diff --git a/gallery_dl/extractor/tumblr.py b/gallery_dl/extractor/tumblr.py
index 6f538811..542a4f2d 100644
--- a/gallery_dl/extractor/tumblr.py
+++ b/gallery_dl/extractor/tumblr.py
@@ -116,8 +116,10 @@ class TumblrExtractor(Extractor):
 
                     if self.original and "/s2048x3072/" in photo["url"] and (
                             photo["width"] == 2048 or photo["height"] == 3072):
-                        photo["url"] = self._original_photo(photo["url"])
-
+                        try:
+                            photo["url"] = self._original_photo(photo["url"])
+                        except Exception:
+                            self._warn_original(photo["url"], post)
                     del photo["original_size"]
                     del photo["alt_sizes"]
                     posts.append(
@@ -138,7 +140,10 @@ class TumblrExtractor(Extractor):
                 # API response, but they can't contain images/videos anyway
                 body = post["reblog"]["comment"] + post["reblog"]["tree_html"]
                 for url in _findall_image(body):
-                    url = self._original_inline_image(url)
+                    try:
+                        url = self._original_inline_image(url)
+                    except Exception:
+                        self._warn_original(url, post)
                     posts.append(self._prepare_image(url, post.copy()))
                 for url in _findall_video(body):
                     url = self._original_video(url)
@@ -218,23 +223,33 @@ class TumblrExtractor(Extractor):
         return self.blog != post.get("reblogged_root_uuid")
 
     def _original_photo(self, url):
-        return self._update_image_token(
-            url.replace("/s2048x3072/", "/s99999x99999/", 1))
+        resized = url.replace("/s2048x3072/", "/s99999x99999/", 1)
+        return self._update_image_token(resized)
 
     def _original_inline_image(self, url):
         if self.original:
-            url, n = self._subn_orig_image("/s99999x99999/", url, 1)
+            resized, n = self._subn_orig_image("/s99999x99999/", url, 1)
             if n:
-                return self._update_image_token(url)
+                return self._update_image_token(resized)
         return self._sub_image(r"https://\1_1280.\2", url)
 
     def _original_video(self, url):
         return self._sub_video(r"https://\1.\2", url)
 
-    def _update_image_token(self, url):
+    def _update_image_token(self, resized):
         headers = {"Accept": "text/html,*/*;q=0.8"}
-        response = self.request(url, headers=headers)
-        return text.extract(response.text, '" src="', '"')[0]
+
+        for _ in range(3):
+            response = self.request(resized, headers=headers)
+            updated = text.extract(response.text, '" src="', '"')[0]
+            if updated != resized:
+                return updated
+
+        raise RuntimeError("invalid token")
+
+    def _warn_original(self, url, post):
+        self.log.warning("Unable to fetch higher-resolution "
+                         "version of %s (%s)", url, post["id"])
 
 
 class TumblrUserExtractor(TumblrExtractor):