diff --git a/.github/workflows/test_cli.yaml b/.github/workflows/test_cli.yaml
index b5f6c863547..3c0e1546efa 100644
--- a/.github/workflows/test_cli.yaml
+++ b/.github/workflows/test_cli.yaml
@@ -134,7 +134,7 @@ jobs:
       - name: Test CLI
         shell: bash
         run: |
-          pytest -v tests/_cli/test_cli*
+          pytest -v tests/_cli/test_cli* --maxfail=2
 
   test_examples:
     needs: [changes, build_wheel]
diff --git a/marimo/_cli/print.py b/marimo/_cli/print.py
index d093dcdfbd5..20e8ea9d3c6 100644
--- a/marimo/_cli/print.py
+++ b/marimo/_cli/print.py
@@ -2,39 +2,77 @@
 
 from __future__ import annotations
 
-from typing import Any
+import os
+import sys
+from typing import Any, cast
 
 from marimo._config.settings import GLOBAL_SETTINGS
 
-# Print helpers
+
+# Check if we're on Windows and if ANSI colors are supported
+def _supports_color() -> bool:
+    if os.environ.get("NO_COLOR") == "1":
+        return False
+
+    # Windows 10 build 14931+ supports ANSI color codes
+    if os.name == "nt":
+        try:
+            import ctypes
+
+            kernel32 = ctypes.windll.kernel32  # type: ignore[attr-defined]
+            # Get Windows version
+            major = sys.getwindowsversion().major  # type: ignore[attr-defined]
+            build = sys.getwindowsversion().build  # type: ignore[attr-defined]
+
+            # Check if Windows 10+ and if VIRTUAL_TERMINAL_PROCESSING is enabled
+            return cast(
+                bool,
+                major >= 10
+                and build >= 14931
+                and kernel32.SetConsoleMode(kernel32.GetStdHandle(-11), 7),  # type: ignore[attr-defined]
+            )
+        except Exception:
+            return False
+    return hasattr(sys.stdout, "isatty") and sys.stdout.isatty()
+
+
+_USE_COLOR = _supports_color()
 
 
 def bold(text: str) -> str:
-    return "\033[1m" + text + "\033[0m"
+    return "\033[1m" + text + "\033[0m" if _USE_COLOR else text
 
 
 def green(text: str, bold: bool = False) -> str:
+    if not _USE_COLOR:
+        return text
     prefix = "\033[32m" if not bold else "\033[1;32m"
     return prefix + text + "\033[0m"
 
 
 def yellow(text: str, bold: bool = False) -> str:
+    if not _USE_COLOR:
+        return text
     prefix = "\033[33m" if not bold else "\033[1;33m"
     return prefix + text + "\033[0m"
 
 
 def orange(text: str, bold: bool = False) -> str:
+    if not _USE_COLOR:
+        return text
     prefix = "\033[33m" if not bold else "\033[1;33m"
     return prefix + text + "\033[0m"
 
 
 def red(text: str, bold: bool = False) -> str:
+    if not _USE_COLOR:
+        return text
     prefix = "\033[31m" if not bold else "\033[1;31m"
     return prefix + text + "\033[0m"
 
 
 def muted(text: str) -> str:
-    return "\033[90m" + text + "\033[0m"
+    return "\033[90m" + text + "\033[0m" if _USE_COLOR else text
 
 
 def echo(*args: Any, **kwargs: Any) -> None:
diff --git a/marimo/_server/print.py b/marimo/_server/print.py
index d35bd7ad2b6..b4648738157 100644
--- a/marimo/_server/print.py
+++ b/marimo/_server/print.py
@@ -38,10 +38,10 @@ def print_startup(
             f"{green('Create or edit notebooks in your browser', bold=True)} {_utf8('📝')}"
         )
     print_()
-    print_tabbed(f"➜  {green('URL')}: {_colorized_url(url)}")
+    print_tabbed(f"{_utf8('➜')}  {green('URL')}: {_colorized_url(url)}")
     if network:
         print_tabbed(
-            f"➜  {green('Network')}: {_colorized_url(_get_network_url(url))}"
+            f"{_utf8('➜')}  {green('Network')}: {_colorized_url(_get_network_url(url))}"
         )
     print_()