diff --git a/README.md b/README.md
index 3fced45..a00b2d9 100644
--- a/README.md
+++ b/README.md
@@ -292,6 +292,7 @@ timeouts:
   captcha_detection: 2.0              # Timeout for captcha iframe detection
   sms_verification: 4.0               # Timeout for SMS verification banners
   gdpr_prompt: 10.0                   # Timeout when handling GDPR dialogs
+  login_detection: 10.0               # Timeout for detecting existing login session via DOM elements
   publishing_result: 300.0            # Timeout for publishing status checks
   publishing_confirmation: 20.0       # Timeout for publish confirmation redirect
   image_upload: 30.0                  # Timeout for image upload and server-side processing
diff --git a/docs/BROWSER_TROUBLESHOOTING.md b/docs/BROWSER_TROUBLESHOOTING.md
index ba977d3..7ed5bd6 100644
--- a/docs/BROWSER_TROUBLESHOOTING.md
+++ b/docs/BROWSER_TROUBLESHOOTING.md
@@ -71,6 +71,29 @@ The bot will also provide specific instructions on how to fix your configuration
 2. Override specific keys under `timeouts` (e.g. `pagination_initial: 20.0`) if only a single selector is problematic.
 3. Keep `retry_enabled` on so that DOM lookups are retried with exponential backoff.
 
+### Issue: Bot fails to detect existing login session
+
+**Symptoms:**
+- Bot re-logins despite being already authenticated
+- Intermittent (50/50) login detection behavior
+- More common with profiles unused for 20+ days
+
+**What `login_detection` controls:**
+- Maximum time (seconds) to wait for user profile DOM elements when checking if already logged in
+- Default: `10.0` seconds (provides ~22.5s total with retry/backoff)
+- Used at startup before attempting login
+
+**When to increase `login_detection`:**
+- Frequent unnecessary re-logins despite being authenticated
+- Slow or unstable network connection
+- Using browser profiles that haven't been active for weeks
+
+**Example:**
+```yaml
+timeouts:
+  login_detection: 15.0  # For slower networks or old sessions
+```
+
 ## Common Issues and Solutions
 
 ### Issue 1: "Failed to connect to browser" with "root" error
diff --git a/schemas/config.schema.json b/schemas/config.schema.json
index b0621bc..d432e15 100644
--- a/schemas/config.schema.json
+++ b/schemas/config.schema.json
@@ -403,6 +403,13 @@
           "title": "Gdpr Prompt",
           "type": "number"
         },
+        "login_detection": {
+          "default": 10.0,
+          "description": "Timeout for detecting existing login session via DOM elements.",
+          "minimum": 1.0,
+          "title": "Login Detection",
+          "type": "number"
+        },
         "publishing_result": {
           "default": 300.0,
           "description": "Timeout for publishing result checks.",
diff --git a/src/kleinanzeigen_bot/__init__.py b/src/kleinanzeigen_bot/__init__.py
index 92f175f..d7b74e0 100644
--- a/src/kleinanzeigen_bot/__init__.py
+++ b/src/kleinanzeigen_bot/__init__.py
@@ -595,6 +595,8 @@ class KleinanzeigenBot(WebScrapingMixin):
     async def login(self) -> None:
         LOG.info("Checking if already logged in...")
         await self.web_open(f"{self.root_url}")
+        if getattr(self, "page", None) is not None:
+            LOG.debug(_("Current page URL after opening homepage: %s"), self.page.url)
 
         if await self.is_logged_in():
             LOG.info("Already logged in as [%s]. Skipping login.", self.config.login.username)
@@ -608,9 +610,15 @@ class KleinanzeigenBot(WebScrapingMixin):
 
         # Sometimes a second login is required
         if not await self.is_logged_in():
+            LOG.debug(_("First login attempt did not succeed, trying second login attempt"))
             await self.fill_login_data_and_send()
             await self.handle_after_login_logic()
 
+            if await self.is_logged_in():
+                LOG.debug(_("Second login attempt succeeded"))
+            else:
+                LOG.warning(_("Second login attempt also failed - login may not have succeeded"))
+
     async def fill_login_data_and_send(self) -> None:
         LOG.info("Logging in as [%s]...", self.config.login.username)
         await self.web_input(By.ID, "login-email", self.config.login.username)
@@ -646,19 +654,34 @@ class KleinanzeigenBot(WebScrapingMixin):
             pass
 
