diff --git a/.github/workflows/check-installers.yml b/.github/workflows/check-installers.yml
index 92dc13f396..9a3757e1bc 100644
--- a/.github/workflows/check-installers.yml
+++ b/.github/workflows/check-installers.yml
@@ -54,7 +54,7 @@ jobs:
       - name: Checkout repository
         uses: actions/checkout@v4
 
-      - name: Run installer 
+      - name: Run installer
         shell: pwsh
         run: |
           $hfTestRoot = Join-Path $env:TEMP ([System.Guid]::NewGuid().ToString())
diff --git a/docs/source/en/guides/cli.md b/docs/source/en/guides/cli.md
index 9cd5e73e77..c377718c19 100644
--- a/docs/source/en/guides/cli.md
+++ b/docs/source/en/guides/cli.md
@@ -28,7 +28,7 @@ On macOS and Linux:
 On Windows:
 
 ```powershell
->>> powershell -c "irm https://hf.co/cli/install.ps1 | iex"
+>>> powershell -ExecutionPolicy ByPass -c "irm https://hf.co/cli/install.ps1 | iex"
 ```
 
 Once installed, you can check that the CLI is correctly setup:
diff --git a/docs/source/en/installation.md b/docs/source/en/installation.md
index 73382afc84..e2c19bb69c 100644
--- a/docs/source/en/installation.md
+++ b/docs/source/en/installation.md
@@ -116,7 +116,7 @@ curl -LsSf https://hf.co/cli/install.sh | sh
 On Windows:
 
 ```powershell
-powershell -c "irm https://hf.co/cli/install.ps1 | iex"
+powershell -ExecutionPolicy ByPass -c "irm https://hf.co/cli/install.ps1 | iex"
 ```
 
 ## Install with conda
diff --git a/src/huggingface_hub/_login.py b/src/huggingface_hub/_login.py
index 4a358293c2..7700ab5b23 100644
--- a/src/huggingface_hub/_login.py
+++ b/src/huggingface_hub/_login.py
@@ -20,8 +20,8 @@
 from typing import Optional
 
 from . import constants
-from .cli._cli_utils import ANSI
 from .utils import (
+    ANSI,
     capture_output,
     get_token,
     is_google_colab,
diff --git a/src/huggingface_hub/cli/_cli_utils.py b/src/huggingface_hub/cli/_cli_utils.py
index 9181dd5569..911aefbe4a 100644
--- a/src/huggingface_hub/cli/_cli_utils.py
+++ b/src/huggingface_hub/cli/_cli_utils.py
@@ -13,14 +13,21 @@
 # limitations under the License.
 """Contains CLI utilities (styling, helpers)."""
 
+import importlib.metadata
 import os
+import time
 from enum import Enum
-from typing import TYPE_CHECKING, Annotated, Optional, Union
+from pathlib import Path
+from typing import TYPE_CHECKING, Annotated, Optional
 
 import click
 import typer
 
-from huggingface_hub import __version__
+from huggingface_hub import __version__, constants
+from huggingface_hub.utils import ANSI, get_session, hf_raise_for_status, installation_method, logging
+
+
+logger = logging.get_logger()
 
 
 if TYPE_CHECKING:
@@ -34,58 +41,6 @@ def get_hf_api(token: Optional[str] = None) -> "HfApi":
     return HfApi(token=token, library_name="hf", library_version=__version__)
 
