diff --git a/gateway/run.py b/gateway/run.py
index 88196d69..daf6b62a 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -673,11 +673,69 @@ def _is_control_interrupt_message(message: Optional[str]) -> bool:
     return normalized in _CONTROL_INTERRUPT_MESSAGES
 
 
+def _skill_slug_from_frontmatter(skill_md: Path) -> tuple[str | None, str | None]:
+    """Derive the /command slug and declared frontmatter name from a SKILL.md.
+
+    Matches the exact normalization used by
+    :func:`agent.skill_commands.scan_skill_commands` so the slug here is the
+    same string a user types after the leading ``/`` (e.g. a skill with
+    frontmatter ``name: Stable Diffusion Image Generation`` resolves to
+    ``stable-diffusion-image-generation`` — NOT the parent directory name,
+    which is commonly shorter/different, e.g. ``stable-diffusion``).
+
+    Using the directory name silently broke :func:`_check_unavailable_skill`
+    for every skill whose directory name drifted from its frontmatter name
+    (19 such skills on a standard install as of 2026-05), causing a generic
+    "unknown command" response where a "disabled — enable with …" or
+    "not installed — install with …" hint was expected.
+
+    Returns ``(slug, declared_name)`` or ``(None, None)`` when the file
+    can't be read or lacks a ``name:`` in its frontmatter.
+    """
+    try:
+        content = skill_md.read_text(encoding="utf-8", errors="replace")
+    except Exception:
+        return None, None
+    if not content.startswith("---"):
+        return None, None
+    end = content.find("\n---", 3)
+    if end < 0:
+        return None, None
+    declared_name: str | None = None
+    for line in content[3:end].splitlines():
+        line = line.strip()
+        if line.startswith("name:"):
+            raw = line.split(":", 1)[1].strip()
+            # Strip YAML quote wrappers if present
+            if len(raw) >= 2 and raw[0] == raw[-1] and raw[0] in ('"', "'"):
+                raw = raw[1:-1]
+            declared_name = raw.strip()
+            break
+    if not declared_name:
+        return None, None
+    slug = declared_name.lower().replace(" ", "-").replace("_", "-")
+    # Mirror _SKILL_INVALID_CHARS and _SKILL_MULTI_HYPHEN from skill_commands
+    import re as _re
+    slug = _re.sub(r"[^a-z0-9-]", "", slug)
+    slug = _re.sub(r"-{2,}", "-", slug).strip("-")
+    if not slug:
+        return None, declared_name
+    return slug, declared_name
+
+
 def _check_unavailable_skill(command_name: str) -> str | None:
     """Check if a command matches a known-but-inactive skill.
 
     Returns a helpful message if the skill exists but is disabled or only
     available as an optional install. Returns None if no match found.
+
+    The slug for each on-disk skill is derived from its frontmatter ``name:``
+    (via :func:`_skill_slug_from_frontmatter`), NOT from its containing
+    directory name — because the two can differ (e.g. directory
+    ``stable-diffusion`` + frontmatter ``Stable Diffusion Image Generation``
+    yields slug ``stable-diffusion-image-generation``). Matching on
+    directory name would miss that slug entirely and fall through to the
+    generic "unknown command" path.
     """
     # Normalize: command uses hyphens, skill names may use hyphens or underscores
     normalized = command_name.lower().replace("_", "-")
@@ -693,8 +751,12 @@ def _check_unavailable_skill(command_name: str) -> str | None:
             for skill_md in skills_dir.rglob("SKILL.md"):
                 if any(part in ('.git', '.github', '.hub', '.archive') for part in skill_md.parts):
                     continue
-                name = skill_md.parent.name.lower().replace("_", "-")
-                if name == normalized and name in disabled:
+                slug, declared_name = _skill_slug_from_frontmatter(skill_md)
+                if not slug or not declared_name:
+                    continue
+                # disabled is keyed by the declared frontmatter name (what
+                # skills.disabled / skills.platform_disabled store).
