diff --git a/src/serena/agent.py b/src/serena/agent.py
index 6f3c203b..ca763b87 100644
--- a/src/serena/agent.py
+++ b/src/serena/agent.py
@@ -25,6 +25,7 @@ from serena.project import Project
 from serena.prompt_factory import SerenaPromptFactory
 from serena.task_executor import TaskExecutor
 from serena.tools import ActivateProjectTool, GetCurrentConfigTool, ReplaceContentTool, Tool, ToolMarker, ToolRegistry
+from serena.util.gui import system_has_usable_display
 from serena.util.inspection import iter_subclasses
 from serena.util.logging import MemoryLogHandler
 from solidlsp.ls_config import Language
@@ -284,11 +285,14 @@ class SerenaAgent:
             dashboard_url = f"http://{dashboard_host}:{port}/dashboard/index.html"
             log.info("Serena web dashboard started at %s", dashboard_url)
             if self.serena_config.web_dashboard_open_on_launch:
-                # open the dashboard URL in the default web browser (using a separate process to control
-                # output redirection)
-                process = multiprocessing.Process(target=self._open_dashboard, args=(dashboard_url,))
-                process.start()
-                process.join(timeout=1)
+                if not system_has_usable_display():
+                    log.warning("Not opening the Serena web dashboard automatically because no usable display was detected.")
+                else:
+                    # open the dashboard URL in the default web browser (using a separate process to control
+                    # output redirection)
+                    process = multiprocessing.Process(target=self._open_dashboard, args=(dashboard_url,))
+                    process.start()
+                    process.join(timeout=1)
             # inform the GUI window (if any)
             if self._gui_log_viewer is not None:
                 self._gui_log_viewer.set_dashboard_url(dashboard_url)
diff --git a/src/serena/util/gui.py b/src/serena/util/gui.py
new file mode 100644
index 00000000..f87236d4
--- /dev/null
+++ b/src/serena/util/gui.py
@@ -0,0 +1,22 @@
+import os
+import platform
+
+
+def system_has_usable_display() -> bool:
+    system = platform.system()
+
+    # macOS and native Windows: assume display is available for desktop usage
+    if system == "Darwin" or system == "Windows":
+        return True
+
+    # Other systems, assumed to be Unix-like (Linux, FreeBSD, Cygwin/MSYS, etc.):
+    # detect display availability since users may operate in CLI contexts
+    else:
+        # Check X11 or Wayland - if environment variables are set to non-empty values, assume display is usable
+        display = os.environ.get("DISPLAY", "")
+        wayland_display = os.environ.get("WAYLAND_DISPLAY", "")
+
+        if display or wayland_display:
+            return True
+
+        return False