diff --git a/services/api-server/src/api_server/html5_ai_structure_controller.py b/services/api-server/src/api_server/html5_ai_structure_controller.py
index 01d3e5e..5472f71 100644
--- a/services/api-server/src/api_server/html5_ai_structure_controller.py
+++ b/services/api-server/src/api_server/html5_ai_structure_controller.py
@@ -85,6 +85,7 @@ async def html5_ai_structure_run(
                     effective_project_id=effective_project_id,
                     input_path=input_path,
                     detected_binary_relative_path=binary_match.get("relative_path"),
+                    detected_binary_relative_paths=binary_match.get("binary_relative_paths"),
                 )
             except HTTPException as error:
                 return render_html5_ai_structure_error(str(error.detail))
@@ -262,7 +263,11 @@ def _detect_binary_tree(input_path: Path) -> dict[str, str] | None:
     if parseable_files or not binary_files:
         return None
     first = binary_files[0]
-    return {"suffix": first.suffix.casefold(), "relative_path": first.relative_to(input_path).as_posix()}
+    return {
+        "suffix": first.suffix.casefold(),
+        "relative_path": first.relative_to(input_path).as_posix(),
+        "binary_relative_paths": [path.relative_to(input_path).as_posix() for path in binary_files],
+    }
 
 
 def _normalize_binary_match(value: str | dict[str, str] | None) -> dict[str, str] | None:
@@ -270,7 +275,7 @@ def _normalize_binary_match(value: str | dict[str, str] | None) -> dict[str, str
         return None
     if isinstance(value, dict):
         return value
-    return {"suffix": value, "relative_path": ""}
+    return {"suffix": value, "relative_path": "", "binary_relative_paths": []}
 
 
 def _enum_text(value: object) -> str:
diff --git a/services/api-server/src/api_server/main.py b/services/api-server/src/api_server/main.py
index bc853b4..59bbf32 100644
--- a/services/api-server/src/api_server/main.py
+++ b/services/api-server/src/api_server/main.py
@@ -588,9 +588,14 @@ async def _start_ai_structure_agent_job(
     effective_project_id: str,
     input_path: str,
     detected_binary_relative_path: str | None = None,
+    detected_binary_relative_paths: list[str] | None = None,
 ) -> AgentImportJob:
     settings = _project_settings_or_404(project_id)
-    binary_files = _ai_structure_binary_files(input_path, detected_binary_relative_path=detected_binary_relative_path)
+    binary_files = _ai_structure_binary_files(
+        input_path,
+        detected_binary_relative_path=detected_binary_relative_path,
+        detected_binary_relative_paths=detected_binary_relative_paths,
+    )
     if not binary_files:
         raise HTTPException(status_code=400, detail="Во входном пути не найдены файлы .cf или .cfe.")
 
@@ -599,15 +604,27 @@ async def _start_ai_structure_agent_job(
     if cf_files and cfe_files:
         raise HTTPException(
             status_code=400,
-            detail="Во входной папке одновременно лежат .cf и .cfe. Укажите конкретный файл, который нужно подготовить для ИИ.",
+            detail=(
+                "Во входной папке одновременно лежат .cf и .cfe. "
+                f"Найдены: {_format_binary_file_list(binary_files)}. "
+                "Укажите конкретный файл, который нужно подготовить для ИИ."
+            ),
         )
     source = ImportSourceKind.CF_FILE if cf_files else ImportSourceKind.CFE_FILE
     agent_id = _agent_id_for_source(settings, ImportSourceKind.CF_FILE)
     if not agent_id:
-        raise HTTPException(status_code=400, detail="В настройках проекта не выбран Windows Agent для CF/CFE.")
+        raise HTTPException(
+            status_code=400,
+            detail="В настройках проекта не выбран Windows Agent для CF/CFE. Откройте настройки проекта и укажите `cf_agent_id`.",
+        )
     agent_status = _agent_status_with_liveness(_agent_statuses.get(agent_id, AgentStatus(agent_id=agent_id)))
     if agent_status.status != "online":
-        raise HTTPException(status_code=409, detail=f"Windows Agent {agent_id} сейчас офлайн. Запустите агент и повторите.")
+        last_seen = str(agent_status.last_seen_at or "").strip()
+        detail = f"Windows Agent {agent_id} сейчас офлайн."
+        if last_seen:
+            detail += f" Последний heartbeat: {last_seen}."
+        detail += " Запустите агент и повторите."
+        raise HTTPException(status_code=409, detail=detail)
 
     agent = settings.agent if isinstance(settings.agent, dict) else {}
     metadata: dict[str, Any] = {
@@ -620,7 +637,10 @@ async def _start_ai_structure_agent_job(
         if len(cf_files) != 1:
             raise HTTPException(
                 status_code=400,
-                detail="Для прямого разбора .cf укажите один конкретный файл .cf, а не папку с несколькими конфигурациями.",
+                detail=(
+                    "Для прямого разбора .cf укажите один конкретный файл .cf, "
+                    f"а не папку с несколькими конфигурациями. Найдены: {_format_binary_file_list(cf_files)}."
+                ),
             )
         local_path = str(cf_files[0])
         metadata["input_mode"] = "cf_file"
@@ -628,7 +648,10 @@ async def _start_ai_structure_agent_job(
         if len(cfe_files) != 1:
             raise HTTPException(
                 status_code=400,
-                detail="Для прямого разбора расширения укажите один конкретный файл .cfe, а не папку с несколькими расширениями.",
+                detail=(
+                    "Для прямого разбора расширения укажите один конкретный файл .cfe, "
+                    f"а не папку с несколькими расширениями. Найдены: {_format_binary_file_list(cfe_files)}."
+                ),
             )
         cfe_file = cfe_files[0]
         local_path = str(cfe_file)
@@ -648,10 +671,19 @@ async def _start_ai_structure_agent_job(
     )
 
