diff --git a/mysql-test/main/having_cond_pushdown.result b/mysql-test/main/having_cond_pushdown.result
index 6b488c2b78812..7afb7e7fbaffc 100644
--- a/mysql-test/main/having_cond_pushdown.result
+++ b/mysql-test/main/having_cond_pushdown.result
@@ -6090,4 +6090,16 @@ EXPLAIN
   }
 }
 drop table t1, t2;
+#
+# MDEV-39916: Crash when pushing "NOT col" from HAVING into WHERE
+#
+CREATE TABLE t1 (a INT);
+INSERT INTO t1 VALUES (0), (1);
+SELECT a
+FROM t1
+GROUP BY a
+HAVING (NOT a) AND TRUE;
+a
+0
+DROP TABLE t1;
 # End of 10.11 tests
diff --git a/mysql-test/main/having_cond_pushdown.test b/mysql-test/main/having_cond_pushdown.test
index 507c5f15bfbf2..9452c8cba94c8 100644
--- a/mysql-test/main/having_cond_pushdown.test
+++ b/mysql-test/main/having_cond_pushdown.test
@@ -1657,4 +1657,18 @@ execute stmt;
 
 drop table t1, t2;
 
+--echo #
+--echo # MDEV-39916: Crash when pushing "NOT col" from HAVING into WHERE
+--echo #
+
+CREATE TABLE t1 (a INT);
+INSERT INTO t1 VALUES (0), (1);
+
+SELECT a
+FROM t1
+GROUP BY a
+HAVING (NOT a) AND TRUE;
+
+DROP TABLE t1;
+
 --echo # End of 10.11 tests
diff --git a/sql/item_cmpfunc.cc b/sql/item_cmpfunc.cc
index 5f2c471de7fba..cb04be003b31f 100644
--- a/sql/item_cmpfunc.cc
+++ b/sql/item_cmpfunc.cc
@@ -6676,7 +6676,9 @@ Item *Item_func_not::neg_transformer(THD *thd)	/* NOT(x)  ->  x */
 bool Item_func_not::fix_fields(THD *thd, Item **ref)
 {
   args[0]->under_not(this);
-  if (args[0]->type() == FIELD_ITEM)
+  if (args[0]->fix_fields_if_needed(thd, &args[0]))
+    return true;
+  if (args[0]->real_item()->type() == FIELD_ITEM)
   {
     /* replace  "NOT <field>" with "<field> == 0" */
     Query_arena backup, *arena;
diff --git a/sql/sql_lex.cc b/sql/sql_lex.cc
index 8a5b1a14bcca7..b0db02ab63f80 100644
--- a/sql/sql_lex.cc
+++ b/sql/sql_lex.cc
@@ -11574,7 +11574,7 @@ Item *st_select_lex::pushdown_from_having_into_where(THD *thd, Item *having)
        list of all its conjuncts saved in attach_to_conds. Otherwise,
        the condition is put into attach_to_conds as the only its element.
   */
-  List_iterator_fast<Item> it(attach_to_conds);
+  List_iterator<Item> it(attach_to_conds);
   Item *item;
   check_cond_extraction_for_grouping_fields(thd, having);
   if (build_pushable_cond_for_having_pushdown(thd, having))
@@ -11638,8 +11638,9 @@ Item *st_select_lex::pushdown_from_having_into_where(THD *thd, Item *having)
                           &Item::field_transformer_for_having_pushdown,
                           (uchar *)this);
 
-    if (item->walk(&Item::cleanup_excluding_immutables_processor, 0, STOP_PTR)
-        || item->fix_fields(thd, NULL))
+    if (item->walk(&Item::cleanup_excluding_immutables_processor, 0,
+                   STOP_PTR) ||
+        item->fix_fields(thd, it.ref()))
     {
       attach_to_conds.empty();
       goto exit;
diff --git a/sql/sql_lex.h b/sql/sql_lex.h
index 8f8d6ce092737..0eea5ae771245 100644
--- a/sql/sql_lex.h
+++ b/sql/sql_lex.h
@@ -1180,7 +1180,13 @@ class st_select_lex: public st_select_lex_node
 
   /* List of references to fields referenced from inner selects */
   List<Item_outer_ref> inner_refs_list;
+
+  /*
+    Pushdown from HAVING into WHERE optimization: conditions from the HAVING
+    clause that should be added into the WHERE.
+  */
   List<Item> attach_to_conds;
+
   /* Saved values of the WHERE and HAVING clauses*/
   Item::cond_result cond_value, having_value;
   /*