diff --git a/packages/pyright-internal/src/analyzer/operations.ts b/packages/pyright-internal/src/analyzer/operations.ts
index 6ffd1233968b..ca2672395fed 100644
--- a/packages/pyright-internal/src/analyzer/operations.ts
+++ b/packages/pyright-internal/src/analyzer/operations.ts
@@ -1037,7 +1037,10 @@ function calcLiteralForBinaryOp(operator: OperatorType, leftType: Type, rightTyp
                             // infinity, so we need to adjust the result if the signs
                             // of the operands are different.
                             if (leftLiteralValue !== rightLiteralValue && leftLiteralValue !== BigInt(0)) {
-                                if (leftLiteralValue < BigInt(0) !== rightLiteralValue < BigInt(0)) {
+                                if (
+                                    leftLiteralValue < BigInt(0) !== rightLiteralValue < BigInt(0) &&
+                                    leftLiteralValue !== rightLiteralValue * BigInt(-1)
+                                ) {
                                     newValue -= BigInt(1);
                                 }
                             }
@@ -1055,9 +1058,13 @@ function calcLiteralForBinaryOp(operator: OperatorType, leftType: Type, rightTyp
                             }
                         }
                     } else if (operator === OperatorType.LeftShift) {
-                        newValue = leftLiteralValue << rightLiteralValue;
+                        if (rightLiteralValue >= BigInt(0)) {
+                            newValue = leftLiteralValue << rightLiteralValue;
+                        }
                     } else if (operator === OperatorType.RightShift) {
-                        newValue = leftLiteralValue >> rightLiteralValue;
+                        if (rightLiteralValue >= BigInt(0)) {
+                            newValue = leftLiteralValue >> rightLiteralValue;
+                        }
                     } else if (operator === OperatorType.BitwiseAnd) {
                         newValue = leftLiteralValue & rightLiteralValue;
                     } else if (operator === OperatorType.BitwiseOr) {
diff --git a/packages/pyright-internal/src/tests/samples/operator8.py b/packages/pyright-internal/src/tests/samples/operator8.py
index 1a3d2b89b021..654658819ab6 100644
--- a/packages/pyright-internal/src/tests/samples/operator8.py
+++ b/packages/pyright-internal/src/tests/samples/operator8.py
@@ -71,6 +71,18 @@ def func1(a: Literal[1, 2], b: Literal[0, 4], c: Literal[3, 4]):
     c10 = 0 // 6
     reveal_type(c10, expected_text="Literal[0]")
 
+    c11 = -6 // 6
+    reveal_type(c11, expected_text="Literal[-1]")
+
+    c12 = 6 // -6
+    reveal_type(c12, expected_text="Literal[-1]")
+
+    c13 = 1 << -1
+    reveal_type(c13, expected_text="int")
+
+    c14 = 1 >> -1
+    reveal_type(c14, expected_text="int")
+
 
 def func2(cond: bool):
     c1 = "Hi " + ("Steve" if cond else "Amy")