diff --git a/docs/upgrade.md b/docs/upgrade.md
index 943d9f41a1..8de9a81e9f 100644
--- a/docs/upgrade.md
+++ b/docs/upgrade.md
@@ -43,7 +43,7 @@ specify self upgrade
 specify self upgrade --tag vX.Y.Z[suffix]
 ```
 
-Bare `specify self upgrade` executes immediately, matching the no-prompt behavior of commands like `pip install -U` and `npm update`. The CLI classifies your runtime into one of: `uv tool`, `pipx`, `uvx (ephemeral)`, source checkout, or unsupported. Only `uv tool` and `pipx` are upgraded automatically; for `uv tool` installs, it runs `uv tool install specify-cli --force --from <git ref>` under the hood so pinned release tags work. The other paths print path-specific guidance and exit 0 without touching anything.
+Bare `specify self upgrade` executes immediately, matching the no-prompt behavior of commands like `pip install -U` and `npm update`. The CLI classifies your runtime into one of: `uv tool`, `pipx`, `uvx (ephemeral)`, source checkout, or unsupported. Only `uv tool` and `pipx` are upgraded automatically; for `uv tool` installs, it runs `uv tool install specify-cli --force --from <git ref>` under the hood so pinned release tags work. On Windows, `uv` cannot replace the tool environment `specify` is running from, so for `uv tool` installs `specify self upgrade` prints that command for you to run once it exits, and exits 0 without touching anything. Stop any other process running from that environment first, such as a `specify mcp` server, or uv can still fail partway through. The other paths print path-specific guidance and exit 0 without touching anything.
 
 Pinned tags must start with `vMAJOR.MINOR.PATCH`. Optional suffixes are limited to dev, alpha/beta/rc, and/or build metadata forms such as `v1.0.0-rc1`, `v0.8.0.dev0`, `v0.8.0+build.42`, or the combination `v1.0.0-rc1+build.42`; branch names, hash refs, `latest`, and bare versions without `v` are rejected.
 
diff --git a/src/specify_cli/_version.py b/src/specify_cli/_version.py
index c8fcad7c7e..4282d976f0 100644
--- a/src/specify_cli/_version.py
+++ b/src/specify_cli/_version.py
@@ -673,6 +673,26 @@ def _installer_binary_name(method: _InstallMethod) -> str | None:
     return None
 
 
+def _runs_from_uv_tool_env_on_windows() -> bool:
+    """Return whether this process runs from a uv tool environment on Windows."""
+    return os.name == "nt" and os.path.isfile(
+        os.path.join(sys.prefix, "uv-receipt.toml")
+    )
+
+
+# Another process from the same tool environment, such as an editor's
+# `specify mcp` server, keeps python.exe locked after this command exits.
+_UV_TOOL_MANUAL_INTRO = (
+    "Stop any other specify process (such as `specify mcp`), then run this "
+    "once this command exits:"
+)
+
+
+def _uv_tool_manual_command(target_tag: str | None) -> str:
+    """Return the uv command a Windows uv-tool user runs after specify exits."""
+    return f"uv tool install specify-cli --force --from {_source_spec(target_tag)}"
+
+
 def _is_path_like_command(value: str) -> bool:
     """Return whether an argv[0] names a path rather than a bare command."""
     return Path(value).parent != Path(".") or "/" in value or "\\" in value
@@ -729,6 +749,12 @@ def _build_upgrade_plan(
         command_preview = (
             f"(installer {_installer_binary_name(method)} not found on PATH)"
         )
+    elif method == _InstallMethod.UV_TOOL and _runs_from_uv_tool_env_on_windows():
+        # self_upgrade prints the uv command instead of running it.
+        command_preview = (
+            "(none — on Windows, uv cannot replace the tool environment specify "
+            "is running from)"
+        )
     else:
         command_preview = (
             _render_argv(argv) if argv is not None else "(none — non-upgradable path)"
diff --git a/src/specify_cli/selfs/command_upgrade.py b/src/specify_cli/selfs/command_upgrade.py
index 1f645c0e45..c950dc2852 100644
--- a/src/specify_cli/selfs/command_upgrade.py
+++ b/src/specify_cli/selfs/command_upgrade.py
@@ -33,7 +33,9 @@ def self_upgrade(
     Detection classifies the runtime into uv-tool / pipx / uvx (ephemeral) /
     source-checkout / unsupported. Only uv-tool and pipx are upgraded
     automatically; the other three paths print path-specific guidance and
-    exit 0.
