An assistant message with 'tool_calls' must be followed by tool messages responding to each 'tool_call_id'

[guizaols]

I'm building a WhatsApp agent with RubyLLM. After a few questions asked and answered the flow just stops because of the error:

DEBUG -- RubyLLM: error: /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/error.rb:61:in `parse_error': An assistant message with 'tool_calls' must be followed by tool messages responding to each 'tool_call_id'. The following tool_call_ids did not have response messages: call_X2wM00xBDQhFbs681BZAZUEt (RubyLLM::BadRequestError)
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/error.rb:49:in `block in call'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-2.13.2/lib/faraday/response.rb:42:in `on_complete'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/error.rb:48:in `call'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-2.13.2/lib/faraday/middleware.rb:56:in `call'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-2.13.2/lib/faraday/middleware.rb:56:in `call'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-retry-2.3.2/lib/faraday/retry/middleware.rb:171:in `block in call'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-retry-2.3.2/lib/faraday/retry/retryable.rb:7:in `with_retries'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-retry-2.3.2/lib/faraday/retry/middleware.rb:167:in `call'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-2.13.2/lib/faraday/middleware.rb:56:in `call'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-2.13.2/lib/faraday/response/logger.rb:25:in `call'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-2.13.2/lib/faraday/rack_builder.rb:153:in `build_response'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-2.13.2/lib/faraday/connection.rb:452:in `run_request'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/faraday-2.13.2/lib/faraday/connection.rb:280:in `post'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/connection.rb:38:in `post'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/provider.rb:77:in `sync_response'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/provider.rb:25:in `complete'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/chat.rb:97:in `complete'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/active_record/acts_as.rb:157:in `complete'
	from /Users/guizaols/.local/share/mise/installs/ruby/3.3.5/lib/ruby/gems/3.3.0/gems/ruby_llm-1.3.1/lib/ruby_llm/active_record/acts_as.rb:151:in `ask'

I get a set of data after a few shots (sometimes it happens in the second attempt). I don't know why this is hapenning

Get data

Chat.last.messages.order(:created_at).pluck(:id, :role, :content, :tool_call_id).map { |data| [data[0], data[1], data[2]&.truncate(100), data[3]] }

Data

[
  ["eec84563-3d1f-4beb-b0a5-a70445d45991", "system", "Você é um assistente...", nil],
  ["39266348-fc40-489c-84df-79260b2a1a31", "user", "quero comprar uma mesa de centro moderna", nil],
  ["382dbe17-dd4b-47b7-b691-06b52cc07b77", "assistant", nil, nil],
  ["527447b5-e6c2-4219-9039-013152908e91", "tool", "Selecionamos as melhores opções para você!", "2aada229-3b28-474e-aff1-ecd91397941c"],
  ["1bd81303-e539-42c1-a902-b228fdcd9f7a", "assistant", "Vou te ajudar a encontrar isso! 😊", nil],
  
  ["2fd36c61-a4ba-43c4-845f-27f5c6063ea5", "system", "Você é um assistente...", nil],
  ["e6f6f9a8-3f5d-4855-af60-256353ca9e4c", "user", "quero comprar uma TIPOIA INFANTIL ESTOFADA CHANTAL", nil],
  ["dd81db67-1ffc-4d03-97db-737a36df7908", "assistant", nil, nil],
  ["e453aa61-c5d4-4689-a6c1-072195327bb6", "tool", "Selecionamos as melhores opções para você!", "30068054-f76d-47e8-9314-f606d2f19a99"],
  ["780d3420-bf61-46b8-b07e-c4f29ccef308", "assistant", "Vou te ajudar a encontrar isso! 😊", nil],
  
  ["4e3c07d5-9e0c-4009-9a86-a7f79414759b", "system", "Você é um assistente...", nil],
  ["522762dd-1178-43af-9517-970d8ddb1322", "user", "quero comprar uma Caixa de som JBL Wind 3", nil],
  ["fed87204-aa93-4e28-8b83-372ab32b2c01", "assistant", nil, nil],
  ["4c4298c2-fe2f-4ba0-aa50-6267cd8eb636", "tool", "Selecionamos as melhores opções para você!", "11b7152d-4f5f-475d-8fc5-080df0fe76c8"],
  ["c9a56bbe-490c-48eb-bb7e-8803a546c790", "assistant", "Vou te ajudar a encontrar isso! 😊", nil],
  
  ["4a59873d-df4f-41a6-b898-1b8f2f5679de", "system", "Você é um assistente...", nil],
  ["fc6022ee-da8e-462c-8be9-920686d219b9", "user", "quero comprar uma chuteira nike total 90 44", nil],
  ["7e821423-4ad8-4c6e-b8d3-8f1642e0ecf7", "assistant", nil, nil],
  ["5d407937-7827-4892-b9bf-b176d055247e", "tool", "", "8df4b7c4-449d-4c25-9777-37ea1296187f"],
  ["14f17a67-f118-4e0e-a3a9-509df4e79b06", "assistant", "Vamos lá! 😊", nil],

  # ERROR!
  ["7061efff-bb54-4630-bc20-aa46e8b37f09", "system", "Você é um assistente...", nil],
  ["1ffe625d-549e-47b8-985b-ccf9da347ff4", "user", "pode ser uma camisa do corinthians", nil]
]

I already try to add manually the tool and assistant message role but with no success.
Does anyone have an ideia about this?

[tpaulshippy]

Do you have a minimal reproducible example?