diff --git a/litellm/proxy/_lazy_openapi_snapshot.json b/litellm/proxy/_lazy_openapi_snapshot.json
index 6f9a2d8c96d..8bce873aa24 100644
--- a/litellm/proxy/_lazy_openapi_snapshot.json
+++ b/litellm/proxy/_lazy_openapi_snapshot.json
@@ -19632,7 +19632,7 @@
                   }
                 }
               },
-              "description": "\n    Unified rate-limit error.\n\n    Every rate-limit condition surfaced by litellm \u2014 whether it originated from\n    an upstream LLM provider, a vendor batch endpoint, or one of litellm's own\n    proxy-side limiters (parallel-requests, dynamic-rate, batch-rate, budget,\n    max-iterations, etc.) \u2014 is raised as an instance of this class.\n\n    The :attr:`category` attribute lets callers distinguish the source. See\n    :class:`RateLimitErrorCategory` for the available values.\n    "
+              "description": "\nUnified rate-limit error.\n\nEvery rate-limit condition surfaced by litellm \u2014 whether it originated from\nan upstream LLM provider, a vendor batch endpoint, or one of litellm's own\nproxy-side limiters (parallel-requests, dynamic-rate, batch-rate, budget,\nmax-iterations, etc.) \u2014 is raised as an instance of this class.\n\nThe :attr:`category` attribute lets callers distinguish the source. See\n:class:`RateLimitErrorCategory` for the available values.\n"
             },
             "500": {
               "content": {
diff --git a/litellm/proxy/client/cli/commands/claude_settings.py b/litellm/proxy/client/cli/commands/claude_settings.py
index f4bebc4a4cb..ffc26d22e84 100644
--- a/litellm/proxy/client/cli/commands/claude_settings.py
+++ b/litellm/proxy/client/cli/commands/claude_settings.py
@@ -22,8 +22,11 @@ from pathlib import Path
 from types import MappingProxyType
 from typing import Final, TypeAlias
 
+import click
+from packaging.version import InvalidVersion, Version
 from pydantic import BaseModel, ConfigDict, JsonValue, TypeAdapter, ValidationError
 
+from litellm._version import version as litellm_version
 from litellm.litellm_core_utils.private_json import (
     commit_staged_json,
     discard_staged_json,
@@ -75,6 +78,7 @@ BACKUP_PATH: Final = Path.home() / ".litellm" / "claude_settings_backup.json"
 AUTOROUTE_BACKUP_PATH: Final = Path.home() / ".litellm" / "autorouter" / "claude_settings_backup.json"
 CONFIGURE_STATE_PATH: Final = Path.home() / ".litellm" / "claude_configure_state.json"
 STATUSLINE_SCRIPT_PATH: Final = Path.home() / ".litellm" / "statusline.py"
+STATUSLINE_VERSION_PREFIX: Final = b"# litellm-statusline-version: "
 
 
 @dataclass(frozen=True, slots=True)
@@ -305,12 +309,37 @@ def statusline_command(script_path: Path, platform: str = sys.platform) -> str:
     return " ".join(quote(token) for token in (sys.executable, str(script_path)))
 
 
-def install_statusline_script(script_path: Path | None = None) -> str:
+def _installed_statusline_version(target: Path) -> Version | None:
+    try:
+        with target.open("rb") as script:
+            header: Final = script.readline(256)
+    except FileNotFoundError:
+        return None
+    if not header.startswith(STATUSLINE_VERSION_PREFIX):
+        return None
+    try:
+        return Version(header.removeprefix(STATUSLINE_VERSION_PREFIX).decode("ascii").strip())
+    except (InvalidVersion, UnicodeDecodeError):
+        return None
+
+
+def install_statusline_script(script_path: Path | None = None, *, package_version: str = litellm_version) -> str:
     target: Final = script_path or STATUSLINE_SCRIPT_PATH
     try:
         ensure_private_dir(target.parent)
-        write_private_bytes(str(target), Path(statusline_script.__file__).read_bytes())
-    except OSError as e:
+        bundled_version: Final = Version(package_version)
+        installed_version: Final = _installed_statusline_version(target)
+        if installed_version is not None and installed_version > bundled_version:
+            click.echo(
+                f"Keeping the status line from LiteLLM {installed_version}; this CLI is {bundled_version}. "
+                "Upgrade the CLI to refresh it.",
+                err=True,
+            )
+            return statusline_command(target)
+        source: Final = Path(statusline_script.__file__).read_bytes()
+        header: Final = STATUSLINE_VERSION_PREFIX + str(bundled_version).encode("ascii") + b"\n"
+        write_private_bytes(str(target), header + source)
+    except (OSError, InvalidVersion) as e:
         raise ClaudeSettingsError(f"Could not install the status line script at {target}: {e}") from e
     return statusline_command(target)
 