+    exit 0. On Windows, uv cannot replace the uv-tool environment specify is
+    running from, so uv-tool installs print the uv command to run once
+    specify exits, and exit 0 without changes.
 
     Exit codes:
       0      success or no-op-success (already on latest, --dry-run, or
@@ -73,6 +75,9 @@ def self_upgrade(
         _parse_version_text,
         _render_argv,
         _run_installer,
+        _runs_from_uv_tool_env_on_windows,
+        _UV_TOOL_MANUAL_INTRO,
+        _uv_tool_manual_command,
         _validate_tag,
         _verify_upgrade,
         console,
@@ -110,6 +115,13 @@ def self_upgrade(
         console.print("Dry run — no changes will be made.")
         for line in plan.preview_summary.splitlines():
             console.print(line)
+        if (
+            plan.method == _InstallMethod.UV_TOOL
+            and plan.installer_argv is not None
+            and _runs_from_uv_tool_env_on_windows()
+        ):
+            console.print(_UV_TOOL_MANUAL_INTRO, soft_wrap=True)
+            console.print(f"  {_uv_tool_manual_command(plan.target_tag)}", soft_wrap=True)
         raise typer.Exit(0)
 
     if plan.method in (
@@ -153,6 +165,21 @@ def self_upgrade(
             console.print(f"Already on requested release: {target_tag}")
             raise typer.Exit(0)
 
+    if plan.method == _InstallMethod.UV_TOOL and _runs_from_uv_tool_env_on_windows():
+        # uv deletes the tool environment before reinstalling it, and Windows
+        # will not delete the python.exe this process is running from, so uv
+        # would leave the environment without its packages. Leave the
+        # reinstall to the user's shell instead.
+        console.print(
+            f"Not upgrading specify-cli {plan.current_version} → {target_tag}: "
+            "on Windows, uv cannot replace the tool environment specify is "
+            "running from. No changes were made.",
+            soft_wrap=True,
+        )
+        console.print(_UV_TOOL_MANUAL_INTRO, soft_wrap=True)
+        console.print(f"  {_uv_tool_manual_command(target_tag)}", soft_wrap=True)
+        raise typer.Exit(0)
+
     installed_version = _parse_version_text(plan.current_version)
     verb = (
         "Downgrading"
diff --git a/tests/specify_cli/test_version_execution.py b/tests/specify_cli/test_version_execution.py
index 9e3f2514fe..eba34884b9 100644
--- a/tests/specify_cli/test_version_execution.py
+++ b/tests/specify_cli/test_version_execution.py
@@ -1,10 +1,12 @@
 """Installer execution, verification, and error-path tests for `specify self upgrade`."""
 
 import errno
+import os
 import subprocess
 from unittest.mock import patch
 
 from specify_cli import app
+from specify_cli._version import _runs_from_uv_tool_env_on_windows
 
 from tests.specify_cli.self_upgrade_helpers import (
     route_opener_open_through_urlopen,  # noqa: F401 (autouse fixture)
@@ -541,3 +543,193 @@ def test_prerelease_failure_degrades_rollback_hint_to_releases_page(
         assert "Previous version was not an exact stable release tag" in out
         assert "https://github.com/github/spec-kit/releases" in out
         assert "git+https://github.com/github/spec-kit.git@v1.0.0rc1" not in out
+
+
+class TestWindowsUvToolEnvironment:
+    """Windows uv-tool installs cannot reinstall the environment they run from."""
