diff --git a/gateway/channel_directory.py b/gateway/channel_directory.py
index 627e525924..402875d4a2 100644
--- a/gateway/channel_directory.py
+++ b/gateway/channel_directory.py
@@ -1,6 +1,6 @@
 """Channel directory -- cached map of reachable channels/contacts per platform.
 
-Built on gateway startup, refreshed every 5 min, saved to ~/.hermes/channel_directory.json.
+Built on gateway startup, refreshed every 5 min, saved to ``<HERMES_HOME>/channel_directory.json``.
 send_message reads it for action="list" and to resolve friendly channel names to IDs.
 """
 
diff --git a/hermes_cli/send_cmd.py b/hermes_cli/send_cmd.py
index 629cd5f74a..87b5fa0e24 100644
--- a/hermes_cli/send_cmd.py
+++ b/hermes_cli/send_cmd.py
@@ -133,7 +133,7 @@ def _list_targets(platform_filter: Optional[str], *, json_mode: bool) -> int:
 
 
 def _load_hermes_env() -> None:
-    """Populate the credential environment from ``~/.hermes/.env`` AND bridge top-level ``config.yaml``
+    """Populate the credential environment from ``<HERMES_HOME>/.env`` AND bridge top-level ``config.yaml``
     keys into it so the gateway config loader sees platform credentials and home channels.
 
     The target is ``os.environ`` for the standalone CLI. Inside a multi-profile host (dashboard console
diff --git a/tests/hermes_cli/test_send_cmd.py b/tests/hermes_cli/test_send_cmd.py
index 57d0b56fe8..e5c255a673 100644
--- a/tests/hermes_cli/test_send_cmd.py
+++ b/tests/hermes_cli/test_send_cmd.py
@@ -376,3 +376,34 @@ def test_load_hermes_env_bom_only_env_is_noop(tmp_path, monkeypatch):
 
     added = {k: v for k, v in os.environ.items() if k not in before}
     assert "\ufeff" not in "".join(added)
+
+
+def test_help_and_empty_list_hint_name_the_resolved_home(tmp_path, monkeypatch, capsys):
+    """``--help`` and the ``--list`` empty-state hint derive their paths from the resolved home instead of a
+    hardcoded ``~/.hermes`` (absent on a Windows install or under a profile home)."""
+    import argparse
+    import sys
+    import types
+
+    home = tmp_path / "AppData" / "Local" / "hermes"
+    home.mkdir(parents=True)
+    monkeypatch.setenv("HERMES_HOME", str(home))
+
+    parser = argparse.ArgumentParser(prog="hermes")
+    send_parser = send_cmd.register_send_subparser(parser.add_subparsers(dest="command"))
+    help_text = send_parser.format_help()
+    assert str(home / ".env") in help_text and str(home / "config.yaml") in help_text
+    assert "~/.hermes" not in help_text
+
+    fake_gw_config = types.ModuleType("gateway.config")
+    fake_gw_config.load_gateway_config = lambda: types.SimpleNamespace(get_connected_platforms=lambda: [])
+    monkeypatch.setitem(sys.modules, "gateway.config", fake_gw_config)
+    fake_dir = types.ModuleType("gateway.channel_directory")
+    fake_dir.load_directory = lambda: {"updated_at": None, "platforms": {}}
+    fake_dir.format_directory_for_display = lambda platforms=None: ""
+    monkeypatch.setitem(sys.modules, "gateway.channel_directory", fake_dir)
+
+    assert send_cmd._list_targets(None, json_mode=False) == 0
+    out = capsys.readouterr().out
+    assert str(home / "channel_directory.json") in out
+    assert "~/.hermes" not in out
diff --git a/tests/tools/test_send_message_tool.py b/tests/tools/test_send_message_tool.py
index 6da8895f6e..0c67840db9 100644
--- a/tests/tools/test_send_message_tool.py
+++ b/tests/tools/test_send_message_tool.py
@@ -1821,3 +1821,24 @@ class TestSendTelegramThreadNotFoundRetry:
         finally:
             if media_path and os.path.exists(media_path):
                 os.unlink(media_path)
+
+
+def test_not_configured_error_names_resolved_home_and_consulted_sources(tmp_path, monkeypatch):
+    """The 'not configured' error names the files this process actually read (resolved home, not a
+    hardcoded ``~/.hermes``) and what each source held, so a Windows/profile home user can fix the right file."""
+    from gateway.config import GatewayConfig
+    from tools.send_message_tool import _resolve_platform_config
+
+    home = tmp_path / "AppData" / "Local" / "hermes"
+    home.mkdir(parents=True)
+    (home / ".env").write_text("FIRECRAWL_API_KEY=x\n", encoding="utf-8")
+    (home / "config.yaml").write_text("platforms:\n  discord:\n    enabled: false\n", encoding="utf-8")
+    monkeypatch.setenv("HERMES_HOME", str(home))
+    monkeypatch.delenv("DISCORD_BOT_TOKEN", raising=False)
+
+    _, _, _, err = _resolve_platform_config("discord", GatewayConfig())
+
+    assert "~/.hermes" not in err
+    assert f"{home / '.env'} (no DISCORD_BOT_TOKEN)" in err
+    assert f"{home / 'config.yaml'} (platforms.discord.enabled: false)" in err
+    assert "environment (DISCORD_BOT_TOKEN unset)" in err
diff --git a/tools/send_message_tool.py b/tools/send_message_tool.py
index 2b98cdcc05..2d038e831d 100644
--- a/tools/send_message_tool.py
+++ b/tools/send_message_tool.py
@@ -304,13 +304,53 @@ def _resolve_platform_config(platform_name, config):
     if not pconfig or not pconfig.enabled:
         pconfig = _weixin_env_pconfig() if platform_name == "weixin" else None
     if pconfig is None:
-        from hermes_constants import get_hermes_home
-        config_path = get_hermes_home() / "config.yaml"
-        return None, None, None, (f"Platform '{platform_name}' is not configured. Set up credentials in "
-                                  f"{config_path} or environment variables.")
+        return None, None, None, _not_configured_error(platform_name, platform, entry)
     return platform, pconfig, entry, None
 