diff --git a/litellm/proxy/client/cli/commands/statusline_script.py b/litellm/proxy/client/cli/commands/statusline_script.py
index 09dd062c888..6264acb39d1 100644
--- a/litellm/proxy/client/cli/commands/statusline_script.py
+++ b/litellm/proxy/client/cli/commands/statusline_script.py
@@ -1,6 +1,6 @@
 """Claude Code status line and Codex Stop hook for auto-routed sessions.
 
-`lite` copies this file verbatim to ~/.litellm/statusline.py and registers it as Claude
+`lite` copies this file with a CLI version header to ~/.litellm/statusline.py and registers it as Claude
 Code's `statusLine` command and as Codex's `[[hooks.Stop]]` command, so it must stay
 standard-library only and must never import litellm. Claude Code re-runs it on every
 status refresh (about every 300ms while typing), so the proxy is asked at most once per
diff --git a/pyproject.toml b/pyproject.toml
index 95da93df41e..8a7d2981c12 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -21,6 +21,7 @@ dependencies = [
     "tiktoken>=0.8.0,<1.0; python_version < '3.14'",
     "tiktoken>=0.12.0,<1.0; python_version >= '3.14'",
     "importlib-metadata>=8.0.0,<9.0",
+    "packaging>=24.0",
     "tokenizers>=0.21.0,<1.0",
     "click>=8.0.0,<9.0",
     "jinja2>=3.1.6,<4.0",
diff --git a/tests/test_litellm/proxy/client/cli/test_claude_settings.py b/tests/test_litellm/proxy/client/cli/test_claude_settings.py
index a48c64eb4a0..f596e1e5d6c 100644
--- a/tests/test_litellm/proxy/client/cli/test_claude_settings.py
+++ b/tests/test_litellm/proxy/client/cli/test_claude_settings.py
@@ -6,6 +6,7 @@ import stat
 import sys
 import time
 from pathlib import Path
+from typing import Final
 from unittest.mock import patch
 
 import pytest
@@ -773,7 +774,7 @@ class TestStatusLine:
 
         script = tmp_path / "lite" / "statusline.py"
         command = install_statusline_script(script)
-        assert script.read_bytes() == pathlib.Path(statusline_script.__file__).read_bytes()
+        assert script.read_bytes().split(b"\n", 1)[1] == pathlib.Path(statusline_script.__file__).read_bytes()
         assert shlex.split(command) == [sys.executable, str(script)]
         assert command == statusline_command(script)
         assert stat.S_IMODE(script.stat().st_mode) == 0o600
@@ -783,11 +784,9 @@ class TestStatusLine:
     def test_a_reinstall_replaces_the_script_in_one_step_and_a_refused_one_leaves_the_old_script_whole(self, tmp_path):
         # Claude Code may be running the script at the moment `lite` reinstalls it; the file it has open
         # must stay complete, and a reinstall that cannot land must not leave a truncated script behind.
-        from litellm.proxy.client.cli.commands import statusline_script
-
         script = tmp_path / "lite" / "statusline.py"
         install_statusline_script(script)
-        bundled = pathlib.Path(statusline_script.__file__).read_bytes()
+        bundled = script.read_bytes()
         with script.open("rb") as running:
             install_statusline_script(script)
             assert running.read() == bundled
@@ -802,6 +801,67 @@ class TestStatusLine:
                 script.parent.chmod(0o700)
             assert script.read_bytes() == bundled
 
