diff --git a/packages/compiler-cli/src/ngtsc/typecheck/src/ts_util.ts b/packages/compiler-cli/src/ngtsc/typecheck/src/ts_util.ts
index 8169a79bdc..a45e491d5c 100644
--- a/packages/compiler-cli/src/ngtsc/typecheck/src/ts_util.ts
+++ b/packages/compiler-cli/src/ngtsc/typecheck/src/ts_util.ts
@@ -9,7 +9,46 @@
 import * as ts from 'typescript';
 import {ClassDeclaration} from '../../reflection';
 
+/**
+ * A `Set` of `ts.SyntaxKind`s of `ts.Expression` which are safe to wrap in a `ts.AsExpression`
+ * without needing to be wrapped in parentheses.
+ *
+ * For example, `foo.bar()` is a `ts.CallExpression`, and can be safely cast to `any` with
+ * `foo.bar() as any`. however, `foo !== bar` is a `ts.BinaryExpression`, and attempting to cast
+ * without the parentheses yields the expression `foo !== bar as any`. This is semantically
+ * equivalent to `foo !== (bar as any)`, which is not what was intended. Thus,
+ * `ts.BinaryExpression`s need to be wrapped in parentheses before casting.
+ */
+//
+const SAFE_TO_CAST_WITHOUT_PARENS: Set<ts.SyntaxKind> = new Set([
+  // Expressions which are already parenthesized can be cast without further wrapping.
+  ts.SyntaxKind.ParenthesizedExpression,
+
+  // Expressions which form a single lexical unit leave no room for precedence issues with the cast.
+  ts.SyntaxKind.Identifier,
+  ts.SyntaxKind.CallExpression,
+  ts.SyntaxKind.NonNullExpression,
+  ts.SyntaxKind.ElementAccessExpression,
+  ts.SyntaxKind.PropertyAccessExpression,
+  ts.SyntaxKind.ArrayLiteralExpression,
+  ts.SyntaxKind.ObjectLiteralExpression,
+
+  // The same goes for various literals.
+  ts.SyntaxKind.StringLiteral,
+  ts.SyntaxKind.NumericLiteral,
+  ts.SyntaxKind.TrueKeyword,
+  ts.SyntaxKind.FalseKeyword,
+  ts.SyntaxKind.NullKeyword,
+  ts.SyntaxKind.UndefinedKeyword,
+]);
+
 export function tsCastToAny(expr: ts.Expression): ts.Expression {
+  // Wrap `expr` in parentheses if needed (see `SAFE_TO_CAST_WITHOUT_PARENS` above).
+  if (!SAFE_TO_CAST_WITHOUT_PARENS.has(expr.kind)) {
+    expr = ts.createParen(expr);
+  }
+
+  // The outer expression is always wrapped in parentheses.
   return ts.createParen(
       ts.createAsExpression(expr, ts.createKeywordTypeNode(ts.SyntaxKind.AnyKeyword)));
 }
diff --git a/packages/compiler-cli/src/ngtsc/typecheck/test/type_check_block_spec.ts b/packages/compiler-cli/src/ngtsc/typecheck/test/type_check_block_spec.ts
index 50ec363108..50f9aa3e08 100644
--- a/packages/compiler-cli/src/ngtsc/typecheck/test/type_check_block_spec.ts
+++ b/packages/compiler-cli/src/ngtsc/typecheck/test/type_check_block_spec.ts
@@ -376,20 +376,31 @@ describe('type check blocks', () => {
     });
 
     describe('config.checkTypeOfBindings', () => {
-      const TEMPLATE = `<div dir [dirInput]="a" [nonDirInput]="b"></div>`;
 
       it('should check types of bindings when enabled', () => {
+        const TEMPLATE = `<div dir [dirInput]="a" [nonDirInput]="b"></div>`;
         const block = tcb(TEMPLATE, DIRECTIVES);
         expect(block).toContain('Dir.ngTypeCtor({ "dirInput": ((ctx).a) })');
         expect(block).toContain('(ctx).b;');
       });
+
       it('should not check types of bindings when disabled', () => {
+        const TEMPLATE = `<div dir [dirInput]="a" [nonDirInput]="b"></div>`;
         const DISABLED_CONFIG:
             TypeCheckingConfig = {...BASE_CONFIG, checkTypeOfInputBindings: false};
         const block = tcb(TEMPLATE, DIRECTIVES, DISABLED_CONFIG);
         expect(block).toContain('Dir.ngTypeCtor({ "dirInput": (((ctx).a as any)) })');
         expect(block).toContain('((ctx).b as any);');
       });
+
+      it('should wrap the cast to any in parentheses when required', () => {
+        const TEMPLATE = `<div dir [dirInput]="a === b"></div>`;
+        const DISABLED_CONFIG:
+            TypeCheckingConfig = {...BASE_CONFIG, checkTypeOfInputBindings: false};
+        const block = tcb(TEMPLATE, DIRECTIVES, DISABLED_CONFIG);
+        expect(block).toContain(
+            'Dir.ngTypeCtor({ "dirInput": (((((ctx).a) === ((ctx).b)) as any)) })');
+      });
     });
 
     describe('config.checkTypeOfOutputEvents', () => {