From 7098719d5bfbeab9ff4fb48f9172d4c31001cd7f Mon Sep 17 00:00:00 2001
From: Jens <1742418+1cu@users.noreply.github.com>
Date: Wed, 28 Jan 2026 06:08:03 +0100
Subject: [PATCH] fix: extend command fails with >25 ads due to pagination
 (#793)

---
 src/kleinanzeigen_bot/__init__.py             |  22 +-
 src/kleinanzeigen_bot/extract.py              | 104 +----
 .../resources/translations.de.yaml            |  29 +-
 .../utils/web_scraping_mixin.py               | 105 +++++
 tests/unit/test_extend_command.py             | 401 ++++++++----------
 tests/unit/test_extract.py                    |  74 ++++
 tests/unit/test_web_scraping_pagination.py    | 181 ++++++++
 7 files changed, 589 insertions(+), 327 deletions(-)
 create mode 100644 tests/unit/test_web_scraping_pagination.py

diff --git a/src/kleinanzeigen_bot/__init__.py b/src/kleinanzeigen_bot/__init__.py
index 3b09559..edf6dd9 100644
--- a/src/kleinanzeigen_bot/__init__.py
+++ b/src/kleinanzeigen_bot/__init__.py
@@ -999,15 +999,23 @@ class KleinanzeigenBot(WebScrapingMixin):  # noqa: PLR0904
         LOG.info("Extending ad '%s' (ID: %s)...", ad_cfg.title, ad_cfg.id)
 
         try:
-            # Navigate to ad management page
-            await self.web_open(f"{self.root_url}/m-meine-anzeigen.html")
-
-            # Find and click "Verlängern" (extend) button for this ad
+            # Navigate to ad management page and find extend button across all pages
             extend_button_xpath = f'//li[@data-adid="{ad_cfg.id}"]//button[contains(., "Verlängern")]'
 
-            try:
-                await self.web_click(By.XPATH, extend_button_xpath)
-            except TimeoutError:
+            async def find_and_click_extend_button(page_num:int) -> bool:
+                """Try to find and click extend button on current page."""
+                try:
+                    extend_button = await self.web_find(By.XPATH, extend_button_xpath, timeout = self._timeout("quick_dom"))
+                    LOG.info("Found extend button on page %s", page_num)
+                    await extend_button.click()
+                    return True  # Success - stop pagination
+                except TimeoutError:
+                    LOG.debug("Extend button not found on page %s", page_num)
+                    return False  # Continue to next page
+
+            success = await self._navigate_paginated_ad_overview(find_and_click_extend_button, page_url = f"{self.root_url}/m-meine-anzeigen.html")
+
+            if not success:
                 LOG.error(" -> FAILED: Could not find extend button for ad ID %s", ad_cfg.id)
                 return False
 
diff --git a/src/kleinanzeigen_bot/extract.py b/src/kleinanzeigen_bot/extract.py
index 03def4b..30cc653 100644
--- a/src/kleinanzeigen_bot/extract.py
+++ b/src/kleinanzeigen_bot/extract.py
@@ -148,104 +148,34 @@ class AdExtractor(WebScrapingMixin):
 
         :return: the links to your ad pages
         """
-        # navigate to "your ads" page
-        await self.web_open("https://www.kleinanzeigen.de/m-meine-anzeigen.html")
-        await self.web_sleep(2000, 3000)  # Consider replacing with explicit waits later
-
-        # Try to find the main ad list container first
-        try:
-            _ = await self.web_find(By.ID, "my-manageitems-adlist")
-        except TimeoutError:
-            LOG.warning("Ad list container #my-manageitems-adlist not found. Maybe no ads present?")
-            return []
-
-        # --- Pagination handling ---
-        multi_page = False
-        pagination_timeout = self._timeout("pagination_initial")
-        try:
-            # Correct selector: Use uppercase '.Pagination'
-            pagination_section = await self.web_find(By.CSS_SELECTOR, ".Pagination", timeout = pagination_timeout)  # Increased timeout slightly
-            # Correct selector: Use 'aria-label'
-            # Also check if the button is actually present AND potentially enabled (though enabled check isn't strictly necessary here, only for clicking later)
-            next_buttons = await self.web_find_all(By.CSS_SELECTOR, 'button[aria-label="Nächste"]', parent = pagination_section)
-            if next_buttons:
-                # Check if at least one 'Nächste' button is not disabled (optional but good practice)
-                enabled_next_buttons = [btn for btn in next_buttons if not btn.attrs.get("disabled")]
-                if enabled_next_buttons:
-                    multi_page = True
-                    LOG.info("Multiple ad pages detected.")
-                else:
-                    LOG.info("Next button found but is disabled. Assuming single effective page.")
-
-            else:
-                LOG.info('No "Naechste" button found within pagination. Assuming single page.')
-        except TimeoutError:
-            # This will now correctly trigger only if the '.Pagination' div itself is not found
-            LOG.info("No pagination controls found. Assuming single page.")
-        except Exception as e:
-            LOG.exception("Error during pagination detection: %s", e)
-            LOG.info("Assuming single page due to error during pagination check.")
-        # --- End Pagination Handling ---
-
         refs:list[str] = []
-        current_page = 1
-        while True:  # Loop reference extraction
-            LOG.info("Extracting ads from page %s...", current_page)
-            # scroll down to load dynamically if necessary
-            await self.web_scroll_page_down()
-            await self.web_sleep(2000, 3000)  # Consider replacing with explicit waits
 
-            # Re-find the ad list container on the current page/state
+        async def extract_page_refs(page_num:int) -> bool:
+            """Extract ad reference URLs from the current page.
+
+            :param page_num: The current page number being processed
+            :return: True to stop pagination (e.g. ads container disappeared), False to continue to next page
+            """
             try:
                 ad_list_container = await self.web_find(By.ID, "my-manageitems-adlist")
                 list_items = await self.web_find_all(By.CLASS_NAME, "cardbox", parent = ad_list_container)
-                LOG.info("Found %s ad items on page %s.", len(list_items), current_page)
-            except TimeoutError:
-                LOG.warning("Could not find ad list container or items on page %s.", current_page)
-                break  # Stop if ads disappear
+                LOG.info("Found %s ad items on page %s.", len(list_items), page_num)
 
-            # Extract references using the CORRECTED selector
-            try:
                 page_refs:list[str] = [str((await self.web_find(By.CSS_SELECTOR, "div h3 a.text-onSurface", parent = li)).attrs["href"]) for li in list_items]
                 refs.extend(page_refs)
-                LOG.info("Successfully extracted %s refs from page %s.", len(page_refs), current_page)
-            except Exception as e:
-                # Log the error if extraction fails for some items, but try to continue
-                LOG.exception("Error extracting refs on page %s: %s", current_page, e)
+                LOG.info("Successfully extracted %s refs from page %s.", len(page_refs), page_num)
+                return False  # Continue to next page
 
