diff --git a/patches/apply_patch.py b/patches/apply_patch.py
index b33cf5d..cb646b2 100644
--- a/patches/apply_patch.py
+++ b/patches/apply_patch.py
@@ -3,6 +3,21 @@ Injeta o registro das rotas aiohttp do skills_api dentro do método start()
 do APIServerAdapter no api_server.py do Hermes.
 
 Idempotente: se o marcador já existir, não faz nada.
+
+Strategy
+--------
+The `web.Application(...)` call may span multiple lines, e.g.:
+
+    self._app = web.Application(
+        middlewares=[...],
+        client_max_size=...,
+    )
+
+We therefore use a two-phase approach:
+  1. Locate the LHS assignment (``<indent><var> = web.Application(``) with a
+     simple MULTILINE regex — this is always a single line.
+  2. From that position, scan forward to find the matching closing parenthesis,
+     correctly handling nested parentheses.
 """
 from __future__ import annotations
 
@@ -12,15 +27,32 @@ from pathlib import Path
 
 MARKER = "# >>> hermes-custom: skills_api <<<"
 
-# Regex: captura uma linha que cria a aiohttp Application, ex:
-#   self._app = web.Application(...)
-#   app = web.Application(...)
-APP_ASSIGN_RE = re.compile(
-    r"^(?P<indent>[ \t]+)(?P<lhs>(?:self\._?app|app))\s*=\s*web\.Application\([^)]*\)\s*$",
+# Phase-1 regex: matches the *start* of the assignment up to and including the
+# opening parenthesis of web.Application.  Does NOT require the call to end on
+# the same line, so it works for both single-line and multi-line forms.
+APP_ASSIGN_START_RE = re.compile(
+    r"^(?P<indent>[ \t]+)(?P<lhs>(?:self\._?app|app))\s*=\s*web\.Application\(",
     re.MULTILINE,
 )
 
 
+def _find_closing_paren(src: str, open_pos: int) -> int:
+    """Return the index of the ')' that closes the '(' at *open_pos*.
+
+    Handles nested parentheses.  Raises ValueError if not found.
+    """
+    depth = 0
+    for i in range(open_pos, len(src)):
+        ch = src[i]
+        if ch == "(":
+            depth += 1
+        elif ch == ")":
+            depth -= 1
+            if depth == 0:
+                return i
+    raise ValueError(f"No matching closing parenthesis found starting at offset {open_pos}")
+
+
 def build_injection(indent: str, app_var: str) -> str:
     lines = [
         "",
@@ -47,17 +79,39 @@ def main(target: str) -> int:
         print("[apply_patch] already applied, skipping")
         return 0
 
-    match = APP_ASSIGN_RE.search(src)
+    # Phase 1 — find the assignment start
+    match = APP_ASSIGN_START_RE.search(src)
     if not match:
+        # Emit a diagnostic snippet to help debug future mismatches
         print(
-            "[apply_patch] ERROR: não encontrei `... = web.Application(...)` no api_server.py",
+            "[apply_patch] ERROR: não encontrei `... = web.Application(` no api_server.py",
             file=sys.stderr,
         )
+        # Print lines that contain "Application" to aid debugging
+        for lineno, line in enumerate(src.splitlines(), 1):
+            if "Application" in line:
+                print(f"[apply_patch] hint line {lineno}: {line!r}", file=sys.stderr)
         return 2
 
     indent = match.group("indent")
     app_var = match.group("lhs")
-    insert_at = match.end()
+
+    # Phase 2 — walk forward to find the matching closing parenthesis
+    open_paren_pos = match.end() - 1  # position of the '(' in web.Application(
+    try:
+        close_paren_pos = _find_closing_paren(src, open_paren_pos)
+    except ValueError as exc:
+        print(f"[apply_patch] ERROR: {exc}", file=sys.stderr)
+        return 2
+
+    # Insert after the closing ')' (and any trailing whitespace on that line)
+    # so we land right after the complete statement.
+    insert_at = close_paren_pos + 1
+    # Advance past an optional trailing comment / whitespace up to the newline
+    newline_pos = src.find("\n", insert_at)
+    if newline_pos != -1:
+        insert_at = newline_pos  # inject before the newline so indentation stays clean
+
     injection = build_injection(indent, app_var)
 
     new_src = src[:insert_at] + injection + src[insert_at:]