path: root/makima/src/orchestration/directive.rs

//! Directive orchestrator — automates the full directive lifecycle.
//!
//! Runs as a background loop, polling every 15s to:
//! 1. Plan: active directives with no steps → spawn planning task
//! 2. Execute: ready steps → spawn execution tasks
//! 3. Monitor: detect task completion → update step status, advance DAG
//! 4. Re-plan: goal updated → spawn new planning task

use sqlx::PgPool;
use uuid::Uuid;

use crate::db::models::{CreateTaskRequest, UpdateTaskRequest};
use crate::db::repository;
use crate::server::state::{DaemonCommand, SharedState};

pub struct DirectiveOrchestrator {
    pool: PgPool,
    state: SharedState,
}

impl DirectiveOrchestrator {
    pub fn new(pool: PgPool, state: SharedState) -> Self {
        Self { pool, state }
    }

    /// Run one orchestration tick — called every 15s.
    pub async fn tick(&mut self) -> Result<(), anyhow::Error> {
        self.phase_planning().await?;
        self.phase_execution().await?;
        self.phase_monitoring().await?;
        self.phase_replanning().await?;
        self.phase_completion().await?;
        Ok(())
    }

    /// Phase 1: Active directives with no steps and no orchestrator task → spawn planning task.
    async fn phase_planning(&self) -> Result<(), anyhow::Error> {
        let directives = repository::get_directives_needing_planning(&self.pool).await?;

        for directive in directives {
            tracing::info!(
                directive_id = %directive.id,
                title = %directive.title,
                "Directive needs planning — spawning planning task"
            );

            let plan = build_planning_prompt(&directive, &[], 1, &[]);

            if let Err(e) = self
                .spawn_orchestrator_task(
                    directive.id,
                    directive.owner_id,
                    format!("Plan: {}", directive.title),
                    plan,
                    directive.repository_url.as_deref(),
                    directive.base_branch.as_deref(),
                )
                .await
            {
                tracing::warn!(
                    directive_id = %directive.id,
                    error = %e,
                    "Failed to spawn planning task"
                );
            }
        }
        Ok(())
    }

    /// Phase 2: Ready steps with no task → create execution task and dispatch.
    /// Also retries pending directive tasks that weren't dispatched previously.
    async fn phase_execution(&self) -> Result<(), anyhow::Error> {
        // Create tasks for ready steps
        let steps = repository::get_ready_steps_for_dispatch(&self.pool).await?;

        for step in steps {
            tracing::info!(
                step_id = %step.step_id,
                directive_id = %step.directive_id,
                step_name = %step.step_name,
                "Dispatching execution task for ready step"
            );

            // Resolve dependency steps to their task IDs for worktree continuation
            let dep_tasks =
                repository::get_step_dependency_tasks(&self.pool, &step.depends_on).await?;
            let mut continue_from_task_id = dep_tasks.first().map(|d| d.task_id);

            // If no dependency tasks resolved, try to continue from previous work:
            // 1) Use the directive's PR branch as base (contains all previous merged work)
            // 2) Fall back to the last completed step's task for worktree continuation
            let effective_base_branch = if continue_from_task_id.is_none() {
                if step.pr_branch.is_some() {
                    tracing::info!(
                        step_id = %step.step_id,
                        pr_branch = ?step.pr_branch,
                        "Step has no deps — using directive PR branch as base"
                    );
                    step.pr_branch.as_deref()
                } else {
                    // No PR branch yet — try to continue from the last completed step's worktree
                    match repository::get_last_completed_step_task_id(
                        &self.pool,
                        step.directive_id,
                    )
                    .await
                    {
                        Ok(Some(task_id)) => {
                            tracing::info!(
                                step_id = %step.step_id,
                                continue_from = %task_id,
                                "Step has no deps, no PR branch — continuing from last completed task"
                            );
                            continue_from_task_id = Some(task_id);
                            step.base_branch.as_deref()
                        }
                        _ => step.base_branch.as_deref(),
                    }
                }
            } else {
                step.base_branch.as_deref()
            };

            let task_plan = step
                .task_plan
                .as_deref()
                .unwrap_or("Execute the step described below.");

