stakpak-server 0.3.62

Stakpak: Your DevOps AI Agent. Generate infrastructure code, debug Kubernetes, configure CI/CD, automate deployments, without giving an LLM the keys to production.
Documentation
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use crate::{
    context::{ContextFile, EnvironmentContext, ProjectContext, SessionContextBuilder},
    message_bridge,
    sandbox::{SandboxConfig, SandboxedMcpServer},
    state::AppState,
    types::SessionHandle,
};
use async_trait::async_trait;
use rmcp::model::{
    CallToolRequestParam, CancelledNotification, CancelledNotificationMethod,
    CancelledNotificationParam, ServerResult,
};
use serde_json::json;
use stakai::{ContentPart, Message, MessageContent, Role};
use stakpak_agent_core::{
    AgentCommand, AgentConfig, AgentEvent, AgentHook, AgentRunContext, BudgetAwareContextReducer,
    CheckpointEnvelopeV1, CompactionConfig, PassthroughCompactionEngine, ProposedToolCall,
    RetryConfig, ToolExecutionResult, ToolExecutor, run_agent,
};
use stakpak_api::CreateCheckpointRequest;
use stakpak_mcp_client::McpClient;
use stakpak_shared::utils::sanitize_text_output;
use std::{path::Path, sync::Arc};
use tokio::sync::{Mutex, mpsc};
use tokio_util::sync::CancellationToken;
use uuid::Uuid;

const MAX_TURNS: usize = 64;
const CHECKPOINT_FLUSH_INTERVAL: std::time::Duration = std::time::Duration::from_secs(5);
pub(crate) const ACTIVE_MODEL_METADATA_KEY: &str = "active_model";

pub fn build_run_context(session_id: Uuid, run_id: Uuid) -> AgentRunContext {
    AgentRunContext { run_id, session_id }
}

pub fn build_checkpoint_envelope(
    run_id: Uuid,
    messages: Vec<stakai::Message>,
    metadata: serde_json::Value,
) -> CheckpointEnvelopeV1 {
    CheckpointEnvelopeV1::new(Some(run_id), messages, metadata)
}

pub fn spawn_session_actor(
    state: AppState,
    session_id: Uuid,
    run_id: Uuid,
    model: stakai::Model,
    user_message: Message,
    caller_context: Vec<ContextFile>,
    sandbox_config: Option<SandboxConfig>,
) -> Result<SessionHandle, String> {
    let (command_tx, command_rx) = mpsc::channel(128);
    let cancel = CancellationToken::new();

    let handle = SessionHandle::new(command_tx, cancel.clone());

    let state_for_task = state.clone();
    tokio::spawn(async move {
        let actor_result = run_session_actor(
            state_for_task.clone(),
            session_id,
            run_id,
            model,
            user_message,
            caller_context,
            command_rx,
            cancel,
            sandbox_config,
        )
        .await;

        let finish_result = actor_result.map(|_| ());
        let _ = state_for_task
            .run_manager
            .mark_run_finished(session_id, run_id, finish_result)
            .await;
    });

    Ok(handle)
}

#[allow(clippy::too_many_arguments)]
async fn run_session_actor(
    state: AppState,
    session_id: Uuid,
    run_id: Uuid,
    model: stakai::Model,
    mut user_message: Message,
    caller_context: Vec<ContextFile>,
    command_rx: mpsc::Receiver<AgentCommand>,
    cancel: CancellationToken,
    sandbox_config: Option<SandboxConfig>,
) -> Result<(), String> {
    let active_checkpoint = state
        .session_store
        .get_active_checkpoint(session_id)
        .await
        .ok();
    let parent_checkpoint_id = active_checkpoint.as_ref().map(|checkpoint| checkpoint.id);

    let (initial_messages, mut initial_metadata) =
        match state.checkpoint_store.load_latest(session_id).await {
            Ok(Some(envelope)) => (envelope.messages, envelope.metadata),
            Ok(None) => {
                let messages = active_checkpoint
                    .as_ref()
                    .map(|checkpoint| {
                        message_bridge::chat_to_stakai(checkpoint.state.messages.clone())
                    })
                    .unwrap_or_default();
                let metadata = active_checkpoint
                    .as_ref()
                    .and_then(|checkpoint| checkpoint.state.metadata.clone())
                    .unwrap_or_else(|| json!({}));
                (messages, metadata)
            }
            Err(error) => {
                return Err(format!("Failed to load checkpoint envelope: {error}"));
            }
        };