 
-class ANSI:
-    """
-    Helper for en.wikipedia.org/wiki/ANSI_escape_code
-    """
-
-    _bold = "\u001b[1m"
-    _gray = "\u001b[90m"
-    _red = "\u001b[31m"
-    _reset = "\u001b[0m"
-    _yellow = "\u001b[33m"
-
-    @classmethod
-    def bold(cls, s: str) -> str:
-        return cls._format(s, cls._bold)
-
-    @classmethod
-    def gray(cls, s: str) -> str:
-        return cls._format(s, cls._gray)
-
-    @classmethod
-    def red(cls, s: str) -> str:
-        return cls._format(s, cls._bold + cls._red)
-
-    @classmethod
-    def yellow(cls, s: str) -> str:
-        return cls._format(s, cls._yellow)
-
-    @classmethod
-    def _format(cls, s: str, code: str) -> str:
-        if os.environ.get("NO_COLOR"):
-            # See https://no-color.org/
-            return s
-        return f"{code}{s}{cls._reset}"
-
-
-def tabulate(rows: list[list[Union[str, int]]], headers: list[str]) -> str:
-    """
-    Inspired by:
-
-    - stackoverflow.com/a/8356620/593036
-    - stackoverflow.com/questions/9535954/printing-lists-as-tabular-data
-    """
-    col_widths = [max(len(str(x)) for x in col) for col in zip(*rows, headers)]
-    row_format = ("{{:{}}} " * len(headers)).format(*col_widths)
-    lines = []
-    lines.append(row_format.format(*headers))
-    lines.append(row_format.format(*["-" * w for w in col_widths]))
-    for row in rows:
-        lines.append(row_format.format(*row))
-    return "\n".join(lines)
-
-
 #### TYPER UTILS
 
 
@@ -150,3 +105,66 @@ class RepoType(str, Enum):
         help="Git revision id which can be a branch name, a tag, or a commit hash.",
     ),
 ]
+
+
+### PyPI VERSION CHECKER
+
+
+def check_cli_update() -> None:
+    """
+    Check whether a newer version of `huggingface_hub` is available on PyPI.
+
+    If a newer version is found, notify the user and suggest updating.
+    If current version is a pre-release (e.g. `1.0.0.rc1`), or a dev version (e.g. `1.0.0.dev1`), no check is performed.
+
+    This function is called at the entry point of the CLI. It only performs the check once every 24 hours, and any error
+    during the check is caught and logged, to avoid breaking the CLI.
+    """
+    try:
+        _check_cli_update()
+    except Exception:
+        # We don't want the CLI to fail on version checks, no matter the reason.
+        logger.debug("Error while checking for CLI update.", exc_info=True)
+
+
+def _check_cli_update() -> None:
+    current_version = importlib.metadata.version("huggingface_hub")
+
+    # Skip if current version is a pre-release or dev version
+    if any(tag in current_version for tag in ["rc", "dev"]):
+        return
+
+    # Skip if already checked in the last 24 hours
+    if os.path.exists(constants.CHECK_FOR_UPDATE_DONE_PATH):
+        mtime = os.path.getmtime(constants.CHECK_FOR_UPDATE_DONE_PATH)
+        if (time.time() - mtime) < 24 * 3600:
+            return
+
+    # Touch the file to mark that we did the check now
+    Path(constants.CHECK_FOR_UPDATE_DONE_PATH).touch()
+
+    # Check latest version from PyPI
+    response = get_session().get("https://pypi.org/pypi/huggingface_hub/json", timeout=2)
+    hf_raise_for_status(response)
+    data = response.json()
+    latest_version = data["info"]["version"]
+
+    # If latest version is different from current, notify user
+    if current_version != latest_version:
+        method = installation_method()
+        if method == "brew":
+            update_command = "brew upgrade huggingface-cli"
+        elif method == "hf_installer" and os.name == "nt":
+            update_command = 'powershell -NoProfile -Command "iwr -useb https://hf.co/cli/install.ps1 | iex"'
+        elif method == "hf_installer":
+            update_command = "curl -LsSf https://hf.co/cli/install.sh | sh -"
+        else:  # unknown => likely pip
+            update_command = "pip install -U huggingface_hub"
+
+        click.echo(
+            ANSI.yellow(
+                f"A new version of huggingface_hub ({latest_version}) is available! "
+                f"You are using version {current_version}.\n"
+                f"To update, run: {ANSI.bold(update_command)}\n",
+            )
+        )
diff --git a/src/huggingface_hub/cli/auth.py b/src/huggingface_hub/cli/auth.py
index ce075b31f6..cb522c918c 100644
--- a/src/huggingface_hub/cli/auth.py
+++ b/src/huggingface_hub/cli/auth.py
@@ -39,8 +39,8 @@
 from huggingface_hub.hf_api import whoami
 
