diff --git a/packages/typescript/src/ast/astnav.ts b/packages/typescript/src/ast/astnav.ts
index f401215034b9d..0b823adb6c5f8 100644
--- a/packages/typescript/src/ast/astnav.ts
+++ b/packages/typescript/src/ast/astnav.ts
@@ -709,8 +709,14 @@ function addSyntheticNodes(children: Node[], pos: number, end: number, parent: N
     scanner.resetTokenState(pos);
     scanner.scan();
     while (pos < end) {
-        const token = scanner.getToken();
-        const tokenEnd = scanner.getTokenEnd();
+        let token = scanner.getToken();
+        let tokenEnd = scanner.getTokenEnd();
+        if (token === SyntaxKind.LessThanLessThanToken && scanner.getTokenStart() < end && tokenEnd > end) {
+            // The parser rescans `<<` as `<` when opening type arguments; mirror that split
+            // when the combined token crosses the next AST child's boundary.
+            token = scanner.reScanLessThanToken();
+            tokenEnd = scanner.getTokenEnd();
+        }
         if (tokenEnd <= end) {
             // An identifier should never appear as trivia between AST children; skip defensively.
             if (token !== SyntaxKind.Identifier) {
diff --git a/packages/typescript/test/sync/ast.test.ts b/packages/typescript/test/sync/ast.test.ts
index 1783da4ac3185..0ccd1a4dd82eb 100644
--- a/packages/typescript/test/sync/ast.test.ts
+++ b/packages/typescript/test/sync/ast.test.ts
@@ -1072,6 +1072,38 @@ describe("RemoteNode + child/token getters", () => {
         });
     });
 
+    test("public getChildren API preserves leaf tokens when type arguments begin with less-than", () => {
+        for (
+            const source of [
+                "type X = ReturnType<<T>(x: T) => number>;",
+                "type X = ReturnType <<T>(x: T) => number>;",
+                "type X = ReturnType/* c */ <<T>(x: T) => number>;",
+                "const x = foo<<T>(x: T) => T>();",
+            ]
+        ) {
+            withFirstStatement(source, (stmt, sf) => {
+                const node = findFirstOfKind(stmt, SyntaxKind.CallExpression)
+                    ?? findFirstOfKind(stmt, SyntaxKind.TypeReference)!;
+                const children = node.getChildren(sf);
+                assertChildInvariants(node, sf);
+
+                const firstLessThan = children.find(child => child.kind === SyntaxKind.LessThanToken);
+                assert.ok(firstLessThan, "expected the public API to expose the opening less-than token");
+                assert.strictEqual(firstLessThan.getStart(sf), source.indexOf("<<"));
+                assert.strictEqual(children.map(child => child.getFullText(sf)).join(""), node.getFullText(sf));
+            });
+        }
+    });
+
+    test("public getChildren API preserves ordinary left-shift tokens", () => {
+        withFirstStatement("const x = a << b;", (stmt, sf) => {
+            const binary = findFirstOfKind(stmt, SyntaxKind.BinaryExpression)!;
+            const children = binary.getChildren(sf);
+            assert.strictEqual(children.filter(child => child.kind === SyntaxKind.LessThanLessThanToken).length, 1);
+            assert.strictEqual(children.filter(child => child.kind === SyntaxKind.LessThanToken).length, 0);
+        });
+    });
+
     test("getChildCount and getChildAt agree with getChildren", () => {
         withFirstStatement("if (x) {}", stmt => {
             const children = stmt.getChildren();