-            if not multi_page:  # only one iteration for single-page overview
-                break
-
-            # --- Navigate to next page ---
-            follow_up_timeout = self._timeout("pagination_follow_up")
-            try:
-                # Find the pagination section again (scope might have changed after scroll/wait)
-                pagination_section = await self.web_find(By.CSS_SELECTOR, ".Pagination", timeout = follow_up_timeout)
-                # Find the "Next" button using the correct aria-label selector and ensure it's not disabled
-                next_button_element = None
-                possible_next_buttons = await self.web_find_all(By.CSS_SELECTOR, 'button[aria-label="Nächste"]', parent = pagination_section)
-                for btn in possible_next_buttons:
-                    if not btn.attrs.get("disabled"):  # Check if the button is enabled
-                        next_button_element = btn
-                        break  # Found an enabled next button
-
-                if next_button_element:
-                    LOG.info("Navigating to next page...")
-                    await next_button_element.click()
-                    current_page += 1
-                    # Wait for page load - consider waiting for a specific element on the new page instead of fixed sleep
-                    await self.web_sleep(3000, 4000)
-                else:
-                    LOG.info('Last ad overview page explored (no enabled "Naechste" button found).')
-                    break
             except TimeoutError:
-                # This might happen if pagination disappears on the last page after loading
-                LOG.info("No pagination controls found after scrolling/waiting. Assuming last page.")
-                break
+                LOG.warning("Could not find ad list container or items on page %s.", page_num)
+                return True  # Stop pagination (ads disappeared)
             except Exception as e:
-                LOG.exception("Error during pagination navigation: %s", e)
-                break
-            # --- End Navigation ---
+                # Continue despite error for resilience against transient web scraping issues
+                # (e.g., DOM structure changes, network glitches). LOG.exception ensures visibility.
+                LOG.exception("Error extracting refs on page %s: %s", page_num, e)
+                return False  # Continue to next page
+
+        await self._navigate_paginated_ad_overview(extract_page_refs)
 
         if not refs:
             LOG.warning("No ad URLs were extracted.")
diff --git a/src/kleinanzeigen_bot/resources/translations.de.yaml b/src/kleinanzeigen_bot/resources/translations.de.yaml
index 4d05f75..4a70845 100644
--- a/src/kleinanzeigen_bot/resources/translations.de.yaml
+++ b/src/kleinanzeigen_bot/resources/translations.de.yaml
@@ -112,6 +112,9 @@ kleinanzeigen_bot/__init__.py:
     " -> FAILED: Timeout while extending ad '%s': %s": " -> FEHLER: Zeitüberschreitung beim Verlängern der Anzeige '%s': %s"
     " -> FAILED: Could not persist extension for ad '%s': %s": " -> FEHLER: Verlängerung der Anzeige '%s' konnte nicht gespeichert werden: %s"
 
+  find_and_click_extend_button:
+    "Found extend button on page %s": "'Verlängern'-Button auf Seite %s gefunden"
+
   finalize_installation_mode:
     "Config file: %s": "Konfigurationsdatei: %s"
     "First run detected, prompting user for installation mode": "Erster Start erkannt, frage Benutzer nach Installationsmodus"
@@ -259,21 +262,11 @@ kleinanzeigen_bot/extract.py:
     "Failed to extract ad ID from URL '%s': %s": "Fehler beim Extrahieren der Anzeigen-ID aus der URL '%s': %s"
 
   extract_own_ads_urls:
-    "Ad list container #my-manageitems-adlist not found. Maybe no ads present?": "Anzeigenlistencontainer #my-manageitems-adlist nicht gefunden. Vielleicht sind keine Anzeigen vorhanden?"
-    "Multiple ad pages detected.": "Mehrere Anzeigenseiten erkannt."
-    "Next button found but is disabled. Assuming single effective page.": "Weiter-Button gefunden, aber deaktiviert. Es wird von einer einzelnen effektiven Seite ausgegangen."
-    "No \"Naechste\" button found within pagination. Assuming single page.": "Kein \"Nächste\"-Button in der Paginierung gefunden. Es wird von einer einzelnen Seite ausgegangen."
-    "No pagination controls found. Assuming single page.": "Keine Paginierungssteuerung gefunden. Es wird von einer einzelnen Seite ausgegangen."
-    "Assuming single page due to error during pagination check.": "Es wird von einer einzelnen Seite ausgegangen wegen eines Fehlers bei der Paginierungsprüfung."
-    "Navigating to next page...": "Navigiere zur nächsten Seite..."
-    "Last ad overview page explored (no enabled \"Naechste\" button found).": "Letzte Anzeigenübersichtsseite erkundet (kein aktivierter \"Nächste\"-Button gefunden)."
-    "No pagination controls found after scrolling/waiting. Assuming last page.": "Keine Paginierungssteuerung nach dem Scrollen/Warten gefunden. Es wird von der letzten Seite ausgegangen."
     "No ad URLs were extracted.": "Es wurden keine Anzeigen-URLs extrahiert."
+
+  extract_page_refs:
     "Could not find ad list container or items on page %s.": "Anzeigenlistencontainer oder Elemente auf Seite %s nicht gefunden."
-    "Error during pagination detection: %s": "Fehler bei der Paginierungserkennung: %s"
-    "Error during pagination navigation: %s": "Fehler bei der Paginierungsnavigation: %s"
     "Error extracting refs on page %s: %s": "Fehler beim Extrahieren der Referenzen auf Seite %s: %s"
-    "Extracting ads from page %s...": "Extrahiere Anzeigen von Seite %s..."
     "Found %s ad items on page %s.": "%s Anzeigen-Elemente auf Seite %s gefunden."
     "Successfully extracted %s refs from page %s.": "%s Referenzen von Seite %s erfolgreich extrahiert."
 
@@ -488,6 +481,18 @@ kleinanzeigen_bot/utils/web_scraping_mixin.py:
     "Combobox missing aria-controls attribute": "Combobox fehlt aria-controls Attribut"
     "No matching option found in combobox: '%s'": "Keine passende Option in Combobox gefunden: '%s'"
 
+  _navigate_paginated_ad_overview:
+    "Failed to open ad overview page at %s: timeout": "Fehler beim Öffnen der Anzeigenübersichtsseite unter %s: Zeitüberschreitung"
+    "Scroll timeout on page %s (non-critical, continuing)": "Zeitüberschreitung beim Scrollen auf Seite %s (nicht kritisch, wird fortgesetzt)"
+    "Page action timed out on page %s": "Seitenaktion hat auf Seite %s eine Zeitüberschreitung erreicht"
+    "Ad list container not found. Maybe no ads present?": "Anzeigenlistencontainer nicht gefunden. Vielleicht sind keine Anzeigen vorhanden?"
+    "Multiple ad pages detected.": "Mehrere Anzeigenseiten erkannt."
+    "No pagination controls found. Assuming single page.": "Keine Paginierungssteuerung gefunden. Es wird von einer einzelnen Seite ausgegangen."
+    "Processing page %s...": "Verarbeite Seite %s..."
+    "Navigating to page %s...": "Navigiere zu Seite %s..."
+    "Last page reached (no enabled 'Naechste' button found).": "Letzte Seite erreicht (kein aktivierter 'Naechste'-Button gefunden)."
+    "No pagination controls found. Assuming last page.": "Keine Paginierungssteuerung gefunden. Es wird von der letzten Seite ausgegangen."
+
   close_browser_session:
     "Closing Browser session...": "Schließe Browser-Sitzung..."
 
