diff --git a/devenv/checks/test.py b/.devenv/checks/test.py
similarity index 100%
rename from devenv/checks/test.py
rename to .devenv/checks/test.py
diff --git a/.github/workflows/bootstrap.yml b/.github/workflows/bootstrap.yml
index 017bcef3..fb82c496 100644
--- a/.github/workflows/bootstrap.yml
+++ b/.github/workflows/bootstrap.yml
@@ -22,7 +22,7 @@ jobs:
     runs-on: ubuntu-22.04
     timeout-minutes: 60
     env:
-      SENTRY_BRANCH: master
+      SENTRY_BRANCH: upgrade-devenv
       SNTY_DEVENV_BRANCH:
         "${{ github.event.pull_request && github.head_ref || github.ref_name }}"
     steps:
@@ -42,11 +42,11 @@ jobs:
   bootstrap-macos-13:
     # This job takes half an hour and costs a lot of money.
     # Let's just run on main commits.
-    if: ${{ github.ref == 'refs/heads/main' }}
+    # if: ${{ github.ref == 'refs/heads/main' }}
     runs-on: macos-13
     timeout-minutes: 60
     env:
-      SENTRY_BRANCH: master
+      SENTRY_BRANCH: upgrade-devenv
       SNTY_DEVENV_BRANCH:
         "${{ github.event.pull_request && github.head_ref || github.ref_name }}"
     steps:
diff --git a/devenv/doctor.py b/devenv/doctor.py
index ee7f2e3c..d0e5e728 100644
--- a/devenv/doctor.py
+++ b/devenv/doctor.py
@@ -74,16 +74,13 @@ def __init__(self, module: ModuleType):
         super().__init__()
 
 
-def load_checks(context: Dict[str, str], match_tags: set[str]) -> List[Check]:
+def load_checks(from_dir: str, match_tags: set[str]) -> List[Check]:
     """
-    Load all checks from the checks directory.
-    Optionally filter by tags.
+    Load checks from a dir and optionally filter by tags.
     If a check doesn't have the required attributes, skip it.
     """
     checks: list[Check] = []
-    for module_finder, module_name, _ in walk_packages(
-        (f'{context["reporoot"]}/devenv/checks',)
-    ):
+    for module_finder, module_name, _ in walk_packages((from_dir,)):
         module_spec = module_finder.find_spec(module_name, None)
 
         # it "should be" impossible to fail these:
@@ -173,12 +170,8 @@ def main(context: Dict[str, str], argv: Sequence[str] | None = None) -> int:
 
     match_tags: set[str] = set(args.tag if args.tag else ())
 
-    repo = context["repo"]
-    if repo not in {"sentry", "getsentry", "devenv"}:
-        print(f"repo {repo} not supported yet!")
-        return 1
-
-    checks = load_checks(context, match_tags)
+    checks_dir = f'{context["reporoot"]}/.devenv/checks'
+    checks = load_checks(checks_dir, match_tags)
 
     if not checks:
         print(f"No checks found for tags: {args.tag}")
diff --git a/devenv/lib/config.py b/devenv/lib/config.py
index ca2f0c48..976a4799 100644
--- a/devenv/lib/config.py
+++ b/devenv/lib/config.py
@@ -10,7 +10,7 @@
 @functools.lru_cache(maxsize=None)
 def get_repo(reporoot: str) -> configparser.ConfigParser:
     config = configparser.ConfigParser()
-    config.read(f"{reporoot}/devenv/config.ini")
+    config.read(f"{reporoot}/.devenv/config.ini")
     return config
 
 
diff --git a/devenv/sync.py b/devenv/sync.py
index e8c5898a..60661d12 100644
--- a/devenv/sync.py
+++ b/devenv/sync.py
@@ -12,12 +12,12 @@
 def main(context: Dict[str, str], argv: Sequence[str] | None = None) -> int:
     reporoot = context["reporoot"]
 