 from .._login import auth_list, auth_switch, login, logout
-from ..utils import get_stored_tokens, get_token, logging
-from ._cli_utils import ANSI, TokenOpt, typer_factory
+from ..utils import ANSI, get_stored_tokens, get_token, logging
+from ._cli_utils import TokenOpt, typer_factory
 
 
 logger = logging.get_logger(__name__)
diff --git a/src/huggingface_hub/cli/cache.py b/src/huggingface_hub/cli/cache.py
index c57f9f207f..35f7540821 100644
--- a/src/huggingface_hub/cli/cache.py
+++ b/src/huggingface_hub/cli/cache.py
@@ -23,8 +23,8 @@
 
 import typer
 
-from ..utils import CachedRepoInfo, CachedRevisionInfo, CacheNotFound, HFCacheInfo, scan_cache_dir
-from ._cli_utils import ANSI, tabulate, typer_factory
+from ..utils import ANSI, CachedRepoInfo, CachedRevisionInfo, CacheNotFound, HFCacheInfo, scan_cache_dir, tabulate
+from ._cli_utils import typer_factory
 
 
 # --- DELETE helpers (from delete_cache.py) ---
diff --git a/src/huggingface_hub/cli/download.py b/src/huggingface_hub/cli/download.py
index 84251cfe39..655e44d0f7 100644
--- a/src/huggingface_hub/cli/download.py
+++ b/src/huggingface_hub/cli/download.py
@@ -44,9 +44,9 @@
 from huggingface_hub import logging
 from huggingface_hub._snapshot_download import snapshot_download
 from huggingface_hub.file_download import DryRunFileInfo, hf_hub_download
-from huggingface_hub.utils import _format_size, disable_progress_bars, enable_progress_bars
+from huggingface_hub.utils import _format_size, disable_progress_bars, enable_progress_bars, tabulate
 
-from ._cli_utils import RepoIdArg, RepoTypeOpt, RevisionOpt, TokenOpt, tabulate
+from ._cli_utils import RepoIdArg, RepoTypeOpt, RevisionOpt, TokenOpt
 
 
 logger = logging.get_logger(__name__)
diff --git a/src/huggingface_hub/cli/hf.py b/src/huggingface_hub/cli/hf.py
index bb8b3b80d0..8306eff084 100644
--- a/src/huggingface_hub/cli/hf.py
+++ b/src/huggingface_hub/cli/hf.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 
 
-from huggingface_hub.cli._cli_utils import typer_factory
+from huggingface_hub.cli._cli_utils import check_cli_update, typer_factory
 from huggingface_hub.cli.auth import auth_cli
 from huggingface_hub.cli.cache import cache_cli
 from huggingface_hub.cli.download import download
@@ -52,6 +52,7 @@
 
 def main():
     logging.set_verbosity_info()
+    check_cli_update()
     app()
 
 
diff --git a/src/huggingface_hub/cli/repo.py b/src/huggingface_hub/cli/repo.py
index 793c1247c8..bb67ba9172 100644
--- a/src/huggingface_hub/cli/repo.py
+++ b/src/huggingface_hub/cli/repo.py
@@ -27,10 +27,9 @@
 import typer
 
 from huggingface_hub.errors import HfHubHTTPError, RepositoryNotFoundError, RevisionNotFoundError
-from huggingface_hub.utils import logging
+from huggingface_hub.utils import ANSI, logging
 
 from ._cli_utils import (
-    ANSI,
     PrivateOpt,
     RepoIdArg,
     RepoType,
diff --git a/src/huggingface_hub/cli/upload_large_folder.py b/src/huggingface_hub/cli/upload_large_folder.py
index fd5d6bb08e..af4fc55836 100644
--- a/src/huggingface_hub/cli/upload_large_folder.py
+++ b/src/huggingface_hub/cli/upload_large_folder.py
@@ -20,9 +20,9 @@
 import typer
 
 from huggingface_hub import logging
-from huggingface_hub.utils import disable_progress_bars
+from huggingface_hub.utils import ANSI, disable_progress_bars
 