diff --git a/src/kleinanzeigen_bot/utils/web_scraping_mixin.py b/src/kleinanzeigen_bot/utils/web_scraping_mixin.py
index fab1ac8..522975a 100644
--- a/src/kleinanzeigen_bot/utils/web_scraping_mixin.py
+++ b/src/kleinanzeigen_bot/utils/web_scraping_mixin.py
@@ -969,6 +969,111 @@ class WebScrapingMixin:
         )
         await self.page.sleep(duration / 1_000)
 
+    async def _navigate_paginated_ad_overview(
+        self,
+        page_action:Callable[[int], Awaitable[bool]],
+        page_url:str = "https://www.kleinanzeigen.de/m-meine-anzeigen.html",
+        *,
+        max_pages:int = 10,
+    ) -> bool:
+        """
+        Navigate through paginated ad overview page, calling page_action on each page.
+
+        This helper guarantees to return a boolean result and never propagates TimeoutError.
+        All timeout conditions are handled internally and logged appropriately.
+
+        Args:
+            page_action: Async callable that receives current_page number and returns True if action succeeded/should stop
+            page_url: URL of the paginated overview page (default: kleinanzeigen ad management page)
+            max_pages: Maximum number of pages to navigate (safety limit)
+
+        Returns:
+            True if page_action returned True on any page, False otherwise
+
+        Example:
+            async def find_ad_callback(page_num: int) -> bool:
+                element = await self.web_find(By.XPATH, "//div[@id='my-ad']")
+                if element:
+                    await element.click()
+                    return True
+                return False
+
+            success = await self._navigate_paginated_ad_overview(find_ad_callback)
+        """
+        try:
+            await self.web_open(page_url)
+        except TimeoutError:
+            LOG.warning("Failed to open ad overview page at %s: timeout", page_url)
+            return False
+
+        await self.web_sleep(2000, 3000)
+
+        # Check if ad list container exists
+        try:
+            _ = await self.web_find(By.ID, "my-manageitems-adlist")
+        except TimeoutError:
+            LOG.warning("Ad list container not found. Maybe no ads present?")
+            return False
+
+        # Check for pagination controls
+        multi_page = False
+        pagination_timeout = self._timeout("pagination_initial")
+        try:
+            pagination_section = await self.web_find(By.CSS_SELECTOR, ".Pagination", timeout = pagination_timeout)
+            next_buttons = await self.web_find_all(By.CSS_SELECTOR, 'button[aria-label="Nächste"]', parent = pagination_section)
+            if next_buttons:
+                enabled_next_buttons = [btn for btn in next_buttons if not btn.attrs.get("disabled")]
+                if enabled_next_buttons:
+                    multi_page = True
+                    LOG.info("Multiple ad pages detected.")
+        except TimeoutError:
+            LOG.info("No pagination controls found. Assuming single page.")
+
+        current_page = 1
+        while current_page <= max_pages:
+            LOG.info("Processing page %s...", current_page)
+
+            try:
+                await self.web_scroll_page_down()
+            except TimeoutError:
+                LOG.debug("Scroll timeout on page %s (non-critical, continuing)", current_page)
+
+            await self.web_sleep(2000, 3000)
+
+            try:
+                if await page_action(current_page):
+                    return True
+            except TimeoutError:
+                LOG.warning("Page action timed out on page %s", current_page)
+                return False
+
+            if not multi_page:
+                break
+
+            follow_up_timeout = self._timeout("pagination_follow_up")
+            try:
+                pagination_section = await self.web_find(By.CSS_SELECTOR, ".Pagination", timeout = follow_up_timeout)
+                next_button_element = None
+                possible_next_buttons = await self.web_find_all(By.CSS_SELECTOR, 'button[aria-label="Nächste"]', parent = pagination_section)
+                for btn in possible_next_buttons:
+                    if not btn.attrs.get("disabled"):
+                        next_button_element = btn
+                        break
+
+                if next_button_element:
+                    LOG.info("Navigating to page %s...", current_page + 1)
+                    await next_button_element.click()
+                    await self.web_sleep(3000, 4000)
+                    current_page += 1
+                else:
+                    LOG.info("Last page reached (no enabled 'Naechste' button found).")
+                    break
+            except TimeoutError:
+                LOG.info("No pagination controls found. Assuming last page.")
+                break
+
+        return False
+
     async def web_request(self, url:str, method:str = "GET", valid_response_codes:int | Iterable[int] = 200, headers:dict[str, str] | None = None) -> Any:
         method = method.upper()
         LOG.debug(" -> HTTP %s [%s]...", method, url)
diff --git a/tests/unit/test_extend_command.py b/tests/unit/test_extend_command.py
index 6e4e1be..a033b46 100644
--- a/tests/unit/test_extend_command.py
+++ b/tests/unit/test_extend_command.py
@@ -5,13 +5,14 @@ import json  # isort: skip
 from datetime import datetime, timedelta
 from pathlib import Path
 from typing import Any
-from unittest.mock import AsyncMock, patch
+from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
 
 from kleinanzeigen_bot import KleinanzeigenBot, misc
 from kleinanzeigen_bot.model.ad_model import Ad
 from kleinanzeigen_bot.utils import dicts
+from kleinanzeigen_bot.utils.web_scraping_mixin import By, Element
 
 
 @pytest.fixture
@@ -34,13 +35,7 @@ def base_ad_config_with_id() -> dict[str, Any]:
         "republication_interval": 7,
         "created_on": "2024-12-07T10:00:00",
         "updated_on": "2024-12-10T15:20:00",
-        "contact": {
-            "name": "Test User",
-            "zipcode": "12345",
-            "location": "Test City",
-            "street": "",
-            "phone": ""
-        }
+        "contact": {"name": "Test User", "zipcode": "12345", "location": "Test City", "street": "", "phone": ""},
     }
 
