipe-server/Cargo.toml
index 1b62caf97c..b82aac2dbe 100644
--- a/screenpipe-server/Cargo.toml
+++ b/screenpipe-server/Cargo.toml
@@ -170,4 +170,5 @@ nix = { version = "0.29", features = ["signal"] }
 windows = { version = "0.58", features = [
     "Win32_System_Threading",
     "Win32_Foundation",
+    "Win32_Networking_WinSock",
 ] }
diff --git a/screenpipe-server/src/auto_destruct.rs b/screenpipe-server/src/auto_destruct.rs
index 553f9c82b0..c479396961 100644
--- a/screenpipe-server/src/auto_destruct.rs
+++ b/screenpipe-server/src/auto_destruct.rs
@@ -2,89 +2,276 @@ use std::process::Command;
 use std::time::Duration;
 use tokio::time::sleep;
 #[cfg(target_os = "windows")]
-use tracing::debug;
-use tracing::info;
-#[cfg(target_os = "windows")]
 use windows::Win32::Foundation::{CloseHandle, HANDLE, STILL_ACTIVE};
 #[cfg(target_os = "windows")]
 use windows::Win32::System::Threading::{
-    GetExitCodeProcess, OpenProcess, PROCESS_QUERY_INFORMATION,
+    CreateJobObjectW, AssignProcessToJobObject, GetExitCodeProcess, OpenProcess, TerminateProcess,
+    PROCESS_QUERY_INFORMATION, PROCESS_TERMINATE, PROCESS_ALL_ACCESS,
 };
+use tracing::{debug, error, info, warn};
+use std::io::Error as IoError;
+use thiserror::Error;
+
+#[cfg(target_os = "windows")]
+#[derive(Error, Debug)]
+pub enum ProcessError {
+    #[error("Failed to open process: {0}")]
+    OpenProcess(IoError),
+    #[error("Failed to terminate process: {0}")]
+    TerminateProcess(IoError),
+    #[error("Process became unresponsive")]
+    Unresponsive,
+    #[error("Port is still in use")]
+    PortInUse,
+    #[error("Failed to kill port: {0}")]
+    KillPort(String),
+}
+
+#[cfg(target_os = "windows")]
+#[derive(Debug)]
+pub struct ProcessStatus {
+    pub terminated: bool,
+    pub exit_code: Option<u32>,
+    pub port_released: bool,
+}
+
+#[cfg(target_os = "windows")]
+pub struct ProcessManager {
+    pid: u32,
+    port: u16,
+    job_handle: HANDLE,
+}
 
 #[cfg(target_os = "windows")]
-fn is_process_alive(pid: u32) -> bool {
-    unsafe {
-        let process: HANDLE = match OpenProcess(PROCESS_QUERY_INFORMATION, false, pid) {
-            Ok(handle) => handle,
-            Err(e) => {
-                debug!("Failed to open process with PID ({}): {:?}", pid, e);
-                return false;
+impl ProcessManager {
+    pub fn new(pid: u32, port: u16) -> windows::core::Result<Self> {
+        unsafe {
+            let job_handle = CreateJobObjectW(None, None)?;
+            let process_handle = OpenProcess(PROCESS_ALL_ACCESS, false, pid)?;
+            AssignProcessToJobObject(job_handle, process_handle)?;
+            CloseHandle(process_handle).expect("Failed to close process handle");
+            Ok(Self {
+                pid,
+                port,
+                job_handle,
+            })
+        }
+    }
+
+    fn is_process_alive(&self) -> Result<bool, ProcessError> {
+        unsafe {
+            let process = OpenProcess(PROCESS_QUERY_INFORMATION | PROCESS_TERMINATE, false, self.pid)
+                .map_err(|e| ProcessError::OpenProcess(IoError::from_raw_os_error(e.code().0)))?;
+            
+            if process.is_invalid() {
+                return Ok(false);
             }
-        };
-        if process.is_invalid() {
-            return false;
-        }
-        let mut exit_code: u32 = 0;
-        let result = GetExitCodeProcess(process, &mut exit_code);
-        CloseHandle(process).expect("Failed to close process handle");
-        if result.is_err() {
-            debug!("Failed to get exit code for process with PID ({})", pid);
-            return false;
-        }
-        exit_code == STILL_ACTIVE.0 as u32
+
+            let mut exit_code: u32 = 0;
+            GetExitCodeProcess(process, &mut exit_code).map_err(|_| ProcessError::Unresponsive)?;
+            CloseHandle(process).expect("Failed to close process handle");
+
+            Ok(exit_code == STILL_ACTIVE.0 as u32)
+        }
     }
-}
 
