diff --git a/.env.enterprise-clean.example b/.env.enterprise-clean.example
index d3d21441..f2401bc0 100644
--- a/.env.enterprise-clean.example
+++ b/.env.enterprise-clean.example
@@ -43,6 +43,19 @@ FRONTEND_SSL_PORT=443
 # nginx работает в HTTP-only режиме.
 CERTS_PATH=./certs
 
+# ======================================================================
+#  LLM CA-сертификаты (скачка по URL на старте контейнера)
+# ======================================================================
+# URL корпоративных CA-сертификатов для LLM-провайдеров.
+# Автоматически скачиваются, конвертируются DER→PEM и устанавливаются
+# в системное хранилище OpenSSL на старте backend-контейнера.
+#
+# Формат: пробел-разделённый список URL
+#
+# Пример:
+#   LLM_CA_CERT_URLS="http://pki.company.com/root-ca.crt http://pki.company.com/intermediate-ca.crt"
+LLM_CA_CERT_URLS=
+
 # ======================================================================
 #  Логирование
 # ======================================================================
diff --git a/backend/src/plugins/llm_analysis/__tests__/test_client_headers.py b/backend/src/plugins/llm_analysis/__tests__/test_client_headers.py
index d36adaba..ec280aa2 100644
--- a/backend/src/plugins/llm_analysis/__tests__/test_client_headers.py
+++ b/backend/src/plugins/llm_analysis/__tests__/test_client_headers.py
@@ -52,4 +52,126 @@ def test_litellm_client_uses_default_bearer_auth():
     assert "Authentication" not in headers
     assert "X-API-Key" not in headers
 # endregion test_litellm_client_uses_default_bearer_auth
+
+
+# region test_get_ssl_verify_default_true [TYPE Function]
+# @RELATION  BINDS_TO -> TestClientHeaders
+# @PURPOSE: _get_ssl_verify defaults to True when LLM_SSL_VERIFY is unset.
+# @PRE  LLM_SSL_VERIFY env var is not set.
+# @POST  Returns True.
+def test_get_ssl_verify_default_true():
+    """Verify default SSL verification is enabled."""
+    assert LLMClient._get_ssl_verify() is True
+# endregion test_get_ssl_verify_default_true
+
+
+# region test_get_ssl_verify_false_values [TYPE Function]
+# @RELATION  BINDS_TO -> TestClientHeaders
+# @PURPOSE: _get_ssl_verify returns False for "false"/"0"/"no"/"off".
+# @PRE  LLM_SSL_VERIFY env var is set to each falsy value.
+# @POST  Returns False.
+def test_get_ssl_verify_false_values(monkeypatch):
+    for val in ("false", "False", "0", "no", "off"):
+        monkeypatch.setenv("LLM_SSL_VERIFY", val)
+        assert LLMClient._get_ssl_verify() is False, f"Expected False for LLM_SSL_VERIFY={val}"
+# endregion test_get_ssl_verify_false_values
+
+
+# region test_get_ssl_verify_true_values [TYPE Function]
+# @RELATION  BINDS_TO -> TestClientHeaders
+# @PURPOSE: _get_ssl_verify returns True for truthy values like "TRUE", "1", "yes".
+# @PRE  LLM_SSL_VERIFY env var is set to truthy values.
+# @POST  Returns True.
+def test_get_ssl_verify_true_values(monkeypatch):
+    for val in ("TRUE", "1", "yes", "on", "true"):
+        monkeypatch.setenv("LLM_SSL_VERIFY", val)
+        assert LLMClient._get_ssl_verify() is True, f"Expected True for LLM_SSL_VERIFY={val}"
+# endregion test_get_ssl_verify_true_values
+
+
+# region test_format_connection_error_no_cause [TYPE Function]
+# @RELATION  BINDS_TO -> TestClientHeaders
+# @PURPOSE: _format_connection_error with single exception (no cause chain).
+# @PRE  Exception has no __cause__ or __context__.
+# @POST  Returns formatted string with only the top-level exception.
+def test_format_connection_error_no_cause():
+    exc = ValueError("test error")
+    result = LLMClient._format_connection_error(exc)
+    assert "ValueError: test error" in result
+    assert "└─" not in result
+# endregion test_format_connection_error_no_cause
+
+
+# region test_format_connection_error_with_cause [TYPE Function]
+# @RELATION  BINDS_TO -> TestClientHeaders
+# @PURPOSE: _format_connection_error with chained exception (__cause__).
