diff --git a/nanobot/agent/tools/web.py b/nanobot/agent/tools/web.py
index 9ac923050..b8aeab47b 100644
--- a/nanobot/agent/tools/web.py
+++ b/nanobot/agent/tools/web.py
@@ -8,7 +8,7 @@ import json
 import os
 import re
 from typing import TYPE_CHECKING, Any
-from urllib.parse import urlparse
+from urllib.parse import quote, urlparse
 
 import httpx
 from loguru import logger
@@ -182,10 +182,10 @@ class WebSearchTool(Tool):
             return await self._search_duckduckgo(query, n)
         try:
             headers = {"Accept": "application/json", "Authorization": f"Bearer {api_key}"}
+            encoded_query = quote(query, safe="")
             async with httpx.AsyncClient(proxy=self.proxy) as client:
                 r = await client.get(
-                    f"https://s.jina.ai/",
-                    params={"q": query},
+                    f"https://s.jina.ai/{encoded_query}",
                     headers=headers,
                     timeout=15.0,
                 )
@@ -197,7 +197,8 @@ class WebSearchTool(Tool):
             ]
             return _format_results(query, items, n)
         except Exception as e:
-            return f"Error: {e}"
+            logger.warning("Jina search failed ({}), falling back to DuckDuckGo", e)
+            return await self._search_duckduckgo(query, n)
 
     async def _search_duckduckgo(self, query: str, n: int) -> str:
         try:
diff --git a/tests/tools/test_web_search_tool.py b/tests/tools/test_web_search_tool.py
index 02bf44395..5445fc67b 100644
--- a/tests/tools/test_web_search_tool.py
+++ b/tests/tools/test_web_search_tool.py
@@ -160,3 +160,70 @@ async def test_searxng_invalid_url():
     tool = _tool(provider="searxng", base_url="not-a-url")
     result = await tool.execute(query="test")
     assert "Error" in result
+
+
+@pytest.mark.asyncio
+async def test_jina_422_falls_back_to_duckduckgo(monkeypatch):
+    class MockDDGS:
+        def __init__(self, **kw):
+            pass
+
+        def text(self, query, max_results=5):
+            return [{"title": "Fallback", "href": "https://ddg.example", "body": "DuckDuckGo fallback"}]
+
+    async def mock_get(self, url, **kw):
+        assert "s.jina.ai" in str(url)
+        raise httpx.HTTPStatusError(
+            "422 Unprocessable Entity",
+            request=httpx.Request("GET", str(url)),
+            response=httpx.Response(422, request=httpx.Request("GET", str(url))),
+        )
+
+    monkeypatch.setattr(httpx.AsyncClient, "get", mock_get)
+    monkeypatch.setattr("ddgs.DDGS", MockDDGS)
+
+    tool = _tool(provider="jina", api_key="jina-key")
+    result = await tool.execute(query="test")
+    assert "DuckDuckGo fallback" in result
+
+
+@pytest.mark.asyncio
+async def test_jina_search_uses_path_encoded_query(monkeypatch):
+    calls = {}
+
+    async def mock_get(self, url, **kw):
+        calls["url"] = str(url)
+        calls["params"] = kw.get("params")
+        return _response(json={
+            "data": [{"title": "Jina Result", "url": "https://jina.ai", "content": "AI search"}]
+        })
+
+    monkeypatch.setattr(httpx.AsyncClient, "get", mock_get)
+    tool = _tool(provider="jina", api_key="jina-key")
+    await tool.execute(query="hello world")
+    assert calls["url"].rstrip("/") == "https://s.jina.ai/hello%20world"
+    assert calls["params"] in (None, {})
+
+
+@pytest.mark.asyncio
+async def test_jina_422_falls_back_to_duckduckgo(monkeypatch):
+    class MockDDGS:
+        def __init__(self, **kw):
+            pass
+
+        def text(self, query, max_results=5):
+            return [{"title": "Fallback", "href": "https://ddg.example", "body": "DuckDuckGo fallback"}]
+
+    async def mock_get(self, url, **kw):
+        raise httpx.HTTPStatusError(
+            "422 Unprocessable Entity",
+            request=httpx.Request("GET", str(url)),
+            response=httpx.Response(422, request=httpx.Request("GET", str(url))),
+        )
+
+    monkeypatch.setattr(httpx.AsyncClient, "get", mock_get)
+    monkeypatch.setattr("ddgs.DDGS", MockDDGS)
+
+    tool = _tool(provider="jina", api_key="jina-key")
+    result = await tool.execute(query="test")
+    assert "DuckDuckGo fallback" in result