diff --git a/backend/apps/agents/core/ws_manager.py b/backend/apps/agents/core/ws_manager.py
index 6996e5cc..78c0d7e3 100644
--- a/backend/apps/agents/core/ws_manager.py
+++ b/backend/apps/agents/core/ws_manager.py
@@ -66,6 +66,8 @@ class ConnectionManager:
     def __init__(self):
         self.connections: dict[str, list[WebSocket]] = {}
         self.global_connections: list[WebSocket] = []
+        # Latched on the first renderer and never cleared: it answers "can a window reach this backend at all", which a momentary socket blip must not un-answer. Only the process dying resets it.
+        self.renderer_ever_attached: bool = False
         # Which dashboard each global socket is currently showing, keyed by id(websocket). active_dashboard_id is the last one activated (the window the user is looking at most recently); a scheduled run targets it so its browser card spawns where the renderer can render it.
         self.global_dashboard_ids: dict[int, str] = {}
         self.active_dashboard_id: Optional[str] = None
@@ -83,6 +85,7 @@ class ConnectionManager:
     async def connect_global(self, websocket: WebSocket):
         await websocket.accept()
         self.global_connections.append(websocket)
+        self.renderer_ever_attached = True
 
     async def connect_main(self, websocket: WebSocket):
         """Register the single Electron-main bridge socket (replaces any stale prior one)."""
diff --git a/backend/apps/agents/manager/permissions/build_effective_tool_lists.py b/backend/apps/agents/manager/permissions/build_effective_tool_lists.py
index b2d44a6a..5a6f17d8 100644
--- a/backend/apps/agents/manager/permissions/build_effective_tool_lists.py
+++ b/backend/apps/agents/manager/permissions/build_effective_tool_lists.py
@@ -18,7 +18,7 @@ from backend.apps.tools_lib.tools_lib import (
     load_all_tools as load_all_tools,
     sanitize_server_name as sanitize_server_name,
 )
-from backend.config.headless import apply_headless_denies
+from backend.config.headless import apply_unreachable_denies
 
 # Mutation/exec tools a read-only session must never reach: Edit (rewrites files), Bash (rm/mv/overwrite),
 # NotebookEdit (rewrites notebooks). Write is intentionally NOT here, the audit needs its one report.
@@ -34,8 +34,8 @@ def build_effective_tool_lists(
     browser_delegation_tools: List[str],
     invoke_agent_tools: List[str],
 ) -> Tuple[List[str], List[str]]:
-    # Same shadow the server registration takes: headless, the renderer-bound built-ins go straight onto disallowed instead of being offered and failing when called.
-    builtin_perms = apply_headless_denies(builtin_perms)
+    # Same shadow the server registration takes: anything that would dead-end goes straight onto disallowed instead of being offered and failing when called.
+    builtin_perms = apply_unreachable_denies(builtin_perms)
     effective_allowed = [
         t for t in session.allowed_tools
         if t in FULL_TOOLS and builtin_perms.get(t, "always_allow") == "always_allow"
diff --git a/backend/apps/agents/manager/register_builtin_mcp_servers.py b/backend/apps/agents/manager/register_builtin_mcp_servers.py
index cc548092..aad257b2 100644
--- a/backend/apps/agents/manager/register_builtin_mcp_servers.py
+++ b/backend/apps/agents/manager/register_builtin_mcp_servers.py
@@ -12,7 +12,7 @@ from typeguard import typechecked
 
 from backend.apps.agents.core.models import AgentSession
 from backend.auth import get_auth_token
-from backend.config.headless import apply_headless_denies
+from backend.config.headless import apply_unreachable_denies
 