    // If sandbox is requested, spawn a sandboxed MCP server for this session.
    // Otherwise, use the shared in-process MCP client.
    let sandbox = if let Some(sandbox_config) = sandbox_config {
        tracing::info!(session_id = %session_id, image = %sandbox_config.image, "Spawning sandbox container for session");
        Some(
            SandboxedMcpServer::spawn(&sandbox_config)
                .await
                .map_err(|e| format!("Failed to start sandbox for session {session_id}: {e}"))?,
        )
    } else {
        None
    };

    let (run_tools, tool_executor): (Vec<stakai::Tool>, Box<dyn ToolExecutor + Send + Sync>) =
        if let Some(ref sandbox) = sandbox {
            (
                sandbox.tools.clone(),
                Box::new(SandboxedToolExecutor {
                    mcp_client: sandbox.client.clone(),
                }),
            )
        } else {
            (
                state.current_mcp_tools().await,
                Box::new(ServerToolExecutor {
                    state: state.clone(),
                }),
            )
        };

    let is_new_session = is_new_session_history(&initial_messages);
    let session_cwd = resolve_session_cwd(&state, session_id).await;
    let environment = EnvironmentContext::snapshot(&session_cwd).await;

    // Combine caller context with pre-loaded remote skills context from AppState.
    // Explicit caller context should force per-turn injection, even on resumed
    // sessions, while startup remote skills remain baseline context.
    let has_runtime_caller_context = !caller_context.is_empty();
    let mut all_caller_context = caller_context;
    all_caller_context.extend(state.current_skills().await);

    let project =
        ProjectContext::discover(Path::new(&session_cwd)).with_caller_context(all_caller_context);

    let session_context = SessionContextBuilder::new()
        .base_system_prompt(state.base_system_prompt.clone().unwrap_or_default())
        .environment(environment)
        .project(project)
        .tools(&run_tools)
        .budget(state.context_budget.clone())
        .build();

    if (is_new_session || has_runtime_caller_context)
        && let Some(context_block) = session_context.user_context_block.as_deref()
    {
        user_message = prepend_context_to_user_message(user_message, context_block);
    }

    let mut baseline_messages = initial_messages.clone();
    baseline_messages.push(user_message.clone());

    let checkpoint_runtime = Arc::new(CheckpointRuntime::new(
        state.clone(),
        session_id,
        run_id,
        model.clone(),
        parent_checkpoint_id,
        baseline_messages,
        initial_metadata.clone(),
    ));

    checkpoint_runtime
        .persist_snapshot()
        .await
        .map_err(|error| format!("Failed to persist baseline checkpoint: {error}"))?;

    let periodic_checkpoint_cancel = CancellationToken::new();
    let periodic_checkpoint_runtime = checkpoint_runtime.clone();
    let periodic_checkpoint_cancel_task = periodic_checkpoint_cancel.clone();
    let periodic_task = tokio::spawn(async move {
        let mut interval = tokio::time::interval(CHECKPOINT_FLUSH_INTERVAL);
        interval.set_missed_tick_behavior(tokio::time::MissedTickBehavior::Delay);

        loop {
            tokio::select! {
                _ = periodic_checkpoint_cancel_task.cancelled() => break,
                _ = interval.tick() => {
                    let _ = periodic_checkpoint_runtime.persist_snapshot().await;
                }
            }
        }
    });

    let (core_event_tx, mut core_event_rx) = mpsc::channel::<AgentEvent>(256);

    let event_state = state.clone();
    let event_forwarder = tokio::spawn(async move {
        while let Some(event) = core_event_rx.recv().await {
            handle_core_event(&event_state, session_id, run_id, event).await;
        }
    });

