Internal Server Error when sending multiple PDFs in conversation

[junuMoon]

Description

When attempting to have a conversation that includes multiple PDF documents with Claude, the API returns a 500 Internal Server Error. The error occurs specifically when trying to send a second PDF after receiving a response for the first one.

Steps to Reproduce

1. Initialize a conversation with Claude API
2. Send first message containing:
   • PDF document (base64 encoded)
   • Text prompt ("1줄 요약")
3. Receive assistant's response
4. Send second message with:
   • Different PDF document (base64 encoded)
   • Text prompt ("1줄요약")
5. API returns 500 Internal Server Error

Code Example

message2 = client.beta.messages.create(
    model="claude-3-5-sonnet-20241022",
    betas=["pdfs-2024-09-25"],
    max_tokens=1024,
    messages=[
        {
            "role": "user",
            "content": [
                {
                    "type": "document",
                    "source": {
                        "type": "base64",
                        "media_type": "application/pdf",
                        "data": base64_string
                    }
                },
                {
                    "type": "text",
                    "text": "1줄 요약"
                }
            ]
        },
        {
            "role": "assistant",
            "content": message.content[0].text
        },
        {
            "role": "user", 
            "content": [
                {
                    "type": "document",
                    "source": {
                        "type": "base64",
                        "media_type": "application/pdf",
                        "data": base64_string2
                    }
                },
                {
                    "type": "text",
                    "text": "1줄요약"
                }
            ]
        }
    ]
)

Error Message

InternalServerError: Error code: 500 - {'type': 'error', 'error': {'type': 'api_error', 'message': 'Internal server error'}}

Environment

• Python SDK Version: (version number)
• Claude Model: claude-3-5-sonnet-20241022
• Beta Features: ["pdfs-2024-09-25"]

Expected Behavior

The API should handle multiple PDF documents in a conversation, allowing for sequential analysis of different documents.

Additional Context

• The first PDF upload and response works correctly
• The error occurs specifically when trying to send a second PDF in the conversation
• Using the latest beta PDF feature as indicated in the betas parameter

Questions

1. Is there a limitation on the number of PDFs that can be processed in a single conversation?
2. Is there a specific way to handle multiple PDF documents in a conversation that I'm missing?
3. Could this be related to the beta status of the PDF feature?

[DavidSnoble]

I am also seeing this error by calling the REST API