diff --git a/headroom/learn/plugins/claude.py b/headroom/learn/plugins/claude.py
index 4589cb5e3..e7ae19584 100644
--- a/headroom/learn/plugins/claude.py
+++ b/headroom/learn/plugins/claude.py
@@ -96,6 +96,11 @@ class ClaudeCodePlugin(LearnPlugin, ConversationScanner):
             if not jsonl_files:
                 continue
 
+            session_project_path = self._project_path_from_session_cwd(jsonl_files)
+            if session_project_path is not None:
+                project_path = session_project_path
+                name = _project_display_name(project_path, entry.name)
+
             projects.append(
                 ProjectInfo(
                     name=name,
@@ -108,6 +113,28 @@ class ClaudeCodePlugin(LearnPlugin, ConversationScanner):
 
         return projects
 
+    @staticmethod
+    def _project_path_from_session_cwd(jsonl_files: list[Path]) -> Path | None:
+        for jsonl_path in sorted(jsonl_files):
+            try:
+                with open(jsonl_path, encoding="utf-8", errors="replace") as f:
+                    for line in f:
+                        if not line.strip():
+                            continue
+                        try:
+                            event = json.loads(line)
+                        except json.JSONDecodeError:
+                            continue
+                        cwd = event.get("cwd")
+                        if isinstance(cwd, str) and cwd:
+                            project_path = Path(cwd)
+                            if project_path.exists():
+                                return project_path
+            except (OSError, UnicodeDecodeError):
+                continue
+        return None
+
+
     def scan_project(
         self, project: ProjectInfo, max_workers: int = 1, include_subagents: bool = True
     ) -> list[SessionData]:
diff --git a/tests/test_learn/test_scanner.py b/tests/test_learn/test_scanner.py
index 49560241a..15b7aa718 100644
--- a/tests/test_learn/test_scanner.py
+++ b/tests/test_learn/test_scanner.py
@@ -8,6 +8,7 @@ making it impossible to reconstruct names formed from three or more tokens.
 
 from __future__ import annotations
 
+import json
 from collections.abc import Generator
 from pathlib import Path
 from uuid import uuid4
@@ -417,6 +418,25 @@ class TestDecodeProjectPath:
         assert projects[0].name == "work"
         assert str(projects[0].project_path).startswith("C:")
 
+    def test_discover_project_prefers_session_cwd_over_ambiguous_folder_name(
+        self, tmp_path: Path
+    ) -> None:
+        nested = tmp_path / "vibe" / "remote"
+        hyphenated = tmp_path / "vibe-remote"
+        nested.mkdir(parents=True)
+        hyphenated.mkdir()
+
+        claude_dir = tmp_path / ".claude"
+        project_dir = claude_dir / "projects" / "C--Users-rod-work-vibe-remote"
+        project_dir.mkdir(parents=True)
+        (project_dir / "session.jsonl").write_text(json.dumps({"cwd": str(hyphenated)}) + "\n")
+
+        projects = ClaudeCodeScanner(claude_dir=claude_dir).discover_projects()
+
+        assert len(projects) == 1
+        assert projects[0].name == "vibe-remote"
+        assert projects[0].project_path == hyphenated
+
     def test_windows_double_dash_encoding_decodes(self) -> None:
         """Real Claude Code encoding has no leading dash: C:\\Users\\x → C--Users-x (#1849).