            // Build merge instructions for additional dependencies (beyond the first)
            let merge_preamble = if dep_tasks.len() > 1 {
                use crate::daemon::worktree::{sanitize_name, short_uuid};
                let merge_lines: Vec<String> = dep_tasks[1..]
                    .iter()
                    .map(|d| {
                        let branch = format!(
                            "makima/task-{}-{}",
                            sanitize_name(&d.task_name),
                            short_uuid(d.task_id)
                        );
                        format!("git merge origin/{} --no-edit", branch)
                    })
                    .collect();
                format!(
                    "IMPORTANT — MERGE DEPENDENCY BRANCHES FIRST:\n\
                     This step continues from one dependency's worktree, but also depends on \
                     additional branches. Before starting work, run:\n\
                     ```\ngit fetch origin\n{}\n```\n\
                     Resolve any merge conflicts sensibly, then proceed.\n\n",
                    merge_lines.join("\n"),
                )
            } else {
                String::new()
            };

            let plan = format!(
                "You are executing a step in directive \"{directive_title}\".\n\n\
                 STEP: {step_name}\n\
                 DESCRIPTION: {description}\n\n\
                 {merge_preamble}\
                 INSTRUCTIONS:\n{task_plan}\n\
                 When done, the system will automatically mark this step as completed.\n\
                 If you cannot complete the task, report the failure clearly.",
                directive_title = step.directive_title,
                step_name = step.step_name,
                description = step.step_description.as_deref().unwrap_or("(none)"),
                merge_preamble = merge_preamble,
                task_plan = task_plan,
            );

            match self
                .spawn_step_task(
                    step.step_id,
                    step.directive_id,
                    step.owner_id,
                    format!("{}: {}", step.directive_title, step.step_name),
                    plan,
                    step.repository_url.as_deref(),
                    effective_base_branch,
                    continue_from_task_id,
                )
                .await
            {
                Ok(()) => {}
                Err(e) => {
                    tracing::warn!(
                        step_id = %step.step_id,
                        error = %e,
                        "Failed to spawn execution task for step"
                    );
                }
            }
        }

        // Retry pending directive tasks that weren't dispatched
        let pending = repository::get_pending_directive_tasks(&self.pool).await?;
        for task in pending {
            if self
                .try_dispatch_task(task.id, task.owner_id, &task.name, &task.plan, task.version)
                .await
            {
                // Task dispatched — mark its step as running if it has one
                if let Some(step_id) = task.directive_step_id {
                    let _ = repository::set_step_running(&self.pool, step_id).await;
                }
            }
        }

        Ok(())
    }

    /// Phase 3: Monitor running steps and orchestrator tasks.
    async fn phase_monitoring(&self) -> Result<(), anyhow::Error> {
        // Check running steps
        let running = repository::get_running_steps_with_tasks(&self.pool).await?;

        for step in running {
            match step.task_status.as_str() {
                "completed" | "merged" | "done" => {
                    tracing::info!(
                        step_id = %step.step_id,
                        directive_id = %step.directive_id,
                        task_id = %step.task_id,
                        "Step task completed — updating step to completed"
                    );
                    let update = crate::db::models::UpdateDirectiveStepRequest {
                        status: Some("completed".to_string()),
                        ..Default::default()
                    };
                    repository::update_directive_step(&self.pool, step.step_id, update).await?;
                    repository::advance_directive_ready_steps(&self.pool, step.directive_id)
                        .await?;
                    repository::check_directive_idle(&self.pool, step.directive_id).await?;
                }
                "failed" | "interrupted" => {
                    tracing::warn!(
                        step_id = %step.step_id,
                        directive_id = %step.directive_id,
                        task_id = %step.task_id,
                        task_status = %step.task_status,
                        "Step task failed — updating step to failed"
                    );
                    let update = crate::db::models::UpdateDirectiveStepRequest {
                        status: Some("failed".to_string()),
                        ..Default::default()
                    };
                    repository::update_directive_step(&self.pool, step.step_id, update).await?;
                    repository::advance_directive_ready_steps(&self.pool, step.directive_id)
                        .await?;
                    repository::check_directive_idle(&self.pool, step.directive_id).await?;
                }
                "paused" => {
                    // Task is paused (e.g., waiting for user answer in reconcile mode)
                    // Keep step in running status — task will auto-resume when answered
                    tracing::debug!(
                        step_id = %step.step_id,
                        directive_id = %step.directive_id,
                        task_id = %step.task_id,
                        "Step task paused (waiting for user response) — keeping step running"
                    );
                }
                _ => {
                    // Still running — do nothing
                }
            }
        }