+# @PRE  Exception has a __cause__.
+# @POST  Returns formatted string with chain.
+def test_format_connection_error_with_cause():
+    inner = ConnectionRefusedError("Connection refused")
+    outer = RuntimeError("API call failed")
+    outer.__cause__ = inner
+    result = LLMClient._format_connection_error(outer)
+    assert "RuntimeError: API call failed" in result
+    assert "└─" in result
+    assert "ConnectionRefusedError: Connection refused" in result
+# endregion test_format_connection_error_with_cause
+
+
+# region test_format_connection_error_deep_chain [TYPE Function]
+# @RELATION  BINDS_TO -> TestClientHeaders
+# @PURPOSE: _format_connection_error with 3-level chain.
+# @PRE  Exception has nested __cause__ chain.
+# @POST  Returns formatted string with all levels.
+def test_format_connection_error_deep_chain():
+    dns = Exception("Name or service not known")
+    ssl = ConnectionError("SSL: CERTIFICATE_VERIFY_FAILED")
+    ssl.__cause__ = dns
+    outer = RuntimeError("Connection error")
+    outer.__cause__ = ssl
+    result = LLMClient._format_connection_error(outer)
+    assert "RuntimeError: Connection error" in result
+    assert "ConnectionError: SSL: CERTIFICATE_VERIFY_FAILED" in result
+    assert "Exception: Name or service not known" in result
+# endregion test_format_connection_error_deep_chain
+
+
+# region test_litellm_client_verify_default [TYPE Function]
+# @RELATION  BINDS_TO -> TestClientHeaders
+# @PURPOSE: LLMClient passes verify=True to httpx.AsyncClient by default.
+# @PRE  LLM_SSL_VERIFY env var is not set.
+# @POST  httpcore pool SSL context has verify_mode=CERT_REQUIRED (2).
+def test_litellm_client_verify_default():
+    """Verify default SSL context with CERT_REQUIRED when LLM_SSL_VERIFY unset."""
+    import ssl
+    client = LLMClient(
+        provider_type=LLMProviderType.LITELLM,
+        api_key="sk-test-verify-key",
+        base_url="http://localhost:4000/v1",
+        default_model="gpt-4o",
+    )
+    pool = client.client._client._transport._pool
+    assert pool._ssl_context.verify_mode == ssl.CERT_REQUIRED, \
+        "verify=True should set verify_mode to CERT_REQUIRED"
+# endregion test_litellm_client_verify_default
+
+
+# region test_litellm_client_verify_disabled [TYPE Function]
+# @RELATION  BINDS_TO -> TestClientHeaders
+# @PURPOSE: LLMClient passes verify=False when LLM_SSL_VERIFY=false.
+# @PRE  LLM_SSL_VERIFY is set to "false".
+# @POST  httpcore pool SSL context has verify_mode=CERT_NONE (0).
+def test_litellm_client_verify_disabled(monkeypatch):
+    monkeypatch.setenv("LLM_SSL_VERIFY", "false")
+    client = LLMClient(
+        provider_type=LLMProviderType.LITELLM,
+        api_key="sk-test-verify-key",
+        base_url="http://localhost:4000/v1",
+        default_model="gpt-4o",
+    )
+    import ssl
+    pool = client.client._client._transport._pool
+    assert pool._ssl_context.verify_mode == ssl.CERT_NONE, \
+        "verify=False should set verify_mode to CERT_NONE"
+# endregion test_litellm_client_verify_disabled
 # endregion TestClientHeaders
diff --git a/backend/src/plugins/llm_analysis/service.py b/backend/src/plugins/llm_analysis/service.py
index d5cd0811..21424e4a 100644
--- a/backend/src/plugins/llm_analysis/service.py
+++ b/backend/src/plugins/llm_analysis/service.py
@@ -2,8 +2,6 @@
 # @BRIEF Services for LLM interaction and dashboard screenshots.
 # @LAYER Plugin
 # @RELATION DEPENDS_ON -> [EXT:Library:tenacity]
-# @RELATION DEPENDS_ON -> [EXT:Library:tenacity]
-# @RELATION DEPENDS_ON -> [EXT:Library:tenacity]
