diff --git a/app/cli.py b/app/cli.py
index 941e25c..4b10816 100644
--- a/app/cli.py
+++ b/app/cli.py
@@ -2,7 +2,6 @@
 import sys
 
 import click
-import requests
 from click_aliases import ClickAliasedGroup
 
 from app.aliases import COMMAND_ALIASES
@@ -10,7 +9,7 @@
 from app.commands.repl import repl
 from app.commands.version import version
 from app.utils.click import ClickColor, CliContextKey, warn
-from app.utils.version import Version
+from app.utils.version import Version, fetch_latest_release_version
 from app.version import __version__
 
 
@@ -39,14 +38,13 @@ def cli(ctx: click.Context, verbose: bool) -> None:
 
     current_version = Version.parse_version_string(__version__)
     ctx.obj[CliContextKey.VERSION] = current_version
-    latest_version = (
-        requests.get(
-            "https://github.com/git-mastery/app/releases/latest", allow_redirects=False
-        )
-        .headers["Location"]
-        .rsplit("/", 1)[-1]
-    )
-    if current_version.is_behind(Version.parse_version_string(latest_version)):
+
+    # Latest version checking is a soft dependency, should not fail operation
+    latest_version, latest_version_error = fetch_latest_release_version()
+    if latest_version_error is not None:
+        warn(latest_version_error)
+
+    if latest_version is not None and current_version.is_behind(latest_version):
         warn(
             click.style(
                 f"Your version of Git-Mastery app {current_version} is behind the latest version {latest_version}.",
diff --git a/app/utils/version.py b/app/utils/version.py
index 600a7ee..de78a83 100644
--- a/app/utils/version.py
+++ b/app/utils/version.py
@@ -1,6 +1,11 @@
 from dataclasses import dataclass
 from typing import Optional
 
+import requests
+
+LATEST_RELEASE_TIMEOUT_SECONDS = 5
+LATEST_RELEASE_URL = "https://github.com/git-mastery/app/releases/latest"
+
 
 @dataclass
 class Version:
@@ -24,7 +29,9 @@ def parse_version_string(version: str) -> "Version":
     def parse(version: str) -> "Version":
         """Parse a plain version string (e.g., '1.2.3')."""
         parts = version.split(".")
-        if ("beta" in version and len(parts) != 4) or ("beta" not in version and len(parts) != 3):
+        if ("beta" in version and len(parts) != 4) or (
+            "beta" not in version and len(parts) != 3
+        ):
             raise ValueError(
                 f"Invalid version string (expected 'MAJOR.MINOR.PATCH[-beta.PRERELEASE]'): {version!r}"
             )
@@ -57,3 +64,18 @@ def __repr__(self) -> str:
         if self.prerelease is not None:
             return f"v{self.major}.{self.minor}.{self.patch}-beta.{self.prerelease}"
         return f"v{self.major}.{self.minor}.{self.patch}"
+
+
+def fetch_latest_release_version() -> tuple[Optional["Version"], Optional[str]]:
+    try:
+        response = requests.get(
+            LATEST_RELEASE_URL,
+            allow_redirects=False,
+            timeout=LATEST_RELEASE_TIMEOUT_SECONDS,
+        )
+        location = response.headers.get("Location")
+        if location is None:
+            return None, "Unable to verify the latest version release"
+        return Version.parse_version_string(location.rsplit("/", 1)[-1]), None
+    except (requests.exceptions.RequestException, ValueError) as e:
+        return None, f"Unable to verify the latest version release: {e}"