diff --git a/pyproject.toml b/pyproject.toml
index 1e3e473c6..057f03014 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -49,7 +49,11 @@ dependencies = [
     # Core: lightweight compression (SmartCrusher, ContentRouter, CCR, TOIN)
     "tiktoken>=0.5.0",            # Tokenizer for all compressors
     "pydantic>=2.0.0",            # Config and data models
-    "litellm>=1.86.2,<2.0",        # Model registry, pricing, and provider support
+    # litellm's own metadata pins requires-python <3.14, and headroom only uses it for
+    # model registry / pricing / non-core providers — all lazily imported and
+    # ImportError-guarded. Marking it 3.14-optional lets headroom install on Python 3.14
+    # (core compression + the Anthropic proxy path never import litellm). See GH #956.
+    "litellm>=1.86.2,<2.0; python_version < '3.14'",  # model registry, pricing, providers (lazy)
     "click>=8.1.0",               # CLI framework
     "rich>=13.0.0",               # Rich terminal output
     "opentelemetry-api>=1.24.0",  # Safe no-op OTEL API for instrumentation
@@ -228,7 +232,7 @@ dev = [
     "pre-commit>=3.0.0",
     "openai>=1.0.0",
     "anthropic>=0.18.0",
-    "litellm>=1.86.2,<2.0",
+    "litellm>=1.86.2,<2.0; python_version < '3.14'",  # see core deps note (GH #956)
     "fastapi>=0.100.0",
     "uvicorn>=0.23.0,<1.0",
     "httpx[http2]>=0.24.0",
diff --git a/tests/test_litellm_optional.py b/tests/test_litellm_optional.py
new file mode 100644
index 000000000..652c39db1
--- /dev/null
+++ b/tests/test_litellm_optional.py
@@ -0,0 +1,54 @@
+"""litellm must be optional on Python 3.14 (GH #956).
+
+litellm's metadata pins requires-python <3.14, so a hard dependency makes
+`pip install headroom-ai` unsatisfiable on 3.14. headroom only uses litellm for
+model registry / pricing / non-core providers (all lazily imported and
+ImportError-guarded), so every litellm requirement must carry a marker that
+skips it on 3.14, and the core paths must degrade gracefully without it.
+"""
+
+from __future__ import annotations
+
+from pathlib import Path
+
+import pytest
+
+try:
+    import tomllib
+except ModuleNotFoundError:  # Python 3.10
+    import tomli as tomllib  # type: ignore[no-redef]
+
+from packaging.requirements import Requirement
+
+PYPROJECT = Path(__file__).resolve().parents[1] / "pyproject.toml"
+
+
+def _litellm_requirements() -> list[Requirement]:
+    data = tomllib.loads(PYPROJECT.read_text(encoding="utf-8"))
+    specs = list(data["project"].get("dependencies", []))
+    for extra in data["project"].get("optional-dependencies", {}).values():
+        specs.extend(extra)
+    return [r for spec in specs if (r := Requirement(spec)).name == "litellm"]
+
+
+def test_every_litellm_requirement_is_skipped_on_py314() -> None:
+    reqs = _litellm_requirements()
+    assert reqs, "expected litellm to be declared in pyproject"
+    for r in reqs:
+        assert r.marker is not None, f"{r}: litellm must carry a python_version marker (GH #956)"
+        assert not r.marker.evaluate({"python_version": "3.14"}), (
+            f"{r}: must be skipped on Python 3.14"
+        )
+        assert r.marker.evaluate({"python_version": "3.13"}), (
+            f"{r}: must still install on Python 3.13"
+        )
+
+
+def test_proxy_cost_degrades_without_litellm(monkeypatch: pytest.MonkeyPatch) -> None:
+    # With litellm absent (its state on 3.14), the proxy cost path must return
+    # None rather than raise.
+    from headroom.proxy import cost
+
+    monkeypatch.setattr(cost, "LITELLM_AVAILABLE", False)
+    monkeypatch.setattr(cost, "litellm", None)
+    assert cost._get_litellm_module() is None