diff --git a/src/jltypes.c b/src/jltypes.c
index dc58cb57bfde6..fbcae4be5a542 100644
--- a/src/jltypes.c
+++ b/src/jltypes.c
@@ -582,6 +582,52 @@ JL_DLLEXPORT jl_value_t *jl_type_union(jl_value_t **ts, size_t n)
     return tu;
 }
 
+jl_value_t *simple_union(jl_value_t *a, jl_value_t *b)
+{
+    size_t nt = count_union_components(&a, 1);
+    nt += count_union_components(&b, 1);
+    jl_value_t **temp;
+    JL_GC_PUSHARGS(temp, nt+1);
+    size_t count = 0;
+    flatten_type_union(&a, 1, temp, &count);
+    flatten_type_union(&b, 1, temp, &count);
+    assert(count == nt);
+    size_t i, j;
+    for (i = 0; i < nt; i++) {
+        int has_free = temp[i] != NULL && jl_has_free_typevars(temp[i]);
+        for (j = 0; j < nt; j++) {
+            if (j != i && temp[i] && temp[j]) {
+                if (temp[i] == jl_bottom_type ||
+                    temp[j] == (jl_value_t*)jl_any_type ||
+                    jl_egal(temp[i], temp[j]) ||
+                    (!has_free && !jl_has_free_typevars(temp[j]) &&
+                        // issue #24521: don't merge Type{T} where typeof(T) varies
+                        !(jl_is_type_type(temp[i]) && jl_is_type_type(temp[j]) && jl_typeof(jl_tparam0(temp[i])) != jl_typeof(jl_tparam0(temp[j]))) &&
+                        jl_subtype(temp[i], temp[j]))) {
+                    temp[i] = NULL;
+                }
+            }
+        }
+    }
+    isort_union(temp, nt);
+    jl_value_t **ptu = &temp[nt];
+    *ptu = jl_bottom_type;
+    int k;
+    for (k = (int)nt-1; k >= 0; --k) {
+        if (temp[k] != NULL) {
+            if (*ptu == jl_bottom_type)
+                *ptu = temp[k];
+            else
+                *ptu = jl_new_struct(jl_uniontype_type, temp[k], *ptu);
+        }
+    }
+    assert(*ptu != NULL);
+    jl_value_t *tu = *ptu;
+    JL_GC_POP();
+    return tu;
+}
+
+
 // unionall types -------------------------------------------------------------
 
 JL_DLLEXPORT jl_value_t *jl_type_unionall(jl_tvar_t *v, jl_value_t *body)
diff --git a/src/subtype.c b/src/subtype.c
index 8f7488dcb27bc..9c6509f90e5a9 100644
--- a/src/subtype.c
+++ b/src/subtype.c
@@ -566,6 +566,7 @@ static int is_any_like(jl_value_t* x, jl_typeenv_t *env) JL_NOTSAFEPOINT
     return 0;
 }
 
+jl_value_t *simple_union(jl_value_t *a, jl_value_t *b);
 // compute a least upper bound of `a` and `b`
 static jl_value_t *simple_join(jl_value_t *a, jl_value_t *b)
 {
@@ -589,13 +590,7 @@ static jl_value_t *simple_join(jl_value_t *a, jl_value_t *b)
         return a;
     if (jl_is_typevar(b) && obviously_egal(a, ((jl_tvar_t*)b)->lb))
         return b;
-    if (!jl_has_free_typevars(a) && !jl_has_free_typevars(b) &&
-        // issue #24521: don't merge Type{T} where typeof(T) varies
-        !(jl_is_type_type(a) && jl_is_type_type(b) && jl_typeof(jl_tparam0(a)) != jl_typeof(jl_tparam0(b)))) {
-        if (jl_subtype(a, b)) return b;
-        if (jl_subtype(b, a)) return a;
-    }
-    return jl_new_struct(jl_uniontype_type, a, b);
+    return simple_union(a, b);
 }
 
 // Compute a greatest lower bound of `a` and `b`
@@ -2759,7 +2754,7 @@ static jl_value_t *omit_bad_union(jl_value_t *u, jl_tvar_t *t)
         b = omit_bad_union(b, t);
         res = a == NULL ? b :
               b == NULL ? a :
-              jl_new_struct(jl_uniontype_type, a, b);
+              simple_join(a, b);
         JL_GC_POP();
     }
     return res;