diff --git a/src/backend/nodes/list.c b/src/backend/nodes/list.c
index 94fb236daf..12847e35ea 100644
--- a/src/backend/nodes/list.c
+++ b/src/backend/nodes/list.c
@@ -906,6 +906,72 @@ list_delete_last(List *list)
 	return list_truncate(list, list_length(list) - 1);
 }
 
+/*
+ * Delete the first N cells of the list.
+ *
+ * The List is pfree'd if the request causes all cells to be deleted.
+ */
+List *
+list_delete_first_n(List *list, int n)
+{
+	check_list_invariants(list);
+
+	/* No-op request? */
+	if (n <= 0)
+		return list;
+
+	/* Delete whole list? */
+	if (n >= list_length(list))
+	{
+		list_free(list);
+		return NIL;
+	}
+
+	/*
+	 * Otherwise, we normally just collapse out the removed elements.  But for
+	 * debugging purposes, move the whole list contents someplace else.
+	 *
+	 * (Note that we *must* keep the contents in the same memory context.)
+	 */
+#ifndef DEBUG_LIST_MEMORY_USAGE
+	memmove(&list->elements[0], &list->elements[n],
+			(list->length - n) * sizeof(ListCell));
+	list->length -= n;
+#else
+	{
+		ListCell   *newelems;
+		int			newmaxlen = list->length - n;
+
+		newelems = (ListCell *)
+			MemoryContextAlloc(GetMemoryChunkContext(list),
+							   newmaxlen * sizeof(ListCell));
+		memcpy(newelems, &list->elements[n], newmaxlen * sizeof(ListCell));
+		if (list->elements != list->initial_elements)
+			pfree(list->elements);
+		else
+		{
+			/*
+			 * As in enlarge_list(), clear the initial_elements[] space and/or
+			 * mark it inaccessible.
+			 */
+#ifdef CLOBBER_FREED_MEMORY
+			wipe_mem(list->initial_elements,
+					 list->max_length * sizeof(ListCell));
+#else
+			VALGRIND_MAKE_MEM_NOACCESS(list->initial_elements,
+									   list->max_length * sizeof(ListCell));
+#endif
+		}
+		list->elements = newelems;
+		list->max_length = newmaxlen;
+		list->length = newmaxlen;
+		check_list_invariants(list);
+	}
+#endif
+
+	return list;
+}
+
 /*
  * Generate the union of two lists. This is calculated by copying
  * list1 via list_copy(), then adding to it all the members of list2
diff --git a/src/backend/storage/sync/sync.c b/src/backend/storage/sync/sync.c
index 4a2ed414b0..023d7413e2 100644
--- a/src/backend/storage/sync/sync.c
+++ b/src/backend/storage/sync/sync.c
@@ -69,6 +69,7 @@ typedef struct
 {
 	FileTag		tag;			/* identifies handler and file */
 	CycleCtr	cycle_ctr;		/* checkpoint_cycle_ctr when request was made */
+	bool		canceled;		/* true if request has been canceled */
 } PendingUnlinkEntry;
 
 static HTAB *pendingOps = NULL;
@@ -195,11 +196,12 @@ void
 SyncPostCheckpoint(void)
 {
 	int			absorb_counter;
+	ListCell   *lc;
 
 	absorb_counter = UNLINKS_PER_ABSORB;
-	while (pendingUnlinks != NIL)
+	foreach(lc, pendingUnlinks)
 	{
-		PendingUnlinkEntry *entry = (PendingUnlinkEntry *) linitial(pendingUnlinks);
+		PendingUnlinkEntry *entry = (PendingUnlinkEntry *) lfirst(lc);
 		char		path[MAXPGPATH];
 
 		/*
@@ -214,6 +216,10 @@ SyncPostCheckpoint(void)
 		if (entry->cycle_ctr == checkpoint_cycle_ctr)
 			break;
 
