diff --git a/src/session_recall/providers/copilot_cli/_labels.py b/src/session_recall/providers/copilot_cli/_labels.py
index 4da82b3..ac6dd81 100644
--- a/src/session_recall/providers/copilot_cli/_labels.py
+++ b/src/session_recall/providers/copilot_cli/_labels.py
@@ -2,12 +2,35 @@
 
 from __future__ import annotations
 
+import posixpath
 from pathlib import Path
 
 from ...util.detect_repo import detect_repo_for_cwd
 
 
+def _is_posixish_path(path_str: str) -> bool:
+    """Return True for POSIX/WSL-style paths even when running on Windows."""
+    return path_str.startswith(("/", "~/"))
+
+
 def _detect_repo_for_path(path_str: str) -> str | None:
+    """Detect a repository for a path without rewriting POSIX paths on Windows.
+
+    Copilot CLI state can contain Linux/WSL-style paths even when this package is
+    executed by Windows Python. Passing those strings through pathlib.Path on
+    Windows rewrites separators (``/work`` -> ``\\work``), which breaks repo
+    detection and changes user-facing local workspace labels.
+    """
+    if _is_posixish_path(path_str):
+        expanded = posixpath.expanduser(path_str)
+        for candidate in (expanded, posixpath.dirname(expanded)):
+            if not candidate:
+                continue
+            repo = detect_repo_for_cwd(candidate)
+            if repo:
+                return repo
+        return None
+
     path = Path(path_str).expanduser()
     candidate = path if path.is_dir() else path.parent
     return detect_repo_for_cwd(str(candidate))
@@ -16,5 +39,6 @@ def _detect_repo_for_path(path_str: str) -> str | None:
 def _local_workspace_label(path_str: str | None) -> str | None:
     if not path_str:
         return None
-    expanded = Path(path_str).expanduser()
-    return f"local:{expanded}"
+    if _is_posixish_path(path_str):
+        return f"local:{posixpath.expanduser(path_str)}"
+    return f"local:{Path(path_str).expanduser()}"
diff --git a/src/session_recall/tests/test_health_schema_multistorage.py b/src/session_recall/tests/test_health_schema_multistorage.py
index de80403..57c9a2d 100644
--- a/src/session_recall/tests/test_health_schema_multistorage.py
+++ b/src/session_recall/tests/test_health_schema_multistorage.py
@@ -82,6 +82,64 @@ def test_health_provider_fallback_mode_json(monkeypatch, capsys):
     assert "Provider:vscode" in names
 
 
+def test_health_discovers_cli_session_state_when_sqlite_db_is_missing(
+    monkeypatch, capsys, tmp_path
+):
+    """Regression for issue #19: health should not require session-store.db.
+
+    Newer Copilot CLI layouts may expose ~/.copilot/session-state/*/events.jsonl
+    without the legacy SQLite session-store.db file.
+    """
+    from session_recall.commands import health
+    from session_recall.providers import discovery
+
+    state_root = tmp_path / "session-state"
+    session_dir = state_root / "abcd1234-0000-0000-0000-000000000000"
+    session_dir.mkdir(parents=True)
+    (session_dir / "events.jsonl").write_text(
+        "\n".join(
+            [
+                json.dumps(
+                    {
+                        "type": "session.start",
+                        "data": {
+                            "sessionId": "abcd1234-0000-0000-0000-000000000000",
+                            "context": {"repository": "owner/repo"},
+                        },
+                        "timestamp": "2026-04-22T10:00:00.000Z",
+                    }
+                ),
+                json.dumps(
+                    {
+                        "type": "user.message",
+                        "data": {"content": "Investigate auth timeout"},
+                        "timestamp": "2026-04-22T10:01:00.000Z",
+                    }
+                ),
+            ]
+        )
+        + "\n",
+        encoding="utf-8",
+    )
+
+    missing_db = str(tmp_path / ".copilot" / "session-store.db")
+    monkeypatch.setattr(health, "DB_PATH", missing_db)
+    monkeypatch.setattr(discovery, "CLI_SESSION_STATE_ROOT", str(state_root))
+
+    args = argparse.Namespace(json=True, provider="all")
+    rc = health.run(args)
+
+    captured = capsys.readouterr()
+    assert rc == 0
+    assert "database not found" not in captured.err
+    out = json.loads(captured.out)
+    assert out["storage_mode"] == "provider-fallback"
+    assert out["providers"]["cli"]["available"] is True
+    names = [d["name"] for d in out["dims"]]
+    assert "SQLite Health Core" in names
+    assert "Provider:cli" in names
+
+
 # ── helpers for integration tests ────────────────────────────────────
 
 
diff --git a/src/session_recall/tests/test_provider_backends.py b/src/session_recall/tests/test_provider_backends.py
index f04e541..4bef207 100644
--- a/src/session_recall/tests/test_provider_backends.py
+++ b/src/session_recall/tests/test_provider_backends.py
@@ -3,11 +3,8 @@
 from __future__ import annotations
 
 import json
-import sys
 from pathlib import Path
 
-import pytest
-
 from session_recall.providers.copilot_cli import CopilotCliProvider
 from session_recall.providers.file import (
     VSCodeProvider,
@@ -16,12 +13,6 @@
     _is_wsl,
 )
 
-# Windows Python rewrites POSIX/WSL session paths (/home/x -> \home\x).
-# Fixed by PR #29; strict so CI flags these once the fix lands.
-posix_paths_on_windows = pytest.mark.xfail(
-    sys.platform == "win32", reason="POSIX paths rewritten on Windows (#29)", strict=True
-)
-
 
 def test_vscode_kind1_inputtext_extraction() -> None:
     row = {
@@ -135,7 +126,6 @@ def test_cli_fallback_prefers_context_repository_field(tmp_path: Path) -> None:
     assert results[0]["repository"] == "dezgit2025/auto-memory"
 
 
-@posix_paths_on_windows
 def test_cli_fallback_uses_tool_path_to_infer_repository(
     monkeypatch, tmp_path: Path
 ) -> None:
@@ -186,7 +176,6 @@ def test_cli_fallback_uses_tool_path_to_infer_repository(
     assert sessions[0]["repository"] == "dezgit2025/auto-memory"
 
 
-@posix_paths_on_windows
 def test_cli_fallback_labels_non_repo_session_as_local_workspace(
     tmp_path: Path,
 ) -> None: