diff --git a/README.md b/README.md
index d607f8f..3fced45 100644
--- a/README.md
+++ b/README.md
@@ -294,6 +294,7 @@ timeouts:
   gdpr_prompt: 10.0                   # Timeout when handling GDPR dialogs
   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
   pagination_initial: 10.0            # Timeout for first pagination lookup
   pagination_follow_up: 5.0           # Timeout for subsequent pagination clicks
   quick_dom: 2.0                      # Generic short DOM timeout (shipping dialogs, etc.)
diff --git a/schemas/config.schema.json b/schemas/config.schema.json
index 0c639fe..b0621bc 100644
--- a/schemas/config.schema.json
+++ b/schemas/config.schema.json
@@ -417,6 +417,13 @@
           "title": "Publishing Confirmation",
           "type": "number"
         },
+        "image_upload": {
+          "default": 30.0,
+          "description": "Timeout for image upload and server-side processing.",
+          "minimum": 5.0,
+          "title": "Image Upload",
+          "type": "number"
+        },
         "pagination_initial": {
           "default": 10.0,
           "description": "Timeout for initial pagination lookup.",
diff --git a/src/kleinanzeigen_bot/__init__.py b/src/kleinanzeigen_bot/__init__.py
index e912f6e..92f175f 100644
--- a/src/kleinanzeigen_bot/__init__.py
+++ b/src/kleinanzeigen_bot/__init__.py
@@ -893,7 +893,7 @@ class KleinanzeigenBot(WebScrapingMixin):
             # delete previous images because we don't know which have changed
             #############################
             img_items = await self.web_find_all(By.CSS_SELECTOR,
-                                                "ul#j-pictureupload-thumbnails > li.ui-sortable-handle")
+                                                "ul#j-pictureupload-thumbnails > li:not(.is-placeholder)")
             for element in img_items:
                 btn = await self.web_find(By.CSS_SELECTOR, "button.pictureupload-thumbnails-remove", parent = element)
                 await btn.click()
@@ -1260,6 +1260,52 @@ class KleinanzeigenBot(WebScrapingMixin):
             await image_upload.send_file(image)
             await self.web_sleep()
 
+        # Wait for all images to be processed and thumbnails to appear
+        expected_count = len(ad_cfg.images)
+        LOG.info(_(" -> waiting for %s to be processed..."), pluralize("image", ad_cfg.images))
+
+        async def check_thumbnails_uploaded() -> bool:
+            try:
+                thumbnails = await self.web_find_all(
+                    By.CSS_SELECTOR,
+                    "ul#j-pictureupload-thumbnails > li:not(.is-placeholder)",
+                    timeout = self._timeout("quick_dom")  # Fast timeout for polling
+                )
+                current_count = len(thumbnails)
+                if current_count < expected_count:
+                    LOG.debug(_(" -> %d of %d images processed"), current_count, expected_count)
+                return current_count == expected_count
+            except TimeoutError:
+                # No thumbnails found yet, continue polling
+                return False
+
+        try:
+            await self.web_await(
+                check_thumbnails_uploaded,
+                timeout = self._timeout("image_upload"),
+                timeout_error_message = _("Image upload timeout exceeded")
+            )
+        except TimeoutError as ex:
+            # Get current count for better error message
+            try:
+                thumbnails = await self.web_find_all(
+                    By.CSS_SELECTOR,
+                    "ul#j-pictureupload-thumbnails > li:not(.is-placeholder)",
+                    timeout = self._timeout("quick_dom")
+                )
+                current_count = len(thumbnails)
+            except TimeoutError:
+                # Still no thumbnails after full timeout
+                current_count = 0
+            raise TimeoutError(
+                _("Not all images were uploaded within timeout. Expected %(expected)d, found %(found)d thumbnails.") % {
+                    "expected": expected_count,
+                    "found": current_count
+                }
+            ) from ex
+
+        LOG.info(_(" -> all images uploaded successfully"))
+
     async def download_ads(self) -> None:
         """
         Determines which download mode was chosen with the arguments, and calls the specified download routine.
diff --git a/src/kleinanzeigen_bot/model/config_model.py b/src/kleinanzeigen_bot/model/config_model.py
index 552a49a..1e224ab 100644
--- a/src/kleinanzeigen_bot/model/config_model.py
+++ b/src/kleinanzeigen_bot/model/config_model.py
@@ -127,6 +127,7 @@ class TimeoutConfig(ContextualModel):
     gdpr_prompt:float = Field(default = 10.0, ge = 1.0, description = "Timeout for GDPR/consent dialogs.")
     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.")
     pagination_initial:float = Field(default = 10.0, ge = 1.0, description = "Timeout for initial pagination lookup.")
     pagination_follow_up:float = Field(default = 5.0, ge = 1.0, description = "Timeout for subsequent pagination navigation.")
     quick_dom:float = Field(default = 2.0, ge = 0.1, description = "Generic short timeout for transient UI.")
diff --git a/src/kleinanzeigen_bot/resources/translations.de.yaml b/src/kleinanzeigen_bot/resources/translations.de.yaml
index ece3787..55827e4 100644
--- a/src/kleinanzeigen_bot/resources/translations.de.yaml
+++ b/src/kleinanzeigen_bot/resources/translations.de.yaml
@@ -112,6 +112,13 @@ kleinanzeigen_bot/__init__.py:
     " -> found %s": "-> %s gefunden"
     "image": "Bild"
     " -> uploading image [%s]": " -> Lade Bild [%s] hoch"
+    " -> waiting for %s to be processed...": " -> Warte auf Verarbeitung von %s..."
+    " -> all images uploaded successfully": " -> Alle Bilder erfolgreich hochgeladen"
+    "Image upload timeout exceeded": "Zeitüberschreitung beim Hochladen der Bilder"
+    "Not all images were uploaded within timeout. Expected %(expected)d, found %(found)d thumbnails.": "Nicht alle Bilder wurden innerhalb der Zeitüberschreitung hochgeladen. Erwartet: %(expected)d, gefunden: %(found)d Miniaturansichten."
+
+  check_thumbnails_uploaded:
+    " -> %d of %d images processed": " -> %d von %d Bildern verarbeitet"
 
   __check_ad_republication:
     " -> SKIPPED: ad [%s] was last published %d days ago. republication is only required every %s days": " -> ÜBERSPRUNGEN: Anzeige [%s] wurde zuletzt vor %d Tagen veröffentlicht. Erneute Veröffentlichung ist erst nach %s Tagen erforderlich"