From d77c8d9364adc1e95b973cfcfc9faf7a3ca0a291 Mon Sep 17 00:00:00 2001
From: w3lld1 <42353747+w3lld1@users.noreply.github.com>
Date: Fri, 10 Jul 2026 02:36:25 +0000
Subject: [PATCH] fix: explain oversized system prompts

---
 .../_internal/transport/subprocess_cli.py     | 28 ++++++++++++
 src/claude_agent_sdk/types.py                 |  5 ++-
 tests/test_transport.py                       | 43 +++++++++++++++++++
 3 files changed, 75 insertions(+), 1 deletion(-)

diff --git a/src/claude_agent_sdk/_internal/transport/subprocess_cli.py b/src/claude_agent_sdk/_internal/transport/subprocess_cli.py
index e9a522d13..db73e2935 100644
--- a/src/claude_agent_sdk/_internal/transport/subprocess_cli.py
+++ b/src/claude_agent_sdk/_internal/transport/subprocess_cli.py
@@ -29,6 +29,24 @@
 
 _DEFAULT_MAX_BUFFER_SIZE = 1024 * 1024  # 1MB buffer limit
 MINIMUM_CLAUDE_CODE_VERSION = "2.0.0"
+_LINUX_MAX_ARG_STRLEN_PAGE_MULTIPLIER = 32
+
+
+def _get_linux_max_arg_strlen() -> int | None:
+    """Return Linux's per-argument execve byte limit, if available."""
+    if platform.system() != "Linux":
+        return None
+
+    try:
+        page_size = os.sysconf("SC_PAGE_SIZE")
+    except (AttributeError, OSError, ValueError):
+        return None
+
+    if not isinstance(page_size, int) or page_size <= 0:
+        return None
+
+    return _LINUX_MAX_ARG_STRLEN_PAGE_MULTIPLIER * page_size
+
 
 # Track live CLI subprocesses so we can terminate them when the parent Python
 # process exits. This mirrors the TypeScript SDK's parent-exit cleanup and
@@ -288,6 +306,16 @@ def _build_command(self) -> list[str]:
         if self._options.system_prompt is None:
             cmd.extend(["--system-prompt", ""])
         elif isinstance(self._options.system_prompt, str):
+            max_arg_strlen = _get_linux_max_arg_strlen()
+            system_prompt_size = len(self._options.system_prompt.encode())
+            if max_arg_strlen is not None and system_prompt_size >= max_arg_strlen:
+                raise CLIConnectionError(
+                    "system_prompt is too large to pass as a command-line "
+                    f"argument on Linux ({system_prompt_size} bytes; "
+                    f"limit is {max_arg_strlen} bytes). Write the prompt to "
+                    "a file and pass system_prompt={'type': 'file', "
+                    "'path': '/path/to/prompt.txt'} instead."
+                )
             cmd.extend(["--system-prompt", self._options.system_prompt])
         else:
             sp = self._options.system_prompt
diff --git a/src/claude_agent_sdk/types.py b/src/claude_agent_sdk/types.py
index 5b7926449..d634d554b 100644
--- a/src/claude_agent_sdk/types.py
+++ b/src/claude_agent_sdk/types.py
@@ -1752,7 +1752,10 @@ class ClaudeAgentOptions:
     system_prompt: str | SystemPromptPreset | SystemPromptFile | None = None
     """System prompt configuration.
 
-    - ``str`` — Use a custom system prompt.
+    - ``str`` — Use a custom system prompt. For very large prompts on Linux,
+      prefer the file form to avoid the kernel's per-argument size limit.
+    - ``{"type": "file", "path": "/path/to/prompt.txt"}`` — Read a custom
+      system prompt from a file.
     - ``{"type": "preset", "preset": "claude_code"}`` — Use Claude Code's default
       system prompt.
     - ``{"type": "preset", "preset": "claude_code", "append": "..."}`` — Default
diff --git a/tests/test_transport.py b/tests/test_transport.py
index d55aa18b0..c1c23f069 100644
--- a/tests/test_transport.py
+++ b/tests/test_transport.py
@@ -137,6 +137,49 @@ def test_build_command_with_system_prompt_string(self):
         assert "--system-prompt" in cmd
         assert "Be helpful" in cmd
 
+    def test_build_command_rejects_oversized_system_prompt_on_linux(self):
+        """Test oversized string prompts get an actionable error on Linux."""
+        from claude_agent_sdk._errors import CLIConnectionError
+
+        transport = SubprocessCLITransport(
+            prompt="test",
+            options=make_options(system_prompt="x" * 64),
+        )
+
+        with (
+            patch(
+                "claude_agent_sdk._internal.transport.subprocess_cli.platform.system",
+                return_value="Linux",
+            ),
+            patch(
+                "claude_agent_sdk._internal.transport.subprocess_cli.os.sysconf",
+                return_value=1,
+            ),
+            pytest.raises(CLIConnectionError) as exc_info,
+        ):
+            transport._build_command()
+
+        message = str(exc_info.value)
+        assert "system_prompt is too large" in message
+        assert "64 bytes" in message
+        assert "system_prompt={'type': 'file'" in message
+
+    def test_build_command_allows_large_system_prompt_off_linux(self):
+        """Test non-Linux platforms keep passing string prompts directly."""
+        transport = SubprocessCLITransport(
+            prompt="test",
+            options=make_options(system_prompt="x" * 16),
+        )
+
+        with patch(
+            "claude_agent_sdk._internal.transport.subprocess_cli.platform.system",
+            return_value="Windows",
+        ):
+            cmd = transport._build_command()
+
+        assert "--system-prompt" in cmd
+        assert cmd[cmd.index("--system-prompt") + 1] == "x" * 16
+
     def test_build_command_with_system_prompt_preset(self):
         """Test building CLI command with system prompt preset."""
         transport = SubprocessCLITransport(