fix(cli): avoid indeterminate self-upgrade no-ops

Author: chordpli

src/specify_cli/__init__.py

@@ -1767,6 +1767,15 @@ def _stable_release_tag_for_version(version_text: str) -> str | None:
     return f"v{release[0]}.{release[1]}.{release[2]}"
 
 
+def _is_comparable_version_text(value: str) -> bool:
+    """Return whether version-like text parses under PEP 440 after tag normalization."""
+    try:
+        Version(_normalize_tag(value))
+        return True
+    except InvalidVersion:
+        return False
+
+
 def _render_argv(argv: list[str]) -> str:
     """Render argv for copy/paste on the current platform."""
     return subprocess.list2cmdline(argv) if os.name == "nt" else shlex.join(argv)
@@ -2713,7 +2722,12 @@ def self_upgrade(
         else "unknown"
     )
     if plan.current_version != "unknown":
-        if tag is None and not _is_newer(target_canonical, plan.current_version):
+        versions_comparable = _is_comparable_version_text(
+            plan.current_version
+        ) and _is_comparable_version_text(target_canonical)
+        if tag is None and versions_comparable and not _is_newer(
+            target_canonical, plan.current_version
+        ):
             if current_canonical == target_canonical:
                 console.print(f"Already on latest release: {plan.target_tag}")
             else:

tests/test_self_upgrade.py

@@ -360,6 +360,27 @@ def test_dev_build_ahead_of_release_reports_newer_noop(
         assert "Already on latest release or newer: 0.7.7.dev0" in strip_ansi(result.output)
         assert mock_run.call_count == 0
 
+    def test_unparseable_current_version_does_not_false_noop(
+        self, uv_tool_argv0, clean_environ
+    ):
+        with patch("specify_cli.urllib.request.urlopen") as mock_urlopen, patch(
+            "specify_cli.subprocess.run"
+        ) as mock_run, patch(
+            "specify_cli.shutil.which", return_value="/usr/bin/uv"
+        ), patch("specify_cli._get_installed_version", return_value="release-main"):
+            mock_urlopen.return_value = _mock_urlopen_response({"tag_name": "v0.7.6"})
+            mock_run.side_effect = [
+                _completed_process(0),
+                _completed_process(0, stdout="specify 0.7.6\n"),
+            ]
+            result = runner.invoke(app, ["self", "upgrade"])
+
+        assert result.exit_code == 0
+        out = strip_ansi(result.output)
+        assert "Already on latest release" not in out
+        assert "Upgrading specify-cli release-main → v0.7.6 via uv tool:" in out
+        assert mock_run.call_count == 2
+
     def test_pinned_older_tag_still_runs_installer(
         self, uv_tool_argv0, clean_environ
     ):