diff --git a/packages/shorebird_cli/lib/src/executables/git.dart b/packages/shorebird_cli/lib/src/executables/git.dart
index 5c092be7..62313540 100644
--- a/packages/shorebird_cli/lib/src/executables/git.dart
+++ b/packages/shorebird_cli/lib/src/executables/git.dart
@@ -1,4 +1,4 @@
-// cspell:words unmatch
+// cspell:words unmatch githubstatus
 import 'dart:io';
 
 import 'package:scoped_deps/scoped_deps.dart';
@@ -10,6 +10,44 @@ final gitRef = create(Git.new);
 /// The [Git] instance available in the current zone.
 Git get git => read(gitRef);
 
+/// {@template git_server_unreachable_exception}
+/// Exception thrown when a git command fails due to a server error.
+/// {@endtemplate}
+class GitServerUnreachableException extends ProcessException {
+  /// {@macro git_server_unreachable_exception}
+  GitServerUnreachableException(
+    super.executable,
+    super.arguments, [
+    super.message = '',
+    super.errorCode = 0,
+  ]);
+}
+
+/// Pattern that matches HTTP server errors (500, 502, 503, 504) or "Internal
+/// Server Error" in git output.
+final _serverErrorPattern = RegExp(
+  'The requested URL returned error: (500|502|503|504)|Internal Server Error',
+);
+
+/// Pattern that extracts the hostname from a git remote URL in stderr.
+/// Matches URLs like `https://github.com/org/repo.git/`.
+final _remoteHostPattern = RegExp(r"https?://([^/']+)");
+
+String _buildServerErrorMessage(String stderr) {
+  final hostMatch = _remoteHostPattern.firstMatch(stderr);
+  final host = hostMatch?.group(1);
+  final serverName = host ?? 'the remote git server';
+
+  final buffer = StringBuffer('Unable to reach $serverName.');
+  if (host == 'github.com') {
+    buffer.write(
+      '\nIf your network connection is working, check '
+      'https://www.githubstatus.com for service status.',
+    );
+  }
+  return buffer.toString();
+}
+
 /// A wrapper around all git related functionality.
 class Git {
   /// Name of the git executable.
@@ -26,10 +64,19 @@ class Git {
       workingDirectory: workingDirectory,
     );
     if (result.exitCode != 0) {
+      final stderr = '${result.stderr}';
+      if (_serverErrorPattern.hasMatch(stderr)) {
+        throw GitServerUnreachableException(
+          executable,
+          arguments,
+          _buildServerErrorMessage(stderr),
+          result.exitCode,
+        );
+      }
       throw ProcessException(
         executable,
         arguments,
-        '${result.stderr}',
+        stderr,
         result.exitCode,
       );
     }
diff --git a/packages/shorebird_cli/test/src/executables/git_test.dart b/packages/shorebird_cli/test/src/executables/git_test.dart
index d04e8b6a..504adb31 100644
--- a/packages/shorebird_cli/test/src/executables/git_test.dart
+++ b/packages/shorebird_cli/test/src/executables/git_test.dart
@@ -1,3 +1,4 @@
+// cspell:words githubstatus
 import 'dart:io';
 
 import 'package:mason_logger/mason_logger.dart';
@@ -37,6 +38,82 @@ void main() {
       when(() => processResult.exitCode).thenReturn(ExitCode.success.code);
     });
 
+    group('server error detection', () {
+      test('includes github.com and status link for GitHub URLs', () async {
+        when(() => processResult.exitCode).thenReturn(128);
+        when(() => processResult.stderr).thenReturn(
+          "fatal: unable to access 'https://github.com/"
+          "shorebirdtech/flutter.git/': "
+          'The requested URL returned error: 500',
+        );
+        expect(
+          () => runWithOverrides(
+            () => git.clone(
+              url: 'https://github.com/shorebirdtech/flutter.git',
+              outputDirectory: './output',
+            ),
+          ),
+          throwsA(
+            isA<GitServerUnreachableException>().having(
+              (e) => e.message,
+              'message',
+              allOf(contains('github.com'), contains('githubstatus.com')),
+            ),
+          ),
+        );
+      });
+
+      test('includes host name for non-GitHub URLs', () async {
+        when(() => processResult.exitCode).thenReturn(128);
+        when(() => processResult.stderr).thenReturn(
+          "fatal: unable to access 'https://gitlab.com/"
+          "org/repo.git/': "
+          'The requested URL returned error: 502',
+        );
+        expect(
+          () => runWithOverrides(() => git.fetch(directory: 'repo')),
+          throwsA(
+            isA<GitServerUnreachableException>().having(
+              (e) => e.message,
+              'message',
+              allOf(
+                contains('gitlab.com'),
+                isNot(contains('githubstatus.com')),
+              ),
+            ),
+          ),
+        );
+      });
+
+      test('falls back to generic message when no URL in stderr', () async {
+        when(() => processResult.exitCode).thenReturn(128);
+        when(
+          () => processResult.stderr,
+        ).thenReturn('remote: Internal Server Error');
+        expect(
+          () => runWithOverrides(() => git.fetch(directory: 'repo')),
+          throwsA(
+            isA<GitServerUnreachableException>().having(
+              (e) => e.message,
+              'message',
+              contains('the remote git server'),
+            ),
+          ),
+        );
+      });
+
+      test('throws ProcessException for non-server errors', () async {
+        when(() => processResult.exitCode).thenReturn(128);
+        when(
+          () => processResult.stderr,
+        ).thenReturn('fatal: repository not found');
+        expect(
+          () => runWithOverrides(() => git.fetch(directory: 'repo')),
+          throwsA(isA<ProcessException>()),
+        );
+      });
+    });
+
     group('clone', () {
       const url = 'https://github.com/shorebirdtech/shorebird';
       const outputDirectory = './output';