 
+def _not_configured_error(platform_name, platform, entry):
+    """Name the resolved home and what each credential source held, so the user edits the file this
+    process actually read (a hardcoded ``~/.hermes`` does not exist on a Windows or profile home)."""
+    from agent.secret_scope import load_env_file
+    from gateway.config import _getenv
+    from gateway.config_env import _ENV_ENABLE_CREDENTIALS
+    from hermes_constants import get_hermes_home
+    home = get_hermes_home()
+    env_names = list(_ENV_ENABLE_CREDENTIALS.get(platform) or (entry.required_env if entry else ()))
+    names = "/".join(env_names) or "credentials"
+    env_path, config_path = home / ".env", home / "config.yaml"
+    dotenv_keys = load_env_file(env_path)
+    dotenv_state = (f"{names} present" if any(n in dotenv_keys for n in env_names) else f"no {names}") \
+        if env_path.exists() else "missing"
+    try:
+        from hermes_cli.config_effective import load_user_config_effective
+        block = (load_user_config_effective(config_path) or {}).get("platforms", {}).get(platform_name)
+    except Exception:
+        block = None
+    if not config_path.exists():
+        config_state = "missing"
+    elif not isinstance(block, dict):
+        config_state = f"no platforms.{platform_name} block"
+    elif block.get("enabled") is False:
+        config_state = f"platforms.{platform_name}.enabled: false"
+    else:
+        config_state = f"platforms.{platform_name} has no token"
+    env_state = f"{names} set" if any(_getenv(n) for n in env_names) else f"{names} unset"
+    msg = (f"Platform '{platform_name}' is not configured. Looked in: {env_path} ({dotenv_state}), "
+           f"{config_path} ({config_state}), environment ({env_state}).")
+    # The gateway can hold a token only in its own process environment; a fresh CLI cannot see it.
+    try:
+        from gateway.status import read_runtime_status, runtime_status_pid_is_live
+        record = read_runtime_status()
+        state = ((record or {}).get("platforms") or {}).get(platform_name, {}).get("state")
+        if state == "connected" and "present" not in dotenv_state and runtime_status_pid_is_live(record):
+            msg += (f" A gateway (pid {record.get('pid')}) running from {home} has {platform_name} connected, "
+                    f"so its credentials live only in that process's environment; add {names} to {env_path}.")
+    except Exception:
+        pass
+    return msg
+
+
 def _home_chat_id(config, platform, platform_name):
     """``(home chat_id, None)`` or ``(None, actionable error)``; Weixin also honours WEIXIN_HOME_CHANNEL."""
     home = config.get_home_channel(platform)
diff --git a/website/docs/guides/pipe-script-output.md b/website/docs/guides/pipe-script-output.md
index a58f408260..b87bf01440 100644
--- a/website/docs/guides/pipe-script-output.md
+++ b/website/docs/guides/pipe-script-output.md
@@ -186,9 +186,19 @@ msg_id=$(hermes send --to discord:#ops --json "build started" \
 **Usually no.** For any bot-token platform — Telegram, Discord, Slack,
 Signal, SMS, WhatsApp Cloud API, and most others — `hermes send` calls
 the platform's REST endpoint directly using credentials from
-`~/.hermes/.env` and `~/.hermes/config.yaml`. It's a standalone subprocess
+`~/.hermes/.env` and `~/.hermes/config.yaml` (or the equivalent files under
+your resolved Hermes home — `%LOCALAPPDATA%\hermes` on Windows, or the profile
+directory when `HERMES_HOME` / `-p` is set). It's a standalone subprocess
 that exits as soon as the message is delivered.
 
+If a platform reports `not configured`, the error lists the exact files it
+read and what each one held, e.g.
+`Looked in: C:\Users\me\AppData\Local\hermes\.env (no DISCORD_BOT_TOKEN),
+C:\Users\me\AppData\Local\hermes\config.yaml (no platforms.discord block),
+environment (DISCORD_BOT_TOKEN unset)`. When a gateway started from the same
+home has that platform connected, the token only exists in the gateway's
+process environment — add it to that home's `.env` so `hermes send` can use it.
+
 A live gateway is only required for **plugin platforms** that rely on a
 persistent adapter connection (for example, a custom plugin that keeps
 a long-lived WebSocket open). In that case you'll get a clear error