 
 @typechecked
@@ -25,8 +25,8 @@ def register_builtin_mcp_servers(
 ) -> Tuple[List[str], List[str]]:
     import backend.apps.agents as p_agents_pkg
     agents_dir = os.path.dirname(p_agents_pkg.__file__)
-    # Headless has no renderer for a webview or a UI component, so we shadow the map once here and let the existing deny short-circuits skip those servers; nothing below may read the un-shadowed one.
-    builtin_perms = apply_headless_denies(builtin_perms)
+    # With no renderer for a webview and no human for a prompt, we shadow the map once here and let the existing deny short-circuits skip those servers; nothing below may read the un-shadowed one.
+    builtin_perms = apply_unreachable_denies(builtin_perms)
     browser_delegation_tools = ["CreateBrowserAgent", "BrowserAgent", "BrowserAgents", "AppAgent"]
     browser_all_denied = all(
         builtin_perms.get(t, "always_allow") == "deny"
diff --git a/backend/apps/health/health.py b/backend/apps/health/health.py
index 5637152c..ed555db0 100644
--- a/backend/apps/health/health.py
+++ b/backend/apps/health/health.py
@@ -1,6 +1,7 @@
 from backend.config.Apps import SubApp
 from contextlib import asynccontextmanager
 from fastapi.responses import PlainTextResponse
+from pydantic import BaseModel, ConfigDict
 from typeguard import typechecked
 from fastapi import status, HTTPException
 
@@ -14,10 +15,33 @@ health = SubApp("health", health_lifespan)
 @typechecked
 async def check() -> PlainTextResponse:
     return PlainTextResponse(
-        content="OK", 
+        content="OK",
         status_code=status.HTTP_200_OK,
         headers={
             "Content-Type": "text/plain",
             "Content-Length": "2"
         }
-    )
\ No newline at end of file
+    )
+
+
+class RendererHealth(BaseModel):
+    """Whether an Electron window is driving this backend, which is what makes browser tools real."""
+
+    model_config = ConfigDict(validate_assignment=True)
+
+    attached: bool
+    ever_attached: bool
+    connections: int
+
+
+@health.router.get("/renderer")
+@typechecked
+async def renderer() -> RendererHealth:
+    """Renderer readiness. The cloud runner blocks on this before it fires a workflow, because a
+    browser step with no window behind it burns turns narrating timeouts at nothing."""
+    from backend.apps.agents.core.ws_manager import ws_manager
+    return RendererHealth(
+        attached=bool(ws_manager.global_connections),
+        ever_attached=ws_manager.renderer_ever_attached,
+        connections=len(ws_manager.global_connections),
+    )
diff --git a/backend/config/headless.py b/backend/config/headless.py
index ccdcbc55..55c086c1 100644
--- a/backend/config/headless.py
+++ b/backend/config/headless.py
@@ -1,18 +1,31 @@
-"""Headless mode: the backend running with no Electron renderer, no display, and no human
-(a Linux container). Single source of truth for the flag and for the tools that dead-end at a
-renderer, so they are dropped from the tool surface up front instead of hanging at call time."""
+"""What the backend can still offer when nobody is sitting in front of it.
+
+Two different absences, and they are not the same absence. `OPENSWARM_HEADLESS=1` says no
+desktop shell owns this process, so no human will answer a prompt and no window arrives on
+its own. A renderer that has never registered on the dashboard WebSocket says there is no
+Electron window to drive a `<webview>` through. A cloud container starts as both and, once
+it boots Electron under a virtual display, becomes only the first.
+
+The browser tools therefore hang off the renderer actually being there, not off the flag,
+which is what lets the same code be right on a laptop, in the runner container, and in
+whatever environment attaches a renderer next.
+"""
 
 import os
-from typing import Dict, FrozenSet
+from typing import Dict, FrozenSet, Set
 
 from typeguard import typechecked
 
-# Each of these ends at the Electron renderer: browser/app delegation drives live webviews, ShowUI (the same gate AskUI rides) draws into the transcript, and AskUserQuestion waits on a person who isn't there.
-HEADLESS_DENIED_TOOLS: FrozenSet[str] = frozenset({
+# Each of these ends at a live Electron renderer: browser and app delegation drive real <webview>s that only the frontend can serialize and click.
+RENDERER_BOUND_TOOLS: FrozenSet[str] = frozenset({
     "CreateBrowserAgent",
     "BrowserAgent",
     "BrowserAgents",
     "AppAgent",
+})
+
+# Each of these ends at a person: ShowUI (the same gate AskUI rides) draws for someone to look at, and AskUserQuestion waits for someone to answer. A renderer nobody is watching does not bring them back.
+HUMAN_BOUND_TOOLS: FrozenSet[str] = frozenset({
     "ShowUI",
     "AskUserQuestion",
 })
@@ -26,9 +39,37 @@ def is_headless() -> bool:
 