 
@@ -50,9 +45,7 @@ class TestExtendCommand:
     @pytest.mark.asyncio
     async def test_run_extend_command_no_ads(self, test_bot:KleinanzeigenBot) -> None:
         """Test running extend command with no ads."""
-        with patch.object(test_bot, "load_config"), \
-                patch.object(test_bot, "load_ads", return_value = []), \
-                patch("kleinanzeigen_bot.UpdateChecker"):
+        with patch.object(test_bot, "load_config"), patch.object(test_bot, "load_ads", return_value = []), patch("kleinanzeigen_bot.UpdateChecker"):
             await test_bot.run(["script.py", "extend"])
             assert test_bot.command == "extend"
             assert test_bot.ads_selector == "all"
@@ -60,11 +53,13 @@ class TestExtendCommand:
     @pytest.mark.asyncio
     async def test_run_extend_command_with_specific_ids(self, test_bot:KleinanzeigenBot) -> None:
         """Test running extend command with specific ad IDs."""
-        with patch.object(test_bot, "load_config"), \
-                patch.object(test_bot, "load_ads", return_value = []), \
-                patch.object(test_bot, "create_browser_session", new_callable = AsyncMock), \
-                patch.object(test_bot, "login", new_callable = AsyncMock), \
-                patch("kleinanzeigen_bot.UpdateChecker"):
+        with (
+            patch.object(test_bot, "load_config"),
+            patch.object(test_bot, "load_ads", return_value = []),
+            patch.object(test_bot, "create_browser_session", new_callable = AsyncMock),
+            patch.object(test_bot, "login", new_callable = AsyncMock),
+            patch("kleinanzeigen_bot.UpdateChecker"),
+        ):
             await test_bot.run(["script.py", "extend", "--ads=12345,67890"])
             assert test_bot.command == "extend"
             assert test_bot.ads_selector == "12345,67890"
@@ -74,19 +69,14 @@ class TestExtendAdsMethod:
     """Tests for the extend_ads() method."""
 
     @pytest.mark.asyncio
-    async def test_extend_ads_skips_unpublished_ad(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_skips_unpublished_ad(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that extend_ads skips ads without an ID (unpublished)."""
         # Create ad without ID
         ad_config = base_ad_config_with_id.copy()
         ad_config["id"] = None
         ad_cfg = Ad.model_validate(ad_config)
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock):
+        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, patch.object(test_bot, "web_sleep", new_callable = AsyncMock):
             mock_request.return_value = {"content": '{"ads": []}'}
 
             await test_bot.extend_ads([("test.yaml", ad_cfg, ad_config)])
@@ -95,16 +85,11 @@ class TestExtendAdsMethod:
             mock_request.assert_called_once()  # Only the API call to get published ads
 
     @pytest.mark.asyncio
-    async def test_extend_ads_skips_ad_not_in_published_list(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_skips_ad_not_in_published_list(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that extend_ads skips ads not found in the published ads API response."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock):
+        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, patch.object(test_bot, "web_sleep", new_callable = AsyncMock):
             # Return empty published ads list
             mock_request.return_value = {"content": '{"ads": []}'}
 
@@ -114,11 +99,7 @@ class TestExtendAdsMethod:
             mock_request.assert_called_once()
 
     @pytest.mark.asyncio
-    async def test_extend_ads_skips_inactive_ad(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_skips_inactive_ad(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that extend_ads skips ads with state != 'active'."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -128,14 +109,16 @@ class TestExtendAdsMethod:
                     "id": 12345,
                     "title": "Test Ad Title",
                     "state": "paused",  # Not active
-                    "endDate": "05.02.2026"
+                    "endDate": "05.02.2026",
                 }
             ]
         }
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+        ):
             mock_request.return_value = {"content": json.dumps(published_ads_json)}
 
             await test_bot.extend_ads([("test.yaml", ad_cfg, base_ad_config_with_id)])
@@ -144,11 +127,7 @@ class TestExtendAdsMethod:
             mock_extend_ad.assert_not_called()
 
     @pytest.mark.asyncio
-    async def test_extend_ads_skips_ad_without_enddate(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_skips_ad_without_enddate(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that extend_ads skips ads without endDate in API response."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -157,15 +136,17 @@ class TestExtendAdsMethod:
                 {
                     "id": 12345,
                     "title": "Test Ad Title",
-                    "state": "active"
+                    "state": "active",
                     # No endDate field
                 }
             ]
         }
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+        ):
             mock_request.return_value = {"content": json.dumps(published_ads_json)}
 
             await test_bot.extend_ads([("test.yaml", ad_cfg, base_ad_config_with_id)])
@@ -174,11 +155,7 @@ class TestExtendAdsMethod:
             mock_extend_ad.assert_not_called()
 
     @pytest.mark.asyncio
-    async def test_extend_ads_skips_ad_outside_window(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_skips_ad_outside_window(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that extend_ads skips ads expiring more than 8 days in the future."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -186,20 +163,13 @@ class TestExtendAdsMethod:
         future_date = misc.now() + timedelta(days = 30)
         end_date_str = future_date.strftime("%d.%m.%Y")
 
-        published_ads_json = {
-            "ads": [
-                {
-                    "id": 12345,
-                    "title": "Test Ad Title",
-                    "state": "active",
-                    "endDate": end_date_str
-                }
-            ]
-        }
+        published_ads_json = {"ads": [{"id": 12345, "title": "Test Ad Title", "state": "active", "endDate": end_date_str}]}
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+        ):
             mock_request.return_value = {"content": json.dumps(published_ads_json)}
 
             await test_bot.extend_ads([("test.yaml", ad_cfg, base_ad_config_with_id)])
@@ -208,11 +178,7 @@ class TestExtendAdsMethod:
             mock_extend_ad.assert_not_called()
 
     @pytest.mark.asyncio
-    async def test_extend_ads_extends_ad_within_window(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_extends_ad_within_window(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that extend_ads extends ads within the 8-day window."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -220,20 +186,13 @@ class TestExtendAdsMethod:
         future_date = misc.now() + timedelta(days = 5)
         end_date_str = future_date.strftime("%d.%m.%Y")
 
-        published_ads_json = {
-            "ads": [
-                {
-                    "id": 12345,
-                    "title": "Test Ad Title",
-                    "state": "active",
-                    "endDate": end_date_str
-                }
-            ]
-        }
+        published_ads_json = {"ads": [{"id": 12345, "title": "Test Ad Title", "state": "active", "endDate": end_date_str}]}
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+        ):
             mock_request.return_value = {"content": json.dumps(published_ads_json)}
             mock_extend_ad.return_value = True
 
@@ -243,11 +202,7 @@ class TestExtendAdsMethod:
             mock_extend_ad.assert_called_once()
 
     @pytest.mark.asyncio
-    async def test_extend_ads_no_eligible_ads(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_no_eligible_ads(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test extend_ads when no ads are eligible for extension."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -255,20 +210,13 @@ class TestExtendAdsMethod:
         future_date = misc.now() + timedelta(days = 30)
         end_date_str = future_date.strftime("%d.%m.%Y")
 
-        published_ads_json = {
-            "ads": [
-                {
-                    "id": 12345,
-                    "title": "Test Ad Title",
-                    "state": "active",
-                    "endDate": end_date_str
-                }
-            ]
-        }
+        published_ads_json = {"ads": [{"id": 12345, "title": "Test Ad Title", "state": "active", "endDate": end_date_str}]}
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+        ):
             mock_request.return_value = {"content": json.dumps(published_ads_json)}
 
             await test_bot.extend_ads([("test.yaml", ad_cfg, base_ad_config_with_id)])
@@ -277,11 +225,7 @@ class TestExtendAdsMethod:
             mock_extend_ad.assert_not_called()
 
     @pytest.mark.asyncio
-    async def test_extend_ads_handles_multiple_ads(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_handles_multiple_ads(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that extend_ads processes multiple ads correctly."""
         ad_cfg1 = Ad.model_validate(base_ad_config_with_id)
 