        // Check orchestrator (planning) tasks
        let orch_tasks = repository::get_orchestrator_tasks_to_check(&self.pool).await?;

        for orch in orch_tasks {
            match orch.task_status.as_str() {
                "completed" | "merged" | "done" => {
                    tracing::info!(
                        directive_id = %orch.directive_id,
                        task_id = %orch.orchestrator_task_id,
                        "Planning task completed — clearing orchestrator task"
                    );
                    repository::clear_orchestrator_task(&self.pool, orch.directive_id).await?;
                    // Advance DAG — planning task should have created steps
                    repository::advance_directive_ready_steps(&self.pool, orch.directive_id)
                        .await?;
                }
                "failed" | "interrupted" => {
                    tracing::warn!(
                        directive_id = %orch.directive_id,
                        task_id = %orch.orchestrator_task_id,
                        "Planning task failed — pausing directive"
                    );
                    repository::clear_orchestrator_task(&self.pool, orch.directive_id).await?;
                    repository::set_directive_status(
                        &self.pool,
                        orch.owner_id,
                        orch.directive_id,
                        "paused",
                    )
                    .await?;
                }
                _ => {}
            }
        }

        Ok(())
    }

    /// Phase 4: Re-planning — goal updated after latest step creation.
    async fn phase_replanning(&self) -> Result<(), anyhow::Error> {
        let directives = repository::get_directives_needing_replanning(&self.pool).await?;

        for directive in directives {
            tracing::info!(
                directive_id = %directive.id,
                title = %directive.title,
                "Directive goal updated — spawning re-planning task"
            );

            let existing_steps =
                repository::list_directive_steps(&self.pool, directive.id).await?;
            let generation =
                repository::get_directive_max_generation(&self.pool, directive.id).await? + 1;
            let goal_history =
                repository::get_directive_goal_history(&self.pool, directive.id, 3).await?;

            let plan =
                build_planning_prompt(&directive, &existing_steps, generation, &goal_history);

            if let Err(e) = self
                .spawn_orchestrator_task(
                    directive.id,
                    directive.owner_id,
                    format!("Re-plan: {}", directive.title),
                    plan,
                    directive.repository_url.as_deref(),
                    directive.base_branch.as_deref(),
                )
                .await
            {
                tracing::warn!(
                    directive_id = %directive.id,
                    error = %e,
                    "Failed to spawn re-planning task"
                );
            }
        }
        Ok(())
    }

    /// Spawn a planning/re-planning task and assign it as the directive's orchestrator task.
    async fn spawn_orchestrator_task(
        &self,
        directive_id: Uuid,
        owner_id: Uuid,
        name: String,
        plan: String,
        repo_url: Option<&str>,
        base_branch: Option<&str>,
    ) -> Result<(), anyhow::Error> {
        let req = CreateTaskRequest {
            contract_id: None,
            name,
            description: Some("Directive planning task".to_string()),
            plan,
            parent_task_id: None,
            is_supervisor: false,
            priority: 0,
            repository_url: repo_url.map(|s| s.to_string()),
            base_branch: base_branch.map(|s| s.to_string()),
            target_branch: None,
            merge_mode: None,
            target_repo_path: None,
            completion_action: None,
            continue_from_task_id: None,
            copy_files: None,
            checkpoint_sha: None,
            branched_from_task_id: None,
            conversation_history: None,
            supervisor_worktree_task_id: None,
            directive_id: Some(directive_id),
            directive_step_id: None,
        };

        let task = repository::create_task_for_owner(&self.pool, owner_id, req).await?;

        repository::assign_orchestrator_task(&self.pool, directive_id, task.id).await?;

        // Cancel any old planning tasks for this directive (superseded by the new one)
        let cancelled =
            repository::cancel_old_planning_tasks(&self.pool, directive_id, task.id).await?;
        if cancelled > 0 {
            tracing::info!(
                directive_id = %directive_id,
                cancelled_count = cancelled,
                "Cancelled old planning tasks superseded by new plan"
            );
        }

        // Try to dispatch to a daemon
        self.try_dispatch_task(task.id, owner_id, &task.name, &task.plan, task.version).await;

