diff --git a/pyproject.toml b/pyproject.toml
index 4b40271..01715b7 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -37,10 +37,16 @@ dependencies = [
 dev = [
   "coverage[toml]>=7.6,<8.0",
   "mypy>=1.10,<2.0",
+  # pip and uv must stay declared here: ./scripts/uv requires .venv/bin/uv and
+  # ./scripts/bootstrap.sh requires .venv/bin/pip, but `uv sync` makes the venv
+  # exactly match the lockfile (and recreates it on interpreter upgrades) —
+  # undeclared, both binaries vanish and the bootstrap chain breaks.
+  "pip>=24.0,<26.0",
   "pre-commit>=4.0,<5.0",
   "pytest>=8.3,<9.0",
   "pytest-asyncio>=0.24,<1.0",
   "ruff>=0.6,<1.0",
+  "uv>=0.4,<1.0",
 ]
 
 [project.scripts]
diff --git a/scripts/bootstrap.sh b/scripts/bootstrap.sh
index 3a05585..cda6263 100755
--- a/scripts/bootstrap.sh
+++ b/scripts/bootstrap.sh
@@ -144,6 +144,11 @@ PYTHON_BIN="$(find_python_312)"
 
 if [[ ! -d "${VENV_DIR}" ]]; then
   "${PYTHON_BIN}" -m venv "${VENV_DIR}"
+elif [[ ! -x "${PIP_BIN}" && ! -x "${UV_BIN}" ]]; then
+  # A uv-recreated venv (e.g. after a Homebrew Python upgrade) contains
+  # neither pip nor uv; rebuild it so the pip -> uv -> sync chain below works.
+  echo "Existing .venv has neither pip nor uv; rebuilding it." >&2
+  "${PYTHON_BIN}" -m venv --clear "${VENV_DIR}"
 fi
 
 if [[ ! -x "${UV_BIN}" ]]; then
diff --git a/tests/test_dev_env_contract.py b/tests/test_dev_env_contract.py
new file mode 100644
index 0000000..e088cc8
--- /dev/null
+++ b/tests/test_dev_env_contract.py
@@ -0,0 +1,26 @@
+"""Contract: the bootstrap chain depends on uv and pip living inside .venv.
+
+``uv sync`` makes the environment exactly match the lockfile, and uv
+recreates the venv outright when the base interpreter changes (e.g. a
+Homebrew Python upgrade). If ``uv`` and ``pip`` are not declared dev
+dependencies they vanish on the next sync or recreation, breaking
+``./scripts/uv`` (which requires ``.venv/bin/uv``) and
+``./scripts/bootstrap.sh`` (which uses ``.venv/bin/pip`` to install uv).
+"""
+
+from __future__ import annotations
+
+import re
+import tomllib
+from pathlib import Path
+
+_PYPROJECT = Path(__file__).resolve().parent.parent / "pyproject.toml"
+
+
+def test_dev_extras_pin_uv_and_pip_for_the_bootstrap_chain() -> None:
+    with open(_PYPROJECT, "rb") as handle:
+        data = tomllib.load(handle)
+    dev = data["project"]["optional-dependencies"]["dev"]
+    names = {re.split(r"[><=\[ ]", item, maxsplit=1)[0] for item in dev}
+    assert "uv" in names, "uv must stay a dev dependency or syncs strip .venv/bin/uv"
+    assert "pip" in names, "pip must stay a dev dependency or bootstrap.sh cannot recover"
diff --git a/uv.lock b/uv.lock
index 34982e4..661981d 100644
--- a/uv.lock
+++ b/uv.lock
@@ -162,10 +162,12 @@ dependencies = [
 dev = [
     { name = "coverage" },
     { name = "mypy" },
+    { name = "pip" },
     { name = "pre-commit" },
     { name = "pytest" },
     { name = "pytest-asyncio" },
     { name = "ruff" },
+    { name = "uv" },
 ]
 
 [package.metadata]
@@ -175,6 +177,7 @@ requires-dist = [
     { name = "keyring", specifier = ">=25.5,<26.0" },
     { name = "mypy", marker = "extra == 'dev'", specifier = ">=1.10,<2.0" },
     { name = "pathspec", specifier = ">=1.0,<2.0" },
+    { name = "pip", marker = "extra == 'dev'", specifier = ">=24.0,<26.0" },
     { name = "pre-commit", marker = "extra == 'dev'", specifier = ">=4.0,<5.0" },
     { name = "prompt-toolkit", specifier = ">=3.0,<4.0" },
     { name = "pydantic", specifier = ">=2.10,<3.0" },
@@ -184,6 +187,7 @@ requires-dist = [
     { name = "rich", specifier = ">=13.7,<14.0" },
     { name = "ruff", marker = "extra == 'dev'", specifier = ">=0.6,<1.0" },
     { name = "typer", specifier = ">=0.12,<1.0" },
+    { name = "uv", marker = "extra == 'dev'", specifier = ">=0.4,<1.0" },
 ]
 provides-extras = ["dev"]
 