@@ -297,46 +241,36 @@ class TestExtendAdsMethod:
 
         published_ads_json = {
             "ads": [
-                {
-                    "id": 12345,
-                    "title": "Test Ad Title",
-                    "state": "active",
-                    "endDate": within_window.strftime("%d.%m.%Y")
-                },
-                {
-                    "id": 67890,
-                    "title": "Second Test Ad",
-                    "state": "active",
-                    "endDate": outside_window.strftime("%d.%m.%Y")
-                }
+                {"id": 12345, "title": "Test Ad Title", "state": "active", "endDate": within_window.strftime("%d.%m.%Y")},
+                {"id": 67890, "title": "Second Test Ad", "state": "active", "endDate": outside_window.strftime("%d.%m.%Y")},
             ]
         }
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+        ):
             mock_request.return_value = {"content": json.dumps(published_ads_json)}
             mock_extend_ad.return_value = True
 
-            await test_bot.extend_ads([
-                ("test1.yaml", ad_cfg1, base_ad_config_with_id),
-                ("test2.yaml", ad_cfg2, ad_config2)
-            ])
+            await test_bot.extend_ads([("test1.yaml", ad_cfg1, base_ad_config_with_id), ("test2.yaml", ad_cfg2, ad_config2)])
 
             # Verify extend_ad was called only once (for the ad within window)
             assert mock_extend_ad.call_count == 1
 
 
 class TestExtendAdMethod:
-    """Tests for the extend_ad() method."""
+    """Tests for the extend_ad() method.
+
+    Note: These tests mock `_navigate_paginated_ad_overview` rather than individual browser methods
+    (web_find, web_click, etc.) because the pagination helper involves complex multi-step browser
+    interactions that would require extensive, brittle mock choreography. Mocking at this level
+    keeps tests focused on extend_ad's own logic (dialog handling, YAML persistence, error paths).
+    """
 
     @pytest.mark.asyncio
-    async def test_extend_ad_success(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any],
-        tmp_path:Path
-    ) -> None:
+    async def test_extend_ad_success(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any], tmp_path:Path) -> None:
         """Test successful ad extension."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -344,27 +278,27 @@ class TestExtendAdMethod:
         ad_file = tmp_path / "test_ad.yaml"
         dicts.save_dict(str(ad_file), base_ad_config_with_id)
 
-        with patch.object(test_bot, "web_open", new_callable = AsyncMock), \
-                patch.object(test_bot, "web_click", new_callable = AsyncMock), \
-                patch("kleinanzeigen_bot.misc.now") as mock_now:
+        with (
+            patch.object(test_bot, "_navigate_paginated_ad_overview", new_callable = AsyncMock) as mock_paginate,
+            patch.object(test_bot, "web_click", new_callable = AsyncMock),
+            patch("kleinanzeigen_bot.misc.now") as mock_now,
+        ):
             # Test mock datetime - timezone not relevant for timestamp formatting test
             mock_now.return_value = datetime(2025, 1, 28, 14, 30, 0)  # noqa: DTZ001
 
+            mock_paginate.return_value = True
+
             result = await test_bot.extend_ad(str(ad_file), ad_cfg, base_ad_config_with_id)
 
             assert result is True
+            assert mock_paginate.call_count == 1
 
             # Verify updated_on was updated in the YAML file
             updated_config = dicts.load_dict(str(ad_file))
             assert updated_config["updated_on"] == "2025-01-28T14:30:00"
 
     @pytest.mark.asyncio
-    async def test_extend_ad_button_not_found(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any],
-        tmp_path:Path
-    ) -> None:
+    async def test_extend_ad_button_not_found(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any], tmp_path:Path) -> None:
         """Test extend_ad when the Verlängern button is not found."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -372,22 +306,17 @@ class TestExtendAdMethod:
         ad_file = tmp_path / "test_ad.yaml"
         dicts.save_dict(str(ad_file), base_ad_config_with_id)
 
-        with patch.object(test_bot, "web_open", new_callable = AsyncMock), \
-                patch.object(test_bot, "web_click", new_callable = AsyncMock) as mock_click:
-            # Simulate button not found by raising TimeoutError
-            mock_click.side_effect = TimeoutError("Button not found")
+        with patch.object(test_bot, "_navigate_paginated_ad_overview", new_callable = AsyncMock) as mock_paginate:
+            # Simulate button not found by having pagination return False (not found on any page)
+            mock_paginate.return_value = False
 
             result = await test_bot.extend_ad(str(ad_file), ad_cfg, base_ad_config_with_id)
 
             assert result is False
+            assert mock_paginate.call_count == 1
 
     @pytest.mark.asyncio
-    async def test_extend_ad_dialog_timeout(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any],
-        tmp_path:Path
-    ) -> None:
+    async def test_extend_ad_dialog_timeout(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any], tmp_path:Path) -> None:
         """Test extend_ad when the confirmation dialog times out (no dialog appears)."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -395,14 +324,18 @@ class TestExtendAdMethod:
         ad_file = tmp_path / "test_ad.yaml"
         dicts.save_dict(str(ad_file), base_ad_config_with_id)
 
-        with patch.object(test_bot, "web_open", new_callable = AsyncMock), \
-                patch.object(test_bot, "web_click", new_callable = AsyncMock) as mock_click, \
-                patch("kleinanzeigen_bot.misc.now") as mock_now:
+        with (
+            patch.object(test_bot, "_navigate_paginated_ad_overview", new_callable = AsyncMock) as mock_paginate,
+            patch.object(test_bot, "web_click", new_callable = AsyncMock) as mock_click,
+            patch("kleinanzeigen_bot.misc.now") as mock_now,
+        ):
             # Test mock datetime - timezone not relevant for timestamp formatting test
             mock_now.return_value = datetime(2025, 1, 28, 14, 30, 0)  # noqa: DTZ001
 
-            # First click (Verlängern button) succeeds, second click (dialog close) times out
-            mock_click.side_effect = [None, TimeoutError("Dialog not found")]
+            # Pagination succeeds (button found and clicked)
+            mock_paginate.return_value = True
+            # Dialog close button times out
+            mock_click.side_effect = TimeoutError("Dialog not found")
 
             result = await test_bot.extend_ad(str(ad_file), ad_cfg, base_ad_config_with_id)
 
@@ -410,12 +343,7 @@ class TestExtendAdMethod:
             assert result is True
 
     @pytest.mark.asyncio
-    async def test_extend_ad_exception_handling(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any],
-        tmp_path:Path
-    ) -> None:
+    async def test_extend_ad_exception_handling(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any], tmp_path:Path) -> None:
         """Test extend_ad propagates unexpected exceptions."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -423,20 +351,15 @@ class TestExtendAdMethod:
         ad_file = tmp_path / "test_ad.yaml"
         dicts.save_dict(str(ad_file), base_ad_config_with_id)
 