 
 @typechecked
-def apply_headless_denies(builtin_perms: Dict[str, str]) -> Dict[str, str]:
-    """The permission map with every renderer-bound tool forced to 'deny' when headless, and the
-    map itself untouched otherwise. Returns a copy so the mode never poisons the live snapshot."""
-    if not is_headless():
+def renderer_reachable() -> bool:
+    """Whether an Electron renderer has ever registered on this backend's dashboard socket.
+
+    Imported inside the call because config sits below apps in the import order; hoisting
+    ws_manager to module scope would close a cycle."""
+    from backend.apps.agents.core.ws_manager import ws_manager
+    return ws_manager.renderer_ever_attached
+
+
+@typechecked
+def denied_tools() -> FrozenSet[str]:
+    """Every builtin that would dead-end in this process, given who is actually attached.
+
+    The renderer-bound set drops only when the shell that would have brought a window is
+    absent AND no window ever showed up. A desktop launch keeps offering them across a
+    socket blip on purpose: browser_agent's dispatch gate is what waits out a reconnect,
+    and a tool pruned at session build never comes back for the life of that session.
+    """
+    denied: Set[str] = set()
+    if is_headless():
+        denied |= HUMAN_BOUND_TOOLS
+        if not renderer_reachable():
+            denied |= RENDERER_BOUND_TOOLS
+    return frozenset(denied)
+
+
+@typechecked
+def apply_unreachable_denies(builtin_perms: Dict[str, str]) -> Dict[str, str]:
+    """The permission map with every currently-unreachable tool forced to 'deny'. Returns a
+    copy so the verdict never poisons the live snapshot."""
+    denied = denied_tools()
+    if not denied:
         return builtin_perms
-    return {**builtin_perms, **{name: "deny" for name in HEADLESS_DENIED_TOOLS}}
+    return {**builtin_perms, **{name: "deny" for name in denied}}
diff --git a/backend/tests/test_headless_mode.py b/backend/tests/test_headless_mode.py
index fdfd07c0..2f884d1e 100644
--- a/backend/tests/test_headless_mode.py
+++ b/backend/tests/test_headless_mode.py
@@ -1,7 +1,9 @@
-"""OPENSWARM_HEADLESS=1 gating: the tools that dead-end at an Electron renderer (browser/app
-delegation, ShowUI/AskUI, AskUserQuestion) must be gone from the effective tool surface, and an
-'ask' must deny on the spot instead of parking on the 600s approval timeout. Every case is paired
-with its headless-off twin, because a gate that can't be seen switching off proves nothing."""
+"""Headless gating: the tools that dead-end must be gone from the effective tool surface, and an
+'ask' must deny on the spot instead of parking on the 600s approval timeout. Two gates, not one:
+ShowUI/AskUI and AskUserQuestion need a person, so OPENSWARM_HEADLESS=1 alone kills them, while
+browser/app delegation only needs a window, so a headless box that boots one (the cloud runner
+under Xvfb) keeps them. Every case is paired with its twin, because a gate that can't be seen
+switching off proves nothing."""
 
 import pytest
 from unittest.mock import AsyncMock, patch
@@ -11,7 +13,8 @@ from backend.apps.agents.manager.permissions import workflow_approval
 from backend.apps.agents.manager.permissions.build_effective_tool_lists import build_effective_tool_lists
 from backend.apps.agents.manager.register_builtin_mcp_servers import register_builtin_mcp_servers
 from backend.apps.agents.manager.streaming.HookContext import HookContext
-from backend.config.headless import HEADLESS_DENIED_TOOLS
+from backend.apps.agents.core.ws_manager import ws_manager
+from backend.config.headless import HUMAN_BOUND_TOOLS, RENDERER_BOUND_TOOLS, denied_tools
 
 BROWSER_DELEGATION = ("CreateBrowserAgent", "BrowserAgent", "BrowserAgents", "AppAgent")
 