    // Use the model's maximum output capacity as the output budget for context
    // window calculations. This is conservative — the actual response may be shorter,
    // but reserving the full limit avoids mid-response context truncation.
    let max_output_tokens = model.limit.output as u32;
    let agent_config = AgentConfig {
        model,
        system_prompt: session_context.system_prompt,
        max_turns: MAX_TURNS,
        max_output_tokens,
        provider_options: None,
        tool_approval: state.tool_approval_policy.clone(),
        retry: RetryConfig::default(),
        compaction: CompactionConfig::default(),
        tools: run_tools,
    };

    let hooks: Vec<Box<dyn AgentHook>> = vec![Box::new(ServerCheckpointHook {
        checkpoint_runtime: checkpoint_runtime.clone(),
    })];

    let compactor = PassthroughCompactionEngine;
    let context_reducer = BudgetAwareContextReducer::new(5, 0.8);
    let run_context = build_run_context(session_id, run_id);

    let run_result = run_agent(
        run_context,
        state.inference.as_ref(),
        &agent_config,
        initial_messages,
        &mut initial_metadata,
        user_message,
        tool_executor.as_ref(),
        &hooks,
        core_event_tx,
        command_rx,
        cancel,
        &compactor,
        &context_reducer,
    )
    .await;

    periodic_checkpoint_cancel.cancel();
    let _ = periodic_task.await;

    // Shut down sandbox container if one was started
    if let Some(sandbox) = sandbox {
        sandbox.shutdown().await;
    }

    state.clear_pending_tools(session_id, run_id).await;

    match &run_result {
        Ok(result) => {
            checkpoint_runtime.update_messages(&result.messages).await;
            checkpoint_runtime.update_metadata(&result.metadata).await;
            checkpoint_runtime
                .persist_snapshot()
                .await
                .map_err(|error| format!("Failed to persist terminal checkpoint: {error}"))?;
        }
        Err(_) => {
            checkpoint_runtime.update_metadata(&initial_metadata).await;
            let _ = checkpoint_runtime.persist_snapshot().await;
        }
    }

    let _ = tokio::time::timeout(std::time::Duration::from_secs(2), event_forwarder).await;

    run_result
        .map(|_| ())
        .map_err(|error| format!("Agent run failed: {error}"))
}

fn is_new_session_history(messages: &[Message]) -> bool {
    !messages
        .iter()
        .any(|message| matches!(message.role, Role::User | Role::Assistant | Role::Tool))
}

async fn resolve_session_cwd(state: &AppState, session_id: Uuid) -> String {
    // 1. Session-specific cwd (set by API caller)
    if let Ok(session) = state.session_store.get_session(session_id).await
        && let Some(cwd) = session.cwd
        && !cwd.trim().is_empty()
    {
        return cwd;
    }

    // 2. Configured project directory (set at server startup, e.g. from `stakpak up`)
    if let Some(project_dir) = &state.project_dir {
        return project_dir.clone();
    }

    // 3. Process working directory
    std::env::current_dir()
        .ok()
        .map(|path| path.to_string_lossy().to_string())
        .unwrap_or_else(|| ".".to_string())
}

fn prepend_context_to_user_message(mut message: Message, context_block: &str) -> Message {
    if context_block.trim().is_empty() {
        return message;
    }

    match &mut message.content {
        MessageContent::Text(text) => {
            let existing = std::mem::take(text);
            *text = if existing.trim().is_empty() {
                context_block.to_string()
            } else {
                format!("{context_block}\n\n{existing}")
            };
        }
        MessageContent::Parts(parts) => {
            let mut prefixed = Vec::with_capacity(parts.len() + 1);
            prefixed.push(ContentPart::text(context_block));
            prefixed.append(parts);
            *parts = prefixed;
        }
    }

    message
}

async fn handle_core_event(state: &AppState, session_id: Uuid, run_id: Uuid, event: AgentEvent) {
    match &event {
        AgentEvent::ToolCallsProposed { tool_calls, .. } => {
            state
                .set_pending_tools(session_id, run_id, tool_calls.clone())
                .await;
        }
        AgentEvent::TurnCompleted { .. }
        | AgentEvent::RunCompleted { .. }
        | AgentEvent::RunError { .. } => {
            state.clear_pending_tools(session_id, run_id).await;
        }
        _ => {}
    }

