diff --git a/py/mpconfig.h b/py/mpconfig.h
index 96cd8c651a..19bae4f88a 100644
--- a/py/mpconfig.h
+++ b/py/mpconfig.h
@@ -79,7 +79,7 @@
 //  - seeeeeee eeeeffff ffffffff ffffffff ffffffff ffffffff ffffffff ffffffff 64-bit fp, e != 0x7ff
 //  - s1111111 11110000 00000000 00000000 00000000 00000000 00000000 00000000 +/- inf
 //  - 01111111 11111000 00000000 00000000 00000000 00000000 00000000 00000000 normalised nan
-//  - 01111111 11111101 00000000 00000000 iiiiiiii iiiiiiii iiiiiiii iiiiiii1 small int
+//  - 01111111 11111101 iiiiiiii iiiiiiii iiiiiiii iiiiiiii iiiiiiii iiiiiii1 small int
 //  - 01111111 11111110 00000000 00000000 qqqqqqqq qqqqqqqq qqqqqqqq qqqqqqq1 str
 //  - 01111111 11111100 00000000 00000000 pppppppp pppppppp pppppppp pppppp00 ptr (4 byte alignment)
 // Stored as O = R + 0x8004000000000000, retrieved as R = O - 0x8004000000000000.
diff --git a/py/obj.h b/py/obj.h
index 31c3ce95c8..10cb48961f 100644
--- a/py/obj.h
+++ b/py/obj.h
@@ -170,8 +170,8 @@ static inline bool MP_OBJ_IS_OBJ(mp_const_obj_t o)
 
 static inline bool MP_OBJ_IS_SMALL_INT(mp_const_obj_t o)
     { return ((((mp_int_t)(o)) & 0xffff000000000000) == 0x0001000000000000); }
-#define MP_OBJ_SMALL_INT_VALUE(o) (((intptr_t)(o)) >> 1)
-#define MP_OBJ_NEW_SMALL_INT(small_int) ((mp_obj_t)(((uintptr_t)(small_int)) << 1) | 0x0001000000000001)
+#define MP_OBJ_SMALL_INT_VALUE(o) (((mp_int_t)((o) << 16)) >> 17)
+#define MP_OBJ_NEW_SMALL_INT(small_int) (((((uint64_t)(small_int)) & 0x7fffffffffff) << 1) | 0x0001000000000001)
 
 static inline bool MP_OBJ_IS_QSTR(mp_const_obj_t o)
     { return ((((mp_int_t)(o)) & 0xffff000000000000) == 0x0002000000000000); }
diff --git a/py/parse.c b/py/parse.c
index f7fe30418c..b80cc8fb1a 100644
--- a/py/parse.c
+++ b/py/parse.c
@@ -369,6 +369,18 @@ STATIC mp_parse_node_t make_node_const_object(parser_t *parser, size_t src_line,
     return (mp_parse_node_t)pn;
 }
 
+STATIC mp_parse_node_t mp_parse_node_new_small_int_checked(parser_t *parser, mp_obj_t o_val) {
+    (void)parser;
+    mp_int_t val = MP_OBJ_SMALL_INT_VALUE(o_val);
+    #if MICROPY_OBJ_REPR == MICROPY_OBJ_REPR_D
+    // A parse node is only 32-bits and the small-int value must fit in 31-bits
+    if (((val ^ (val << 1)) & 0xffffffff80000000) != 0) {
+        return make_node_const_object(parser, 0, o_val);
+    }
+    #endif
+    return mp_parse_node_new_small_int(val);
+}
+
 STATIC void push_result_token(parser_t *parser, const rule_t *rule) {
     mp_parse_node_t pn;
     mp_lexer_t *lex = parser->lexer;
@@ -380,7 +392,7 @@ STATIC void push_result_token(parser_t *parser, const rule_t *rule) {
         if (rule->rule_id == RULE_atom
             && (elem = mp_map_lookup(&parser->consts, MP_OBJ_NEW_QSTR(id), MP_MAP_LOOKUP)) != NULL) {
             if (MP_OBJ_IS_SMALL_INT(elem->value)) {
-                pn = mp_parse_node_new_small_int(MP_OBJ_SMALL_INT_VALUE(elem->value));
+                pn = mp_parse_node_new_small_int_checked(parser, elem->value);
             } else {
                 pn = make_node_const_object(parser, lex->tok_line, elem->value);
             }
@@ -394,7 +406,7 @@ STATIC void push_result_token(parser_t *parser, const rule_t *rule) {
     } else if (lex->tok_kind == MP_TOKEN_INTEGER) {
         mp_obj_t o = mp_parse_num_integer(lex->vstr.buf, lex->vstr.len, 0, lex);
         if (MP_OBJ_IS_SMALL_INT(o)) {
-            pn = mp_parse_node_new_small_int(MP_OBJ_SMALL_INT_VALUE(o));
+            pn = mp_parse_node_new_small_int_checked(parser, o);
         } else {
             pn = make_node_const_object(parser, lex->tok_line, o);
         }
@@ -686,7 +698,7 @@ STATIC bool fold_constants(parser_t *parser, const rule_t *rule, size_t num_args
         pop_result(parser);
     }
     if (MP_OBJ_IS_SMALL_INT(arg0)) {
-        push_result_node(parser, mp_parse_node_new_small_int(MP_OBJ_SMALL_INT_VALUE(arg0)));
+        push_result_node(parser, mp_parse_node_new_small_int_checked(parser, arg0));
     } else {
         // TODO reuse memory for parse node struct?
         push_result_node(parser, make_node_const_object(parser, 0, arg0));
diff --git a/py/smallint.h b/py/smallint.h
index 42679a78fb..6a3c75236c 100644
--- a/py/smallint.h
+++ b/py/smallint.h
@@ -50,10 +50,10 @@
 
 #elif MICROPY_OBJ_REPR == MICROPY_OBJ_REPR_D
 
-#define MP_SMALL_INT_MIN ((mp_int_t)(((mp_int_t)0xffffffff80000000) >> 1))
-#define MP_SMALL_INT_FITS(n) ((((n) ^ ((n) << 1)) & 0xffffffff80000000) == 0)
+#define MP_SMALL_INT_MIN ((mp_int_t)(((mp_int_t)0xffff800000000000) >> 1))
+#define MP_SMALL_INT_FITS(n) ((((n) ^ ((n) << 1)) & 0xffff800000000000) == 0)
 // Mask to truncate mp_int_t to positive value
-#define MP_SMALL_INT_POSITIVE_MASK ~(0xffffffff80000000 | (0xffffffff80000000 >> 1))
+#define MP_SMALL_INT_POSITIVE_MASK ~(0xffff800000000000 | (0xffff800000000000 >> 1))
 
 #endif