-pub async fn watch_pid(pid: u32) -> bool {
-    info!("starting to watch for app termination (pid: {})", pid);
+    fn get_port_pids(&self) -> Vec<u32> {
+        let netstat_output = Command::new("netstat")
+            .args(&["-ano"])
+            .output()
+            .expect("failed to execute netstat");
 
-    loop {
-        #[cfg(target_os = "windows")]
-        {
-            // Try Windows API first
-            if !is_process_alive(pid) {
-                debug!("Process ({}) not found via windows api", pid);
-                return true;
+        let output = String::from_utf8_lossy(&netstat_output.stdout);
+        let mut pids = Vec::new();
+
+        for line in output.lines() {
+            if line.contains(&format!(":{}", self.port)) {
+                if let Some(pid_str) = line.split_whitespace().last() {
+                    if let Ok(pid) = pid_str.parse::<u32>() {
+                        pids.push(pid);
+                    }
+                }
+            }
+        }
+        pids
+    }
+
+    fn kill_port_forcefully(&self) -> Result<(), ProcessError> {
+        // First try using killport crate
+        if let Err(e) = killport::kill(self.port as u16) {
+            warn!("killport failed: {:?}, trying alternative methods", e);
+        }
+
+        // Then try killing all processes using the port
+        for pid in self.get_port_pids() {
+            unsafe {
+                if let Ok(process) = OpenProcess(PROCESS_TERMINATE, false, pid) {
+                    let _ = TerminateProcess(process, 1);
+                    CloseHandle(process).expect("Failed to close process handle");
+                }
+            }
+        }
+
+        // Verify port is released
+        if self.is_port_in_use() {
+            Err(ProcessError::KillPort(format!("Failed to release port {}", self.port)))
+        } else {
+            Ok(())
+        }
+    }
+
+    fn is_port_in_use(&self) -> bool {
+        let netstat_output = Command::new("netstat")
+            .args(&["-ano"])
+            .output()
+            .expect("failed to execute netstat");
+
+        let output = String::from_utf8_lossy(&netstat_output.stdout);
+        output.contains(&format!(":{}", self.port))
+    }
+
+    async fn try_graceful_shutdown(&self) -> Result<(), ProcessError> {
+        for _ in 0..3 {
+            if !self.is_process_alive()? {
+                // Even if process is dead, ensure port is released
+                if !self.is_port_in_use() {
+                    return Ok(());
+                }
+            }
+            sleep(Duration::from_secs(1)).await;
+        }
+        Err(ProcessError::Unresponsive)
+    }
+
+    pub async fn force_terminate(&self) -> Result<(), ProcessError> {
+        // First try normal process termination
+        unsafe {
+            let process = OpenProcess(PROCESS_TERMINATE, false, self.pid)
+                .map_err(|e| ProcessError::OpenProcess(IoError::from_raw_os_error(e.code().0)))?;
+
+            if !process.is_invalid() {
+                TerminateProcess(process, 1)
+                    .map_err(|e| ProcessError::TerminateProcess(IoError::from_raw_os_error(e.code().0)))?;
+                CloseHandle(process).expect("Failed to close process handle");
             }
+        }
+
+        // Then ensure port is released
+        if self.is_port_in_use() {
+            self.kill_port_forcefully()?;
+        }
+
+        Ok(())
+    }
 