@@ -45,11 +48,45 @@ def p_ctx() -> HookContext:
     )
 
 
-def test_the_denied_set_is_exactly_the_renderer_bound_tools():
-    assert HEADLESS_DENIED_TOOLS == frozenset(BROWSER_DELEGATION) | {"ShowUI", "AskUserQuestion"}
+@pytest.fixture
+def no_renderer(monkeypatch):
+    """No window has ever attached, the state a container starts in."""
+    monkeypatch.setattr(ws_manager, "renderer_ever_attached", False, raising=False)
 
 
-def test_headless_drops_the_renderer_bound_servers_and_tools(monkeypatch):
+@pytest.fixture
+def renderer_attached(monkeypatch):
+    """A window registered on the dashboard socket, the state the runner waits for."""
+    monkeypatch.setattr(ws_manager, "renderer_ever_attached", True, raising=False)
+
+
+def test_the_two_denied_sets_split_by_what_they_actually_need():
+    assert RENDERER_BOUND_TOOLS == frozenset(BROWSER_DELEGATION)
+    assert HUMAN_BOUND_TOOLS == frozenset({"ShowUI", "AskUserQuestion"})
+
+
+def test_a_renderer_buys_back_the_browser_tools_but_never_the_human_ones(monkeypatch, renderer_attached):
+    monkeypatch.setenv("OPENSWARM_HEADLESS", "1")
+    assert denied_tools() == HUMAN_BOUND_TOOLS
+
+
+def test_a_desktop_launch_denies_nothing_even_before_its_window_loads(monkeypatch, no_renderer):
+    monkeypatch.delenv("OPENSWARM_HEADLESS", raising=False)
+    assert denied_tools() == frozenset()
+
+
+def test_headless_with_a_renderer_offers_the_browser_server_again(monkeypatch, renderer_attached):
+    monkeypatch.setenv("OPENSWARM_HEADLESS", "1")
+    mcp_servers, allowed, disallowed = p_run_the_real_pipeline()
+    assert "openswarm-browser-agent" in mcp_servers
+    for tool in BROWSER_DELEGATION:
+        assert f"mcp__openswarm-browser-agent__{tool}" in allowed
+    # Still nobody to answer, so the human-bound pair stays gone.
+    assert "openswarm-ui" not in mcp_servers
+    assert "AskUserQuestion" in disallowed
+
+
+def test_headless_drops_the_renderer_bound_servers_and_tools(monkeypatch, no_renderer):
     monkeypatch.setenv("OPENSWARM_HEADLESS", "1")
     mcp_servers, allowed, disallowed = p_run_the_real_pipeline()
     assert "openswarm-browser-agent" not in mcp_servers
@@ -66,7 +103,7 @@ def test_headless_drops_the_renderer_bound_servers_and_tools(monkeypatch):
     assert "openswarm-apps" in mcp_servers
 
 
-def test_without_headless_every_one_of_them_is_offered(monkeypatch):
+def test_without_headless_every_one_of_them_is_offered(monkeypatch, no_renderer):
     monkeypatch.delenv("OPENSWARM_HEADLESS", raising=False)
     mcp_servers, allowed, _ = p_run_the_real_pipeline()
     assert "openswarm-browser-agent" in mcp_servers
@@ -87,7 +124,7 @@ def test_askuserquestion_survives_when_the_ui_server_is_absent(monkeypatch):
     assert "AskUserQuestion" not in allowed and "AskUserQuestion" in disallowed
 
 
-def test_only_the_exact_flag_value_turns_headless_on(monkeypatch):
+def test_only_the_exact_flag_value_turns_headless_on(monkeypatch, no_renderer):
     monkeypatch.setenv("OPENSWARM_HEADLESS", "0")
     _, allowed, _ = p_run_the_real_pipeline()
     assert "mcp__openswarm-ui__ShowUI" in allowed
diff --git a/openswarm-runner/runner/backend_process.py b/openswarm-runner/runner/boot/backend_process.py
similarity index 100%
rename from openswarm-runner/runner/backend_process.py
rename to openswarm-runner/runner/boot/backend_process.py