diff --git a/pyfa.py b/pyfa.py
index 706af752c..9c8d0b14a 100755
--- a/pyfa.py
+++ b/pyfa.py
@@ -150,6 +150,12 @@ def _process_args(self, largs, rargs, values):
         mf = MainFrame(options.title)
         ErrorHandler.SetParent(mf)
 
+        # Start ESI token validation, this helps avoid token expiry
+        from service.esi import Esi
+        esi = Esi.getInstance()
+        esi.startTokenValidation()
+        pyfalog.info("ESI token validation started")
+
         if options.profile_path:
             profile_path = os.path.join(options.profile_path, 'pyfa-{}.profile'.format(datetime.datetime.now().strftime('%Y%m%d_%H%M%S')))
             pyfalog.debug("Starting pyfa with a profiler, saving to {}".format(profile_path))
diff --git a/service/esi.py b/service/esi.py
index 35d92a56f..e176e223f 100644
--- a/service/esi.py
+++ b/service/esi.py
@@ -25,6 +25,44 @@
 _t = wx.GetTranslation
 
 
+class EsiTokenValidationThread(threading.Thread):
+    def __init__(self, callback=None):
+        threading.Thread.__init__(self)
+        self.name = "EsiTokenValidation"
+        self.callback = callback
+        self.running = True
+
+    def run(self):
+        with config.logging_setup.threadbound():
+            try:
+                esi = Esi.getInstance()
+                chars = esi.getSsoCharacters()
+
+                for char in chars:
+                    if not self.running:
+                        return
+
+                    if char.is_token_expired():
+                        pyfalog.info(f"Token expired for {char.characterName}, attempting refresh")
+                        try:
+                            esi.refresh(char)
+                            eos.db.save(char)
+                            pyfalog.info(f"Successfully refreshed token for {char.characterName}")
+                        except Exception as e:
+                            pyfalog.error(f"Failed to refresh token for {char.characterName}: {e}")
+                    else:
+                        pyfalog.debug(f"Token valid for {char.characterName}")
+
+            except Exception as e:
+                pyfalog.error(f"Error validating ESI tokens: {e}")
+            finally:
+                if self.callback:
+                    wx.CallAfter(self.callback)
+
+    def stop(self):
+        self.running = False
+
+
 class Esi(EsiAccess):
     _instance = None
 
@@ -194,3 +232,9 @@ def handleServerRequest(self, message):
         pyfalog.debug("Handling SSO login with: {0}", message)
 
         self.handleLogin(message['code'])
+
+    def startTokenValidation(self):
+        pyfalog.debug("Starting ESI token validation thread")
+        tokenValidationThread = EsiTokenValidationThread()
+        tokenValidationThread.daemon = True
+        tokenValidationThread.start()