diff --git a/hermes_cli/tools_config.py b/hermes_cli/tools_config.py
index 45255e670e96..a9612a2dbedb 100644
--- a/hermes_cli/tools_config.py
+++ b/hermes_cli/tools_config.py
@@ -4266,7 +4266,30 @@ def tools_command(args=None, first_install: bool = False, config: dict = None):
                 all_current,
                 force_fresh=True,
             )
-            if new_enabled != all_current:
+            selected_to_configure = [
+                ts_key for ts_key in sorted(new_enabled)
+                if (TOOL_CATEGORIES.get(ts_key) or TOOLSET_ENV_REQUIREMENTS.get(ts_key))
+                and _toolset_needs_configuration_prompt(
+                    ts_key,
+                    config,
+                    force_fresh=True,
+                )
+            ]
+
+            selected_to_configure_set = set(selected_to_configure)
+
+            if selected_to_configure:
+                print()
+                print(color(f"  Configuring {len(selected_to_configure)} selected tool(s):", Colors.YELLOW))
+                for ts_key in selected_to_configure:
+                    label = next((l for k, l, _ in _get_effective_configurable_toolsets() if k == ts_key), ts_key)
+                    print(color(f"    • {label}", Colors.DIM))
+                print(color("  You can skip any tool you don't need right now.", Colors.DIM))
+                print()
+                for ts_key in selected_to_configure:
+                    _configure_toolset(ts_key, config)
+
+            if new_enabled != all_current or selected_to_configure:
                 for pk in platform_keys:
                     prev = _get_platform_tools(config, pk, include_default_mcp_servers=False)
                     # Scope the printed diff to the checklist's universe (see
@@ -4284,8 +4307,13 @@ def tools_command(args=None, first_install: bool = False, config: dict = None):
                         for ts in sorted(removed):
                             label = next((l for k, l, _ in _get_effective_configurable_toolsets() if k == ts), ts)
                             print(color(f"    - {label}", Colors.RED))
-                    # Configure API keys for newly enabled tools
-                    for ts_key in sorted(added):
+                    # Configure API keys for newly enabled tools not already
+                    # handled by the global selected-tool pass above. This
+                    # preserves the old per-platform enable flow but avoids
+                    # dropping users back to the main menu when a selected tool
+                    # was already enabled globally and only lacked provider
+                    # configuration.
+                    for ts_key in sorted(added - selected_to_configure_set):
                         if (TOOL_CATEGORIES.get(ts_key) or TOOLSET_ENV_REQUIREMENTS.get(ts_key)):
                             if _toolset_needs_configuration_prompt(
                                 ts_key,
diff --git a/tests/hermes_cli/test_tools_config.py b/tests/hermes_cli/test_tools_config.py
index d640061335fa..8074581cc537 100644
--- a/tests/hermes_cli/test_tools_config.py
+++ b/tests/hermes_cli/test_tools_config.py
@@ -893,6 +893,52 @@ def test_reconfigure_lists_enabled_web_without_existing_provider_config(monkeypa
     assert configured == ["web"]
 
 
+def test_configure_all_platforms_configures_selected_tool_missing_provider(monkeypatch):
+    """Regression: `hermes tools` → Configure all platforms → Web Search
+    must enter provider/API-key setup even when Web was already enabled on all
+    configured platforms, so the checklist selection itself has no diff.
+    """
+    config = {"platform_toolsets": {"cli": ["web"], "telegram": ["web"]}}
+    configured = []
+
+    monkeypatch.setattr(
+        "hermes_cli.tools_config._get_enabled_platforms",
+        lambda: ["cli", "telegram"],
+    )
+
+    menu_calls = 0
+
+    def choose_by_label(_question, choices, default=0):
+        nonlocal menu_calls
+        menu_calls += 1
+        wanted = "Configure all platforms" if menu_calls == 1 else "Done"
+        for idx, choice in enumerate(choices):
+            if wanted in choice:
+                return idx
+        return default
+
+    monkeypatch.setattr("hermes_cli.tools_config._prompt_choice", choose_by_label)
+    monkeypatch.setattr(
+        "hermes_cli.tools_config._prompt_toolset_checklist",
+        lambda *args, **kwargs: {"web"},
+    )
+    monkeypatch.setattr(
+        "hermes_cli.tools_config._toolset_needs_configuration_prompt",
+        lambda ts_key, config, **kwargs: ts_key == "web",
+    )
+    monkeypatch.setattr(
+        "hermes_cli.tools_config._configure_toolset",
+        lambda ts_key, config, **kwargs: configured.append(ts_key),
+    )
+    monkeypatch.setattr("hermes_cli.tools_config.save_config", lambda config: None)
+
+    tools_command(first_install=False, config=config)
+
+    assert configured == ["web"]
+    assert config["platform_toolsets"]["cli"] == ["web"]
+    assert config["platform_toolsets"]["telegram"] == ["web"]
+
+
 def test_first_install_nous_auto_configures_managed_defaults(monkeypatch):
     monkeypatch.setattr("hermes_cli.nous_subscription.managed_nous_tools_enabled", lambda: True)
     config = {