        Ok(())
    }

    /// Spawn an execution task for a step.
    /// Links the task to the step but only marks the step as 'running' once dispatched.
    async fn spawn_step_task(
        &self,
        step_id: Uuid,
        directive_id: Uuid,
        owner_id: Uuid,
        name: String,
        plan: String,
        repo_url: Option<&str>,
        base_branch: Option<&str>,
        continue_from_task_id: Option<Uuid>,
    ) -> Result<(), anyhow::Error> {
        let req = CreateTaskRequest {
            contract_id: None,
            name,
            description: Some("Directive step execution task".to_string()),
            plan,
            parent_task_id: None,
            is_supervisor: false,
            priority: 0,
            repository_url: repo_url.map(|s| s.to_string()),
            base_branch: base_branch.map(|s| s.to_string()),
            target_branch: None,
            merge_mode: None,
            target_repo_path: None,
            completion_action: Some("branch".to_string()),
            continue_from_task_id,
            copy_files: None,
            checkpoint_sha: None,
            branched_from_task_id: None,
            conversation_history: None,
            supervisor_worktree_task_id: None,
            directive_id: Some(directive_id),
            directive_step_id: Some(step_id),
        };

        let task = repository::create_task_for_owner(&self.pool, owner_id, req).await?;

        // Link the task to the step (sets task_id) but keep step as 'ready' for now
        repository::link_task_to_step(&self.pool, step_id, task.id).await?;

        // Only mark step as 'running' if we can actually dispatch the task
        if self
            .try_dispatch_task(task.id, owner_id, &task.name, &task.plan, task.version)
            .await
        {
            repository::set_step_running(&self.pool, step_id).await?;
        }

        Ok(())
    }

    /// Try to dispatch a task to an available daemon. Returns true if dispatched.
    async fn try_dispatch_task(
        &self,
        task_id: Uuid,
        owner_id: Uuid,
        task_name: &str,
        plan: &str,
        version: i32,
    ) -> bool {
        let Some(daemon_id) = self.state.find_alternative_daemon(owner_id, &[]) else {
            tracing::info!(
                task_id = %task_id,
                "No daemon available for directive task — leaving pending for retry"
            );
            return false;
        };

        // Update task status to starting and assign daemon
        let update_req = UpdateTaskRequest {
            status: Some("starting".to_string()),
            daemon_id: Some(daemon_id),
            version: Some(version),
            ..Default::default()
        };

        match repository::update_task_for_owner(&self.pool, task_id, owner_id, update_req).await {
            Ok(Some(updated_task)) => {
                let command = DaemonCommand::SpawnTask {
                    task_id,
                    task_name: task_name.to_string(),
                    plan: plan.to_string(),
                    repo_url: updated_task.repository_url.clone(),
                    base_branch: updated_task.base_branch.clone(),
                    target_branch: updated_task.target_branch.clone(),
                    parent_task_id: None,
                    depth: 0,
                    is_orchestrator: false,
                    target_repo_path: None,
                    completion_action: updated_task.completion_action.clone(),
                    continue_from_task_id: updated_task.continue_from_task_id,
                    copy_files: None,
                    contract_id: None,
                    is_supervisor: false,
                    autonomous_loop: false,
                    resume_session: false,
                    conversation_history: None,
                    patch_data: None,
                    patch_base_sha: None,
                    local_only: false,
                    auto_merge_local: false,
                    supervisor_worktree_task_id: None,
                    directive_id: updated_task.directive_id,
                };

                if let Err(e) = self.state.send_daemon_command(daemon_id, command).await {
                    tracing::warn!(
                        task_id = %task_id,
                        daemon_id = %daemon_id,
                        error = %e,
                        "Failed to send SpawnTask to daemon for directive task"
                    );
                    return false;
                } else {
                    tracing::info!(
                        task_id = %task_id,
                        daemon_id = %daemon_id,
                        "Dispatched directive task to daemon"
                    );
                    return true;
                }
            }
            Ok(None) => {
                tracing::warn!(task_id = %task_id, "Task not found when trying to dispatch");
            }
            Err(e) => {
                tracing::warn!(task_id = %task_id, error = %e, "Failed to update task for dispatch");
            }
        }
        false
    }

