diff --git a/py/parsenum.c b/py/parsenum.c
index e18002306a25..4239f2dcd4d0 100644
--- a/py/parsenum.c
+++ b/py/parsenum.c
@@ -64,7 +64,7 @@ typedef mp_int_t parsed_int_t;
 typedef unsigned long long parsed_int_t;
 
 #define PARSED_INT_MUL_OVERFLOW mp_mul_ull_overflow
-#define PARSED_INT_FITS(I) ((I) <= (unsigned long long)LLONG_MAX)
+#define PARSED_INT_FITS(I) ((I) <= (unsigned long long)LLONG_MAX + 1)
 #endif
 
 mp_obj_t mp_parse_num_integer(const char *restrict str_, size_t len, int base, mp_lexer_t *lex) {
@@ -135,8 +135,11 @@ mp_obj_t mp_parse_num_integer(const char *restrict str_, size_t len, int base, m
 have_ret_val:
     #else
     // The PARSED_INT_FITS check above ensures parsed_val won't overflow signed long long
-    long long signed_val = parsed_val;
-    if (neg) {
+    long long signed_val = -parsed_val;
+    if (!neg) {
+        if (signed_val == LLONG_MIN) {
+            goto overflow;
+        }
         signed_val = -signed_val;
     }
     ret_val = mp_obj_new_int_from_ll(signed_val); // Could be large or small int
diff --git a/tests/basics/int_64_basics.py b/tests/basics/int_64_basics.py
index 2a161dac0ba1..ef76793317ec 100644
--- a/tests/basics/int_64_basics.py
+++ b/tests/basics/int_64_basics.py
@@ -151,3 +151,11 @@
     print((1 << 48) << -6)
 except ValueError as e:
     print(e)
+
+# Test that the most extreme 64 bit integer values all parse with int()
+print(int("-9223372036854775807"))
+print(int("-9223372036854775808"))
+print(int("9223372036854775807"))
+
+# Test that the most negative 64 bit integer can be formed via arithmetic
+print(-9223372036854775807-1)