I’m building a chat interface that connects to Claude’s API via API Connector. The chat works for 2-3 messages, then breaks. Claude loses all conversation history and starts fresh. The Problem: After 2-3 exchanges, I get either: “messages.X: all messages must have non-empty content” error Bl…

Yes. Role should be an option set. You’ll have System, Assistant, and User probably. Their IDs can be system, assistant, and user respectively (essentially what you’re passing to the AI). Could you just lowercase the display and use that? Possibly, but the display is a display intended to be readab…

[image] gregoryjameslessard: Is there a plugin that properly handles the messages array with JSON escaping? [image] robot ᴺᴱᵂ ᴾᴸᵁᴳᴵᴺ Claude AI - ChatGPT-Like Streaming with Your App Data [Native RAG] - ( Prompt+Model Hiding, Web Search, Vision, Tools (Functions), Toke…

Thank you! I’ll check out this plugin. Does it handle multi-turn conversation history automatically?

Hi @gregoryjameslessard The easiest way to debug this is to copy your API call in the workflow, and prepend a link to a https://webhook.site / request catcher URL to the API call URL (you can do this by making the URL an optional parameter in the API Call). That will forward your raw request to t…

[image] georgecollier: The easiest way to debug this is to copy your API call in the workflow, and prepend a link to a https://webhook.site / request catcher URL to the API call URL (you can do this by making the URL an optional parameter in the API Call). That will forward your raw request to …

[image] gregoryjameslessard: For the webhook.site approach — do I just prepend the webhook URL to my actual API endpoint URL? So it would be something like https://webhook.site/my-unique-id/https://api.anthropic.com/v1/messages? Yeah I mean this example is for OpenAI schema but principle appl…

[image] georgecollier: Some here on the forum will beg you to though :upside_down_face: lmfao

This is exactly what I needed — thank you! So to confirm my understanding: I create a Messages data type with role and content fields, then when building the API call I use: Do a search for Messages (where Conversation = current conversation):format as text With each item formatted as: {"role": …

Perfect — option set for roles makes total sense. I’ll set it up as: Option Set: MessageRole System (ID: system) Assistant (ID: assistant) User (ID: user) Then reference the ID attribute in the :formatted as JSON safe call instead of the display. This has been incredibly helpful — you’…

On a tangentially related note, you might consider using https://openrouter.ai instead of Anthropic directly, because you can use any provider’s models with one API call.

Claude API conversation history breaks after 2-3 messages - JSON escaping issue

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redvivi January 9, 2026, 2:26pm 2

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Claude API conversation history breaks after 2-3 messages - JSON escaping issue

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