 # @INVARIANT Screenshots must be 1920px width and capture full page height.
 # @DATA_CONTRACT DashboardSpec -> Screenshot + Analysis
 # @RATIONALE Extracted all hardcoded timeouts into named module-level constants (PLAYWRIGHT_NAVIGATION_TIMEOUT_MS, PLAYWRIGHT_WAIT_TIMEOUT_MS, PLAYWRIGHT_SHORT_TIMEOUT_MS, HTTP_REQUEST_TIMEOUT_MS, SCREENSHOT_SERVICE_TIMEOUT_MS, LLM_HTTP_TIMEOUT_S) and DEFAULT_USER_AGENT. Zero remaining numeric timeout literals.
@@ -907,7 +905,14 @@ class LLMClient:
         # It routes to upstream providers transparently, and the default Authorization header
         # is sufficient. No additional headers like HTTP-Referer or X-API-Key are required.
 
-        http_client = httpx.AsyncClient(headers=default_headers, timeout=LLM_HTTP_TIMEOUT_S)
+        ssl_verify = self._get_ssl_verify()
+        logger.info(f"[LLMClient.__init__]   SSL Verify: {ssl_verify} (set LLM_SSL_VERIFY=false to disable)")
+
+        http_client = httpx.AsyncClient(
+            headers=default_headers,
+            timeout=LLM_HTTP_TIMEOUT_S,
+            verify=ssl_verify,
+        )
         self.client = AsyncOpenAI(
             api_key=self.api_key,
             base_url=base_url,
@@ -916,6 +921,28 @@ class LLMClient:
         )
     # endregion LLMClient.__init__
 
+    # region LLMClient._get_ssl_verify [TYPE Function]
+    # @PURPOSE Resolve SSL verification flag from environment.
+    # @POST Returns False when LLM_SSL_VERIFY env var is "false"/"0"/"no" (case-insensitive).
+    @staticmethod
+    def _get_ssl_verify() -> bool:
+        raw = os.getenv("LLM_SSL_VERIFY", "true").strip().lower()
+        return raw not in ("false", "0", "no", "off")
+    # endregion LLMClient._get_ssl_verify
+
+    # region LLMClient._format_connection_error [TYPE Function]
+    # @PURPOSE Format exception chain for diagnostics, extracting httpx cause details.
+    # @POST Returns a human-readable string with the full error chain.
+    @staticmethod
+    def _format_connection_error(exc: Exception) -> str:
+        parts = [f"{type(exc).__name__}: {exc!s}"]
+        cause = exc.__cause__ or exc.__context__
+        while cause:
+            parts.append(f"  └─ {type(cause).__name__}: {cause!s}")
+            cause = cause.__cause__ or cause.__context__
+        return "\n".join(parts)