-        with patch.object(test_bot, "web_open", new_callable = AsyncMock) as mock_open:
-            # Simulate unexpected exception
-            mock_open.side_effect = Exception("Unexpected error")
+        with patch.object(test_bot, "_navigate_paginated_ad_overview", new_callable = AsyncMock) as mock_paginate:
+            # Simulate unexpected exception during pagination
+            mock_paginate.side_effect = Exception("Unexpected error")
 
             with pytest.raises(Exception, match = "Unexpected error"):
                 await test_bot.extend_ad(str(ad_file), ad_cfg, base_ad_config_with_id)
 
     @pytest.mark.asyncio
-    async def test_extend_ad_updates_yaml_file(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any],
-        tmp_path:Path
-    ) -> None:
+    async def test_extend_ad_updates_yaml_file(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any], tmp_path:Path) -> None:
         """Test that extend_ad correctly updates the YAML file with new timestamp."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -445,12 +368,17 @@ class TestExtendAdMethod:
         original_updated_on = base_ad_config_with_id["updated_on"]
         dicts.save_dict(str(ad_file), base_ad_config_with_id)
 
-        with patch.object(test_bot, "web_open", new_callable = AsyncMock), \
-                patch.object(test_bot, "web_click", new_callable = AsyncMock), \
-                patch("kleinanzeigen_bot.misc.now") as mock_now:
+        with (
+            patch.object(test_bot, "_navigate_paginated_ad_overview", new_callable = AsyncMock) as mock_paginate,
+            patch.object(test_bot, "web_click", new_callable = AsyncMock),
+            patch("kleinanzeigen_bot.misc.now") as mock_now,
+        ):
             # Test mock datetime - timezone not relevant for timestamp formatting test
             mock_now.return_value = datetime(2025, 1, 28, 14, 30, 0)  # noqa: DTZ001
 
+            # Pagination succeeds (button found and clicked)
+            mock_paginate.return_value = True
+
             await test_bot.extend_ad(str(ad_file), ad_cfg, base_ad_config_with_id)
 
             # Load the updated file and verify the timestamp changed
@@ -458,16 +386,67 @@ class TestExtendAdMethod:
             assert updated_config["updated_on"] != original_updated_on
             assert updated_config["updated_on"] == "2025-01-28T14:30:00"
 
+    @pytest.mark.asyncio
+    async def test_extend_ad_with_web_mocks(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any], tmp_path:Path) -> None:
+        """Test extend_ad with web-level mocks to exercise the find_and_click_extend_button callback."""
+        ad_cfg = Ad.model_validate(base_ad_config_with_id)
+
+        # Create temporary YAML file
+        ad_file = tmp_path / "test_ad.yaml"
+        dicts.save_dict(str(ad_file), base_ad_config_with_id)
+
+        extend_button_mock = AsyncMock()
+        extend_button_mock.click = AsyncMock()
+
+        pagination_section = MagicMock()
+
+        find_call_count = {"count": 0}
+
+        async def mock_web_find(selector_type:By, selector_value:str, **kwargs:Any) -> Element:
+            find_call_count["count"] += 1
+            # Ad list container (called by pagination helper)
+            if selector_type == By.ID and selector_value == "my-manageitems-adlist":
+                return MagicMock()
+            # Pagination section (called by pagination helper)
+            if selector_type == By.CSS_SELECTOR and selector_value == ".Pagination":
+                # Raise TimeoutError on first call (pagination detection) to indicate single page
+                if find_call_count["count"] == 2:
+                    raise TimeoutError("No pagination")
+                return pagination_section
+            # Extend button (called by find_and_click_extend_button callback)
+            if selector_type == By.XPATH and "Verlängern" in selector_value:
+                return extend_button_mock
+            raise TimeoutError(f"Unexpected find: {selector_type} {selector_value}")
+
+        with (
+            patch.object(test_bot, "web_open", new_callable = AsyncMock),
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "web_find", new_callable = AsyncMock, side_effect = mock_web_find),
+            patch.object(test_bot, "web_find_all", new_callable = AsyncMock, return_value = []),
+            patch.object(test_bot, "web_scroll_page_down", new_callable = AsyncMock),
+            patch.object(test_bot, "web_click", new_callable = AsyncMock),
+            patch.object(test_bot, "_timeout", return_value = 10),
+            patch("kleinanzeigen_bot.misc.now") as mock_now,
+        ):
+            # Test mock datetime - timezone not relevant for timestamp formatting test
+            mock_now.return_value = datetime(2025, 1, 28, 15, 0, 0)  # noqa: DTZ001
+
+            result = await test_bot.extend_ad(str(ad_file), ad_cfg, base_ad_config_with_id)
+
+            assert result is True
+            # Verify the extend button was found and clicked
+            extend_button_mock.click.assert_awaited_once()
+
+            # Verify updated_on was updated
+            updated_config = dicts.load_dict(str(ad_file))
+            assert updated_config["updated_on"] == "2025-01-28T15:00:00"
+
 
 class TestExtendEdgeCases:
     """Tests for edge cases and boundary conditions."""
 
     @pytest.mark.asyncio
-    async def test_extend_ads_exactly_8_days(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_exactly_8_days(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that ads expiring exactly in 8 days are eligible for extension."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -475,20 +454,13 @@ class TestExtendEdgeCases:
         future_date = misc.now() + timedelta(days = 8)
         end_date_str = future_date.strftime("%d.%m.%Y")
 
-        published_ads_json = {
-            "ads": [
-                {
-                    "id": 12345,
-                    "title": "Test Ad Title",
-                    "state": "active",
-                    "endDate": end_date_str
-                }
-            ]
-        }
+        published_ads_json = {"ads": [{"id": 12345, "title": "Test Ad Title", "state": "active", "endDate": end_date_str}]}
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+        ):
             mock_request.return_value = {"content": json.dumps(published_ads_json)}
             mock_extend_ad.return_value = True
 
@@ -498,11 +470,7 @@ class TestExtendEdgeCases:
             mock_extend_ad.assert_called_once()
 
     @pytest.mark.asyncio
-    async def test_extend_ads_exactly_9_days(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_exactly_9_days(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that ads expiring in exactly 9 days are not eligible for extension."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -510,20 +478,13 @@ class TestExtendEdgeCases:
         future_date = misc.now() + timedelta(days = 9)
         end_date_str = future_date.strftime("%d.%m.%Y")
 
-        published_ads_json = {
-            "ads": [
-                {
-                    "id": 12345,
-                    "title": "Test Ad Title",
-                    "state": "active",
-                    "endDate": end_date_str
-                }
-            ]
-        }
+        published_ads_json = {"ads": [{"id": 12345, "title": "Test Ad Title", "state": "active", "endDate": end_date_str}]}
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+        ):
             mock_request.return_value = {"content": json.dumps(published_ads_json)}
 
             await test_bot.extend_ads([("test.yaml", ad_cfg, base_ad_config_with_id)])
@@ -532,11 +493,7 @@ class TestExtendEdgeCases:
             mock_extend_ad.assert_not_called()
 
