diff --git a/app/cli.py b/app/cli.py
index 74703f9..add4e57 100644
--- a/app/cli.py
+++ b/app/cli.py
@@ -1,10 +1,11 @@
 import logging
+import platform
 import sys
 
 import click
 import requests
 
-from app.commands import check, download, progress, setup, verify
+from app.commands import check, download, progress, setup, update, verify
 from app.commands.version import version
 from app.utils.click import ClickColor, CliContextKey, warn
 from app.utils.version import Version
@@ -43,14 +44,20 @@ def cli(ctx, verbose) -> None:
                 fg=ClickColor.BRIGHT_RED,
             )
         )
-        warn("We strongly recommend upgrading your app.")
-        warn(
-            f"Follow the update guide here: {click.style('https://git-mastery.github.io/app/update', bold=True)}"
-        )
+        # Auto-update only supported on macOS
+        # TODO: Add support for other platforms
+        if platform.system().lower() == "darwin":
+            warn("Attempting automatic update...")
+            ctx.invoke(update)
+        else:
+            warn("We strongly recommend upgrading your app.")
+            warn(
+                f"Follow the update guide here: {click.style('https://git-mastery.github.io/app/update', bold=True)}"
+            )
 
 
 def start() -> None:
-    commands = [check, download, progress, setup, verify, version]
+    commands = [check, download, progress, setup, update, verify, version]
     for command in commands:
         cli.add_command(command)
     cli(obj={})
diff --git a/app/commands/__init__.py b/app/commands/__init__.py
index 1455c3e..e4ef1fc 100644
--- a/app/commands/__init__.py
+++ b/app/commands/__init__.py
@@ -1,8 +1,9 @@
-__all__ = ["check", "download", "progress", "setup", "verify", "version"]
+__all__ = ["check", "download", "progress", "setup", "update", "verify", "version"]
 
 from .check import check
 from .download import download
 from .progress.progress import progress
 from .setup_folder import setup
+from .update import update
 from .verify import verify
 from .version import version
diff --git a/app/commands/update.py b/app/commands/update.py
new file mode 100644
index 0000000..51e40f7
--- /dev/null
+++ b/app/commands/update.py
@@ -0,0 +1,42 @@
+import logging
+import platform
+import subprocess
+
+import click
+
+from app.utils.click import info, success, warn
+
+logger = logging.getLogger(__name__)
+
+
+def is_macos() -> bool:
+    return platform.system().lower() == "darwin"
+
+
+def run_brew_update() -> bool:
+    """Updates Git-Mastery via Homebrew for macOS."""
+    try:
+        command = ["sh", "-c", "brew update && brew upgrade gitmastery"]
+        info(f"Running: {click.style(' '.join(command), bold=True)}")
+        result = subprocess.run(command)
+        return result.returncode == 0
+    except Exception as e:
+        logger.error(f"Failed to run update command: {e}")
+        return False
+
+
+@click.command()
+def update() -> None:
+    """Update Git-Mastery to the latest version."""
+    if not is_macos():
+        info(
+            "Auto-update is currently only supported on macOS. "
+            "Please follow the update guide: https://git-mastery.github.io/app/update"
+        )
+        return
+
+    info("Detected macOS. Starting update via Homebrew...")
+    if run_brew_update():
+        success("Git-Mastery has been updated successfully!")
+    else:
+        warn("Update command finished with errors. Please check the output above.")