@@ -373,6 +377,15 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/ef/3c/2c197d226f9ea224a9ab8d197933f9da0ae0aac5b6e0f884e2b8d9c8e9f7/pathspec-1.0.4-py3-none-any.whl", hash = "sha256:fb6ae2fd4e7c921a165808a552060e722767cfa526f99ca5156ed2ce45a5c723", size = 55206, upload-time = "2026-01-27T03:59:45.137Z" },
 ]
 
+[[package]]
+name = "pip"
+version = "25.3"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/fe/6e/74a3f0179a4a73a53d66ce57fdb4de0080a8baa1de0063de206d6167acc2/pip-25.3.tar.gz", hash = "sha256:8d0538dbbd7babbd207f261ed969c65de439f6bc9e5dbd3b3b9a77f25d95f343", size = 1803014, upload-time = "2025-10-25T00:55:41.394Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/44/3c/d717024885424591d5376220b5e836c2d5293ce2011523c9de23ff7bf068/pip-25.3-py3-none-any.whl", hash = "sha256:9655943313a94722b7774661c21049070f6bbb0a1516bf02f7c8d5d9201514cd", size = 1778622, upload-time = "2025-10-25T00:55:39.247Z" },
+]
+
 [[package]]
 name = "platformdirs"
 version = "4.9.4"
@@ -668,6 +681,32 @@ wheels = [
     { url = "https://files.pythonhosted.org/packages/dc/9b/47798a6c91d8bdb567fe2698fe81e0c6b7cb7ef4d13da4114b41d239f65d/typing_inspection-0.4.2-py3-none-any.whl", hash = "sha256:4ed1cacbdc298c220f1bd249ed5287caa16f34d44ef4e9c3d0cbad5b521545e7", size = 14611, upload-time = "2025-10-01T02:14:40.154Z" },
 ]
 
