diff --git a/.evergreen/install-cli.sh b/.evergreen/install-cli.sh
index 2f72ccf9..f1d5fac1 100755
--- a/.evergreen/install-cli.sh
+++ b/.evergreen/install-cli.sh
@@ -69,7 +69,7 @@ if ! command -V uv &>/dev/null; then
   echo "Installing uv using pip..."
   venvcreate "$DRIVERS_TOOLS_PYTHON" "$_venv_dir"
   # Install uv into the newly created venv.
-  python -m pip install -q --force-reinstall -r requirements-cli.txt
+  python -m pip install -q --force-reinstall uv
   _suffix=""
   # Symlink uv and uvx binaries.
   _install_dir="${DRIVERS_TOOLS}/.bin"
@@ -99,32 +99,40 @@ uv venv venv &>/dev/null
 popd >/dev/null # $SCRIPT_DIR
 pushd "$TARGET_DIR" >/dev/null
 
+# uv requires UV_TOOL_BIN_DIR is `C:\a\b\c` instead of `/cygdrive/c/a/b/c` on Windows.
+if [[ "${OSTYPE:?}" == cygwin ]]; then
+  UV_TOOL_BIN_DIR="$(cygpath -aw .)"
+else
+  UV_TOOL_BIN_DIR="$(pwd)"
+fi
+export UV_TOOL_BIN_DIR
+
+# Pin the uv binary version used by subsequent commands.
+uv tool install -q --force "uv~=0.8.0"
+PATH="${UV_TOOL_BIN_DIR:?}:${PATH:-}"
+command -V uv
+uv --version
+
+# Workaround for https://github.com/astral-sh/uv/issues/5815.
+uv export --quiet --frozen --format requirements.txt -o uv-requirements.txt
+
+# Support overriding lockfile dependencies.
+if [[ ! -f "${DRIVERS_TOOLS_INSTALL_CLI_OVERRIDES:-}" ]]; then
+  printf "" >|"${DRIVERS_TOOLS_INSTALL_CLI_OVERRIDES:="uv-override-dependencies.txt"}"
+fi
+
 declare uv_install_args
 uv_install_args=(
   --quiet
   --force
   --editable
-  --with certifi
+  --with-requirements uv-requirements.txt
+  --overrides "${DRIVERS_TOOLS_INSTALL_CLI_OVERRIDES:?}"
 )
+uv tool install "${uv_install_args[@]:?}" .
 
-# Preserve pymongo compatibility with the requested server version.
-case "${MONGODB_VERSION:-"latest"}" in
-3.6) uv_install_args+=(--with "pymongo<4.11") ;;
-4.0) uv_install_args+=(--with "pymongo<4.14") ;;
-esac
-
-# On Windows, we have to do a bit of path manipulation.
-if [ "Windows_NT" == "${OS:-}" ]; then
-  TMP_DIR=$(cygpath -m "$(mktemp -d)")
-  PATH="$SCRIPT_DIR/venv/Scripts:$PATH"
-  UV_TOOL_BIN_DIR=${TMP_DIR} uv tool install "${uv_install_args[@]:?}" .
-  filenames=$(ls ${TMP_DIR})
-  for filename in $filenames; do
-    mv $TMP_DIR/$filename "$1/${filename//.exe/}"
-  done
-  rm -rf $TMP_DIR
-else
-  UV_TOOL_BIN_DIR=$(pwd) uv tool install "${uv_install_args[@]:?}" .
-fi
+# Support running tool executables on Windows without including the ".exe" suffix.
+find . -maxdepth 1 -type f -name '*.exe' -exec \
+  bash -c "ln -sf \"\$0\" \"\$(echo \"\$0\" | sed -E -e 's|(.*)\.exe|\1|')\"" {} \;
 
 popd >/dev/null # "$TARGET_DIR"
diff --git a/.evergreen/orchestration/pyproject.toml b/.evergreen/orchestration/pyproject.toml
index 8f0fb4a9..482c7d09 100644
--- a/.evergreen/orchestration/pyproject.toml
+++ b/.evergreen/orchestration/pyproject.toml
@@ -6,7 +6,7 @@ build-backend = "hatchling.build"
 name = "drivers-orchestration"
 version = "0.1.0"
 description = 'Scripts for drivers orchestration'
-requires-python = ">=3.8"
+requires-python = ">=3.9"
 license = "MIT"
 keywords = []
 authors = [
diff --git a/.evergreen/orchestration/setup.sh b/.evergreen/orchestration/setup.sh
index 055f2f56..de142734 100755
--- a/.evergreen/orchestration/setup.sh
+++ b/.evergreen/orchestration/setup.sh
@@ -3,10 +3,20 @@
 
 set -o errexit
 
-SCRIPT_DIR=$(dirname ${BASH_SOURCE[0]})
-. $SCRIPT_DIR/../handle-paths.sh
+SCRIPT_DIR="$(dirname "${BASH_SOURCE[0]}")"
+. "${SCRIPT_DIR:?}/../handle-paths.sh"
+
+export DRIVERS_TOOLS_INSTALL_CLI_OVERRIDES
+DRIVERS_TOOLS_INSTALL_CLI_OVERRIDES="${SCRIPT_DIR:?}/uv-override-dependencies.txt"
+printf "" >|"${DRIVERS_TOOLS_INSTALL_CLI_OVERRIDES:?}"
+
+# Preserve pymongo compatibility with the requested server version.
+case "${MONGODB_VERSION:-"latest"}" in
+3.6) echo "pymongo<4.11" >>"${DRIVERS_TOOLS_INSTALL_CLI_OVERRIDES:?}" ;;
+4.0) echo "pymongo<4.14" >>"${DRIVERS_TOOLS_INSTALL_CLI_OVERRIDES:?}" ;;
+esac
 