-from ._cli_utils import ANSI, PrivateOpt, RepoIdArg, RepoType, RepoTypeOpt, RevisionOpt, TokenOpt, get_hf_api
+from ._cli_utils import PrivateOpt, RepoIdArg, RepoType, RepoTypeOpt, RevisionOpt, TokenOpt, get_hf_api
 
 
 logger = logging.get_logger(__name__)
diff --git a/src/huggingface_hub/constants.py b/src/huggingface_hub/constants.py
index 2ca29cf294..90ba0a5889 100644
--- a/src/huggingface_hub/constants.py
+++ b/src/huggingface_hub/constants.py
@@ -163,6 +163,10 @@ def _as_int(value: Optional[str]) -> Optional[int]:
 
 HF_HUB_OFFLINE = _is_true(os.environ.get("HF_HUB_OFFLINE") or os.environ.get("TRANSFORMERS_OFFLINE"))
 
+# File created to mark that the version check has been done.
+# Check is performed once per 24 hours at most.
+CHECK_FOR_UPDATE_DONE_PATH = os.path.join(HF_HOME, ".check_for_update_done")
+
 # If set, log level will be set to DEBUG and all requests made to the Hub will be logged
 # as curl commands for reproducibility.
 HF_DEBUG = _is_true(os.environ.get("HF_DEBUG"))
diff --git a/src/huggingface_hub/utils/__init__.py b/src/huggingface_hub/utils/__init__.py
index 7817bfe0d4..bccc01174d 100644
--- a/src/huggingface_hub/utils/__init__.py
+++ b/src/huggingface_hub/utils/__init__.py
@@ -85,6 +85,7 @@
     get_tensorboard_version,
     get_tf_version,
     get_torch_version,
+    installation_method,
     is_aiohttp_available,
     is_colab_enterprise,
     is_fastai_available,
@@ -109,6 +110,7 @@
 from ._safetensors import SafetensorsFileMetadata, SafetensorsRepoMetadata, TensorInfo
 from ._subprocess import capture_output, run_interactive_subprocess, run_subprocess
 from ._telemetry import send_telemetry
+from ._terminal import ANSI, tabulate
 from ._typing import is_jsonable, is_simple_optional_type, unwrap_simple_optional_type
 from ._validators import validate_hf_hub_args, validate_repo_id
 from ._xet import (
diff --git a/src/huggingface_hub/utils/_cache_manager.py b/src/huggingface_hub/utils/_cache_manager.py
index 2d927cf278..3ec03f35e8 100644
--- a/src/huggingface_hub/utils/_cache_manager.py
+++ b/src/huggingface_hub/utils/_cache_manager.py
@@ -24,9 +24,9 @@
 
 from huggingface_hub.errors import CacheNotFound, CorruptedCacheException
 
-from ..cli._cli_utils import tabulate
 from ..constants import HF_HUB_CACHE
 from . import logging
+from ._terminal import tabulate
 
 
 logger = logging.get_logger(__name__)
diff --git a/src/huggingface_hub/utils/_http.py b/src/huggingface_hub/utils/_http.py
index b172379417..f98dfda517 100644
--- a/src/huggingface_hub/utils/_http.py
+++ b/src/huggingface_hub/utils/_http.py
@@ -716,9 +716,9 @@ def _curlify(request: httpx.Request) -> str:
     flat_parts = []
     for k, v in parts:
         if k:
-            flat_parts.append(quote(k))
+            flat_parts.append(quote(str(k)))
         if v:
-            flat_parts.append(quote(v))
+            flat_parts.append(quote(str(v)))
 
