diff --git a/changes/11564.fix.md b/changes/11564.fix.md
new file mode 100644
index 00000000000..f528deff836
--- /dev/null
+++ b/changes/11564.fix.md
@@ -0,0 +1 @@
+Fix the installer hanging on the WSL/LiveCD environment warning when run with `--headless` because the "Press Enter to continue" prompt could not receive keystrokes; in headless mode it now auto-proceeds after printing the warning.
diff --git a/src/ai/backend/install/widgets.py b/src/ai/backend/install/widgets.py
index 65bd5662cd3..1dae0de379d 100644
--- a/src/ai/backend/install/widgets.py
+++ b/src/ai/backend/install/widgets.py
@@ -97,7 +97,12 @@ async def wait_continue(self) -> None:
         """
         Block until the user concludes the dialog.
         If the user cancels, the result will be None.
+        In headless mode there is no terminal-attached UI to receive the Enter
+        keypress, so we auto-proceed instead of blocking forever.
         """
+        if self.app.is_headless:
+            self.write(Text.from_markup("\n[dim](headless mode: auto-continuing)[/]\n"))
+            return
         self.write(Text.from_markup("\nPress [bold]Enter[/] to continue...\n"))
         self._continue.clear()
         await self._continue.wait()