+                if slug == normalized and declared_name in disabled:
                     return (
                         f"The **{command_name}** skill is installed but disabled.\n"
                         f"Enable it with: `hermes skills config`"
@@ -706,8 +768,10 @@ def _check_unavailable_skill(command_name: str) -> str | None:
         optional_dir = get_optional_skills_dir(repo_root / "optional-skills")
         if optional_dir.exists():
             for skill_md in optional_dir.rglob("SKILL.md"):
-                name = skill_md.parent.name.lower().replace("_", "-")
-                if name == normalized:
+                slug, _declared = _skill_slug_from_frontmatter(skill_md)
+                if not slug:
+                    continue
+                if slug == normalized:
                     # Build install path: official/<category>/<name>
                     rel = skill_md.parent.relative_to(optional_dir)
                     parts = list(rel.parts)
diff --git a/tests/gateway/test_unavailable_skill_hint.py b/tests/gateway/test_unavailable_skill_hint.py
new file mode 100644
index 00000000..8b28d13a
--- /dev/null
+++ b/tests/gateway/test_unavailable_skill_hint.py
@@ -0,0 +1,185 @@
+"""Tests for gateway.run._check_unavailable_skill.
+
+Regression coverage for the dir-name-vs-frontmatter-name drift bug.
+The hint function used to compare the skill's parent-directory name
+against the typed command and the disabled list. That silently missed
+every skill whose directory name differs from its declared frontmatter
+name (~19 skills on a standard install), so users typing a real slug
+like ``/stable-diffusion-image-generation`` got a generic "unknown
+command" response instead of the intended "disabled — enable with …"
+or "not installed — install with …" hint.
+
+These tests pin the fixed behavior:
+
+* Slug is derived from the frontmatter ``name:`` (exactly matching
+  :func:`agent.skill_commands.scan_skill_commands`), so the slug differs
+  from the directory name when the declared name is multi-word.
+* ``disabled`` membership is checked by the declared name, because that
+  is what :func:`hermes_cli.skills_config.save_disabled_skills` stores.
+"""
+from __future__ import annotations
+
+from pathlib import Path
+from unittest.mock import patch
+
+import pytest
+
+
+@pytest.fixture
+def tmp_skills(tmp_path: Path, monkeypatch: pytest.MonkeyPatch) -> Path:
+    """Isolated skills dir + HERMES_HOME so the real user config is untouched."""
+    home = tmp_path / ".hermes"
+    home.mkdir()
+    (home / "skills").mkdir()
+    monkeypatch.setenv("HERMES_HOME", str(home))
+    monkeypatch.setattr(Path, "home", lambda: tmp_path)
+    return home / "skills"
+
+
+def _write_skill(skills_dir: Path, rel: str, frontmatter_name: str) -> Path:
+    """Create a SKILL.md at ``<skills_dir>/<rel>/SKILL.md``."""
+    skill_dir = skills_dir / rel
+    skill_dir.mkdir(parents=True, exist_ok=True)
+    skill_md = skill_dir / "SKILL.md"
+    skill_md.write_text(
+        f"---\nname: {frontmatter_name}\ndescription: test skill\n---\nBody.\n",
+        encoding="utf-8",
+    )
+    return skill_md
+
+
+def test_frontmatter_slug_matched_even_when_dir_name_differs(
+    tmp_skills: Path, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    """Directory ``stable-diffusion`` + frontmatter ``Stable Diffusion Image Generation``.
+
+    Command typed: ``stable-diffusion-image-generation`` (the slug the
+    agent actually registers). The old dir-name-based check would have
+    compared ``stable-diffusion`` to the typed command and missed.
+    """
+    from gateway import run as gateway_run
+
+    _write_skill(tmp_skills, "mlops/stable-diffusion", "Stable Diffusion Image Generation")
+
+    # Config disables by declared name (matches what `hermes skills config` writes).
+    monkeypatch.setattr(
+        "gateway.run._get_disabled_skill_names",
+        lambda: {"Stable Diffusion Image Generation"},
+        raising=False,
+    )
+    with patch(
+        "tools.skills_tool._get_disabled_skill_names",
+        return_value={"Stable Diffusion Image Generation"},
+    ), patch(
+        "agent.skill_utils.get_all_skills_dirs",
+        return_value=[tmp_skills],
+    ):
+        msg = gateway_run._check_unavailable_skill("stable-diffusion-image-generation")
+
+    assert msg is not None, (
+        "expected a 'disabled' hint for the frontmatter-derived slug; "
+        "the old code compared the dir name 'stable-diffusion' and returned None"
+    )
+    assert "disabled" in msg.lower()
+    assert "hermes skills config" in msg
+
+
+def test_unknown_command_still_returns_none(
+    tmp_skills: Path,
+) -> None:
+    """A command that matches no on-disk skill still returns None."""