+    # endregion LLMClient._format_connection_error
+
     # region LLMClient._supports_json_response_format [TYPE Function]
     # @PURPOSE Detect whether provider/model is likely compatible with response_format=json_object.
     # @PRE Client initialized with base_url and default_model.
@@ -1035,7 +1062,10 @@ class LLMClient:
                 await asyncio.sleep(wait_time)
                 raise
             except Exception as e:
-                logger.error(f"[get_json_completion] LLM call failed: {e!s}")
+                logger.error(
+                    f"[get_json_completion] LLM call failed.\n"
+                    f"{self._format_connection_error(e)}"
+                )
                 raise
 
             if not response or not hasattr(response, 'choices') or not response.choices:
diff --git a/docker-compose.enterprise-clean.yml b/docker-compose.enterprise-clean.yml
index 0fa208e2..34d81cdd 100644
--- a/docker-compose.enterprise-clean.yml
+++ b/docker-compose.enterprise-clean.yml
@@ -48,6 +48,8 @@ services:
       FEATURES__HEALTH_MONITOR: ${FEATURES__HEALTH_MONITOR:-true}
       # Путь до сертификатов внутри контейнера — всегда /opt/certs
       CERTS_PATH: /opt/certs
+      # URL CA-сертификатов для LLM-провайдеров (скачка на старте, DER→PEM конвертация)
+      LLM_CA_CERT_URLS: ${LLM_CA_CERT_URLS:-}
     ports:
       - "${BACKEND_HOST_PORT:-8001}:8000"
     volumes:
diff --git a/docker-compose.yml b/docker-compose.yml
index 0289e23f..c35257b3 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -37,6 +37,7 @@ services:
       INITIAL_ADMIN_PASSWORD: ${INITIAL_ADMIN_PASSWORD:-}
       FEATURES__DATASET_REVIEW: ${FEATURES__DATASET_REVIEW:-true}
       FEATURES__HEALTH_MONITOR: ${FEATURES__HEALTH_MONITOR:-true}
+      LLM_CA_CERT_URLS: ${LLM_CA_CERT_URLS:-}
     ports:
       - "${BACKEND_HOST_PORT:-8001}:8000"
     volumes:
diff --git a/docker/backend.entrypoint.sh b/docker/backend.entrypoint.sh
index 5e140579..4791dff8 100755
--- a/docker/backend.entrypoint.sh
+++ b/docker/backend.entrypoint.sh
@@ -75,6 +75,143 @@ install_certificates() {
 }
 # #endregion docker.backend.entrypoint.install_certificates
 
+# ======================================================================
+#  install_llm_ca_certs — скачка и установка CA-сертификатов по URL
+# ======================================================================
+# #region docker.backend.entrypoint.install_llm_ca_certs [C:4] [TYPE Function]
+# @BRIEF Скачивает PEM/DER-сертификаты из LLM_CA_CERT_URLS, конвертирует DER→PEM,
+#   устанавливает в системное хранилище, создаёт хеш-симлинки и при необходимости
+#   добавляет в ca-certificates.crt напрямую (fallback для OpenSSL 3-совместимости).
+# @PRE LLM_CA_CERT_URLS — строка с URL через пробел; curl и openssl установлены.
+# @POST Сертификаты доступны в /etc/ssl/certs/ca-certificates.crt.
+#   Хеш-симлинки созданы для каждого сертификата.
+# @SIDE_EFFECT Скачивает файлы из внешних URL. Модифицирует /etc/ssl/certs/.
+# @LAYER Infrastructure
+# @EXAMPLE:
+#   LLM_CA_CERT_URLS="http://pki.company.com/root.crt http://pki.company.com/intermediate.crt"
+install_llm_ca_certs() {
+  local urls="${LLM_CA_CERT_URLS:-}"
+  if [ -z "$urls" ]; then
+    echo "[entrypoint] LLM_CA_CERT_URLS не задан — пропускаем скачку сертификатов"
+    return 0
+  fi
+
+  local work_dir="/tmp/llm-ca-certs"
+  local target_dir="/usr/local/share/ca-certificates/llm"
+  mkdir -p "$work_dir" "$target_dir"
+
+  echo "[entrypoint] === Скачивание и установка LLM CA-сертификатов ==="
+  local index=0
+  local downloaded_names=""
+
+  for url in $urls; do
+    url="$(echo "$url" | xargs)"  # trim
+    [ -z "$url" ] && continue
+    index=$((index + 1))
+
+    # Определяем имя файла из URL, или генерируем
+    local filename
+    filename="$(basename "$url" | sed 's/[?#].*//')"
+    if [ -z "$filename" ] || [ "$filename" = "." ] || [ "$filename" = ".." ]; then
+      filename="llm-ca-${index}.crt"
+    fi
+
+    local raw_file="${work_dir}/${filename}"
+    local pem_file="${target_dir}/$(echo "$filename" | sed 's/\.[^.]*$//').pem"
+
+    echo "[entrypoint]   [${index}] Скачивание: ${url}"
+
+    # Скачиваем с retry 3 раза
+    local attempt=0
+    local success=0
+    while [ $attempt -lt 3 ]; do
+      attempt=$((attempt + 1))
+      if curl -sS --connect-timeout 10 --max-time 30 -o "$raw_file" "$url" 2>/dev/null; then
+        success=1
+        break
+      fi
+      echo "[entrypoint]   ⚠ Попытка ${attempt}/3 не удалась, повтор через 2с..."