+    @pytest.mark.parametrize(
+        ("installed_version", "older_version"),
+        (("2.10.0", "2.9.0"), ("2.1.0", "2.1.0rc1"), ("2.1.0rc1", "2.1.0.dev2"), ("2.1.0.post1", "2.1.0")),
+    )
+    def test_an_older_cli_preserves_the_newer_footer(
+        self, tmp_path: Path, capsys: pytest.CaptureFixture[str], installed_version: str, older_version: str
+    ) -> None:
+        script: Final = tmp_path / "statusline.py"
+        command: Final = install_statusline_script(script, package_version=installed_version)
+        installed: Final = script.read_bytes()
+        modified: Final = script.stat().st_mtime_ns
+
+        assert install_statusline_script(script, package_version=older_version) == command
+
+        assert script.read_bytes() == installed
+        assert script.stat().st_mtime_ns == modified
+        assert f"Keeping the status line from LiteLLM {installed_version}" in capsys.readouterr().err
+
+    @pytest.mark.parametrize(
+        "old_header", (b"", b"# litellm-statusline-version: invalid\n", b"# litellm-statusline-version: \xff\n")
+    )
+    def test_a_legacy_or_damaged_version_marker_is_repaired(self, tmp_path: Path, old_header: bytes) -> None:
+        from litellm.proxy.client.cli.commands import statusline_script
+
+        script: Final = tmp_path / "statusline.py"
+        script.write_bytes(old_header + b"print('old footer')\n")
+
+        install_statusline_script(script, package_version="2.1.0")
+
+        assert script.read_bytes() == (
+            b"# litellm-statusline-version: 2.1.0\n" + Path(statusline_script.__file__).read_bytes()
+        )
+
+    @pytest.mark.parametrize("next_version", ("2.1.0", "2.2.0"))
+    def test_an_equal_or_newer_cli_refreshes_the_footer(self, tmp_path: Path, next_version: str) -> None:
+        from litellm.proxy.client.cli.commands import statusline_script
+
+        script: Final = tmp_path / "statusline.py"
+        script.write_bytes(b"# litellm-statusline-version: 2.1.0\nprint('old footer')\n")
+
+        install_statusline_script(script, package_version=next_version)
+
+        assert script.read_bytes() == (
+            f"# litellm-statusline-version: {next_version}\n".encode() + Path(statusline_script.__file__).read_bytes()
+        )
+
+    def test_configure_keeps_a_newer_footer_while_updating_settings(
+        self, tmp_path: Path, capsys: pytest.CaptureFixture[str]
+    ) -> None:
+        script: Final = tmp_path / "statusline.py"
+        script.write_bytes(b"# litellm-statusline-version: 999999.0.0\nprint('newer footer')\n")
+        installed: Final = script.read_bytes()
+        rig: Final = _Rig(tmp_path, {"theme": "dark"})
+
+        rig.configure(script_path=script)
+
+        assert script.read_bytes() == installed
+        assert rig.read()["statusLine"]["command"] == statusline_command(script)
+        assert rig.read()["env"]["ANTHROPIC_BASE_URL"] == PROXY
+        assert "Keeping the status line" in capsys.readouterr().err
+
     def test_configure_installs_it_and_unconfigure_removes_only_ours(self, tmp_path):
         rig = _Rig(tmp_path, {"theme": "dark"})
         script = tmp_path / "statusline.py"
diff --git a/uv.lock b/uv.lock
index 543581cbc23..e1d4ab791c6 100644
--- a/uv.lock
+++ b/uv.lock
@@ -4521,6 +4521,7 @@ dependencies = [
     { name = "jinja2" },
     { name = "jsonschema" },
     { name = "openai" },
+    { name = "packaging" },
     { name = "pydantic" },
     { name = "pydantic-settings" },
     { name = "python-dotenv" },
@@ -4802,6 +4803,7 @@ requires-dist = [
     { name = "numpydoc", marker = "extra == 'utils'", specifier = ">=1.8.0,<2.0" },
     { name = "nvidia-riva-client", marker = "extra == 'stt-nvidia-riva'", specifier = ">=2.15.0" },
     { name = "openai", specifier = ">=2.20.0,<3.0.0" },
+    { name = "packaging", specifier = ">=24.0" },
     { name = "opentelemetry-api", marker = "extra == 'proxy-runtime'", specifier = "==1.28.0" },
     { name = "opentelemetry-exporter-otlp", marker = "extra == 'proxy-runtime'", specifier = "==1.28.0" },
     { name = "opentelemetry-instrumentation-fastapi", marker = "extra == 'proxy-runtime'", specifier = "==0.49b0" },