From e5cac812fa15a4b50bc10bbb1ca8e826af59767a Mon Sep 17 00:00:00 2001
From: Corey Weathers <corey.weathers@deepgram.com>
Date: Fri, 9 Oct 2026 09:40:45 -0400
Subject: [PATCH] test(core): expect E44 on Windows when a refresh lands over
 0.3.x

#126 asserted that landing new skill folders over a record written by deepctl 0.3.x
prints nothing. #130 made Windows skip the 0.3.x cleanup and print E44
once. Each passed on its own branch; together on main every Windows job
fails. The test now has three named cases: native, forced-windows (the
Windows branch on POSIX, skipped on Windows where native already is), and
removed. The Windows branch expects one E44 for the recorded path, the
POSIX branch silence, and both assert that the 0.3.x path leaves the
record, the v03 flag is cleared, and a second refresh prints nothing
(on Windows a stale path would print E44 again). Both sides of the E44
match normalize whitespace so a console wrap cannot split them. The
comment names deepctl as the actor: the cleanup runs after any tool's
folders land, from dg skills, dg login and dg plugin.
---
 .../tests/unit/test_skill_generator.py        | 46 +++++++++++++++----
 1 file changed, 38 insertions(+), 8 deletions(-)

diff --git a/packages/deepctl-core/tests/unit/test_skill_generator.py b/packages/deepctl-core/tests/unit/test_skill_generator.py
index d2eaa96..cb41210 100644
--- a/packages/deepctl-core/tests/unit/test_skill_generator.py
+++ b/packages/deepctl-core/tests/unit/test_skill_generator.py
@@ -3045,29 +3045,59 @@ def test_fresh_install_ignores_the_records(self, tmp_path, monkeypatch, capsys):
         assert disk_state()["skill_folders"]["claude"]["skills_ref"] == "x"
         assert capsys.readouterr().err == ""
 
-    @pytest.mark.parametrize("removed", [False, True])
+    @pytest.mark.parametrize(
+        ("removed", "windows"),
+        [
+            pytest.param(False, False, id="native"),
+            pytest.param(
+                False,
+                True,
+                id="forced-windows",
+                marks=pytest.mark.skipif(
+                    os.name == "nt", reason="the native case already covers Windows"
+                ),
+            ),
+            pytest.param(True, False, id="removed"),
+        ],
+    )
     def test_03x_only_tool_still_gets_folders_on_refresh(
-        self, tmp_path, monkeypatch, capsys, removed
+        self, tmp_path, monkeypatch, capsys, removed, windows
     ):
+        # Run the Windows branch on POSIX too; never force the POSIX branch on Windows.
+        if windows:
+            monkeypatch.setattr(sg, "_WINDOWS", True)
         legacy = {"paths": [str(tmp_path / "legacy" / "deepgram.md")]}
         write_state({"installed_skills": {"claude": legacy}, "auto_update": True})
 
         def remove():
             write_state({"installed_skills": {}, "auto_update": True})
 
+        plan = [(gen("claude"), REF)]
         done = self._refresh(
-            monkeypatch,
-            make_bundle(tmp_path),
-            remove if removed else None,
-            plan=[(gen("claude"), REF)],
+            monkeypatch, make_bundle(tmp_path), remove if removed else None, plan=plan
         )
         _, err = capsys.readouterr()
         if removed:
             assert done == [] and not root().exists()
             assert err.count(_msg("E31", gen("claude"))) == 1
         else:
-            assert done == [("claude", 2)] and err == ""
-            assert disk_state()["skill_folders"]["claude"]["skills_ref"] == REF
+            assert done == [("claude", 2)]
+            if sg._WINDOWS:
+                # On Windows, deepctl leaves 0.3.x files alone and prints E44 once.
+                # Both sides normalize whitespace so a wrap cannot split the match.
+                e44 = " ".join(_msg("E44", paths=legacy["paths"][0]).split())
+                assert " ".join(err.split()).count(e44) == 1
+            else:
+                assert err == ""
+            state = disk_state()
+            assert state["skill_folders"]["claude"]["skills_ref"] == REF
+            # The 0.3.x path leaves the record; on Windows a stale one reprints E44.
+            assert state["installed_skills"]["claude"]["paths"] == [
+                str(root() / n) for n in ("api", "docs")
+            ]
+            assert "v03" not in state["skill_folders"]["claude"]
+            again = self._refresh(monkeypatch, make_bundle(tmp_path), plan=plan)
+            assert again == [("claude", 2)] and capsys.readouterr().err == ""
 
     def test_refresh_never_overwrites_a_newer_copy_of_the_same_ref(
         self, tmp_path, monkeypatch, capsys