     @pytest.mark.asyncio
-    async def test_extend_ads_date_parsing_german_format(
-        self,
-        test_bot:KleinanzeigenBot,
-        base_ad_config_with_id:dict[str, Any]
-    ) -> None:
+    async def test_extend_ads_date_parsing_german_format(self, test_bot:KleinanzeigenBot, base_ad_config_with_id:dict[str, Any]) -> None:
         """Test that extend_ads correctly parses German date format (DD.MM.YYYY)."""
         ad_cfg = Ad.model_validate(base_ad_config_with_id)
 
@@ -547,15 +504,17 @@ class TestExtendEdgeCases:
                     "id": 12345,
                     "title": "Test Ad Title",
                     "state": "active",
-                    "endDate": "05.02.2026"  # German format: DD.MM.YYYY
+                    "endDate": "05.02.2026",  # German format: DD.MM.YYYY
                 }
             ]
         }
 
-        with patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request, \
-                patch.object(test_bot, "web_sleep", new_callable = AsyncMock), \
-                patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad, \
-                patch("kleinanzeigen_bot.misc.now") as mock_now:
+        with (
+            patch.object(test_bot, "web_request", new_callable = AsyncMock) as mock_request,
+            patch.object(test_bot, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_bot, "extend_ad", new_callable = AsyncMock) as mock_extend_ad,
+            patch("kleinanzeigen_bot.misc.now") as mock_now,
+        ):
             # Mock now() to return a date where 05.02.2026 would be within 8 days
             # Test mock datetime - timezone not relevant for date comparison test
             mock_now.return_value = datetime(2026, 1, 28)  # noqa: DTZ001
diff --git a/tests/unit/test_extract.py b/tests/unit/test_extract.py
index 626ab7d..3e977e0 100644
--- a/tests/unit/test_extract.py
+++ b/tests/unit/test_extract.py
@@ -662,6 +662,80 @@ class TestAdExtractorNavigation:
         assert refs == ["/s-anzeige/page-one/111", "/s-anzeige/page-two/222"]
         next_button_enabled.click.assert_awaited()  # triggered once during navigation
 
+    @pytest.mark.asyncio
+    async def test_extract_own_ads_urls_timeout_in_callback(self, test_extractor:AdExtractor) -> None:
+        """Test that TimeoutError in extract_page_refs callback stops pagination."""
+        with (
+            patch.object(test_extractor, "web_open", new_callable = AsyncMock),
+            patch.object(test_extractor, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_extractor, "web_find", new_callable = AsyncMock) as mock_web_find,
+            patch.object(test_extractor, "web_find_all", new_callable = AsyncMock, return_value = []),
+            patch.object(test_extractor, "web_scroll_page_down", new_callable = AsyncMock),
+            patch.object(test_extractor, "web_execute", new_callable = AsyncMock),
+        ):
+            # Setup: ad list container exists, but web_find_all for cardbox raises TimeoutError
+            ad_list_container_mock = MagicMock()
+
+            call_count = {"count": 0}
+
+            def mock_find_side_effect(*args:Any, **kwargs:Any) -> Element:
+                call_count["count"] += 1
+                if call_count["count"] == 1:
+                    # First call: ad list container (before pagination loop)
+                    return ad_list_container_mock
+                # Second call: ad list container (inside callback)
+                return ad_list_container_mock
+
+            mock_web_find.side_effect = mock_find_side_effect
+
+            # Make web_find_all for cardbox raise TimeoutError (simulating missing ad items)
+            async def mock_find_all_side_effect(*args:Any, **kwargs:Any) -> list[Element]:
+                raise TimeoutError("Ad items not found")
+
+            with patch.object(test_extractor, "web_find_all", new_callable = AsyncMock, side_effect = mock_find_all_side_effect):
+                refs = await test_extractor.extract_own_ads_urls()
+
+            # Pagination should stop (TimeoutError in callback returns True)
+            assert refs == []
+
+    @pytest.mark.asyncio
+    async def test_extract_own_ads_urls_generic_exception_in_callback(self, test_extractor:AdExtractor) -> None:
+        """Test that generic Exception in extract_page_refs callback continues pagination."""
+        with (
+            patch.object(test_extractor, "web_open", new_callable = AsyncMock),
+            patch.object(test_extractor, "web_sleep", new_callable = AsyncMock),
+            patch.object(test_extractor, "web_find", new_callable = AsyncMock) as mock_web_find,
+            patch.object(test_extractor, "web_scroll_page_down", new_callable = AsyncMock),
+        ):
+            # Setup: ad list container exists, but web_find_all raises generic Exception
+            ad_list_container_mock = MagicMock()
+
+            call_count = {"count": 0}
+
+            def mock_find_side_effect(*args:Any, **kwargs:Any) -> Element:
+                call_count["count"] += 1
+                if call_count["count"] == 1:
+                    # First call: ad list container (before pagination loop)
+                    return ad_list_container_mock
+                # Second call: pagination check - raise TimeoutError to indicate no pagination
+                if call_count["count"] == 2:
+                    raise TimeoutError("No pagination")
+                # Third call: ad list container (inside callback)
+                return ad_list_container_mock
+
+            mock_web_find.side_effect = mock_find_side_effect
+
+            # Make web_find_all raise a generic exception
+            async def mock_find_all_side_effect(*args:Any, **kwargs:Any) -> list[Element]:
+                raise AttributeError("Unexpected error")
+
+            with patch.object(test_extractor, "web_find_all", new_callable = AsyncMock, side_effect = mock_find_all_side_effect):
+                refs = await test_extractor.extract_own_ads_urls()
+
+            # Pagination should continue despite exception (callback returns False)
+            # Since it's a single page (no pagination), refs should be empty
+            assert refs == []
+
 