    state.events.publish(session_id, Some(run_id), event).await;
}

#[derive(Clone)]
struct ServerToolExecutor {
    state: AppState,
}

#[async_trait]
impl ToolExecutor for ServerToolExecutor {
    async fn execute_tool_call(
        &self,
        run: &AgentRunContext,
        tool_call: &ProposedToolCall,
        cancel: &CancellationToken,
    ) -> Result<ToolExecutionResult, stakpak_agent_core::AgentError> {
        Ok(execute_mcp_tool_call(&self.state, run.session_id, run.run_id, tool_call, cancel).await)
    }
}

/// Tool executor that routes calls through a per-session sandboxed MCP client.
#[derive(Clone)]
struct SandboxedToolExecutor {
    mcp_client: Arc<McpClient>,
}

#[async_trait]
impl ToolExecutor for SandboxedToolExecutor {
    async fn execute_tool_call(
        &self,
        run: &AgentRunContext,
        tool_call: &ProposedToolCall,
        cancel: &CancellationToken,
    ) -> Result<ToolExecutionResult, stakpak_agent_core::AgentError> {
        Ok(execute_mcp_tool_call_with_client(
            &self.mcp_client,
            run.session_id,
            run.run_id,
            tool_call,
            cancel,
        )
        .await)
    }
}

struct CheckpointRuntime {
    state: AppState,
    session_id: Uuid,
    run_id: Uuid,
    active_model: stakai::Model,
    inner: Mutex<CheckpointRuntimeInner>,
}

struct CheckpointRuntimeInner {
    parent_checkpoint_id: Option<Uuid>,
    latest_messages: Vec<Message>,
    latest_metadata: serde_json::Value,
    last_persisted_signature: Option<String>,
    dirty: bool,
}

impl CheckpointRuntime {
    fn new(
        state: AppState,
        session_id: Uuid,
        run_id: Uuid,
        active_model: stakai::Model,
        parent_checkpoint_id: Option<Uuid>,
        latest_messages: Vec<Message>,
        latest_metadata: serde_json::Value,
    ) -> Self {
        Self {
            state,
            session_id,
            run_id,
            active_model,
            inner: Mutex::new(CheckpointRuntimeInner {
                parent_checkpoint_id,
                latest_messages,
                latest_metadata,
                last_persisted_signature: None,
                dirty: true,
            }),
        }
    }

    async fn update_messages(&self, messages: &[Message]) {
        let mut guard = self.inner.lock().await;
        guard.latest_messages = messages.to_vec();
        guard.dirty = true;
    }

    async fn update_metadata(&self, metadata: &serde_json::Value) {
        let mut guard = self.inner.lock().await;
        guard.latest_metadata = metadata.clone();
        guard.dirty = true;
    }

    async fn persist_snapshot(&self) -> Result<Uuid, String> {
        let mut guard = self.inner.lock().await;
        self.persist_if_needed(&mut guard).await
    }

    async fn persist_if_needed(&self, guard: &mut CheckpointRuntimeInner) -> Result<Uuid, String> {
        if !guard.dirty
            && let Some(checkpoint_id) = guard.parent_checkpoint_id
        {
            return Ok(checkpoint_id);
        }

        let signature = checkpoint_signature(&guard.latest_messages, &guard.latest_metadata)?;
        let changed = guard.last_persisted_signature.as_deref() != Some(signature.as_str());
        let should_persist = guard.parent_checkpoint_id.is_none() || (guard.dirty && changed);

        if !should_persist {
            guard.dirty = false;
            if let Some(checkpoint_id) = guard.parent_checkpoint_id {
                return Ok(checkpoint_id);
            }
        }

        let checkpoint_id = persist_checkpoint(
            &self.state,
            self.session_id,
            self.run_id,
            &self.active_model,
            guard.parent_checkpoint_id,
            &guard.latest_messages,
            &guard.latest_metadata,
        )
        .await?;

        guard.parent_checkpoint_id = Some(checkpoint_id);
        guard.last_persisted_signature = Some(signature);
        guard.dirty = false;