    /// Phase 5: Completion — spawn PR-creation tasks for idle directives.
    async fn phase_completion(&self) -> Result<(), anyhow::Error> {
        // Part 1: Spawn completion tasks for idle directives
        let directives = repository::get_idle_directives_needing_completion(&self.pool).await?;

        for directive in directives {
            // Atomically claim this directive for completion using a placeholder.
            // This prevents a concurrent tick from also spawning a completion task.
            let placeholder_id = Uuid::new_v4();
            let claimed = repository::claim_directive_for_completion(
                &self.pool,
                directive.id,
                placeholder_id,
            )
            .await?;

            if !claimed {
                tracing::debug!(
                    directive_id = %directive.id,
                    "Directive already claimed for completion — skipping"
                );
                continue;
            }

            tracing::info!(
                directive_id = %directive.id,
                title = %directive.title,
                "Directive idle — spawning completion task for PR"
            );

            let step_tasks = repository::get_completed_step_tasks(&self.pool, directive.id).await?;
            if step_tasks.is_empty() {
                // Release the claim since there's nothing to complete
                let _ = repository::clear_completion_task(&self.pool, directive.id).await;
                continue;
            }

            let base_branch = directive
                .base_branch
                .as_deref()
                .unwrap_or("main");

            let directive_branch = format!(
                "makima/directive-{}-{}",
                crate::daemon::worktree::sanitize_name(&directive.title),
                crate::daemon::worktree::short_uuid(directive.id),
            );

            // Compute step branch names using the same formula as execute_completion_action
            let step_branches: Vec<String> = step_tasks
                .iter()
                .map(|st| {
                    format!(
                        "makima/{}-{}",
                        crate::daemon::worktree::sanitize_name(&st.task_name),
                        crate::daemon::worktree::short_uuid(st.task_id),
                    )
                })
                .collect();

            let prompt = build_completion_prompt(
                &directive,
                &step_tasks,
                &step_branches,
                &directive_branch,
                base_branch,
            );

            match self
                .spawn_completion_task(
                    directive.id,
                    directive.owner_id,
                    format!("PR: {}", directive.title),
                    prompt,
                    directive.repository_url.as_deref(),
                    directive.base_branch.as_deref(),
                )
                .await
            {
                Ok(task_id) => {
                    // Store pr_branch on directive immediately
                    let update = crate::db::models::UpdateDirectiveRequest {
                        pr_branch: Some(directive_branch.clone()),
                        ..Default::default()
                    };
                    let _ = repository::update_directive_for_owner(
                        &self.pool,
                        directive.owner_id,
                        directive.id,
                        update,
                    )
                    .await;
                    // Replace placeholder with the real task ID
                    repository::assign_completion_task(&self.pool, directive.id, task_id).await?;
                }
                Err(e) => {
                    tracing::warn!(
                        directive_id = %directive.id,
                        error = %e,
                        "Failed to spawn completion task — releasing claim"
                    );
                    // Release the claim so it can be retried on the next tick
                    let _ = repository::clear_completion_task(&self.pool, directive.id).await;
                }
            }
        }

        // Part 2: Monitor completion tasks
        let checks = repository::get_completion_tasks_to_check(&self.pool).await?;

        for check in checks {
            match check.task_status.as_str() {
                "completed" | "merged" | "done" => {
                    tracing::info!(
                        directive_id = %check.directive_id,
                        task_id = %check.completion_task_id,
                        "Completion task finished"
                    );

                    // If directive has no pr_url yet, try to extract from task output
                    if check.pr_url.is_none() {
                        match self.extract_pr_url_from_task(check.completion_task_id).await {
                            Ok(Some(url)) => {
                                tracing::info!(
                                    directive_id = %check.directive_id,
                                    pr_url = %url,
                                    "Extracted PR URL from completion task output"
                                );
                                let update = crate::db::models::UpdateDirectiveRequest {
                                    pr_url: Some(url),
                                    ..Default::default()
                                };
                                let _ = repository::update_directive_for_owner(
                                    &self.pool,
                                    check.owner_id,
                                    check.directive_id,
                                    update,
                                )
                                .await;
                            }
                            Ok(None) => {
                                if check.task_name.starts_with("Verify PR:") {
                                    // Verification task failed to find/create PR — mark directive completed (one-shot)
                                    tracing::warn!(
                                        directive_id = %check.directive_id,
                                        task_id = %check.completion_task_id,
                                        "Verification task finished but no PR URL found — marking directive completed"
                                    );
                                    let update = crate::db::models::UpdateDirectiveRequest {
                                        status: Some("completed".to_string()),
                                        ..Default::default()
                                    };
                                    let _ = repository::update_directive_for_owner(
                                        &self.pool,
                                        check.owner_id,
                                        check.directive_id,
                                        update,
                                    )
                                    .await;
                                } else {
                                    tracing::warn!(
                                        directive_id = %check.directive_id,
                                        task_id = %check.completion_task_id,
                                        "Completion task finished but no PR URL found — will spawn verifier"
                                    );
                                }
                            }
                            Err(e) => {
                                tracing::warn!(
                                    directive_id = %check.directive_id,
                                    error = %e,
                                    "Failed to extract PR URL from completion task output"
                                );
                            }
                        }
                    }

