diff --git a/openbb_terminal/terminal_helper.py b/openbb_terminal/terminal_helper.py
index 63a0ab3801b..a7dee8dbbf4 100644
--- a/openbb_terminal/terminal_helper.py
+++ b/openbb_terminal/terminal_helper.py
@@ -9,7 +9,8 @@ import logging
 import os
 import subprocess  # nosec
 import sys
-from typing import List, Optional
+from typing import List, Union
+from packaging import version
 
 # IMPORTATION THIRDPARTY
 import requests
@@ -220,19 +221,19 @@ def check_for_updates() -> None:
         r = None
 
     if r is not None and r.status_code == 200:
-        latest_version = r.json()["tag_name"]
-        latest_version_number = get_version_number(tag=latest_version)
-        current_version_number = get_version_number(tag=obbff.VERSION)
+        latest_tag_name = r.json()["tag_name"]
+        latest_version = version.parse(latest_tag_name)
+        current_version = version.parse(obbff.VERSION)
 
-        if latest_version_number and current_version_number:
+        if check_valid_versions(latest_version, current_version):
 
-            if current_version_number == latest_version_number:
+            if current_version == latest_version:
                 console.print("[green]You are using the latest stable version[/green]")
             else:
                 console.print(
                     "[yellow]You are not using the latest stable version[/yellow]"
                 )
-                if current_version_number < latest_version_number:
+                if current_version < latest_version:
                     console.print(
                         "[yellow]Check for updates at https://openbb.co/products/terminal#get-started[/yellow]"
                     )
@@ -252,21 +253,18 @@ def check_for_updates() -> None:
     console.print("\n")
 
 
-def get_version_number(tag: str) -> Optional[str]:
-    """Get the release number from a tag."""
-
-    if not tag.startswith("v") and len(tag.split(".")) != 3:
-        return None
-
-    if tag.startswith("v"):
-        tag = tag[1:]
-
-    if "rc" in tag.split(".")[-1]:
-        tag_split = tag.split(".")
-        tag_split[-1] = tag_split[-1].split("rc")[0]
-        tag = ".".join(tag_split)
-
-    return tag
+def check_valid_versions(
+    latest_version: Union[version.LegacyVersion, version.Version],
+    current_version: Union[version.LegacyVersion, version.Version],
+) -> bool:
+    if (
+        not latest_version
+        or not current_version
+        or not isinstance(latest_version, version.Version)
+        or not isinstance(current_version, version.Version)
+    ):
+        return False
+    return True
 
 
 def welcome_message():
diff --git a/tests/openbb_terminal/test_terminal_helper.py b/tests/openbb_terminal/test_terminal_helper.py
index 674d3331ed6..54d79916bb4 100644
--- a/tests/openbb_terminal/test_terminal_helper.py
+++ b/tests/openbb_terminal/test_terminal_helper.py
@@ -2,6 +2,7 @@ import sys
 import unittest
 from contextlib import contextmanager
 from unittest.mock import patch
+import pytest
 
