diff --git a/api/routes.py b/api/routes.py
index efae299c..b28bd2f4 100644
--- a/api/routes.py
+++ b/api/routes.py
@@ -6967,7 +6967,7 @@ def _handle_chat_start(handler, body, diag=None):
         attachments = _normalize_chat_attachments(body.get("attachments") or [])[:20]
         diag.stage("resolve_workspace") if diag else None
         try:
-            workspace = str(resolve_trusted_workspace(body.get("workspace") or s.workspace))
+            workspace = _resolve_chat_workspace_with_recovery(s, body.get("workspace"))
         except ValueError as e:
             return bad(handler, str(e))
         requested_model = body.get("model") or s.model
@@ -7000,6 +7000,24 @@ def _handle_chat_start(handler, body, diag=None):
 
 
 
+def _resolve_chat_workspace_with_recovery(s, requested_workspace) -> str:
+    """Recover stale implicit session workspaces without hiding explicit errors."""
+    explicit = requested_workspace not in (None, "")
+    candidate = requested_workspace if explicit else getattr(s, "workspace", None)
+    try:
+        return str(resolve_trusted_workspace(candidate))
+    except ValueError:
+        if explicit:
+            raise
+    fallback = str(resolve_trusted_workspace(get_last_workspace()))
+    s.workspace = fallback
+    try:
+        s.save()
+    except Exception:
+        pass
+    return fallback
+
+
 def _normalize_chat_attachments(raw_attachments):
     """Normalize attachment payloads from the browser.
 
diff --git a/api/workspace.py b/api/workspace.py
index 5ec8ec9e..97c768f6 100644
--- a/api/workspace.py
+++ b/api/workspace.py
@@ -64,7 +64,7 @@ def _profile_default_workspace() -> str:
       2. 'default_workspace' — alternate explicit key
       3. 'terminal.cwd'      — hermes-agent terminal working dir (most common)
 
-    Falls back to the boot-time DEFAULT_WORKSPACE constant.
+    Falls back to the live DEFAULT_WORKSPACE from api.config.
     """
     try:
         from api.config import get_config
@@ -86,7 +86,12 @@ def _profile_default_workspace() -> str:
                     return str(p)
     except (ImportError, Exception):
         logger.debug("Failed to load profile default workspace config")
-    return str(_BOOT_DEFAULT_WORKSPACE)
+    try:
+        from api.config import DEFAULT_WORKSPACE as _LIVE_DEFAULT_WORKSPACE
+
+        return str(Path(_LIVE_DEFAULT_WORKSPACE).expanduser().resolve())
+    except Exception:
+        return str(Path(_BOOT_DEFAULT_WORKSPACE).expanduser().resolve())
 
 
 # ── Public API ──────────────────────────────────────────────────────────────
diff --git a/tests/test_workspace_stale_recovery.py b/tests/test_workspace_stale_recovery.py
new file mode 100644
index 00000000..31141525
--- /dev/null
+++ b/tests/test_workspace_stale_recovery.py
@@ -0,0 +1,71 @@
+from pathlib import Path
+from types import SimpleNamespace
+
+import pytest
+
+from api import config as api_config
+from api import routes, workspace
+
+
+def test_profile_default_workspace_uses_live_config_default(monkeypatch, tmp_path):
+    live_default = tmp_path / "live-default"
+    live_default.mkdir()
+
+    monkeypatch.setattr(api_config, "DEFAULT_WORKSPACE", live_default)
+    monkeypatch.setattr(api_config, "get_config", lambda: {})
+
+    assert workspace._profile_default_workspace() == str(live_default.resolve())
+
+
+def test_resolve_chat_workspace_with_recovery_repairs_missing_implicit_workspace(monkeypatch, tmp_path):
+    fallback = tmp_path / "fallback"
+    fallback.mkdir()
+    stale = tmp_path / "deleted-workspace"
+
+    def fake_resolve(value):
+        if value == str(stale):
+            raise ValueError(f"Path does not exist: {stale}")
+        return Path(value).resolve()
+
+    saved = {"count": 0}
+
+    def fake_save():
+        saved["count"] += 1
+
+    session = SimpleNamespace(session_id="sess-1", workspace=str(stale), save=fake_save)
+
+    monkeypatch.setattr(routes, "resolve_trusted_workspace", fake_resolve)
+    monkeypatch.setattr(routes, "get_last_workspace", lambda: str(fallback))
+
+    resolved = routes._resolve_chat_workspace_with_recovery(session, None)
+
+    assert resolved == str(fallback.resolve())
+    assert session.workspace == str(fallback.resolve())
+    assert saved["count"] == 1
+
+
+def test_resolve_chat_workspace_with_recovery_preserves_explicit_errors(monkeypatch, tmp_path):
+    fallback = tmp_path / "fallback"
+    fallback.mkdir()
+    stale = tmp_path / "deleted-workspace"
+
+    def fake_resolve(value):
+        if value == str(stale):
+            raise ValueError(f"Path does not exist: {stale}")
+        return Path(value).resolve()
+
+    saved = {"count": 0}
+
+    def fake_save():
+        saved["count"] += 1
+
+    session = SimpleNamespace(session_id="sess-2", workspace=str(fallback), save=fake_save)
+
+    monkeypatch.setattr(routes, "resolve_trusted_workspace", fake_resolve)
+    monkeypatch.setattr(routes, "get_last_workspace", lambda: str(fallback))
+
+    with pytest.raises(ValueError, match="Path does not exist"):
+        routes._resolve_chat_workspace_with_recovery(session, str(stale))
+
+    assert session.workspace == str(fallback)
+    assert saved["count"] == 0