diff --git a/src/Win_Client.py b/src/Win_Client.py
index d8c8c9b..894db8c 100644
--- a/src/Win_Client.py
+++ b/src/Win_Client.py
@@ -24,17 +24,46 @@ CONFIG_FILE_NAME = "client_config.json"
 STATE_FILE_NAME = "client_state.json"
 
 
-def enroll_client_if_needed(hub_url: str, enrollment_secret: str, cert_dir: str, client_id: str, hostname: str, os_type: str = "windows"):
-    """Bootstraps client enrollment if certificates are missing."""
+def is_cert_expiring_soon(cert_path: str, threshold_days: int = 30) -> bool:
+    """Checks if client certificate at cert_path is expiring within threshold_days."""
+    if not os.path.exists(cert_path):
+        return True
+    try:
+        from cryptography import x509
+        with open(cert_path, "r", encoding="utf-8") as f:
+            cert = x509.load_pem_x509_certificate(f.read().encode("utf-8"))
+        expiry = getattr(cert, "not_valid_after_utc", None)
+        if expiry is None:
+            expiry = cert.not_valid_after.replace(tzinfo=timezone.utc)
+        now = datetime.now(timezone.utc)
+        return expiry <= (now + timedelta(days=threshold_days))
+    except Exception:
+        return True
+
+
+def enroll_client_if_needed(
+    hub_url: str,
+    enrollment_secret: str,
+    cert_dir: str,
+    client_id: str,
+    hostname: str,
+    os_type: str = "windows",
+    force_renew: bool = False,
+    threshold_days: int = 30
+):
+    """Bootstraps client enrollment if certificates are missing or expiring soon."""
     os.makedirs(cert_dir, exist_ok=True)
     ca_path = os.path.join(cert_dir, "ca.crt")
     cert_path = os.path.join(cert_dir, "client.crt")
     key_path = os.path.join(cert_dir, "client.key")
 
-    if os.path.exists(ca_path) and os.path.exists(cert_path) and os.path.exists(key_path):
-        return True
+    if not force_renew and os.path.exists(ca_path) and os.path.exists(cert_path) and os.path.exists(key_path):
+        if not is_cert_expiring_soon(cert_path, threshold_days=threshold_days):
+            return True
+        print(f"[*] Client certificate at {cert_path} is expiring within {threshold_days} days. Auto-renewing...")
 
-    print(f"[*] Bootstrapping client enrollment with LOGAR Hub at {hub_url}...")
+    action_name = "re-enrolling" if os.path.exists(cert_path) else "enrolling"
+    print(f"[*] Bootstrapping client {action_name} with LOGAR Hub at {hub_url}...")
     enroll_endpoint = f"{hub_url.rstrip('/')}/api/client/enroll"
     payload = {
         "client_id": client_id,
@@ -64,7 +93,7 @@ def enroll_client_if_needed(hub_url: str, enrollment_secret: str, cert_dir: str,
     except Exception:
         pass
 
-    print(f"[+] Client enrolled successfully! Certificates saved to {os.path.abspath(cert_dir)}")
+    print(f"[+] Client certificates updated successfully in {os.path.abspath(cert_dir)}")
     return True
 
 
@@ -269,6 +298,7 @@ def send_encrypted_logs_over_socket(config: dict, logs: list):
     machine_id = get_machine_identifier()
 
     # Attempt automatic enrollment bootstrap if certs are missing and secret is provided
+    hub_url = None
     if enrollment_secret:
         hermes_host = config.get("hermes_host", server_host)
         hermes_port = config.get("hermes_port", 8443)
@@ -285,7 +315,22 @@ def send_encrypted_logs_over_socket(config: dict, logs: list):
 
     if has_mtls_certs:
         print(f"[*] Connecting to LOGAR server at {server_host}:{server_port} over mTLS (TLS 1.3)...")
-        with get_tls_socket(server_host, server_port, cert_dir) as sock:
+        sock = None
+        try:
+            sock = get_tls_socket(server_host, server_port, cert_dir)
+        except (ssl.SSLError, ssl.CertificateError, ConnectionResetError) as tls_err:
+            if enrollment_secret and hub_url:
+                print(f"[!] TLS handshake error ({tls_err}). Re-enrolling with LOGAR Hub...")
+                try:
+                    enroll_client_if_needed(hub_url, enrollment_secret, cert_dir, machine_id, machine_id, os_type="windows", force_renew=True)
+                    sock = get_tls_socket(server_host, server_port, cert_dir)
+                except Exception as retry_err:
+                    print(f"[!] Re-enrollment or reconnection retry failed: {retry_err}")
+                    raise
+            else:
+                raise
+
+        with sock:
             payload = {
                 "server": machine_id,
                 "timestamp": datetime.now(timezone.utc).isoformat(),