diff --git a/plugins/_code_execution/helpers/tty_session.py b/plugins/_code_execution/helpers/tty_session.py
index d39537ae1..bd8013d79 100644
--- a/plugins/_code_execution/helpers/tty_session.py
+++ b/plugins/_code_execution/helpers/tty_session.py
@@ -97,10 +97,20 @@ class TTYSession:
     async def send(self, data: str | bytes):
         if self._proc is None:
             raise RuntimeError("TTYSpawn is not started")
+        if self._pty_master is None and not _IS_WIN:
+            raise RuntimeError("TTYSpawn PTY is closed")
+        if getattr(self._proc, "returncode", None) is not None:
+            raise RuntimeError("TTYSpawn process has exited")
         if isinstance(data, str):
             data = data.encode(self.encoding)
-        self._proc.stdin.write(data)  # type: ignore
-        await self._proc.stdin.drain()  # type: ignore
+        try:
+            self._proc.stdin.write(data)  # type: ignore
+            await self._proc.stdin.drain()  # type: ignore
+        except OSError as e:
+            if e.errno in (errno.EBADF, errno.EIO, errno.EINVAL):
+                self._pty_master = None
+                raise RuntimeError("TTYSpawn PTY is closed") from e
+            raise
 
     async def sendline(self, line: str):
         await self.send(line + "\n")
diff --git a/plugins/_code_execution/tools/code_execution_tool.py b/plugins/_code_execution/tools/code_execution_tool.py
index 6ebec1d61..45566b00f 100644
--- a/plugins/_code_execution/tools/code_execution_tool.py
+++ b/plugins/_code_execution/tools/code_execution_tool.py
@@ -194,12 +194,11 @@ class CodeExecution(Tool):
                 )
 
             except Exception as e:
-                if i == 1:
-                    PrintStyle.error(str(e))
-                    await self.prepare_state(cfg, reset=True, session=session)
+                PrintStyle.error(str(e))
+                await self.prepare_state(cfg, reset=True, session=session)
+                if i == 0:
                     continue
-                else:
-                    raise e
+                raise e
 
     def format_command_for_output(self, command: str):
         short_cmd = command[:250]