        Ok(checkpoint_id)
    }
}

struct ServerCheckpointHook {
    checkpoint_runtime: Arc<CheckpointRuntime>,
}

#[async_trait]
impl AgentHook for ServerCheckpointHook {
    async fn before_inference(
        &self,
        _run: &AgentRunContext,
        messages: &[Message],
        _model: &stakai::Model,
    ) -> Result<(), stakpak_agent_core::AgentError> {
        self.checkpoint_runtime.update_messages(messages).await;
        Ok(())
    }

    async fn after_inference(
        &self,
        _run: &AgentRunContext,
        messages: &[Message],
        _model: &stakai::Model,
    ) -> Result<(), stakpak_agent_core::AgentError> {
        self.checkpoint_runtime.update_messages(messages).await;
        Ok(())
    }

    async fn after_tool_execution(
        &self,
        _run: &AgentRunContext,
        _tool_call: &ProposedToolCall,
        messages: &[Message],
    ) -> Result<(), stakpak_agent_core::AgentError> {
        self.checkpoint_runtime.update_messages(messages).await;
        Ok(())
    }

    async fn on_error(
        &self,
        _run: &AgentRunContext,
        _error: &stakpak_agent_core::AgentError,
        messages: &[Message],
    ) -> Result<(), stakpak_agent_core::AgentError> {
        self.checkpoint_runtime.update_messages(messages).await;
        let _ = self.checkpoint_runtime.persist_snapshot().await;
        Ok(())
    }
}

async fn execute_mcp_tool_call(
    state: &AppState,
    session_id: Uuid,
    run_id: Uuid,
    tool_call: &ProposedToolCall,
    cancel: &CancellationToken,
) -> ToolExecutionResult {
    let Some(mcp_client) = state.mcp_client.as_ref() else {
        return ToolExecutionResult::Completed {
            result: "MCP client is not initialized".to_string(),
            is_error: true,
        };
    };

    execute_mcp_tool_call_with_client(mcp_client, session_id, run_id, tool_call, cancel).await
}

async fn execute_mcp_tool_call_with_client(
    mcp_client: &McpClient,
    session_id: Uuid,
    run_id: Uuid,
    tool_call: &ProposedToolCall,
    cancel: &CancellationToken,
) -> ToolExecutionResult {
    let metadata = Some(serde_json::Map::from_iter([
        (
            "session_id".to_string(),
            serde_json::Value::String(session_id.to_string()),
        ),
        (
            "run_id".to_string(),
            serde_json::Value::String(run_id.to_string()),
        ),
        (
            "tool_call_id".to_string(),
            serde_json::Value::String(tool_call.id.clone()),
        ),
    ]));

    let arguments = match &tool_call.arguments {
        serde_json::Value::Object(map) => Some(map.clone()),
        serde_json::Value::Null => None,
        other => Some(serde_json::Map::from_iter([(
            "input".to_string(),
            other.clone(),
        )])),
    };

    let request_handle = match stakpak_mcp_client::call_tool(
        mcp_client,
        CallToolRequestParam {
            name: tool_call.name.clone().into(),
            arguments,
        },
        metadata,
    )
    .await
    {
        Ok(handle) => handle,
        Err(error) => {
            return ToolExecutionResult::Completed {
                result: format!("MCP tool call failed: {error}"),
                is_error: true,
            };
        }
    };

    let peer_for_cancel = request_handle.peer.clone();
    let request_id = request_handle.id.clone();

    tokio::select! {
        _ = cancel.cancelled() => {
            let notification = CancelledNotification {
                method: CancelledNotificationMethod,
                params: CancelledNotificationParam {
                    request_id,
                    reason: Some("user cancel".to_string()),
                },
                extensions: Default::default(),
            };

