diff --git a/packages/core/tools/src/py-types.ts b/packages/core/tools/src/py-types.ts
index 22e459bc3e..6e69541fb9 100644
--- a/packages/core/tools/src/py-types.ts
+++ b/packages/core/tools/src/py-types.ts
@@ -259,7 +259,17 @@ function renderType(schema: unknown, className: string, state: RenderState): str
           continue
         }
         if (frame.kind === 'oneOf') {
-          finish(frame.childTypes.join(' | '))
+          // Concatenate with `+` (not `Array.join`): V8 builds a lazy
+          // ConsString, so a deep oneOf chain materializes once at the root
+          // instead of re-materializing the accumulated string at every level
+          // (which `join` would, making it Θ(depth²)). This matches the array
+          // arm's template-literal laziness and ts-types' composable-document
+          // approach — the whole walk stays linear in schema depth.
+          let union = ''
+          for (const [index, childType] of frame.childTypes.entries()) {
+            union = index === 0 ? childType : `${union} | ${childType}`
+          }
+          finish(union)
           continue
         }
         /* jscpd:ignore-end */
diff --git a/packages/core/tools/tests/py-types.spec.ts b/packages/core/tools/tests/py-types.spec.ts
index 89db13d852..aa0bc30cff 100644
--- a/packages/core/tools/tests/py-types.spec.ts
+++ b/packages/core/tools/tests/py-types.spec.ts
@@ -469,6 +469,20 @@ describe('renderToolsSdkPy', () => {
     expect(type.length).toBe('list['.length * 20000 + 'str'.length + ']'.repeat(20000).length)
   })
 
+  it('renders a deeply nested oneOf chain in linear time (no per-level re-materialization)', () => {
+    // Each level is a two-branch oneOf whose first branch recurses; joining the
+    // accumulated union string at every level would be Theta(depth^2). The `+`
+    // (ConsString) concatenation keeps it linear, like the array arm.
+    const depth = 20000
+    let deep: Record<string, unknown> = { type: 'string' }
+    for (let i = 0; i < depth; i++) deep = { oneOf: [deep, { type: 'null' }] }
+    const type = jsonSchemaToPy(deep)
+    // depth levels of ` | None` appended to the innermost `str`.
+    expect(type.startsWith('str | None')).toBe(true)
+    expect(type.endsWith(' | None')).toBe(true)
+    expect(type.length).toBe('str'.length + ' | None'.length * depth)
+  })
+
   it('emits pass for a subscript-only tool set (comments are not statements)', () => {
     const t: ToolSdkSchema = {
       name: 'my-exotic.tool',