+    from gateway import run as gateway_run
+
+    _write_skill(tmp_skills, "creative/ascii-art", "ascii-art")
+
+    with patch(
+        "tools.skills_tool._get_disabled_skill_names", return_value=set()
+    ), patch(
+        "agent.skill_utils.get_all_skills_dirs", return_value=[tmp_skills]
+    ):
+        assert gateway_run._check_unavailable_skill("no-such-skill") is None
+
+
+def test_matched_but_not_disabled_returns_none(
+    tmp_skills: Path,
+) -> None:
+    """A skill that exists and isn't disabled shouldn't produce a hint."""
+    from gateway import run as gateway_run
+
+    _write_skill(tmp_skills, "creative/ascii-art", "ascii-art")
+
+    with patch(
+        "tools.skills_tool._get_disabled_skill_names", return_value=set()
+    ), patch(
+        "agent.skill_utils.get_all_skills_dirs", return_value=[tmp_skills]
+    ):
+        assert gateway_run._check_unavailable_skill("ascii-art") is None
+
+
+def test_slug_normalization_strips_non_alnum(
+    tmp_skills: Path,
+) -> None:
+    """Frontmatter ``C++ Code Review`` → slug ``c-code-review`` (``+`` stripped)."""
+    from gateway import run as gateway_run
+
+    _write_skill(tmp_skills, "software-development/cpp-review", "C++ Code Review")
+
+    with patch(
+        "tools.skills_tool._get_disabled_skill_names",
+        return_value={"C++ Code Review"},
+    ), patch(
+        "agent.skill_utils.get_all_skills_dirs", return_value=[tmp_skills]
+    ):
+        msg = gateway_run._check_unavailable_skill("c-code-review")
+
+    assert msg is not None
+    assert "disabled" in msg.lower()
+
+
+def test_optional_skill_uses_frontmatter_slug(
+    tmp_path: Path, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    """Same drift bug applies to the optional-skills branch.
+
+    Before: directory name was matched against the typed command, so an
+    optional skill at ``optional-skills/mlops/stable-diffusion/SKILL.md``
+    with frontmatter ``Stable Diffusion Image Generation`` returned None
+    when the user typed the real slug.
+    """
+    from gateway import run as gateway_run
+
+    # Build an isolated optional-skills dir
+    optional = tmp_path / "optional-skills"
+    skill_dir = optional / "mlops" / "stable-diffusion"
+    skill_dir.mkdir(parents=True)
+    (skill_dir / "SKILL.md").write_text(
+        "---\nname: Stable Diffusion Image Generation\ndescription: test\n---\n",
+        encoding="utf-8",
+    )
+
+    # Point the optional lookup at our tmp dir. The source reads from
+    # ``get_optional_skills_dir(repo_root / "optional-skills")`` — we
+    # can't easily retarget ``repo_root``, so patch the resolver.
+    monkeypatch.setattr(
+        "hermes_constants.get_optional_skills_dir",
+        lambda _default: optional,
+        raising=False,
+    )
+
+    # Ensure the "disabled" branch doesn't match anything so we fall
+    # through to the optional-skills branch.
+    empty_skills = tmp_path / "empty-skills"
+    empty_skills.mkdir()
+    with patch(
+        "tools.skills_tool._get_disabled_skill_names", return_value=set()
+    ), patch(
+        "agent.skill_utils.get_all_skills_dirs", return_value=[empty_skills]
+    ):
+        msg = gateway_run._check_unavailable_skill("stable-diffusion-image-generation")
+
+    assert msg is not None, (
+        "optional-skills branch should recognize the frontmatter-derived slug; "
+        "the old dir-name-based check returned None here too"
+    )
+    assert "not installed" in msg.lower()
+    assert "official/mlops/stable-diffusion" in msg