diff --git a/crates/oxc_formatter/src/parentheses/expression.rs b/crates/oxc_formatter/src/parentheses/expression.rs
index c42440332f15d..a3bc6c73b5ba5 100644
--- a/crates/oxc_formatter/src/parentheses/expression.rs
+++ b/crates/oxc_formatter/src/parentheses/expression.rs
@@ -638,16 +638,44 @@ impl<'a> NeedsParentheses<'a> for AstNode<'a, TSSatisfiesExpression<'a>> {
 
 impl<'a> NeedsParentheses<'a> for AstNode<'a, TSTypeAssertion<'a>> {
     fn needs_parentheses(&self, f: &Formatter<'_, 'a>) -> bool {
-        matches!(
-            self.parent,
-            AstNodes::ComputedMemberExpression(_)
-                | AstNodes::StaticMemberExpression(_)
-                | AstNodes::PrivateFieldExpression(_)
-                | AstNodes::IdentifierReference(_)
-                | AstNodes::AssignmentExpression(_)
-                | AstNodes::AssignmentTargetWithDefault(_)
-                | AstNodes::UpdateExpression(_)
-        )
+        match self.parent {
+            AstNodes::TSAsExpression(_) | AstNodes::TSSatisfiesExpression(_) => true,
+            AstNodes::BinaryExpression(binary) => {
+                matches!(binary.operator, BinaryOperator::ShiftLeft)
+            }
+            _ => type_cast_like_needs_parens(self.span(), self.parent),
+        }
+    }
+}
+
+fn type_cast_like_needs_parens(span: Span, parent: &AstNodes<'_>) -> bool {
+    #[expect(clippy::match_same_arms)]
+    match parent {
+        AstNodes::ExportDefaultDeclaration(_)
+        | AstNodes::TSTypeAssertion(_)
+        | AstNodes::UnaryExpression(_)
+        | AstNodes::AwaitExpression(_)
+        | AstNodes::TSNonNullExpression(_)
+        // Callee
+        | AstNodes::CallExpression(_)
+        | AstNodes::NewExpression(_)
+        // template tag
+        | AstNodes::TaggedTemplateExpression(_)
+        // in spread
+        | AstNodes::JSXSpreadChild(_)
+        | AstNodes::SpreadElement(_)
+        | AstNodes::JSXSpreadAttribute(_)
+        // static member
+        | AstNodes::StaticMemberExpression(_) => true,
+        AstNodes::ComputedMemberExpression(member) => {
+            member.object.span() == span
+        }
+        // assignment left hand side
+        AstNodes::UpdateExpression(_) | AstNodes::AssignmentTargetWithDefault(_) => true,
+        AstNodes::AssignmentExpression(assignment) => {
+            assignment.left.span() == span
+        }
+        _ => is_class_extends(span, parent),
     }
 }
 
diff --git a/tasks/coverage/snapshots/formatter_typescript.snap b/tasks/coverage/snapshots/formatter_typescript.snap
index afb15e9ebd0d1..32ab0f1165eed 100644
--- a/tasks/coverage/snapshots/formatter_typescript.snap
+++ b/tasks/coverage/snapshots/formatter_typescript.snap
@@ -2,15 +2,13 @@ commit: 261630d6
 
 formatter_typescript Summary:
 AST Parsed     : 8816/8816 (100.00%)
-Positive Passed: 8774/8816 (99.52%)
+Positive Passed: 8775/8816 (99.53%)
 Mismatch: tasks/coverage/typescript/tests/cases/compiler/amdLikeInputDeclarationEmit.ts
 
 Expect to Parse: tasks/coverage/typescript/tests/cases/compiler/arrayFromAsync.ts
 `await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules`await` is only allowed within async functions and at the top levels of modules
 Mismatch: tasks/coverage/typescript/tests/cases/compiler/callOfConditionalTypeWithConcreteBranches.ts
 
-Expect to Parse: tasks/coverage/typescript/tests/cases/compiler/castExpressionParentheses.ts
-Unexpected token
 Expect to Parse: tasks/coverage/typescript/tests/cases/compiler/castFunctionExpressionShouldBeParenthesized.ts
 Expected a semicolon or an implicit semicolon after a statement, but found none
 Mismatch: tasks/coverage/typescript/tests/cases/compiler/coAndContraVariantInferences3.ts
diff --git a/tasks/prettier_conformance/snapshots/prettier.ts.snap.md b/tasks/prettier_conformance/snapshots/prettier.ts.snap.md
index 61a108ac0a00d..486daa7e81ad3 100644
--- a/tasks/prettier_conformance/snapshots/prettier.ts.snap.md
+++ b/tasks/prettier_conformance/snapshots/prettier.ts.snap.md
@@ -1,4 +1,4 @@
-ts compatibility: 386/573 (67.36%)
+ts compatibility: 389/573 (67.89%)
 
 # Failed
 
@@ -50,7 +50,6 @@ ts compatibility: 386/573 (67.36%)
 | typescript/comments/type_literals.ts | 💥 | 68.97% |
 | typescript/comments/union.ts | 💥 | 5.26% |
 | typescript/compiler/anyIsAssignableToObject.ts | 💥 | 75.00% |
-| typescript/compiler/castOfAwait.ts | 💥 | 87.50% |
 | typescript/compiler/castTest.ts | 💥 | 96.67% |
 | typescript/compiler/contextualSignatureInstantiation2.ts | 💥 | 88.89% |
 | typescript/compiler/indexSignatureWithInitializer.ts | 💥 | 75.00% |
@@ -68,7 +67,6 @@ ts compatibility: 386/573 (67.36%)
 | typescript/conformance/classes/classDeclarations/classAbstractKeyword/classAbstractMixedWithModifiers.ts | 💥 | 86.67% |
 | typescript/conformance/classes/classDeclarations/classHeritageSpecification/classExtendingClass.ts | 💥 | 96.77% |
 | typescript/conformance/es6/Symbols/symbolProperty15.ts | 💥 | 73.33% |
-| typescript/conformance/expressions/functionCalls/callWithSpreadES6.ts | 💥 | 97.96% |
 | typescript/conformance/types/ambient/ambientDeclarations.ts | 💥 | 90.00% |
 | typescript/conformance/types/functions/functionOverloadCompatibilityWithVoid01.ts | 💥 | 75.00% |
 | typescript/conformance/types/functions/functionOverloadCompatibilityWithVoid02.ts | 💥 | 75.00% |
@@ -172,7 +170,6 @@ ts compatibility: 386/573 (67.36%)
 | typescript/type-alias/conditional.ts | 💥 | 23.33% |
 | typescript/type-alias/issue-100857.ts | 💥 | 67.61% |
 | typescript/type-alias/issue-9874.ts | 💥 | 0.00% |
-| typescript/type-arguments-bit-shift-left-like/1.ts | 💥 | 0.00% |
 | typescript/type-arguments-bit-shift-left-like/3.ts | 💥 | 0.00% |
 | typescript/type-arguments-bit-shift-left-like/5.tsx | 💥 | 0.00% |
 | typescript/typeof/typeof.ts | 💥 | 25.00% |