diff --git a/graalpython/com.oracle.graal.python.test/src/tests/test_int.py b/graalpython/com.oracle.graal.python.test/src/tests/test_int.py
index a6934f0e9c..cc2810a67b 100644
--- a/graalpython/com.oracle.graal.python.test/src/tests/test_int.py
+++ b/graalpython/com.oracle.graal.python.test/src/tests/test_int.py
@@ -853,6 +853,15 @@ def test_WrongInput(self):
         self.assertRaises(OverflowError, (256).to_bytes, 1, 'big', signed=True)
         self.assertRaises(OverflowError, (256).to_bytes, 1, 'little', signed=False)
         self.assertRaises(OverflowError, (256).to_bytes, 1, 'little', signed=True)
+        self.assertRaises(OverflowError, (32768).to_bytes, 2, 'big', signed=True)
+        self.assertRaises(OverflowError, (32768).to_bytes, 2, 'little', signed=True)
+        self.assertRaises(OverflowError, (-32769).to_bytes, 2, 'big', signed=True)
+        self.assertRaises(OverflowError, (-32769).to_bytes, 2, 'little', signed=True)
+        self.assertRaises(OverflowError, (-5242881).to_bytes, 2, 'big', signed=True)
+        self.assertRaises(OverflowError, (-5242881).to_bytes, 2, 'little', signed=True)
+        self.assertRaises(OverflowError, self.MyInt(32768).to_bytes, 2, 'big', signed=True)
+        self.assertRaises(OverflowError, self.MyInt(-32769).to_bytes, 2, 'big', signed=True)
+        self.assertRaises(OverflowError, self.MyInt(-5242881).to_bytes, 2, 'big', signed=True)
         self.assertRaises(OverflowError, (-1).to_bytes, 2, 'big', signed=False)
         self.assertRaises(OverflowError, (-1).to_bytes, 2, 'little', signed=False)
         self.assertRaises(OverflowError, (1).to_bytes, 0, 'big')
diff --git a/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/builtins/objects/ints/IntBuiltins.java b/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/builtins/objects/ints/IntBuiltins.java
index 63c8209d8c..2c81fcea3d 100644
--- a/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/builtins/objects/ints/IntBuiltins.java
+++ b/graalpython/com.oracle.graal.python/src/com/oracle/graal/python/builtins/objects/ints/IntBuiltins.java
@@ -2327,25 +2327,29 @@ public static byte[] fromLong(long self, int byteCount, boolean isBigEndian, boo
             byte[] bytes = new byte[byteCount];
             long number = self;
 
-            while (number != 0 && 0 <= index && index <= (byteCount - 1)) {
+            while (number != signByte && 0 <= index && index <= (byteCount - 1)) {
                 bytes[index] = (byte) (number & 0xFF);
-                if (number == signByte) {
-                    number = 0;
-                }
                 number >>= 8;
                 index += delta;
             }
 
-            if (overflowProfile.profile(inliningTarget, !signed && number != 0 || (signed && bytes.length == 1 && bytes[0] != self) || (byteCount == 0 && self != 0 && self != -1))) {
-                throw raiseNode.raise(inliningTarget, PythonErrorType.OverflowError, ErrorMessages.MESSAGE_INT_TO_BIG);
-            }
-
             if (signed) {
                 while (0 <= index && index <= (byteCount - 1)) {
                     bytes[index] = signByte;
                     index += delta;
                 }
             }
+
+            boolean overflow = number != signByte;
+            if (signed && byteCount > 0) {
+                int mostSignificantByte = isBigEndian ? bytes[0] : bytes[byteCount - 1];
+                if ((mostSignificantByte < 0) != (self < 0)) {
+                    overflow = true;
+                }
+            }
+            if (overflowProfile.profile(inliningTarget, overflow)) {
+                throw raiseNode.raise(inliningTarget, PythonErrorType.OverflowError, ErrorMessages.MESSAGE_INT_TO_BIG);
+            }
             return bytes;
         }