Anthropic API bug: 500 error when reusing container with bash_code_execution_output in conversation history

containerBugRepro.ts

/**
 * Bug Reproduction: 500 error when reusing container with bash_code_execution_output in conversation history
 *
 * Steps to reproduce:
 * 1. Upload a file with container_upload
 * 2. Make a request that generates bash_code_execution_output file references
 * 3. Try to reuse the container with the full conversation history
 *
 * Expected: Second request succeeds
 * Actual: Second request fails with 500 Internal Server Error
 *
 * Workaround: Filter out bash_code_execution_output file references from the assistant content
 */

import { Anthropic } from '@anthropic-ai/sdk';
import { createReadStream } from 'fs';

const anthropic = new Anthropic();

async function main() {
  console.log("Step 1: Upload file and make first request...");

  // Upload a file
  const fileObject = await anthropic.beta.files.upload({
    file: createReadStream("test_data.csv"),
  });

  // First request with file upload
  const response1 = await anthropic.beta.messages.create({
    model: "claude-sonnet-4-5",
    betas: ["code-execution-2025-08-25", "files-api-2025-04-14"],
    max_tokens: 4096,
    messages: [{
      role: "user",
      content: [
        { type: "text", text: "Analyze this CSV and save a summary to analysis.json" },
        { type: "container_upload", file_id: fileObject.id }
      ]
    }],
    tools: [{
      type: "code_execution_20250825",
      name: "code_execution"
    }]
  });

  console.log("✓ First request succeeded");

  const containerId = response1.container!.id;
  console.log(`Container ID: ${containerId}`);

  // Check if response has bash_code_execution_output file references
  const hasFileOutputs = JSON.stringify(response1.content).includes("bash_code_execution_output");
  console.log(`Response has file outputs: ${hasFileOutputs}\n`);

  console.log("Step 2: Reuse container with conversation history (will fail)...");

  // BUG: This causes a 500 error when response1.content includes
  // bash_code_execution_output file references in tool results
  try {
    const response2 = await anthropic.beta.messages.create({
      container: containerId,
      model: "claude-sonnet-4-5",
      betas: ["code-execution-2025-08-25", "files-api-2025-04-14"],
      max_tokens: 4096,
      messages: [
        {
          role: "user",
          content: "Analyze this CSV and save a summary to analysis.json",
        },
        {
          role: "assistant",
          content: response1.content, // This causes 500 error
        },
        {
          role: "user",
          content: "What was the total sales?",
        }
      ],
      tools: [{
        type: "code_execution_20250825",
        name: "code_execution"
      }]
    });
    console.log("✓ Second request succeeded");
  } catch (error: any) {
    console.error("✗ Second request failed with error:");
    console.error(`Status: ${error.status}`);
    console.error(`Message: ${error.message}`);
    console.error(`Request ID: ${error.requestID}\n`);
  }

  console.log("Step 3: Reuse container with filtered conversation history (workaround)...");

  // WORKAROUND: Filter out bash_code_execution_output file references
  const filteredContent = response1.content.map((block: any) => {
    if (block.type === "bash_code_execution_tool_result" && block.content?.content) {
      return {
        ...block,
        content: {
          ...block.content,
          content: block.content.content.filter((c: any) => c.type !== "bash_code_execution_output")
        }
      };
    }
    return block;
  });

  try {
    const response3 = await anthropic.beta.messages.create({
      container: containerId,
      model: "claude-sonnet-4-5",
      betas: ["code-execution-2025-08-25", "files-api-2025-04-14"],
      max_tokens: 4096,
      messages: [
        {
          role: "user",
          content: "Analyze this CSV and save a summary to analysis.json",
        },
        {
          role: "assistant",
          content: filteredContent, // Use filtered content
        },
        {
          role: "user",
          content: "What was the total sales?",
        }
      ],
      tools: [{
        type: "code_execution_20250825",
        name: "code_execution"
      }]
    });
    console.log("✓ Third request succeeded with workaround!");
  } catch (error: any) {
    console.error("✗ Third request also failed:");
    console.error(`Status: ${error.status}`);
    console.error(`Message: ${error.message}`);
  }
}

main().catch(console.error);

output.txt

➜ bun ./containerBugRepro.ts 
Step 1: Upload file and make first request...
✓ First request succeeded
Container ID: container_011CTkUQG4YRQUgVoDxBme5n
Response has file outputs: true

Step 2: Reuse container with conversation history (will fail)...
✗ Second request failed with error:
Status: 500
Message: 500 {"type":"error","error":{"type":"api_error","message":"Internal server error"},"request_id":"req_011CTkU
TaLDwSYRp5MeuiJYo"}                                                                                                  Request ID: req_011CTkUTaLDwSYRp5MeuiJYo

Step 3: Reuse container with filtered conversation history (workaround)...
✓ Third request succeeded with workaround!

test_data.csv