 from openbb_terminal import terminal_helper
 from tests.helpers.helpers import check_print
@@ -39,3 +40,51 @@ class TestMainHelper(unittest.TestCase):
     def test_reset(self, mock):
         # pylint: disable=unused-argument
         terminal_helper.reset()
+
+
+@pytest.mark.vcr(record_mode="none")
+@pytest.mark.record_stdout
+@pytest.mark.parametrize(
+    "last_release, current_release",
+    [
+        ("v0.0.1", "v0.0.1"),
+        ("v0.0.2", "v0.0.1"),
+        ("v0.0.1", "v0.0.2"),
+        ("v1.9.0", "v1.10.0"),
+        ("v1.10.0", "v1.9.0"),
+        ("xyz", "v1.9.0"),
+        ("2.0.0", "2.0.0rc1"),
+        ("2.0.0rc1", "2.0.0"),
+        ("2.0.0rc1", "2.0.0rc2"),
+        ("2.0.0rc2", "2.0.0rc1"),
+        ("3.41.99", "88.123.456"),
+        ("88.123.456", "3.41.99"),
+        ("3.41.99", "3.41.99"),
+        ("3.41.99", "3.41.99rc1"),
+        ("8.10.01", "8.1.01"),
+    ],
+)
+def test_check_for_updates(mocker, last_release, current_release):
+    # MOCK GET
+    attrs = {
+        "status_code": 200,
+        "json.return_value": {
+            "url": "mock_url",
+            "assets_url": "mock_url",
+            "upload_url": "mock_url",
+            "html_url": "mock_url",
+            "node_id": "mock_node_id",
+            "tag_name": last_release,
+            "name": "mock_terminal_name",
+        },
+    }
+    mock_response = mocker.Mock(**attrs)
+    mocker.patch(target="requests.get", new=mocker.Mock(return_value=mock_response))
+
+    # MOCK FF VERSION
+    mocker.patch(
+        target="openbb_terminal.feature_flags.VERSION",
+        new=current_release,
+    )
+
+    terminal_helper.check_for_updates()
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0-2.0.0rc1].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0-2.0.0rc1].txt
new file mode 100644
index 00000000000..ebb1d30e693
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0-2.0.0rc1].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]Check for updates at https://openbb.co/products/terminal#get-started[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc1-2.0.0].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc1-2.0.0].txt
new file mode 100644
index 00000000000..1829b0d4e81
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc1-2.0.0].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]You are using an unreleased version[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc1-2.0.0rc2].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc1-2.0.0rc2].txt
new file mode 100644
index 00000000000..1829b0d4e81
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc1-2.0.0rc2].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]You are using an unreleased version[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc2-2.0.0rc1].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc2-2.0.0rc1].txt
new file mode 100644
index 00000000000..ebb1d30e693
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[2.0.0rc2-2.0.0rc1].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]Check for updates at https://openbb.co/products/terminal#get-started[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-3.41.99].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-3.41.99].txt
new file mode 100644
index 00000000000..9e44b60e915
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-3.41.99].txt
@@ -0,0 +1,3 @@
+[green]You are using the latest stable version[/green]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-3.41.99rc1].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-3.41.99rc1].txt
new file mode 100644
index 00000000000..ebb1d30e693
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-3.41.99rc1].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]Check for updates at https://openbb.co/products/terminal#get-started[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-88.123.456].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-88.123.456].txt
new file mode 100644
index 00000000000..1829b0d4e81
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[3.41.99-88.123.456].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]You are using an unreleased version[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[8.10.01-8.1.01].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[8.10.01-8.1.01].txt
new file mode 100644
index 00000000000..ebb1d30e693
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[8.10.01-8.1.01].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]Check for updates at https://openbb.co/products/terminal#get-started[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[88.123.456-3.41.99].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[88.123.456-3.41.99].txt
new file mode 100644
index 00000000000..ebb1d30e693
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[88.123.456-3.41.99].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]Check for updates at https://openbb.co/products/terminal#get-started[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.1-v0.0.1].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.1-v0.0.1].txt
new file mode 100644
index 00000000000..9e44b60e915
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.1-v0.0.1].txt
@@ -0,0 +1,3 @@
+[green]You are using the latest stable version[/green]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.1-v0.0.2].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.1-v0.0.2].txt
new file mode 100644
index 00000000000..1829b0d4e81
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.1-v0.0.2].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]You are using an unreleased version[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.2-v0.0.1].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.2-v0.0.1].txt
new file mode 100644
index 00000000000..ebb1d30e693
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v0.0.2-v0.0.1].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]Check for updates at https://openbb.co/products/terminal#get-started[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v1.10.0-v1.9.0].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v1.10.0-v1.9.0].txt
new file mode 100644
index 00000000000..ebb1d30e693
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v1.10.0-v1.9.0].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]Check for updates at https://openbb.co/products/terminal#get-started[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v1.9.0-v1.10.0].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v1.9.0-v1.10.0].txt
new file mode 100644
index 00000000000..1829b0d4e81
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[v1.9.0-v1.10.0].txt
@@ -0,0 +1,4 @@
+[yellow]You are not using the latest stable version[/yellow]
+[yellow]You are using an unreleased version[/yellow]
+
+
diff --git a/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[xyz-v1.9.0].txt b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[xyz-v1.9.0].txt
new file mode 100644
index 00000000000..11cd4741d9c
--- /dev/null
+++ b/tests/openbb_terminal/txt/test_terminal_helper/test_check_for_updates[xyz-v1.9.0].txt
@@ -0,0 +1,3 @@
+[red]You are using an unrecognized version.[/red]
+
+