diff --git a/hermes_cli/auth.py b/hermes_cli/auth.py
index f85a421e33..6fa7653637 100644
--- a/hermes_cli/auth.py
+++ b/hermes_cli/auth.py
@@ -1356,16 +1356,33 @@ def _logged_in_oauth_active_provider(*, skip_free_tier: bool = False) -> Optiona
 
 
 def _config_model_provider() -> Tuple[Any, Optional[str]]:
-    """``(model_cfg, provider)`` from config.yaml when ``model.provider`` names a registry provider.
+    """``(model_cfg, provider)`` from config.yaml when ``model.provider`` names a registry provider
+    or a custom OpenAI-compatible endpoint (``custom``, ``custom:<name>``, ``vllm``/``ollama``/...).
 
     The normal chat/gateway path resolves config.provider upstream in resolve_requested_provider();
-    this is the safety net for the lone direct caller (main.py resolve_provider("auto"))."""
+    this is the safety net for the direct ``resolve_provider("auto")`` callers. A configured custom
+    endpoint is explicit intent like any registry pin: without this rung the boot inventory
+    (``free_tier_bootstrap``) read a llama.cpp/vLLM install as "nothing configured" and the
+    dashboard's Ink chat parked every session on Setup Required while ``hermes chat`` worked
+    (#108383)."""
     try:
         from hermes_cli.config import load_config
         model_cfg = (load_config() or {}).get("model")
         provider = model_cfg.get("provider") if isinstance(model_cfg, dict) else None
         provider = provider.strip().lower() if isinstance(provider, str) else ""
-        return model_cfg, (provider if provider in PROVIDER_REGISTRY else None)
+        provider = _plugin_aliases().get(provider, provider)
+        if provider == "custom" or provider.startswith("custom:"):
+            return model_cfg, "custom"
+        if provider in PROVIDER_REGISTRY:
+            return model_cfg, provider
+        # No provider pin but a base_url the bare-custom runtime rung would honour (a loopback
+        # llama.cpp/vLLM/ollama server) — same explicit intent, spelled by URL.
+        base_url = str(model_cfg.get("base_url") or "").strip() if isinstance(model_cfg, dict) else ""
+        if base_url:
+            from hermes_cli.runtime_provider import _config_base_url_trustworthy_for_bare_custom
+            if _config_base_url_trustworthy_for_bare_custom(base_url, provider):
+                return model_cfg, "custom"
+        return model_cfg, None
     except Exception as e:
         logger.debug("Could not read config.yaml model.provider for auto-resolution: %s", e)
         return None, None
diff --git a/tests/hermes_cli/test_resolve_provider_custom_endpoint.py b/tests/hermes_cli/test_resolve_provider_custom_endpoint.py
new file mode 100644
index 0000000000..1e6b2792e6
--- /dev/null
+++ b/tests/hermes_cli/test_resolve_provider_custom_endpoint.py
@@ -0,0 +1,74 @@
+"""A configured custom (OpenAI-compatible) endpoint is explicit provider intent.
+
+Regression for #108383: ``resolve_provider("auto")`` recognised only registry providers from
+``model.provider``, so the boot inventory (``free_tier_bootstrap``) read a llama.cpp / vLLM /
+ollama install as "nothing configured" and ``setup.status`` reported ``provider_configured:
+False`` — the dashboard's Ink chat parked every new session on "Setup Required" while
+``hermes chat`` (which resolves the runtime directly) worked against the same config.
+"""
+
+from __future__ import annotations
+
+import pytest
+
+
+@pytest.fixture
+def isolated_home(tmp_path, monkeypatch):
+    home = tmp_path / "hermes"
+    home.mkdir()
+    (home / ".env").write_text("", encoding="utf-8")
+    monkeypatch.setenv("HERMES_HOME", str(home))
+    monkeypatch.delenv("HERMES_GUEST_ONBOARDING", raising=False)
+    for var in ("OPENAI_API_KEY", "OPENROUTER_API_KEY", "ANTHROPIC_API_KEY", "OPENAI_BASE_URL",
+                "OPENROUTER_BASE_URL", "HERMES_INFERENCE_PROVIDER", "NOUS_API_KEY"):
+        monkeypatch.delenv(var, raising=False)
+    monkeypatch.setattr("agent.bedrock_adapter.has_aws_credentials", lambda: False)
+    from hermes_cli import free_tier_bootstrap as fb
+    fb.reset_for_tests()
+    return home
+
+
+@pytest.mark.parametrize(
+    "model_block",
+    [
+        pytest.param(
+            "model:\n  default: nvidia/Nemotron\n  provider: custom\n"
+            "  base_url: http://127.0.0.1:8000/v1\n  api_key: dummy\n",
+            id="provider-custom",
+        ),
+        pytest.param(
+            "model:\n  default: qwen3\n  provider: vllm\n  base_url: http://127.0.0.1:8000/v1\n",
+            id="local-server-alias",
+        ),
+        pytest.param(
+            "model:\n  default: qwen3\n  base_url: http://localhost:8080/v1\n",
+            id="loopback-base-url-only",
+        ),
+    ],
+)
+def test_configured_custom_endpoint_resolves_as_a_provider(isolated_home, model_block):
+    (isolated_home / "config.yaml").write_text(model_block, encoding="utf-8")
+    from hermes_cli.auth import resolve_provider
+    from hermes_cli.free_tier_bootstrap import run_bootstrap
+
+    assert resolve_provider("auto") == "custom"
+    record = run_bootstrap(announce=False)
+    assert record.provider_configured is True
+    assert record.other_providers is True
+    assert record.inference_provider == "custom"
+
+
+def test_stale_remote_base_url_without_a_custom_pin_is_not_a_provider(isolated_home):
+    """The URL rung follows the runtime's own trust rule: a non-loopback ``base_url`` left behind
+    under another provider's pin is not custom intent (#14676), so a blank machine still reads
+    as unconfigured."""
+    (isolated_home / "config.yaml").write_text(
+        "model:\n  default: some/model\n  provider: openrouter\n  base_url: https://api.z.ai/v1\n",
+        encoding="utf-8",
+    )
+    from hermes_cli.auth import AuthError, resolve_provider
+    from hermes_cli.free_tier_bootstrap import run_bootstrap
+
+    with pytest.raises(AuthError):
+        resolve_provider("auto")
+    assert run_bootstrap(announce=False).provider_configured is False