            let _ = peer_for_cancel.send_notification(notification.into()).await;
            ToolExecutionResult::Cancelled
        }
        server_result = request_handle.await_response() => {
            match server_result {
                Ok(ServerResult::CallToolResult(result)) => {
                    ToolExecutionResult::Completed {
                        result: render_call_tool_result(&result),
                        is_error: result.is_error.unwrap_or(false),
                    }
                }
                Ok(_) => ToolExecutionResult::Completed {
                    result: "Unexpected MCP response type".to_string(),
                    is_error: true,
                },
                Err(error) => ToolExecutionResult::Completed {
                    result: format!("MCP tool execution error: {error}"),
                    is_error: true,
                },
            }
        }
    }
}

fn render_call_tool_result(result: &rmcp::model::CallToolResult) -> String {
    let rendered = result
        .content
        .iter()
        .filter_map(|content| content.raw.as_text().map(|text| text.text.clone()))
        .collect::<Vec<_>>()
        .join("\n");

    if !rendered.is_empty() {
        return sanitize_text_output(&rendered);
    }

    if result.content.is_empty() {
        return "<empty tool result>".to_string();
    }

    "<non-text tool result omitted for safety>".to_string()
}

fn checkpoint_signature(
    messages: &[Message],
    metadata: &serde_json::Value,
) -> Result<String, String> {
    serde_json::to_string(&(messages, metadata))
        .map_err(|error| format!("Failed to serialize checkpoint messages: {error}"))
}

async fn persist_checkpoint(
    state: &AppState,
    session_id: Uuid,
    run_id: Uuid,
    active_model: &stakai::Model,
    parent_id: Option<Uuid>,
    messages: &[Message],
    metadata: &serde_json::Value,
) -> Result<Uuid, String> {
    // TODO(ahmed): Migrate server/session checkpoint storage to `Vec<stakai::Message>` directly
    // and remove the ChatMessage adapter conversion (`message_bridge::stakai_to_chat`).
    let mut request = CreateCheckpointRequest::new(message_bridge::stakai_to_chat(messages))
        .with_metadata(metadata.clone());

    if let Some(parent_id) = parent_id {
        request = request.with_parent(parent_id);
    }

    let checkpoint = state
        .session_store
        .create_checkpoint(session_id, &request)
        .await
        .map_err(|error| error.to_string())?;

    let mut envelope_metadata = if metadata.is_object() {
        metadata.clone()
    } else {
        json!({})
    };

    if let Some(obj) = envelope_metadata.as_object_mut() {
        obj.insert(
            "session_id".to_string(),
            serde_json::Value::String(session_id.to_string()),
        );
        obj.insert(
            "checkpoint_id".to_string(),
            serde_json::Value::String(checkpoint.id.to_string()),
        );
        obj.insert(
            ACTIVE_MODEL_METADATA_KEY.to_string(),
            serde_json::Value::String(format!("{}/{}", active_model.provider, active_model.id)),
        );
    }

    let envelope = build_checkpoint_envelope(run_id, messages.to_vec(), envelope_metadata);

    state
        .checkpoint_store
        .save_latest(session_id, &envelope)
        .await
        .map_err(|error| {
            format!(
                "Failed to persist checkpoint envelope for session {}: {}",
                session_id, error
            )
        })?;

    Ok(checkpoint.id)
}

#[cfg(test)]
mod tests {
    use super::*;
    use rmcp::model::{CallToolResult, Content};
    use serde_json::json;
    use stakai::{ContentPart, Message, MessageContent, Role};

    #[test]
    fn run_id_is_not_regenerated_when_building_run_context() {
        let session_id = Uuid::new_v4();
        let run_id = Uuid::new_v4();

        let run_context = build_run_context(session_id, run_id);

        assert_eq!(run_context.session_id, session_id);
        assert_eq!(run_context.run_id, run_id);
    }

    #[test]
    fn checkpoint_envelope_carries_same_run_id() {
        let run_id = Uuid::new_v4();
        let envelope = build_checkpoint_envelope(
            run_id,
            vec![Message::new(Role::User, "hello")],
            json!({"turn": 1}),
        );

        assert_eq!(envelope.run_id, Some(run_id));
    }

    #[test]
    fn render_call_tool_result_sanitizes_text_blocks() {
        let result = CallToolResult::success(vec![Content::text("ok\u{0007}done")]);

        assert_eq!(render_call_tool_result(&result), "okdone");
    }

    #[test]
    fn render_call_tool_result_omits_non_text_blocks() {
        let result = CallToolResult::success(vec![Content::image("dGVzdA==", "image/png")]);

        assert_eq!(
            render_call_tool_result(&result),
            "<non-text tool result omitted for safety>"
        );
    }