+[[package]]
+name = "uv"
+version = "0.11.20"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/80/09/c29c0b90bc9308cfa6f5d77ce9b38ce97852210fda17d79019c7bcf9c3a1/uv-0.11.20.tar.gz", hash = "sha256:a246f30931cbc93d0a39d0cfc75be045fddd45773a734ddf8afa869aabc46c63", size = 4237464, upload-time = "2026-06-10T17:20:05.905Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/6b/8a/25fc4d94ad3896e636466ee1fb03c4077f7a151c19cb25c1e6a731fa9cbf/uv-0.11.20-py3-none-linux_armv6l.whl", hash = "sha256:f867fd0807e39653fd101e16f2292ff488de14b5ffbb86a5678a87a27aa58ea0", size = 23713010, upload-time = "2026-06-10T17:19:32.058Z" },
+    { url = "https://files.pythonhosted.org/packages/02/7d/bbaad5f0c616f7824149a4ac0271db14107b859b36bd75d16db1486c495f/uv-0.11.20-py3-none-macosx_10_12_x86_64.whl", hash = "sha256:f3bacc52778775cef671867ddab744b50c4183bc3cd6419a5fb4eb01a02f9526", size = 22918378, upload-time = "2026-06-10T17:19:20.828Z" },
+    { url = "https://files.pythonhosted.org/packages/39/3e/e3d39361b95c262b43ccfe260f41184da71c536a08f39d4ad59ab962e459/uv-0.11.20-py3-none-macosx_11_0_arm64.whl", hash = "sha256:c9f2062096e146b351fd5da3cd43e15a5c43bfa37166c509d884dab3dbb72f03", size = 21716975, upload-time = "2026-06-10T17:19:51.552Z" },
+    { url = "https://files.pythonhosted.org/packages/24/30/9031204d7b592d1595322d7506944793728a74795a8c4a3c38bc4a8985f0/uv-0.11.20-py3-none-manylinux_2_17_aarch64.manylinux2014_aarch64.musllinux_1_1_aarch64.whl", hash = "sha256:8fe143572a1f02d536c4e9c6994f0c89d9fa58ff6e5d91de55f61660658c694b", size = 23571826, upload-time = "2026-06-10T17:19:46.206Z" },
+    { url = "https://files.pythonhosted.org/packages/98/c3/7f9f00c7a152e67d59ae5f25635d19ac4252929dd6ac454cdb1dee3119fa/uv-0.11.20-py3-none-manylinux_2_17_armv7l.manylinux2014_armv7l.musllinux_1_1_armv7l.whl", hash = "sha256:3d00754be09a381030829526f7ff47c06d0e28ca90760c4439be48e71c1bf13a", size = 23249218, upload-time = "2026-06-10T17:19:26.603Z" },
+    { url = "https://files.pythonhosted.org/packages/35/a9/1ce58670a89c25d4a8b84532207183b5a97b3623d9b9151afe641499fbc8/uv-0.11.20-py3-none-manylinux_2_17_armv7l.manylinux2014_armv7l.whl", hash = "sha256:edb59d33e602fc462b6ed8fde66d404445294de41ad4de31039f7a2c41153601", size = 23302149, upload-time = "2026-06-10T17:20:01.111Z" },
+    { url = "https://files.pythonhosted.org/packages/61/cf/3a498a315364f906bd655a94fa6b5f74f5240dc90875d6ab67ef28c081ec/uv-0.11.20-py3-none-manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:14026b64ccbe0174e4fcf107f585f5d23f0f5b9f5b3e8b28394fe63fff3e60ff", size = 24652804, upload-time = "2026-06-10T17:19:16.692Z" },
+    { url = "https://files.pythonhosted.org/packages/ff/8c/68e4a805e3b49d834e95b3838e53a623d2e0ad956bb44e681ece54b3308b/uv-0.11.20-py3-none-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:73dcaf5543d1b24e4c6fa4c19af033ed015304171c132670ebe9ef01ddec3d17", size = 25660209, upload-time = "2026-06-10T17:20:08.156Z" },
+    { url = "https://files.pythonhosted.org/packages/a6/de/e8e205a79b9a39454c5da5c2695e4911a42860a4404739e32802e599af0c/uv-0.11.20-py3-none-manylinux_2_17_s390x.manylinux2014_s390x.whl", hash = "sha256:cac8ca5d187dc5040b1c22c83f6ed789195c3fc06b6a5a2b32c747c603f07820", size = 24866467, upload-time = "2026-06-10T17:19:37.981Z" },
+    { url = "https://files.pythonhosted.org/packages/7e/38/f844d125db277d8ce0c921f0219078d292d0ee72d314d0c12f4cf510aa40/uv-0.11.20-py3-none-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:61588768f04a24b0b4d87b43f03b4521ba66d5eec3ab1aca37cb59b1d52337db", size = 24957448, upload-time = "2026-06-10T17:19:40.979Z" },
+    { url = "https://files.pythonhosted.org/packages/ab/7d/b0e28abfa41c424d2a3df83be2b00b2fbe3ad5795baf7361262c6d800a62/uv-0.11.20-py3-none-manylinux_2_28_aarch64.whl", hash = "sha256:2d307d47b1a0cf8f76aa69bde850be407bca9482c13cff066142e586a5c57e77", size = 23671087, upload-time = "2026-06-10T17:19:54.595Z" },
+    { url = "https://files.pythonhosted.org/packages/80/ff/92bce88101ce61d708e888db6ab7f5ebf4ccd61f54d3316e7e48a4be56a5/uv-0.11.20-py3-none-manylinux_2_31_riscv64.musllinux_1_1_riscv64.whl", hash = "sha256:bb5839cbb68d7469925fe1599dacd16cefdb7698a7adeaf9c8e4d8a7cd4122bf", size = 24324677, upload-time = "2026-06-10T17:19:43.534Z" },
+    { url = "https://files.pythonhosted.org/packages/0f/90/d308bd88c7a53cae93f7fe13ce5c621895b8fb94e37911660a3de7283b67/uv-0.11.20-py3-none-manylinux_2_31_riscv64.whl", hash = "sha256:efefbd491ba443b326fdd344d7efc89c1de8a006cab5bc639a4d5ce9d1dd1ab9", size = 24429959, upload-time = "2026-06-10T17:19:29.352Z" },
+    { url = "https://files.pythonhosted.org/packages/e5/e6/b87c941b93b61dceaa11f4f8d02760de7aa7d1c58ea24a2298e7c5aafb4f/uv-0.11.20-py3-none-musllinux_1_1_i686.whl", hash = "sha256:daa41b97386699212b2266a80c178140c5396e3c444ff5553f68f79812334e41", size = 23880515, upload-time = "2026-06-10T17:19:23.733Z" },
+    { url = "https://files.pythonhosted.org/packages/53/ab/11b07641f8387177889f4341a36318561208c18703837bc47163244aa11b/uv-0.11.20-py3-none-musllinux_1_1_x86_64.whl", hash = "sha256:37ca61eddb940d1c698fce46d63789adfda3033344dabab0e18e2958e1a69771", size = 25171603, upload-time = "2026-06-10T17:19:34.848Z" },
+    { url = "https://files.pythonhosted.org/packages/b4/7d/62af57509c7007600ce11cd5222b2cb84d5cd8f80f427a499d1b44ef3601/uv-0.11.20-py3-none-win32.whl", hash = "sha256:32893ee9f94657fbf89e22638ac88850db4529d454f102bfa7ceea5fc9fe8d77", size = 22570328, upload-time = "2026-06-10T17:19:48.808Z" },
+    { url = "https://files.pythonhosted.org/packages/66/35/c9ee48cdce11f5cdac9e2be41a5446bae7382cde18d2ce1050bcd81dc05a/uv-0.11.20-py3-none-win_amd64.whl", hash = "sha256:4836044213bb23a3be1f5550db340d3a19babe1dfc3ca1313544e8b614085ce9", size = 25228859, upload-time = "2026-06-10T17:19:57.824Z" },
+    { url = "https://files.pythonhosted.org/packages/8b/8d/00a382c2f8f44b328cf98f734a3fcd72957698c30bed2392bd241b573384/uv-0.11.20-py3-none-win_arm64.whl", hash = "sha256:442ae26f47bf6e58b072e99dbfd6d5296ab90308574b2c02adff1dace051008d", size = 23664943, upload-time = "2026-06-10T17:20:03.774Z" },
+]
+
 [[package]]
 name = "virtualenv"
 version = "21.2.0"