 class TestAdExtractorContent:
     """Tests for content extraction functionality."""
diff --git a/tests/unit/test_web_scraping_pagination.py b/tests/unit/test_web_scraping_pagination.py
new file mode 100644
index 0000000..0feadf5
--- /dev/null
+++ b/tests/unit/test_web_scraping_pagination.py
@@ -0,0 +1,181 @@
+# SPDX-FileCopyrightText: © Sebastian Thomschke and contributors
+# SPDX-License-Identifier: AGPL-3.0-or-later
+# SPDX-ArtifactOfProjectHomePage: https://github.com/Second-Hand-Friends/kleinanzeigen-bot/
+"""Tests for the _navigate_paginated_ad_overview helper method."""
+
+from typing import Any
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+from kleinanzeigen_bot.utils.web_scraping_mixin import By, Element, WebScrapingMixin
+
+
+class TestNavigatePaginatedAdOverview:
+    """Tests for _navigate_paginated_ad_overview method."""
+
+    @pytest.mark.asyncio
+    async def test_single_page_action_succeeds(self) -> None:
+        """Test pagination on single page where action succeeds."""
+        mixin = WebScrapingMixin()
+
+        # Mock callback that succeeds
+        callback = AsyncMock(return_value = True)
+
+        with (
+            patch.object(mixin, "web_open", new_callable = AsyncMock),
+            patch.object(mixin, "web_sleep", new_callable = AsyncMock),
+            patch.object(mixin, "web_find", new_callable = AsyncMock) as mock_find,
+            patch.object(mixin, "web_find_all", new_callable = AsyncMock, return_value = []),
+            patch.object(mixin, "web_scroll_page_down", new_callable = AsyncMock),
+            patch.object(mixin, "_timeout", return_value = 10),
+        ):
+            # Ad list container exists
+            mock_find.return_value = MagicMock()
+
+            result = await mixin._navigate_paginated_ad_overview(callback)
+
+            assert result is True
+            callback.assert_awaited_once_with(1)
+
+    @pytest.mark.asyncio
+    async def test_single_page_action_returns_false(self) -> None:
+        """Test pagination on single page where action returns False."""
+        mixin = WebScrapingMixin()
+
+        # Mock callback that returns False (doesn't find what it's looking for)
+        callback = AsyncMock(return_value = False)
+
+        with (
+            patch.object(mixin, "web_open", new_callable = AsyncMock),
+            patch.object(mixin, "web_sleep", new_callable = AsyncMock),
+            patch.object(mixin, "web_find", new_callable = AsyncMock) as mock_find,
+            patch.object(mixin, "web_find_all", new_callable = AsyncMock, return_value = []),
+            patch.object(mixin, "web_scroll_page_down", new_callable = AsyncMock),
+            patch.object(mixin, "_timeout", return_value = 10),
+        ):
+            # Ad list container exists
+            mock_find.return_value = MagicMock()
+
+            result = await mixin._navigate_paginated_ad_overview(callback)
+
+            assert result is False
+            callback.assert_awaited_once_with(1)
+
+    @pytest.mark.asyncio
+    async def test_multi_page_action_succeeds_on_page_2(self) -> None:
+        """Test pagination across multiple pages where action succeeds on page 2."""
+        mixin = WebScrapingMixin()
+
+        # Mock callback that returns False on page 1, True on page 2
+        callback_results = [False, True]
+        callback = AsyncMock(side_effect = callback_results)
+
+        pagination_section = MagicMock()
+        next_button_enabled = MagicMock()
+        next_button_enabled.attrs = {}  # No "disabled" attribute = enabled
+        next_button_enabled.click = AsyncMock()
+
+        find_call_count = {"count": 0}
+
+        async def mock_find_side_effect(selector_type:By, selector_value:str, **kwargs:Any) -> Element:
+            find_call_count["count"] += 1
+            if selector_type == By.ID and selector_value == "my-manageitems-adlist":
+                return MagicMock()  # Ad list container
+            if selector_type == By.CSS_SELECTOR and selector_value == ".Pagination":
+                return pagination_section
+            raise TimeoutError("Unexpected find")
+
+        find_all_call_count = {"count": 0}
+
+        async def mock_find_all_side_effect(selector_type:By, selector_value:str, **kwargs:Any) -> list[Element]:
+            find_all_call_count["count"] += 1
+            if selector_type == By.CSS_SELECTOR and 'aria-label="Nächste"' in selector_value:
+                # Return enabled next button on both calls (initial detection and navigation)
+                return [next_button_enabled]
+            return []
+
+        with (
+            patch.object(mixin, "web_open", new_callable = AsyncMock),
+            patch.object(mixin, "web_sleep", new_callable = AsyncMock),
+            patch.object(mixin, "web_find", new_callable = AsyncMock, side_effect = mock_find_side_effect),
+            patch.object(mixin, "web_find_all", new_callable = AsyncMock, side_effect = mock_find_all_side_effect),
+            patch.object(mixin, "web_scroll_page_down", new_callable = AsyncMock),
+            patch.object(mixin, "_timeout", return_value = 10),
+        ):
+            result = await mixin._navigate_paginated_ad_overview(callback)
+
+            assert result is True
+            assert callback.await_count == 2
+            next_button_enabled.click.assert_awaited_once()
+
+    @pytest.mark.asyncio
+    async def test_web_open_raises_timeout(self) -> None:
+        """Test that TimeoutError on web_open is caught and returns False."""
+        mixin = WebScrapingMixin()
+
+        callback = AsyncMock()
+
+        with patch.object(mixin, "web_open", new_callable = AsyncMock, side_effect = TimeoutError("Page load timeout")):
+            result = await mixin._navigate_paginated_ad_overview(callback)
+
+            assert result is False
+            callback.assert_not_awaited()  # Callback should not be called
+
+    @pytest.mark.asyncio
+    async def test_ad_list_container_not_found(self) -> None:
+        """Test that missing ad list container returns False."""
+        mixin = WebScrapingMixin()
+
+        callback = AsyncMock()
+
+        with (
+            patch.object(mixin, "web_open", new_callable = AsyncMock),
+            patch.object(mixin, "web_sleep", new_callable = AsyncMock),
+            patch.object(mixin, "web_find", new_callable = AsyncMock, side_effect = TimeoutError("Container not found")),
+        ):
+            result = await mixin._navigate_paginated_ad_overview(callback)
+
+            assert result is False
+            callback.assert_not_awaited()
+
+    @pytest.mark.asyncio
+    async def test_web_scroll_timeout_continues(self) -> None:
+        """Test that TimeoutError on web_scroll_page_down is non-fatal and pagination continues."""
+        mixin = WebScrapingMixin()
+
+        callback = AsyncMock(return_value = True)
+
+        with (
+            patch.object(mixin, "web_open", new_callable = AsyncMock),
+            patch.object(mixin, "web_sleep", new_callable = AsyncMock),
+            patch.object(mixin, "web_find", new_callable = AsyncMock, return_value = MagicMock()),
+            patch.object(mixin, "web_find_all", new_callable = AsyncMock, return_value = []),
+            patch.object(mixin, "web_scroll_page_down", new_callable = AsyncMock, side_effect = TimeoutError("Scroll timeout")),
+            patch.object(mixin, "_timeout", return_value = 10),
+        ):
+            result = await mixin._navigate_paginated_ad_overview(callback)
+
+            # Should continue and call callback despite scroll timeout
+            assert result is True
+            callback.assert_awaited_once_with(1)
+
+    @pytest.mark.asyncio
+    async def test_page_action_raises_timeout(self) -> None:
+        """Test that TimeoutError from page_action is caught and returns False."""
+        mixin = WebScrapingMixin()
+
+        callback = AsyncMock(side_effect = TimeoutError("Action timeout"))
+
+        with (
+            patch.object(mixin, "web_open", new_callable = AsyncMock),
+            patch.object(mixin, "web_sleep", new_callable = AsyncMock),
+            patch.object(mixin, "web_find", new_callable = AsyncMock, return_value = MagicMock()),
+            patch.object(mixin, "web_find_all", new_callable = AsyncMock, return_value = []),
+            patch.object(mixin, "web_scroll_page_down", new_callable = AsyncMock),
+            patch.object(mixin, "_timeout", return_value = 10),
+        ):
+            result = await mixin._navigate_paginated_ad_overview(callback)
+
+            assert result is False
+            callback.assert_awaited_once_with(1)