diff --git a/hermes_cli/tools_config.py b/hermes_cli/tools_config.py
index 5edb227d95..b3df18d932 100644
--- a/hermes_cli/tools_config.py
+++ b/hermes_cli/tools_config.py
@@ -1822,7 +1822,7 @@ def _reconfigure_tool(config: dict):
         cat = TOOL_CATEGORIES.get(ts_key)
         reqs = TOOLSET_ENV_REQUIREMENTS.get(ts_key)
         if cat or reqs:
-            if _toolset_has_keys(ts_key, config):
+            if _toolset_has_keys(ts_key, config) or _toolset_enabled_for_reconfigure(ts_key, config):
                 configurable.append((ts_key, ts_label))
 
     if not configurable:
@@ -1848,6 +1848,28 @@ def _reconfigure_tool(config: dict):
     save_config(config)
 
 
+def _toolset_enabled_for_reconfigure(ts_key: str, config: dict) -> bool:
+    """Return True if a configurable toolset is enabled anywhere.
+
+    Reconfigure must include enabled-but-unconfigured categories so users can
+    finish provider/API-key setup without disabling and re-enabling the toolset.
+    """
+    for platform in PLATFORMS:
+        if not _toolset_allowed_for_platform(ts_key, platform):
+            continue
+        try:
+            enabled = _get_platform_tools(
+                config,
+                platform,
+                include_default_mcp_servers=False,
+            )
+        except Exception:
+            continue
+        if ts_key in enabled:
+            return True
+    return False
+
+
 def _configure_tool_category_for_reconfig(ts_key: str, cat: dict, config: dict):
     """Reconfigure a tool category - provider selection + API key update."""
     icon = cat.get("icon", "")
diff --git a/tests/hermes_cli/test_tools_config.py b/tests/hermes_cli/test_tools_config.py
index d5b8aec3b7..abe211f4fb 100644
--- a/tests/hermes_cli/test_tools_config.py
+++ b/tests/hermes_cli/test_tools_config.py
@@ -8,6 +8,7 @@ from hermes_cli.tools_config import (
     _configure_provider,
     _get_platform_tools,
     _platform_toolset_summary,
+    _reconfigure_tool,
     _save_platform_tools,
     _toolset_has_keys,
     CONFIGURABLE_TOOLSETS,
@@ -468,6 +469,33 @@ def test_local_browser_provider_is_saved_explicitly(monkeypatch):
     assert config["browser"]["cloud_provider"] == "local"
 
 
+def test_reconfigure_lists_enabled_web_without_existing_provider_config(monkeypatch):
+    config = {"platform_toolsets": {"cli": ["web"]}}
+    seen = {}
+    configured = []
+
+    monkeypatch.setattr(
+        "hermes_cli.tools_config._toolset_has_keys",
+        lambda ts_key, config=None: False,
+    )
+
+    def fake_prompt_choice(question, choices, default=0):
+        seen["choices"] = choices
+        return 0
+
+    monkeypatch.setattr("hermes_cli.tools_config._prompt_choice", fake_prompt_choice)
+    monkeypatch.setattr(
+        "hermes_cli.tools_config._configure_tool_category_for_reconfig",
+        lambda ts_key, cat, config: configured.append(ts_key),
+    )
+    monkeypatch.setattr("hermes_cli.tools_config.save_config", lambda config: None)
+
+    _reconfigure_tool(config)
+
+    assert any("Web Search" in choice for choice in seen["choices"])
+    assert configured == ["web"]
+
+
 def test_first_install_nous_auto_configures_managed_defaults(monkeypatch):
     monkeypatch.setattr("hermes_cli.tools_config.managed_nous_tools_enabled", lambda: True)
     monkeypatch.setattr("hermes_cli.nous_subscription.managed_nous_tools_enabled", lambda: True)