+      sleep 2
+    done
+
+    if [ "$success" -eq 0 ]; then
+      echo "[entrypoint]   ❌ Не удалось скачать: ${url} — пропускаем"
+      continue
+    fi
+
+    # Определяем формат: PEM или DER
+    if openssl x509 -in "$raw_file" -inform PEM -noout 2>/dev/null; then
+      echo "[entrypoint]   ✓ Формат: PEM"
+      cp "$raw_file" "$pem_file"
+    elif openssl x509 -in "$raw_file" -inform DER -noout 2>/dev/null; then
+      echo "[entrypoint]   ↻ Формат: DER — конвертируем в PEM"
+      openssl x509 -in "$raw_file" -inform DER -out "$pem_file" -outform PEM
+    else
+      echo "[entrypoint]   ❌ Неизвестный формат (не PEM и не DER) — пропускаем"
+      rm -f "$raw_file"
+      continue
+    fi
+
+    chmod 644 "$pem_file"
+    echo "[entrypoint]   ✅ Установлен: $(basename "$pem_file")"
+    downloaded_names="$downloaded_names $(basename "$pem_file" .pem)"
+    rm -f "$raw_file"
+  done
+
+  if [ -z "$(ls -A "$target_dir" 2>/dev/null)" ]; then
+    echo "[entrypoint] Нет скачанных сертификатов — пропускаем"
+    rm -rf "$work_dir"
+    return 0
+  fi
+
+  # Обновляем системное хранилище
+  echo "[entrypoint] --- Обновление системного хранилища CA-сертификатов ---"
+  update-ca-certificates --fresh 2>&1 | sed 's/^/[entrypoint]   /'
+
+  # Проверяем, попали ли сертификаты в бандл, и создаём хеш-симлинки
+  echo "[entrypoint] --- Валидация установки сертификатов ---"
+  local all_ok=true
+
+  for pem in "$target_dir"/*.pem; do
+    [ -f "$pem" ] || continue
+    local cert_name
+    cert_name="$(basename "$pem" .pem)"
+    local cert_subject
+    cert_subject="$(openssl x509 -in "$pem" -noout -subject 2>/dev/null | head -1 || echo "unknown")"
+
+    # Проверяем есть ли в ca-certificates.crt
+    if grep -q "$cert_name" /etc/ssl/certs/ca-certificates.crt 2>/dev/null || \
+       grep -qF "$(openssl x509 -in "$pem" -noout -serial 2>/dev/null)" /etc/ssl/certs/ca-certificates.crt 2>/dev/null; then
+      echo "[entrypoint]   ✅ ${cert_name} — в ca-certificates.crt (${cert_subject})"
+    else
+      echo "[entrypoint]   ⚠ ${cert_name} — НЕ в ca-certificates.crt. Добавляем напрямую..."
+      cat "$pem" >> /etc/ssl/certs/ca-certificates.crt
+      echo "[entrypoint]   ➕ Добавлен напрямую в ca-certificates.crt"
+    fi
+
+    # Создаём хеш-симлинку в /etc/ssl/certs/
+    local hash_val
+    hash_val="$(openssl x509 -in "$pem" -noout -hash 2>/dev/null || true)"
+    if [ -n "$hash_val" ]; then
+      local link_path="/etc/ssl/certs/${hash_val}.0"
+      if [ ! -L "$link_path" ]; then
+        ln -sf "$pem" "$link_path"
+        echo "[entrypoint]   🔗 Создана симлинка: ${hash_val}.0 → ${cert_name}"
+      fi
+    fi
+  done
+
+  # Проверяем итоговое количество
+  local total_in_bundle
+  total_in_bundle="$(awk -v cmd='openssl x509 -noout -subject' '/BEGIN/{close(cmd)};{print | cmd}' \
+    < /etc/ssl/certs/ca-certificates.crt 2>/dev/null | wc -l || echo "0")"
+  echo "[entrypoint] ✅ Всего сертификатов в bundle: ${total_in_bundle}"
+
+  rm -rf "$work_dir"
+  echo "[entrypoint] === Установка LLM CA-сертификатов завершена ==="
+}
+# #endregion docker.backend.entrypoint.install_llm_ca_certs
+
 # ======================================================================
 #  bootstrap_admin — создание admin пользователя
 # ======================================================================
@@ -149,6 +286,7 @@ install_playwright() {
 # ======================================================================
 
 install_certificates
+install_llm_ca_certs
 install_playwright
 
 # Check DB state: empty, legacy (tables exist but no alembic), or managed