 # Install CLIs into this directory (default path for $PROJECT_ORCHESTRATION_HOME
 # and $MONGO_ORCHESTRATION_HOME) and the parent directory ($DRIVERS_TOOLS).
-bash $SCRIPT_DIR/../install-cli.sh $SCRIPT_DIR/..
-bash $SCRIPT_DIR/../install-cli.sh $SCRIPT_DIR
+bash "${SCRIPT_DIR:?}/../install-cli.sh" "${SCRIPT_DIR:?}/.."
+bash "${SCRIPT_DIR:?}/../install-cli.sh" "${SCRIPT_DIR:?}"
diff --git a/.evergreen/orchestration/uv.lock b/.evergreen/orchestration/uv.lock
new file mode 100644
index 00000000..db4bdf84
--- /dev/null
+++ b/.evergreen/orchestration/uv.lock
@@ -0,0 +1,282 @@
+version = 1
+revision = 3
+requires-python = ">=3.9"
+
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+version = "0.13.4"
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+name = "certifi"
+version = "2025.8.3"
+source = { registry = "https://pypi.org/simple" }
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diff --git a/.evergreen/requirements-cli.txt b/.evergreen/requirements-cli.txt
deleted file mode 100644
index dc553f86..00000000
--- a/.evergreen/requirements-cli.txt
+++ /dev/null
@@ -1,8 +0,0 @@
-#
-# This file is autogenerated by pip-compile with Python 3.9
-# by the following command:
-#
-#    pip-compile --output-file=requirements-cli.txt requirements-in-cli.txt
-#
-uv==0.7.21
-    # via -r requirements-in-cli.txt
diff --git a/.evergreen/requirements-in-cli.txt b/.evergreen/requirements-in-cli.txt
deleted file mode 100644
index 60cc5e6a..00000000
--- a/.evergreen/requirements-in-cli.txt
+++ /dev/null
@@ -1 +0,0 @@
-uv
diff --git a/.evergreen/uv.lock b/.evergreen/uv.lock
new file mode 100644
index 00000000..89209803
--- /dev/null
+++ b/.evergreen/uv.lock
@@ -0,0 +1,8 @@
+version = 1
+revision = 3
+requires-python = ">=3.9"
+
+[[package]]
+name = "drivers-evergreen-tools"
+version = "0.1.0"
+source = { editable = "." }
diff --git a/.gitignore b/.gitignore
index e71f1a76..92eb0c94 100644
--- a/.gitignore
+++ b/.gitignore
@@ -136,6 +136,8 @@ container_id.txt
 bin
 perf-report.md
 perf-report.txt
+uv-requirements.txt
+uv-override-dependencies.txt
 
 # Azure functions.
 .python_packages/
diff --git a/README.md b/README.md
index a8f78d07..34a326a2 100644
--- a/README.md
+++ b/README.md
@@ -105,6 +105,34 @@ export TLS_PEM_KEY_FILE=<path-to>/server.pem
 export TLS_CA_FILE=<path-to>/ca.pem
 ```
 
+## Updating Dependencies
+
+The MongoDB server management scripts under [`.evergreen/orchestration`](https://github.com/mongodb-labs/drivers-evergreen-tools/tree/master/.evergreen/orchestration)
+depend on [PyMongo](https://pymongo.readthedocs.io/en/stable/). Package dependencies are pinned by the
+[`.evergreen/orchestration/uv.lock`](https://github.com/eramongodb/drivers-evergreen-tools/blob/master/.evergreen/orchestration/uv.lock)
+lockfile. When the lockfile is updated, ensure the updated PyMongo version still supports old server versions which are
+still in use by downstream projects.
+
+If a [recent release](https://pymongo.readthedocs.io/en/stable/changelog.html) of PyMongo drops support for an old
+server version that is still in use by downstream projects, add a dependency override to
+[`.evergreen/orchestration/setup.sh`](https://github.com/mongodb-labs/drivers-evergreen-tools/blob/master/.evergreen/orchestration/setup.sh).
+Otherwise, an error similar to the following may occur during mongo-orchestration operations (e.g. with server 4.0 and
+PyMongo 4.14):
+
+```
+[ERROR] mongo_orchestration.apps:68 - ...
+Traceback (most recent call last):
+  ...
+  File ".../drivers-orchestration/lib/python3.13/site-packages/pymongo/synchronous/topology.py", line 369, in _select_servers_loop
+    self._description.check_compatible()
+    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~^^
+  File ".../drivers-orchestration/lib/python3.13/site-packages/pymongo/topology_description.py", line 168, in check_compatible
+    raise ConfigurationError(self._incompatible_err)
+pymongo.errors.ConfigurationError: Server at localhost:27017 reports wire version 7, but this version of PyMongo requires at least 8 (MongoDB 4.2).
+```
+
+The dependency override may be removed once all downstream projects have also dropped support for the old server version.
+
 ## Linters and Formatters
 
 This repo uses [pre-commit](https://pre-commit.com/) for managing linting and formatting of the codebase.