     async def is_logged_in(self) -> bool:
+        # Use login_detection timeout (10s default) instead of default (5s)
+        # to allow sufficient time for client-side JavaScript rendering after page load.
+        # This is especially important for older sessions (20+ days) that require
+        # additional server-side validation time.
+        login_check_timeout = self._timeout("login_detection")
+        effective_timeout = self._effective_timeout("login_detection")
+        username = self.config.login.username.lower()
+        LOG.debug(_("Starting login detection (timeout: %.1fs base, %.1fs effective with multiplier/backoff)"), login_check_timeout, effective_timeout)
+
+        # Try to find the standard element first
         try:
-            # Try to find the standard element first
-            user_info = await self.web_text(By.CLASS_NAME, "mr-medium")
-            if self.config.login.username.lower() in user_info.lower():
+            user_info = await self.web_text(By.CLASS_NAME, "mr-medium", timeout = login_check_timeout)
+            if username in user_info.lower():
+                LOG.debug(_("Login detected via .mr-medium element"))
                 return True
         except TimeoutError:
-            try:
-                # If standard element not found, try the alternative
-                user_info = await self.web_text(By.ID, "user-email")
-                if self.config.login.username.lower() in user_info.lower():
-                    return True
-            except TimeoutError:
-                return False
+            LOG.debug(_("Timeout waiting for .mr-medium element after %.1fs"), effective_timeout)
+
+        # If standard element not found or didn't contain username, try the alternative
+        try:
+            user_info = await self.web_text(By.ID, "user-email", timeout = login_check_timeout)
+            if username in user_info.lower():
+                LOG.debug(_("Login detected via #user-email element"))
+                return True
+        except TimeoutError:
+            LOG.debug(_("Timeout waiting for #user-email element after %.1fs"), effective_timeout)
+
+        LOG.debug(_("No login detected - neither .mr-medium nor #user-email found with username"))
         return False
 
     async def delete_ads(self, ad_cfgs:list[tuple[str, Ad, dict[str, Any]]]) -> None:
diff --git a/src/kleinanzeigen_bot/model/config_model.py b/src/kleinanzeigen_bot/model/config_model.py
index 1e224ab..5506f14 100644
--- a/src/kleinanzeigen_bot/model/config_model.py
+++ b/src/kleinanzeigen_bot/model/config_model.py
@@ -125,6 +125,7 @@ class TimeoutConfig(ContextualModel):
     captcha_detection:float = Field(default = 2.0, ge = 0.1, description = "Timeout for captcha iframe detection.")
     sms_verification:float = Field(default = 4.0, ge = 0.1, description = "Timeout for SMS verification prompts.")
     gdpr_prompt:float = Field(default = 10.0, ge = 1.0, description = "Timeout for GDPR/consent dialogs.")
+    login_detection:float = Field(default = 10.0, ge = 1.0, description = "Timeout for detecting existing login session via DOM elements.")
     publishing_result:float = Field(default = 300.0, ge = 10.0, description = "Timeout for publishing result checks.")
     publishing_confirmation:float = Field(default = 20.0, ge = 1.0, description = "Timeout for publish confirmation redirect.")
     image_upload:float = Field(default = 30.0, ge = 5.0, description = "Timeout for image upload and server-side processing.")
diff --git a/src/kleinanzeigen_bot/resources/translations.de.yaml b/src/kleinanzeigen_bot/resources/translations.de.yaml
index 55827e4..b91b8c4 100644
--- a/src/kleinanzeigen_bot/resources/translations.de.yaml
+++ b/src/kleinanzeigen_bot/resources/translations.de.yaml
@@ -61,8 +61,20 @@ kleinanzeigen_bot/__init__.py:
 
   login:
     "Checking if already logged in...": "Überprüfe, ob bereits eingeloggt..."
+    "Current page URL after opening homepage: %s": "Aktuelle Seiten-URL nach dem Öffnen der Startseite: %s"
     "Already logged in as [%s]. Skipping login.": "Bereits eingeloggt als [%s]. Überspringe Anmeldung."
     "Opening login page...": "Öffne Anmeldeseite..."
+    "First login attempt did not succeed, trying second login attempt": "Erster Anmeldeversuch war nicht erfolgreich, versuche zweiten Anmeldeversuch"
+    "Second login attempt succeeded": "Zweiter Anmeldeversuch erfolgreich"
+    "Second login attempt also failed - login may not have succeeded": "Zweiter Anmeldeversuch ebenfalls fehlgeschlagen - Anmeldung möglicherweise nicht erfolgreich"
+
+  is_logged_in:
+    "Starting login detection (timeout: %.1fs base, %.1fs effective with multiplier/backoff)": "Starte Login-Erkennung (Timeout: %.1fs Basis, %.1fs effektiv mit Multiplikator/Backoff)"
+    "Login detected via .mr-medium element": "Login erkannt über .mr-medium Element"
+    "Timeout waiting for .mr-medium element after %.1fs": "Timeout beim Warten auf .mr-medium Element nach %.1fs"
+    "Login detected via #user-email element": "Login erkannt über #user-email Element"
+    "Timeout waiting for #user-email element after %.1fs": "Timeout beim Warten auf #user-email Element nach %.1fs"
+    "No login detected - neither .mr-medium nor #user-email found with username": "Kein Login erkannt - weder .mr-medium noch #user-email mit Benutzername gefunden"
 
   handle_after_login_logic:
     "# Device verification message detected. Please follow the instruction displayed in the Browser.": "# Nachricht zur Geräteverifizierung erkannt. Bitte den Anweisungen im Browser folgen."