diff --git a/tests/tui_gateway/test_projects_rpc.py b/tests/tui_gateway/test_projects_rpc.py
index 9e1a6f5256..1cd5a320c2 100644
--- a/tests/tui_gateway/test_projects_rpc.py
+++ b/tests/tui_gateway/test_projects_rpc.py
@@ -5,6 +5,7 @@ from __future__ import annotations
 import contextlib
 import os
 import subprocess
+import threading
 from pathlib import Path
 
 import pytest
@@ -511,6 +512,51 @@ def test_explicit_desktop_and_terminal_cwds_are_context_workspaces():
     ) is False
 
 
+@pytest.mark.parametrize(
+    ("explicit_cwd", "launch_artifact"),
+    [(True, False), (False, True)],
+)
+def test_desktop_agent_rebuild_preserves_workspace_provenance(
+    monkeypatch, explicit_cwd, launch_artifact
+):
+    captured = {}
+    session = {
+        "agent": object(),
+        "attached_images": [],
+        "cwd": "/picked/repo" if explicit_cwd else "/opt/hermes",
+        "edit_snapshots": {},
+        "explicit_cwd": explicit_cwd,
+        "history": ["old"],
+        "history_lock": threading.Lock(),
+        "history_version": 0,
+        "image_counter": 0,
+        "running": False,
+        "session_key": "stored-session",
+        "show_reasoning": False,
+        "source": "desktop",
+        "tool_progress_mode": "off",
+        "tool_started_at": {},
+    }
+
+    def _make_agent(*_args, **kwargs):
+        captured.update(kwargs)
+        return object()
+
+    monkeypatch.setattr(server, "_set_session_context", lambda _key: [])
+    monkeypatch.setattr(server, "_clear_session_context", lambda _tokens: None)
+    monkeypatch.setattr(server, "_make_agent", _make_agent)
+    monkeypatch.setattr(server, "_config_model_target", lambda: None)
+    monkeypatch.setattr(server, "_load_show_reasoning", lambda: False)
+    monkeypatch.setattr(server, "_load_tool_progress_mode", lambda: "off")
+    monkeypatch.setattr(server, "_session_info", lambda *_args: {})
+    monkeypatch.setattr(server, "_emit", lambda *_args: None)
+    monkeypatch.setattr(server, "_restart_slash_worker", lambda *_args: None)
+
+    server._reset_session_agent("live-session", session)
+
+    assert captured["context_cwd_is_launch_artifact"] is launch_artifact
+
+
 def test_home_container_dirs_are_never_a_workspace(tmp_path):
     """`/home` and `/Users` hold homes; they are not workspaces themselves.
 
diff --git a/tests/tui_gateway/test_session_db_ownership_teardown.py b/tests/tui_gateway/test_session_db_ownership_teardown.py
index 766629a7a0..c3cb310c11 100644
--- a/tests/tui_gateway/test_session_db_ownership_teardown.py
+++ b/tests/tui_gateway/test_session_db_ownership_teardown.py
@@ -368,6 +368,34 @@ def test_deferred_build_transfers_the_handle_on_success(
     assert session["agent"]._owns_session_db is True
 
 
+def test_deferred_build_uses_the_preserved_desktop_workspace_provenance(
+    build_env, registered, monkeypatch
+):
+    captured: dict = {}
+
+    def _fake_make_agent(*_args, session_db=None, **kwargs):
+        captured.update(kwargs)
+        return types.SimpleNamespace(_session_db=session_db, _owns_session_db=False)
+
+    monkeypatch.setattr(server, "_make_agent", _fake_make_agent)
+    monkeypatch.setattr(
+        server, "_session_source", lambda current: current.get("source")
+    )
+    sid, session = "sid-workspace", _session(build_env.profile_home)
+    session.update(
+        {
+            "cwd": "C:/picked/repo",
+            "explicit_cwd": True,
+            "source": "desktop",
+        }
+    )
+    registered(sid, session)
+
+    _run_build(sid, session)
+
+    assert captured["context_cwd_is_launch_artifact"] is False
+
+
 def test_deferred_build_closes_the_handle_when_the_session_is_reaped_midbuild(
     build_env, registered, monkeypatch
 ):
diff --git a/tests/tui_gateway/test_session_resume_db_ownership.py b/tests/tui_gateway/test_session_resume_db_ownership.py
index e1cdf63927..e14d79a031 100644
--- a/tests/tui_gateway/test_session_resume_db_ownership.py
+++ b/tests/tui_gateway/test_session_resume_db_ownership.py
@@ -134,6 +134,28 @@ def test_resume_closes_profile_db_when_session_not_found(profile_dbs):
     assert scoped[0].closed == 1
 
