diff --git a/mysql-test/r/ctype_collate.result b/mysql-test/r/ctype_collate.result
index 7e9513f06e9..8bcd488cb69 100644
--- a/mysql-test/r/ctype_collate.result
+++ b/mysql-test/r/ctype_collate.result
@@ -611,3 +611,22 @@ check table t1 extended;
 Table	Op	Msg_type	Msg_text
 test.t1	check	status	OK
 drop table t1;
+select least(_latin1'a',_latin2'b',_latin5'c' collate latin5_turkish_ci);
+least(_latin1'a',_latin2'b',_latin5'c' collate latin5_turkish_ci)
+a
+create table t1
+select least(_latin1'a',_latin2'b',_latin5'c' collate latin5_turkish_ci) as f1;
+show create table t1;
+Table	Create Table
+t1	CREATE TABLE `t1` (
+  `f1` varchar(1) character set latin5 NOT NULL default ''
+) ENGINE=MyISAM DEFAULT CHARSET=latin1
+drop table t1;
+select case _latin1'a' when _latin2'b' then 1 when _latin5'c' collate
+latin5_turkish_ci then 2 else 3 end;
+case _latin1'a' when _latin2'b' then 1 when _latin5'c' collate
+latin5_turkish_ci then 2 else 3 end
+3
+select concat(_latin1'a',_latin2'b',_latin5'c' collate latin5_turkish_ci);
+concat(_latin1'a',_latin2'b',_latin5'c' collate latin5_turkish_ci)
+abc
diff --git a/mysql-test/t/ctype_collate.test b/mysql-test/t/ctype_collate.test
index cfef8dfe81a..6b6abbcfbcc 100644
--- a/mysql-test/t/ctype_collate.test
+++ b/mysql-test/t/ctype_collate.test
@@ -229,3 +229,17 @@ insert into t1 set a=0x6c;
 insert into t1 set a=0x4c98;
 check table t1 extended;
 drop table t1;
+
+#
+# Bug#41627 Illegal mix of collations in LEAST / GREATEST / CASE
+#
+select least(_latin1'a',_latin2'b',_latin5'c' collate latin5_turkish_ci);
+create table t1
+select least(_latin1'a',_latin2'b',_latin5'c' collate latin5_turkish_ci) as f1;
+show create table t1;
+drop table t1;
+
+select case _latin1'a' when _latin2'b' then 1 when _latin5'c' collate
+latin5_turkish_ci then 2 else 3 end;
+
+select concat(_latin1'a',_latin2'b',_latin5'c' collate latin5_turkish_ci);
diff --git a/sql/item.cc b/sql/item.cc
index f32828629cf..c80d1b7a455 100644
--- a/sql/item.cc
+++ b/sql/item.cc
@@ -1498,7 +1498,8 @@ bool DTCollation::aggregate(DTCollation &dt, uint flags)
     else
     {
       // Cannot apply conversion
-      set(0, DERIVATION_NONE, 0);
+      set(&my_charset_bin, DERIVATION_NONE,
+          (dt.repertoire|repertoire));
       return 1;
     }
   }
@@ -1581,15 +1582,31 @@ bool agg_item_collations(DTCollation &c, const char *fname,
 {
   uint i;
   Item **arg;
+  bool unknown_cs= 0;
+
   c.set(av[0]->collation);
   for (i= 1, arg= &av[item_sep]; i < count; i++, arg++)
   {
     if (c.aggregate((*arg)->collation, flags))
     {
+      if (c.derivation == DERIVATION_NONE &&
+          c.collation == &my_charset_bin)
+      {
+        unknown_cs= 1;
+        continue;
+      }
       my_coll_agg_error(av, count, fname, item_sep);
       return TRUE;
     }
   }
+
+  if (unknown_cs &&
+      c.derivation != DERIVATION_EXPLICIT)
+  {
+    my_coll_agg_error(av, count, fname, item_sep);
+    return TRUE;
+  }
+
   if ((flags & MY_COLL_DISALLOW_NONE) &&
       c.derivation == DERIVATION_NONE)
   {