     return " ".join(flat_parts)
 
diff --git a/src/huggingface_hub/utils/_runtime.py b/src/huggingface_hub/utils/_runtime.py
index dd390df87c..445be52baf 100644
--- a/src/huggingface_hub/utils/_runtime.py
+++ b/src/huggingface_hub/utils/_runtime.py
@@ -19,7 +19,8 @@
 import platform
 import sys
 import warnings
-from typing import Any
+from pathlib import Path
+from typing import Any, Literal
 
 from .. import __version__, constants
 
@@ -322,6 +323,49 @@ def is_colab_enterprise() -> bool:
     return os.environ.get("VERTEX_PRODUCT") == "COLAB_ENTERPRISE"
 
 
+# Check how huggingface_hub has been installed
+
+
+def installation_method() -> Literal["brew", "hf_installer", "unknown"]:
+    """Return the installation method of the current environment.
+
+    - "hf_installer" if installed via the official installer script
+    - "brew" if installed via Homebrew
+    - "unknown" otherwise
+    """
+    if _is_brew_installation():
+        return "brew"
+    elif _is_hf_installer_installation():
+        return "hf_installer"
+    else:
+        return "unknown"
+
+
+def _is_brew_installation() -> bool:
+    """Check if running from a Homebrew installation.
+
+    Note: AI-generated by Claude.
+    """
+    exe_path = Path(sys.executable).resolve()
+    exe_str = str(exe_path)
+
+    # Check common Homebrew paths
+    # /opt/homebrew (Apple Silicon), /usr/local (Intel)
+    return "/Cellar/" in exe_str or "/opt/homebrew/" in exe_str or exe_str.startswith("/usr/local/Cellar/")
+
+
+def _is_hf_installer_installation() -> bool:
+    """Return `True` if the current environment was set up via the official hf installer script.
+
+    i.e. using one of
+        curl -LsSf https://hf.co/cli/install.sh | sh
+        powershell -ExecutionPolicy ByPass -c "irm https://hf.co/cli/install.ps1 | iex"
+    """
+    venv = sys.prefix  # points to venv root if active
+    marker = Path(venv) / ".hf_installer_marker"
+    return marker.exists()
+
+
 def dump_environment_info() -> dict[str, Any]:
     """Dump information about the machine to help debugging issues.
 
@@ -366,6 +410,9 @@ def dump_environment_info() -> dict[str, Any]:
     except Exception:
         pass
 