+		/* Skip over any canceled entries */
+		if (entry->canceled)
+			continue;
+
 		/* Unlink the file */
 		if (syncsw[entry->tag.handler].sync_unlinkfiletag(&entry->tag,
 														  path) < 0)
@@ -231,15 +237,13 @@ SyncPostCheckpoint(void)
 						 errmsg("could not remove file \"%s\": %m", path)));
 		}
 
-		/* And remove the list entry */
-		pendingUnlinks = list_delete_first(pendingUnlinks);
-		pfree(entry);
+		/* Mark the list entry as canceled, just in case */
+		entry->canceled = true;
 
 		/*
 		 * As in ProcessSyncRequests, we don't want to stop absorbing fsync
 		 * requests for a long time when there are many deletions to be done.
-		 * We can safely call AbsorbSyncRequests() at this point in the loop
-		 * (note it might try to delete list entries).
+		 * We can safely call AbsorbSyncRequests() at this point in the loop.
 		 */
 		if (--absorb_counter <= 0)
 		{
@@ -247,6 +251,26 @@ SyncPostCheckpoint(void)
 			absorb_counter = UNLINKS_PER_ABSORB;
 		}
 	}
+
+	/*
+	 * If we reached the end of the list, we can just remove the whole list
+	 * (remembering to pfree all the PendingUnlinkEntry objects).  Otherwise,
+	 * we must keep the entries at or after "lc".
+	 */
+	if (lc == NULL)
+	{
+		list_free_deep(pendingUnlinks);
+		pendingUnlinks = NIL;
+	}
+	else
+	{
+		int			ntodelete = list_cell_number(pendingUnlinks, lc);
+
+		for (int i = 0; i < ntodelete; i++)
+			pfree(list_nth(pendingUnlinks, i));
+
+		pendingUnlinks = list_delete_first_n(pendingUnlinks, ntodelete);
+	}
 }
 
 /*
@@ -486,17 +510,14 @@ RememberSyncRequest(const FileTag *ftag, SyncRequestType type)
 				entry->canceled = true;
 		}
 
-		/* Remove matching unlink requests */
+		/* Cancel matching unlink requests */
 		foreach(cell, pendingUnlinks)
 		{
 			PendingUnlinkEntry *entry = (PendingUnlinkEntry *) lfirst(cell);
 
 			if (entry->tag.handler == ftag->handler &&
 				syncsw[ftag->handler].sync_filetagmatches(ftag, &entry->tag))
-			{
-				pendingUnlinks = foreach_delete_current(pendingUnlinks, cell);
-				pfree(entry);
-			}
+				entry->canceled = true;
 		}
 	}
 	else if (type == SYNC_UNLINK_REQUEST)
@@ -508,6 +529,7 @@ RememberSyncRequest(const FileTag *ftag, SyncRequestType type)
 		entry = palloc(sizeof(PendingUnlinkEntry));
 		entry->tag = *ftag;
 		entry->cycle_ctr = checkpoint_cycle_ctr;
+		entry->canceled = false;
 
 		pendingUnlinks = lappend(pendingUnlinks, entry);
 
diff --git a/src/include/nodes/pg_list.h b/src/include/nodes/pg_list.h
index 30f98c4595..c3f47db888 100644
--- a/src/include/nodes/pg_list.h
+++ b/src/include/nodes/pg_list.h
@@ -564,6 +564,7 @@ extern pg_nodiscard List *list_delete_int(List *list, int datum);
 extern pg_nodiscard List *list_delete_oid(List *list, Oid datum);
 extern pg_nodiscard List *list_delete_first(List *list);
 extern pg_nodiscard List *list_delete_last(List *list);
+extern pg_nodiscard List *list_delete_first_n(List *list, int n);
 extern pg_nodiscard List *list_delete_nth_cell(List *list, int n);
 extern pg_nodiscard List *list_delete_cell(List *list, ListCell *cell);