+
+    def test_windows_uv_tool_prints_command_without_running_installer(
+        self, uv_tool_argv0, clean_environ
+    ):
+        with patch("specify_cli.authentication.http.urllib.request.urlopen") as mock_urlopen, patch(
+            "specify_cli._version.shutil.which", return_value="uv"
+        ), patch("specify_cli._version.subprocess.run") as mock_run, patch(
+            "specify_cli._version._get_installed_version", return_value="1.2.2"
+        ), patch(
+            "specify_cli._version._runs_from_uv_tool_env_on_windows", return_value=True
+        ):
+            mock_urlopen.return_value = mock_urlopen_response({"tag_name": "v1.2.4"})
+            result = runner.invoke(app, ["self", "upgrade"])
+
+        assert result.exit_code == 0
+        out = strip_ansi(result.output)
+        assert "Not upgrading specify-cli 1.2.2 → v1.2.4" in out
+        assert (
+            "  uv tool install specify-cli --force --from "
+            "git+https://github.com/github/spec-kit.git@v1.2.4"
+        ) in out
+        assert "Upgrade failed" not in out
+        assert mock_run.call_count == 0
+
+    def test_windows_pipx_still_runs_installer(self, pipx_argv0, clean_environ):
+        with patch("specify_cli.authentication.http.urllib.request.urlopen") as mock_urlopen, patch(
+            "specify_cli._version.shutil.which", return_value="pipx"
+        ), patch("specify_cli._version.subprocess.run") as mock_run, patch(
+            "specify_cli._version._get_installed_version", return_value="1.2.2"
+        ), patch(
+            "specify_cli._version._runs_from_uv_tool_env_on_windows", return_value=True
+        ):
+            mock_urlopen.return_value = mock_urlopen_response({"tag_name": "v1.2.4"})
+            mock_run.side_effect = [
+                _completed_process(0),  # installer
+                _completed_process(0, stdout="specify 1.2.4\n"),  # verify
+            ]
+            result = runner.invoke(app, ["self", "upgrade"])
+
+        assert result.exit_code == 0
+        assert "Upgraded specify-cli: 1.2.2 → 1.2.4" in strip_ansi(result.output)
+        assert mock_run.call_count == 2
+
+    def test_windows_uv_tool_dry_run_previews_manual_command(
+        self, uv_tool_argv0, clean_environ
+    ):
+        with patch("specify_cli.authentication.http.urllib.request.urlopen") as mock_urlopen, patch(
+            "specify_cli._version.shutil.which", return_value="uv"
+        ), patch("specify_cli._version.subprocess.run") as mock_run, patch(
+            "specify_cli._version._get_installed_version", return_value="1.2.2"
+        ), patch(
+            "specify_cli._version._runs_from_uv_tool_env_on_windows", return_value=True
+        ):
+            mock_urlopen.return_value = mock_urlopen_response({"tag_name": "v1.2.4"})
+            result = runner.invoke(app, ["self", "upgrade", "--dry-run"])
+
+        assert result.exit_code == 0
+        out = strip_ansi(result.output)
+        assert "Dry run — no changes will be made." in out
+        assert "Target version: v1.2.4" in out
+        assert (
+            "Command that would be executed: (none — on Windows, uv cannot "
+            "replace the tool environment specify is running from)"
+        ) in " ".join(out.split())
+        assert (
+            "Stop any other specify process (such as `specify mcp`), then run "
+            "this once this command exits:\n"
+            "  uv tool install specify-cli --force --from "
+            "git+https://github.com/github/spec-kit.git@v1.2.4\n"
+        ) in out
+        assert mock_run.call_count == 0
+
+    def test_windows_uv_tool_dry_run_with_tag_previews_pinned_command(
+        self, uv_tool_argv0, clean_environ
+    ):
+        with patch("specify_cli.authentication.http.urllib.request.urlopen") as mock_urlopen, patch(
+            "specify_cli._version.shutil.which", return_value="uv"
+        ), patch("specify_cli._version.subprocess.run") as mock_run, patch(
+            "specify_cli._version._get_installed_version", return_value="1.2.2"
+        ), patch(
+            "specify_cli._version._runs_from_uv_tool_env_on_windows", return_value=True
+        ):
+            result = runner.invoke(
+                app, ["self", "upgrade", "--dry-run", "--tag", "v1.2.0"]
+            )
+
+        assert result.exit_code == 0
+        assert (
+            "\n  uv tool install specify-cli --force --from "
+            "git+https://github.com/github/spec-kit.git@v1.2.0\n"
+        ) in strip_ansi(result.output)
+        mock_urlopen.assert_not_called()
+        assert mock_run.call_count == 0
+
+    def test_windows_uv_tool_dry_run_matches_real_run_command(