+    # How huggingface_hub has been installed?
+    info["Installation method"] = installation_method()
+
     # Installed dependencies
     info["Torch"] = get_torch_version()
     info["httpx"] = get_httpx_version()
diff --git a/src/huggingface_hub/utils/_terminal.py b/src/huggingface_hub/utils/_terminal.py
new file mode 100644
index 0000000000..6463b4b3cc
--- /dev/null
+++ b/src/huggingface_hub/utils/_terminal.py
@@ -0,0 +1,69 @@
+# Copyright 2025 The HuggingFace Team. All rights reserved.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+"""Contains utilities to print stuff to the terminal (styling, helpers)."""
+
+import os
+from typing import Union
+
+
+class ANSI:
+    """
+    Helper for en.wikipedia.org/wiki/ANSI_escape_code
+    """
+
+    _bold = "\u001b[1m"
+    _gray = "\u001b[90m"
+    _red = "\u001b[31m"
+    _reset = "\u001b[0m"
+    _yellow = "\u001b[33m"
+
+    @classmethod
+    def bold(cls, s: str) -> str:
+        return cls._format(s, cls._bold)
+
+    @classmethod
+    def gray(cls, s: str) -> str:
+        return cls._format(s, cls._gray)
+
+    @classmethod
+    def red(cls, s: str) -> str:
+        return cls._format(s, cls._bold + cls._red)
+
+    @classmethod
+    def yellow(cls, s: str) -> str:
+        return cls._format(s, cls._yellow)
+
+    @classmethod
+    def _format(cls, s: str, code: str) -> str:
+        if os.environ.get("NO_COLOR"):
+            # See https://no-color.org/
+            return s
+        return f"{code}{s}{cls._reset}"
+
+
+def tabulate(rows: list[list[Union[str, int]]], headers: list[str]) -> str:
+    """
+    Inspired by:
+
+    - stackoverflow.com/a/8356620/593036
+    - stackoverflow.com/questions/9535954/printing-lists-as-tabular-data
+    """
+    col_widths = [max(len(str(x)) for x in col) for col in zip(*rows, headers)]
+    row_format = ("{{:{}}} " * len(headers)).format(*col_widths)
+    lines = []
+    lines.append(row_format.format(*headers))
+    lines.append(row_format.format(*["-" * w for w in col_widths]))
+    for row in rows:
+        lines.append(row_format.format(*row))
+    return "\n".join(lines)
diff --git a/tests/test_utils_cli.py b/tests/test_utils_terminal.py
similarity index 97%
rename from tests/test_utils_cli.py
rename to tests/test_utils_terminal.py
index 5e6cdedeab..5b5f39bf5e 100644
--- a/tests/test_utils_cli.py
+++ b/tests/test_utils_terminal.py
@@ -2,7 +2,7 @@
 import unittest
 from unittest import mock
 
-from huggingface_hub.cli._cli_utils import ANSI, tabulate
+from huggingface_hub.utils._terminal import ANSI, tabulate
 
 
 class TestCLIUtils(unittest.TestCase):
diff --git a/utils/installers/install.ps1 b/utils/installers/install.ps1
index 8fd82e39d9..cb7f507cb8 100644
--- a/utils/installers/install.ps1
+++ b/utils/installers/install.ps1
@@ -1,5 +1,5 @@
 # Hugging Face CLI Installer for Windows
-# Usage: powershell -c "irm https://hf.co/cli/install.ps1 | iex"
+# Usage: powershell -ExecutionPolicy ByPass -c "irm https://hf.co/cli/install.ps1 | iex"
 # Or: curl -LsSf https://hf.co/cli/install.ps1 | pwsh -
 
 <#
@@ -223,6 +223,10 @@ function New-VirtualEnvironment {
     }
     if (-not $?) { throw "Failed to create virtual environment" }
 
+    # Mark this installation as installer-managed
+    $markerFile = Join-Path $VENV_DIR ".hf_installer_marker"
+    New-Item -Path $markerFile -ItemType File -Force | Out-Null
+
     # Use the venv's python -m pip for deterministic upgrades
     $script:VenvPython = Join-Path $SCRIPTS_DIR "python.exe"
     Write-Log "Upgrading pip..."
diff --git a/utils/installers/install.sh b/utils/installers/install.sh
index d8030ea585..011fcfb30c 100755
--- a/utils/installers/install.sh
+++ b/utils/installers/install.sh
@@ -180,7 +180,7 @@ detect_os() {
 
 # Install Python if not available
 python_version_supported() {
-    "$1" - <<'PY' >/dev/null 2>&1
+    "$1" <<'PY' >/dev/null 2>&1
 import sys
 sys.exit(0 if sys.version_info >= (3, 9) else 1)
 PY
@@ -268,6 +268,9 @@ create_venv() {
 
     run_command "Failed to create virtual environment at $VENV_DIR" "$PYTHON_CMD" -m venv "$VENV_DIR"
 
+    # Mark this installation as installer-managed
+    touch "$VENV_DIR/.hf_installer_marker"
+
     # Use the venv python for pip management
     log_info "Upgrading pip..."
     run_command "Failed to upgrade pip" "$VENV_DIR/bin/python" -m pip install --upgrade pip