-    if not os.path.exists(f"{reporoot}/devenv/sync.py"):
-        print(f"{reporoot}/devenv/sync.py not found!")
+    if not os.path.exists(f"{reporoot}/.devenv/sync.py"):
+        print(f"{reporoot}/.devenv/sync.py not found!")
         return 1
 
     spec = importlib.util.spec_from_file_location(
-        "sync", f"{reporoot}/devenv/sync.py"
+        "sync", f"{reporoot}/.devenv/sync.py"
     )
     module = importlib.util.module_from_spec(spec)  # type: ignore
     spec.loader.exec_module(module)  # type: ignore
diff --git a/tests/doctor/test_load_checks.py b/tests/doctor/test_load_checks.py
index e2b8ae85..d3a7a0af 100644
--- a/tests/doctor/test_load_checks.py
+++ b/tests/doctor/test_load_checks.py
@@ -6,15 +6,15 @@
 
 from devenv import doctor
 
+here = os.path.join(os.path.dirname(__file__))
+
 
 def test_load_checks_no_checks() -> None:
-    assert doctor.load_checks({"reporoot": "not a real path"}, set()) == []
+    assert doctor.load_checks(here, set()) == []
 
 
 def test_load_checks_test_checks(capsys: pytest.CaptureFixture[str]) -> None:
-    loaded_checks = doctor.load_checks(
-        {"reporoot": os.path.join(os.path.dirname(__file__))}, set()
-    )
+    loaded_checks = doctor.load_checks(f"{here}/devenv/checks", set())
     loaded_check_names = [check.name for check in loaded_checks]
     assert len(loaded_check_names) == 5
     assert "passing check" in loaded_check_names
@@ -34,18 +34,14 @@ def test_load_checks_test_checks(capsys: pytest.CaptureFixture[str]) -> None:
 
 
 def test_load_checks_only_passing_tag() -> None:
-    loaded_checks = doctor.load_checks(
-        {"reporoot": os.path.join(os.path.dirname(__file__))}, {"pass"}
-    )
+    loaded_checks = doctor.load_checks(f"{here}/devenv/checks", {"pass"})
     loaded_check_names = [check.name for check in loaded_checks]
     assert len(loaded_check_names) == 1
     assert "passing check" in loaded_check_names
 
 
 def test_load_checks_only_failing_tag() -> None:
-    loaded_checks = doctor.load_checks(
-        {"reporoot": os.path.join(os.path.dirname(__file__))}, {"fail"}
-    )
+    loaded_checks = doctor.load_checks(f"{here}/devenv/checks", {"fail"})
     loaded_check_names = [check.name for check in loaded_checks]
     assert len(loaded_check_names) == 2
     assert "failing check" in loaded_check_names
@@ -54,16 +50,14 @@ def test_load_checks_only_failing_tag() -> None:
 
 def test_load_checks_passing_and_failing_tag() -> None:
     loaded_checks = doctor.load_checks(
-        {"reporoot": os.path.join(os.path.dirname(__file__))}, {"pass", "fail"}
+        f"{here}/devenv/checks", {"pass", "fail"}
     )
     loaded_check_names = [check.name for check in loaded_checks]
     assert len(loaded_check_names) == 0
 
 
 def test_load_checks_test_tag() -> None:
-    loaded_checks = doctor.load_checks(
-        {"reporoot": os.path.join(os.path.dirname(__file__))}, {"test"}
-    )
+    loaded_checks = doctor.load_checks(f"{here}/devenv/checks", {"test"})
     loaded_check_names = [check.name for check in loaded_checks]
     assert len(loaded_check_names) == 5
     assert "passing check" in loaded_check_names
diff --git a/tests/lib/test_venv.py b/tests/lib/test_venv.py
index 12e32444..43b12707 100644
--- a/tests/lib/test_venv.py
+++ b/tests/lib/test_venv.py
@@ -35,8 +35,8 @@
 
 def test_get_ensure(tmp_path: pathlib.Path) -> None:
     reporoot = f"{tmp_path}/ops"
-    os.makedirs(f"{reporoot}/devenv")
-    with open(f"{reporoot}/devenv/config.ini", "w") as f:
+    os.makedirs(f"{reporoot}/.devenv")
+    with open(f"{reporoot}/.devenv/config.ini", "w") as f:
         f.write(mock_config)
 
     venv_dir, python_version, requirements, editable_paths, bins = venv.get(