-            // Fallback to Command approach
-            let pid_output = Command::new("tasklist")
-                .args(&["/FI", &format!("PID eq {}", pid), "/NH", "/FO", "CSV"])
-                .output()
-                .expect("failed to check pid");
-
-            let app_output = Command::new("tasklist")
-                .args(&[
-                    "/FI",
-                    "IMAGENAME eq screenpipe-app.exe",
-                    "/NH",
-                    "/FO",
-                    "CSV",
-                ])
-                .output()
-                .expect("failed to check app name");
-
-            let pid_alive = String::from_utf8_lossy(&pid_output.stdout).contains(&pid.to_string());
-            let app_alive = !String::from_utf8_lossy(&app_output.stdout).is_empty();
-
-            info!("pid alive: {}, app alive: {}", pid_alive, app_alive);
-
-            if !pid_alive || !app_alive {
-                return true;
+    pub async fn watch_and_cleanup(&self) -> Result<ProcessStatus, ProcessError> {
+        info!("starting enhanced process monitoring (pid: {}, port: {})", self.pid, self.port);
+        
+        let mut consecutive_fails = 0;
+        let max_fails = 3;
+
+        loop {
+            match self.is_process_alive() {
+                Ok(false) => {
+                    debug!("Process ({}) not found via Windows API", self.pid);
+                    break;
+                }
+                Ok(true) => {
+                    consecutive_fails = 0;
+                }
+                Err(e) => {
+                    consecutive_fails += 1;
+                    error!("Error checking process status: {:?}", e);
+                    if consecutive_fails >= max_fails {
+                        return Err(ProcessError::Unresponsive);
+                    }
+                }
             }
+
+            sleep(Duration::from_secs(1)).await;
+        }
+
+        // Try graceful shutdown first
+        if let Err(e) = self.try_graceful_shutdown().await {
+            warn!("Graceful shutdown failed: {:?}, attempting force terminate", e);
+            self.force_terminate().await?;
+        }
+
+        // If port is still in use after process termination, force kill it
+        if self.is_port_in_use() {
+            warn!("Port {} still in use after process termination, force killing", self.port);
+            self.kill_port_forcefully()?;
+        }
+
+        let mut port_released = false;
+        for _ in 0..5 {
+            if !self.is_port_in_use() {
+                port_released = true;
+                break;
+            }
+            sleep(Duration::from_secs(1)).await;
+        }
+
+        if !port_released {
+            return Err(ProcessError::PortInUse);
         }
 
-        #[cfg(not(target_os = "windows"))]
-        {
-            let output = Command::new("ps")
-                .args(&["-p", &pid.to_string()])
-                .output()
-                .expect("failed to execute process check command");
+        Ok(ProcessStatus {
+            terminated: true,
+            exit_code: None,
+            port_released,
+        })
+    }
+}
+
+#[cfg(target_os = "windows")]
+impl Drop for ProcessManager {
+    fn drop(&mut self) {
+        unsafe {
+            CloseHandle(self.job_handle).expect("Failed to close job handle");
+        }
+    }
+}
 
-            if !output.status.success() || output.stdout.is_empty() {
-                return true;
+#[cfg(target_os = "windows")]
+pub async fn watch_pid(pid: u32) -> bool {
+    let port = 3030;
+    match ProcessManager::new(pid, port) {
+        Ok(manager) => {
+            match manager.watch_and_cleanup().await {
+                Ok(status) => {
+                    info!(
+                        "Process terminated successfully. Port released: {}",
+                        status.port_released
+                    );
+                    true
+                }
+                Err(e) => {
+                    error!("Failed to manage process: {:?}", e);
+                    false
+                }
             }
         }
+        Err(e) => {
+            error!("Failed to create process manager: {:?}", e);
+            false
+        }
+    }
+}
+
+#[cfg(not(target_os = "windows"))]
+pub async fn watch_pid(pid: u32) -> bool {
+    info!("starting to watch for app termination (pid: {})", pid);
+
+    loop {
+        let output = Command::new("ps")
+            .args(&["-p", &pid.to_string()])
+            .output()
+            .expect("failed to execute process check command");
+
+        if !output.status.success() || output.stdout.is_empty() {
+            return true;
+        }
 
         sleep(Duration::from_secs(1)).await;
     }