+        self, uv_tool_argv0, clean_environ
+    ):
+        outputs = {}
+        for args in (["self", "upgrade", "--dry-run"], ["self", "upgrade"]):
+            with patch(
+                "specify_cli.authentication.http.urllib.request.urlopen"
+            ) as mock_urlopen, patch(
+                "specify_cli._version.shutil.which", return_value="uv"
+            ), patch("specify_cli._version.subprocess.run") as mock_run, patch(
+                "specify_cli._version._get_installed_version", return_value="1.2.2"
+            ), patch(
+                "specify_cli._version._runs_from_uv_tool_env_on_windows",
+                return_value=True,
+            ):
+                mock_urlopen.return_value = mock_urlopen_response({"tag_name": "v1.2.4"})
+                result = runner.invoke(app, args)
+            assert result.exit_code == 0
+            assert mock_run.call_count == 0
+            outputs[len(args)] = strip_ansi(result.output)
+
+        manual_steps = (
+            "Stop any other specify process (such as `specify mcp`), then run "
+            "this once this command exits:\n"
+            "  uv tool install specify-cli --force --from "
+            "git+https://github.com/github/spec-kit.git@v1.2.4\n"
+        )
+        assert manual_steps in outputs[3]
+        assert manual_steps in outputs[2]
+
+    def test_non_windows_uv_tool_dry_run_still_previews_installer(
+        self, uv_tool_argv0, clean_environ
+    ):
+        with patch("specify_cli.authentication.http.urllib.request.urlopen") as mock_urlopen, patch(
+            "specify_cli._version.shutil.which", return_value="uv"
+        ), patch("specify_cli._version.subprocess.run"), patch(
+            "specify_cli._version._get_installed_version", return_value="1.2.2"
+        ), patch(
+            "specify_cli._version._runs_from_uv_tool_env_on_windows", return_value=False
+        ):
+            mock_urlopen.return_value = mock_urlopen_response({"tag_name": "v1.2.4"})
+            result = runner.invoke(app, ["self", "upgrade", "--dry-run"])
+
+        assert result.exit_code == 0
+        out = strip_ansi(result.output)
+        assert (
+            "Command that would be executed: uv tool install specify-cli --force "
+            "--from git+https://github.com/github/spec-kit.git@v1.2.4"
+        ) in " ".join(out.split())
+        assert "then run this once this command exits" not in out
+
+    def test_windows_uv_tool_dry_run_without_uv_reports_missing_installer(
+        self, uv_tool_argv0, clean_environ
+    ):
+        with patch("specify_cli.authentication.http.urllib.request.urlopen") as mock_urlopen, patch(
+            "specify_cli._version.shutil.which", return_value=None
+        ), patch("specify_cli._version.subprocess.run") as mock_run, patch(
+            "specify_cli._version._get_installed_version", return_value="1.2.2"
+        ), patch(
+            "specify_cli._version._runs_from_uv_tool_env_on_windows", return_value=True
+        ):
+            mock_urlopen.return_value = mock_urlopen_response({"tag_name": "v1.2.4"})
+            result = runner.invoke(app, ["self", "upgrade", "--dry-run"])
+
+        assert result.exit_code == 0
+        out = strip_ansi(result.output)
+        assert "Command that would be executed: (installer uv not found on PATH)" in out
+        assert "then run this once this command exits" not in out
+        assert mock_run.call_count == 0
+
+    def test_help_mentions_windows_uv_tool_exception(self):
+        result = runner.invoke(app, ["self", "upgrade", "--help"])
+        assert result.exit_code == 0
+        out = " ".join(strip_ansi(result.output).split())
+        assert "On Windows, uv cannot replace the uv-tool environment" in out
+
+    def test_detects_uv_tool_environment_on_windows(self, tmp_path, monkeypatch):
+        (tmp_path / "uv-receipt.toml").write_text("[tool]\n")
+        monkeypatch.setattr("sys.prefix", str(tmp_path))
+        monkeypatch.setattr(os, "name", "nt")
+        assert _runs_from_uv_tool_env_on_windows() is True
+
+    def test_ignores_environment_without_uv_receipt(self, tmp_path, monkeypatch):
+        monkeypatch.setattr("sys.prefix", str(tmp_path))
+        monkeypatch.setattr(os, "name", "nt")
+        assert _runs_from_uv_tool_env_on_windows() is False
+
+    def test_ignores_uv_tool_environment_off_windows(self, tmp_path, monkeypatch):
+        (tmp_path / "uv-receipt.toml").write_text("[tool]\n")
+        monkeypatch.setattr("sys.prefix", str(tmp_path))
+        monkeypatch.setattr(os, "name", "posix")
+        assert _runs_from_uv_tool_env_on_windows() is False