 
+def test_deferred_desktop_resume_keeps_stored_workspace_provenance(
+    profile_dbs, monkeypatch, tmp_path
+):
+    workspace = tmp_path / "workspace"
+    workspace.mkdir()
+
+    def _factory(db_path=None, **kwargs):
+        db = _RecordingDB(db_path=db_path, **kwargs)
+        db.rows["s1"] = {"id": "s1", "cwd": str(workspace)}
+        profile_dbs.append(db)
+        return db
+
+    monkeypatch.setattr("hermes_state.SessionDB", _factory)
+
+    resp = _resume(session_id="s1", profile="work", source="desktop")
+    session = server._sessions[resp["result"]["session_id"]]
+
+    assert session["cwd"] == str(workspace)
+    assert session["explicit_cwd"] is True
+    assert server._context_cwd_is_launch_artifact(session) is False
+
+
 def test_resume_closes_profile_db_when_reopen_fails(profile_dbs, monkeypatch):
     """The 'resume failed' early return must not leak the handle."""
 
diff --git a/tui_gateway/methods_session.py b/tui_gateway/methods_session.py
index 8b32c05188..485456a87f 100644
--- a/tui_gateway/methods_session.py
+++ b/tui_gateway/methods_session.py
@@ -689,6 +689,7 @@ def _(rid, params: dict) -> dict:
                 profile_home=profile_home,
                 lazy=True,
                 todo_state=_todo_state_from_history(history),
+                explicit_cwd=bool(profile_resume_cwd),
             )
             if (live := _claim_or_reuse_live(sid, target, record, lease)) is not None:
                 return _reuse_live_response(*live)
@@ -760,6 +761,7 @@ def _(rid, params: dict) -> dict:
                 profile_home=profile_home,
                 model_override=overrides.get("model_override"),
                 resume_runtime_overrides=overrides or None,
+                explicit_cwd=bool(profile_resume_cwd),
             )
             record["resume_history_ready"] = threading.Event()
             record["resume_hydrating"] = True
@@ -860,6 +862,7 @@ def _(rid, params: dict) -> dict:
                 model_override=overrides.get("model_override"),
                 resume_runtime_overrides=overrides or None,
                 todo_state=_todo_state_from_history(history),
+                explicit_cwd=bool(profile_resume_cwd),
             )
             if (live := _claim_or_reuse_live(sid, target, record, lease)) is not None:
                 return _reuse_live_response(*live)
@@ -998,6 +1001,7 @@ def _(rid, params: dict) -> dict:
                         cwd=profile_resume_cwd,
                         session_db=db,
                         source=source,
+                        explicit_cwd=bool(profile_resume_cwd),
                     )
                     # Ownership TRANSFER — the registered session's agent now
                     # holds this handle for its whole life, and _init_session
@@ -3324,6 +3328,7 @@ def _(rid, params: dict) -> dict:
                 session_db=branch_db,
                 source=source,
                 profile_home=parent_home,
+                explicit_cwd=bool(session.get("explicit_cwd")),
             )
             # Ownership TRANSFER — the branched session's agent holds this
             # handle for its whole life and closes it on teardown. Drop is
diff --git a/tui_gateway/server.py b/tui_gateway/server.py
index 106f8d1fde..d10ff2c865 100644
--- a/tui_gateway/server.py
+++ b/tui_gateway/server.py
@@ -3221,7 +3221,12 @@ def _start_agent_build(sid: str, session: dict) -> None:
                 # Lazy-resumed (watch) sessions carry the stored conversation
                 # id — pass it through so the upgrade continues that session
                 # instead of starting a fresh one under the same key.
-                kw = {"session_db": session_db}
+                kw = {
+                    "session_db": session_db,
+                    "context_cwd_is_launch_artifact": (
+                        _context_cwd_is_launch_artifact(current)
+                    ),
+                }
                 if resume_sid := current.get("resume_session_id"):
                     kw["session_id"] = resume_sid
                 kw["platform_override"] = _session_source(current)
@@ -8672,6 +8677,9 @@ def _reset_session_agent(sid: str, session: dict) -> dict:
             session["session_key"],
             session_id=session["session_key"],
             platform_override=_session_source(session),
+            context_cwd_is_launch_artifact=(
+                _context_cwd_is_launch_artifact(session)
+            ),
         )
     finally:
         _clear_session_context(tokens)
@@ -9041,6 +9049,7 @@ def _init_session(
     session_db=None,
     source: str | None = None,
     profile_home: str | None = None,
+    explicit_cwd: bool = False,
 ):
     now = time.time()
     with _sessions_lock:
@@ -9057,6 +9066,7 @@ def _init_session(
             "attached_images": [],
             "image_counter": 0,
             "cwd": cwd or _completion_cwd(),
+            "explicit_cwd": bool(explicit_cwd),
             "cols": cols,
             "slash_worker": None,
             "show_reasoning": _load_show_reasoning(),
@@ -10462,6 +10472,7 @@ def _deferred_session_record(
     model_override=None,
     resume_runtime_overrides: dict | None = None,
     todo_state: dict | None = None,
+    explicit_cwd: bool = False,
 ) -> dict:
     """A live-session record whose AIAgent is built later (lazy watch / cold
     resume) — _init_session's shape minus the agent."""
@@ -10478,7 +10489,7 @@ def _deferred_session_record(
         "cwd": cwd,
         "display_history_prefix": display_history_prefix or [],
         "edit_snapshots": {},
-        "explicit_cwd": False,
+        "explicit_cwd": bool(explicit_cwd),
         "history": history,
         "history_lock": threading.Lock(),
         "history_version": 0,