 
-def _ai_structure_binary_files(raw_input_path: str, detected_binary_relative_path: str | None = None) -> list[Path]:
+def _ai_structure_binary_files(
+    raw_input_path: str,
+    detected_binary_relative_path: str | None = None,
+    detected_binary_relative_paths: list[str] | None = None,
+) -> list[Path]:
     lowered = raw_input_path.strip().casefold()
     if lowered.endswith(".cf") or lowered.endswith(".cfe"):
         return [Path(raw_input_path)]
+    if detected_binary_relative_paths:
+        return [
+            Path(ntpath.join(raw_input_path, relative_path.replace("/", "\\")))
+            for relative_path in detected_binary_relative_paths
+        ]
     if detected_binary_relative_path:
         windows_path = ntpath.join(raw_input_path, detected_binary_relative_path.replace("/", "\\"))
         return [Path(windows_path)]
@@ -663,6 +695,14 @@ def _ai_structure_binary_files(raw_input_path: str, detected_binary_relative_pat
     return sorted(path for path in input_path.rglob("*") if path.is_file() and path.suffix.casefold() in {".cf", ".cfe"})
 
 
+def _format_binary_file_list(paths: list[Path]) -> str:
+    visible = [path.name for path in paths[:5]]
+    result = ", ".join(visible)
+    if len(paths) > 5:
+        result += f" и еще {len(paths) - 5}"
+    return result
+
+
 def _cancel_stale_extension_install_jobs(project_id: str, selected_agent_id: str) -> None:
     now = _current_timestamp()
     for job in list(_agent_import_jobs.values()):
diff --git a/services/api-server/tests/test_api.py b/services/api-server/tests/test_api.py
index 4a5e806..6e02f0d 100644
--- a/services/api-server/tests/test_api.py
+++ b/services/api-server/tests/test_api.py
@@ -2015,9 +2015,62 @@ def test_html5_ai_structure_routes_unc_directory_with_cf_through_windows_agent(m
     assert copied_targets
     assert started["input_path"] == r"\\192.168.220.200\mst\1c\MARKA\CODEX\CF"
     assert started["detected_binary_relative_path"] == "base.cf"
+    assert started["detected_binary_relative_paths"] == ["base.cf"]
     assert "agent-import-test" in saved_runs
 
 
+def test_html5_ai_structure_reports_multiple_binary_files_in_directory(tmp_path: Path):
+    first = tmp_path / "first.cf"
+    second = tmp_path / "second.cf"
+    first.write_bytes(b"cf-1")
+    second.write_bytes(b"cf-2")
+    client = TestClient(app)
+    project_id = f"ai-many-{uuid4()}"
+    agent_id = f"win-agent-{uuid4()}"
+
+    settings = client.post(
+        f"/projects/{project_id}/settings",
+        json={"name": "AI Many", "structure_source": "CF_FILE", "agent": {"cf_agent_id": agent_id}},
+    )
+    assert settings.status_code == 200
+    heartbeat = client.post("/agent/heartbeat", json={"agent_id": agent_id, "host": "test-host"})
+    assert heartbeat.status_code == 200
+
+    queued = client.post(
+        f"/html5/projects/{project_id}/ai-structure/run",
+        data={"project_id": project_id, "input_path": str(tmp_path), "output_path": str(tmp_path / 'out')},
+    )
+    assert queued.status_code == 200
+    assert "один конкретный файл .cf" in queued.text
+    assert "first.cf" in queued.text
+    assert "second.cf" in queued.text
+
+
+def test_html5_ai_structure_reports_offline_agent_with_last_seen(tmp_path: Path):
+    cf_input = tmp_path / "demo.cf"
+    cf_input.write_bytes(b"binary-cf")
+    client = TestClient(app)
+    project_id = f"ai-offline-{uuid4()}"
+    agent_id = f"win-agent-{uuid4()}"
+
+    settings = client.post(
+        f"/projects/{project_id}/settings",
+        json={"name": "AI Offline", "structure_source": "CF_FILE", "agent": {"cf_agent_id": agent_id}},
+    )
+    assert settings.status_code == 200
+    heartbeat = client.post("/agent/heartbeat", json={"agent_id": agent_id, "host": "test-host"})
+    assert heartbeat.status_code == 200
+    main._agent_statuses[agent_id].last_seen_at = "2020-01-01T00:00:00+00:00"
+
+    queued = client.post(
+        f"/html5/projects/{project_id}/ai-structure/run",
+        data={"project_id": project_id, "input_path": str(cf_input), "output_path": str(tmp_path / 'out')},
+    )
+    assert queued.status_code == 200
+    assert "сейчас офлайн" in queued.text
+    assert "Последний heartbeat" in queued.text
+
+
 def test_import_full_replace_replaces_current_normalized_project(tmp_path: Path):
     first = tmp_path / "first"
     second = tmp_path / "second"