    #[test]
    fn checkpoint_signature_changes_when_messages_change() {
        let messages_a = vec![Message::new(Role::User, "hello")];
        let messages_b = vec![
            Message::new(Role::User, "hello"),
            Message::new(Role::Assistant, "hi"),
        ];

        let sig_a = checkpoint_signature(&messages_a, &json!({}))
            .unwrap_or_else(|error| panic!("signature failed: {error}"));
        let sig_b = checkpoint_signature(&messages_b, &json!({}))
            .unwrap_or_else(|error| panic!("signature failed: {error}"));

        assert_ne!(sig_a, sig_b);
    }

    #[test]
    fn checkpoint_signature_changes_when_metadata_changes() {
        let messages = vec![Message::new(Role::User, "hello")];

        let sig_a = checkpoint_signature(&messages, &json!({}))
            .unwrap_or_else(|error| panic!("signature failed: {error}"));
        let sig_b = checkpoint_signature(&messages, &json!({"trimmed_up_to_message_index": 5}))
            .unwrap_or_else(|error| panic!("signature failed: {error}"));

        assert_ne!(sig_a, sig_b);
    }

    #[test]
    fn is_new_session_empty_history() {
        assert!(is_new_session_history(&[]));
    }

    #[test]
    fn is_new_session_system_only() {
        let messages = vec![Message::new(Role::System, "you are an agent")];
        assert!(is_new_session_history(&messages));
    }

    #[test]
    fn is_not_new_session_with_user_message() {
        let messages = vec![Message::new(Role::User, "hello")];
        assert!(!is_new_session_history(&messages));
    }

    #[test]
    fn is_not_new_session_with_system_and_user() {
        let messages = vec![
            Message::new(Role::System, "system"),
            Message::new(Role::User, "hello"),
        ];
        assert!(!is_new_session_history(&messages));
    }

    #[test]
    fn is_not_new_session_with_assistant() {
        let messages = vec![Message::new(Role::Assistant, "hi there")];
        assert!(!is_new_session_history(&messages));
    }

    #[test]
    fn prepend_context_to_text_message() {
        let msg = Message::new(Role::User, "how do I deploy?");
        let result = prepend_context_to_user_message(msg, "<context>env info</context>");

        let text = result.text().unwrap_or_default();
        assert!(
            text.starts_with("<context>env info</context>"),
            "context should be prepended"
        );
        assert!(
            text.contains("how do I deploy?"),
            "original text should be preserved"
        );
    }

    #[test]
    fn prepend_context_to_empty_text_message() {
        let msg = Message::new(Role::User, "  ");
        let result = prepend_context_to_user_message(msg, "<context>env info</context>");

        let text = result.text().unwrap_or_default();
        assert_eq!(text, "<context>env info</context>");
    }

    #[test]
    fn prepend_context_to_parts_message() {
        let msg = Message {
            role: Role::User,
            content: MessageContent::Parts(vec![ContentPart::text("original text")]),
            name: None,
            provider_options: None,
        };
        let result = prepend_context_to_user_message(msg, "<context>env info</context>");

        if let MessageContent::Parts(parts) = &result.content {
            assert_eq!(parts.len(), 2, "should have context part + original part");
            if let ContentPart::Text { text, .. } = &parts[0] {
                assert_eq!(text, "<context>env info</context>");
            } else {
                panic!("first part should be text");
            }
        } else {
            panic!("expected Parts content");
        }
    }

    #[test]
    fn prepend_empty_context_is_noop() {
        let msg = Message::new(Role::User, "hello");
        let result = prepend_context_to_user_message(msg, "   ");

        assert_eq!(result.text().unwrap_or_default(), "hello");
    }
}