diff --git a/guardrails/cli/configure.py b/guardrails/cli/configure.py
index c1acd612b..f1b9a8d08 100644
--- a/guardrails/cli/configure.py
+++ b/guardrails/cli/configure.py
@@ -12,7 +12,7 @@
 from guardrails.cli.hub.console import console
 from guardrails.cli.server.hub_client import AuthenticationError, get_auth
 from guardrails.cli.telemetry import trace_if_enabled
-
+from guardrails.cli.version import version_warnings_if_applicable
 
 DEFAULT_TOKEN = ""
 DEFAULT_ENABLE_METRICS = True
@@ -78,6 +78,7 @@ def configure(
         help="Clear the existing token from the configuration file.",
     ),
 ):
+    version_warnings_if_applicable(console)
     trace_if_enabled("configure")
     existing_token = _get_default_token()
     last4 = existing_token[-4:] if existing_token else ""
diff --git a/guardrails/cli/hub/install.py b/guardrails/cli/hub/install.py
index 641bd2397..844b05a87 100644
--- a/guardrails/cli/hub/install.py
+++ b/guardrails/cli/hub/install.py
@@ -5,7 +5,9 @@
 
 from guardrails.cli.hub.hub import hub_command
 from guardrails.cli.logger import logger
+from guardrails.cli.hub.console import console
 from guardrails.cli.telemetry import trace_if_enabled
+from guardrails.cli.version import version_warnings_if_applicable
 
 
 @hub_command.command()
@@ -40,6 +42,8 @@ def confirm():
                 " local models for local inference?",
             )
 
+        version_warnings_if_applicable(console)
+
         install_multiple(
             package_uris,
             install_local_models=local_models,
diff --git a/guardrails/cli/start.py b/guardrails/cli/start.py
index 21183b835..d29bbf03d 100644
--- a/guardrails/cli/start.py
+++ b/guardrails/cli/start.py
@@ -5,6 +5,8 @@
 from guardrails.cli.hub.utils import pip_process
 from guardrails.cli.logger import logger
 from guardrails.cli.telemetry import trace_if_enabled
+from guardrails.cli.version import version_warnings_if_applicable
+from guardrails.cli.hub.console import console
 
 
 def api_is_installed() -> bool:
@@ -39,5 +41,6 @@ def start(
     from guardrails_api.cli.start import start  # type: ignore
 
     logger.info("Starting Guardrails server")
+    version_warnings_if_applicable(console)
     trace_if_enabled("start")
     start(env, config, port)
diff --git a/guardrails/cli/version.py b/guardrails/cli/version.py
new file mode 100644
index 000000000..f82f3793f
--- /dev/null
+++ b/guardrails/cli/version.py
@@ -0,0 +1,31 @@
+import contextlib
+import requests
+import semver
+from importlib.metadata import version
+from rich.console import Console
+
+
+GUARDRAILS_PACKAGE_NAME = "guardrails-ai"
+
+
+def get_guardrails_version():
+    return version(GUARDRAILS_PACKAGE_NAME)
+
+
+def version_warnings_if_applicable(console: Console):
+    current_version = get_guardrails_version()
+
+    with contextlib.suppress(Exception):
+        res = requests.get(f"https://pypi.org/pypi/{GUARDRAILS_PACKAGE_NAME}/json")
+        version_info = res.json()
+        info = version_info.get("info", {})
+        latest_version = info.get("version")
+
+        is_update_available = semver.compare(latest_version, current_version) > 0
+
+        if is_update_available:
+            console.print(
+                "[yellow]There is a newer version of Guardrails "
+                f"available {latest_version}. Your current version "
+                f"is {current_version}[/yellow]!"
+            )
diff --git a/poetry.lock b/poetry.lock
index 24b48dec6..4d5e43f7f 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -6823,6 +6823,17 @@ files = [
 cryptography = ">=2.0"
 jeepney = ">=0.6"
 
+[[package]]
+name = "semver"
+version = "3.0.2"
+description = "Python helper for Semantic Versioning (https://semver.org)"
+optional = false
+python-versions = ">=3.7"
+files = [
+    {file = "semver-3.0.2-py3-none-any.whl", hash = "sha256:b1ea4686fe70b981f85359eda33199d60c53964284e0cfb4977d243e37cf4bf4"},
+    {file = "semver-3.0.2.tar.gz", hash = "sha256:6253adb39c70f6e51afed2fa7152bcd414c411286088fb4b9effb133885ab4cc"},
+]
+
 [[package]]
 name = "send2trash"
 version = "1.8.3"
@@ -8419,4 +8430,4 @@ vectordb = ["faiss-cpu", "numpy"]
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.9"
-content-hash = "6253610141bb5686330057ae658550f9257aabe83ee7b279b783a7f4418a26a6"
+content-hash = "25d043e207ef2c57ecc4c4cb6fb288ecccea69cc1f2e7894f3c56e7919f17a43"
diff --git a/pyproject.toml b/pyproject.toml
index 7d0c1eb91..12c3cceef 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -61,6 +61,7 @@ diff-match-patch = "^20230430"
 guardrails-api = ">=0.0.1"
 mlflow = {version = ">=2.0.1", optional = true}
 uvloop = {version = "^0.20.0", optional = true}
+semver = "^3.0.2"
 
 [tool.poetry.extras]
 sql = ["sqlvalidator", "sqlalchemy", "sqlglot"]