diff --git a/instaloader/instaloader.py b/instaloader/instaloader.py
index 950e6ce..15fa555 100644
--- a/instaloader/instaloader.py
+++ b/instaloader/instaloader.py
@@ -1010,7 +1010,10 @@ class Instaloader:
                 enabled=self.resume_prefix is not None
         ) as (is_resuming, start_index):
             for number, post in enumerate(posts, start=start_index + 1):
-                if (max_count is not None and number > max_count) or not takewhile(post):
+                should_stop = not takewhile(post)
+                if should_stop and post.is_pinned:
+                    continue
+                if (max_count is not None and number > max_count) or should_stop:
                     break
                 if displayed_count is not None:
                     self.context.log("[{0:{w}d}/{1:{w}d}] ".format(number, displayed_count,
@@ -1042,7 +1045,7 @@ class Instaloader:
                         except PostChangedException:
                             post_changed = True
                             continue
-                    if fast_update and not downloaded and not post_changed:
+                    if fast_update and not downloaded and not post_changed and not post.is_pinned:
                         # disengage fast_update for first post when resuming
                         if not is_resuming or number > 0:
                             break
diff --git a/instaloader/nodeiterator.py b/instaloader/nodeiterator.py
index b5fabae..a49656d 100644
--- a/instaloader/nodeiterator.py
+++ b/instaloader/nodeiterator.py
@@ -76,7 +76,8 @@ class NodeIterator(Iterator[T]):
                  node_wrapper: Callable[[Dict], T],
                  query_variables: Optional[Dict[str, Any]] = None,
                  query_referer: Optional[str] = None,
-                 first_data: Optional[Dict[str, Any]] = None):
+                 first_data: Optional[Dict[str, Any]] = None,
+                 is_first: Optional[Callable[[T], bool]] = None):
         self._context = context
         self._query_hash = query_hash
         self._edge_extractor = edge_extractor
@@ -91,6 +92,7 @@ class NodeIterator(Iterator[T]):
         else:
             self._data = self._query()
         self._first_node: Optional[Dict] = None
+        self._is_first = is_first
 
     def _query(self, after: Optional[str] = None) -> Dict:
         pagination_variables = {'first': NodeIterator._graphql_page_length}  # type: Dict[str, Any]
@@ -128,8 +130,12 @@ class NodeIterator(Iterator[T]):
                 self._page_index, self._total_index = page_index, total_index
                 raise
             item = self._node_wrapper(node)
-            if self._first_node is None:
-                self._first_node = node
+            if self._is_first is not None:
+                if self._is_first(item):
+                    self._first_node = node
+            else:
+                if self._first_node is None:
+                    self._first_node = node
             return item
         if self._data['page_info']['has_next_page']:
             query_response = self._query(self._data['page_info']['end_cursor'])
@@ -168,7 +174,13 @@ class NodeIterator(Iterator[T]):
         """
         If this iterator has produced any items, returns the first item produced.
 
+        It is possible to override what is considered the first item (for example, to consider the
+        newest item in case items are not in strict chronological order) by passing a callback
+        function as the `is_first` parameter when creating the class.
+
         .. versionadded:: 4.8
+        .. versionchanged:: 4.9.2
+           What is considered the first item can be overridden.
         """
         return self._node_wrapper(self._first_node) if self._first_node is not None else None
 
diff --git a/instaloader/structures.py b/instaloader/structures.py
index 5efa541..adaa222 100644
--- a/instaloader/structures.py
+++ b/instaloader/structures.py
@@ -7,7 +7,7 @@ from contextlib import suppress
 from datetime import datetime
 from itertools import islice
 from pathlib import Path
-from typing import Any, Dict, Iterable, Iterator, List, Optional, Tuple, Union
+from typing import Any, Callable, Dict, Iterable, Iterator, List, Optional, Tuple, Union
 from unicodedata import normalize
 
 from . import __version__
@@ -644,6 +644,13 @@ class Post:
                                       loc.get('lat'), loc.get('lng'))
         return self._location
 
+    @property
+    def is_pinned(self) -> bool:
+        """True if this Post has been pinned by at least one user.
+
+        .. versionadded: 4.9.2"""
+        return 'pinned_for_users' in self._node and bool(self._node['pinned_for_users'])
+
 
 class Profile:
     """
@@ -970,6 +977,7 @@ class Profile:
             {'id': self.userid},
             'https://www.instagram.com/{0}/'.format(self.username),
             self._metadata('edge_owner_to_timeline_media'),
+            Profile._make_is_newest_checker()
         )
 
     def get_saved_posts(self) -> NodeIterator[Post]:
@@ -1003,6 +1011,7 @@ class Profile:
             lambda n: Post(self._context, n, self if int(n['owner']['id']) == self.userid else None),
             {'id': self.userid},
             'https://www.instagram.com/{0}/'.format(self.username),
+            is_first=Profile._make_is_newest_checker()
         )
 
     def get_igtv_posts(self) -> NodeIterator[Post]:
@@ -1020,8 +1029,22 @@ class Profile:
             {'id': self.userid},
             'https://www.instagram.com/{0}/channel/'.format(self.username),
             self._metadata('edge_felix_video_timeline'),
+            Profile._make_is_newest_checker()
         )
 
+    @staticmethod
+    def _make_is_newest_checker() -> Callable[[Post], bool]:
+        newest_date: Optional[datetime] = None
+        def is_newest(p: Post) -> bool:
+            nonlocal newest_date
+            post_date = p.date_local
+            if newest_date is None or post_date > newest_date:
+                newest_date = post_date
+                return True
+            else:
+                return False
+        return is_newest
+
     def get_followers(self) -> NodeIterator['Profile']:
         """
         Retrieve list of followers of given profile.