                    repository::clear_completion_task(&self.pool, check.directive_id).await?;
                }
                "failed" | "interrupted" => {
                    tracing::warn!(
                        directive_id = %check.directive_id,
                        task_id = %check.completion_task_id,
                        "Completion task failed"
                    );
                    repository::clear_completion_task(&self.pool, check.directive_id).await?;
                }
                _ => {
                    // Still running
                }
            }
        }

        // Part 3: Spawn verification tasks for directives with pr_branch but no pr_url
        let verify_directives =
            repository::get_directives_needing_verification(&self.pool).await?;

        for directive in verify_directives {
            let placeholder_id = Uuid::new_v4();
            let claimed = repository::claim_directive_for_completion(
                &self.pool,
                directive.id,
                placeholder_id,
            )
            .await?;

            if !claimed {
                continue;
            }

            tracing::info!(
                directive_id = %directive.id,
                title = %directive.title,
                "Directive has pr_branch but no pr_url — spawning verification task"
            );

            let pr_branch = directive.pr_branch.as_deref().unwrap_or("unknown");
            let base_branch = directive.base_branch.as_deref().unwrap_or("main");
            let prompt = build_verification_prompt(&directive, pr_branch, base_branch);

            match self
                .spawn_completion_task(
                    directive.id,
                    directive.owner_id,
                    format!("Verify PR: {}", directive.title),
                    prompt,
                    directive.repository_url.as_deref(),
                    directive.base_branch.as_deref(),
                )
                .await
            {
                Ok(task_id) => {
                    repository::assign_completion_task(&self.pool, directive.id, task_id).await?;
                }
                Err(e) => {
                    tracing::warn!(
                        directive_id = %directive.id,
                        error = %e,
                        "Failed to spawn verification task — releasing claim"
                    );
                    let _ = repository::clear_completion_task(&self.pool, directive.id).await;
                }
            }
        }

        Ok(())
    }

    /// Spawn a completion task that creates/updates a PR from step branches.
    async fn spawn_completion_task(
        &self,
        directive_id: Uuid,
        owner_id: Uuid,
        name: String,
        plan: String,
        repo_url: Option<&str>,
        base_branch: Option<&str>,
    ) -> Result<Uuid, anyhow::Error> {
        let req = CreateTaskRequest {
            contract_id: None,
            name,
            description: Some("Directive PR completion task".to_string()),
            plan,
            parent_task_id: None,
            is_supervisor: false,
            priority: 0,
            repository_url: repo_url.map(|s| s.to_string()),
            base_branch: base_branch.map(|s| s.to_string()),
            target_branch: None,
            merge_mode: None,
            target_repo_path: None,
            completion_action: None,
            continue_from_task_id: None,
            copy_files: None,
            checkpoint_sha: None,
            branched_from_task_id: None,
            conversation_history: None,
            supervisor_worktree_task_id: None,
            directive_id: Some(directive_id),
            directive_step_id: None,
        };

        let task = repository::create_task_for_owner(&self.pool, owner_id, req).await?;

        // Try to dispatch to a daemon
        self.try_dispatch_task(task.id, owner_id, &task.name, &task.plan, task.version)
            .await;

        Ok(task.id)
    }

    /// Extract a GitHub PR URL from a completion task's output events.
    /// Searches task output for patterns like `https://github.com/.../pull/123`.
    async fn extract_pr_url_from_task(
        &self,
        task_id: Uuid,
    ) -> Result<Option<String>, anyhow::Error> {
        let events = repository::get_task_output(&self.pool, task_id, Some(500)).await?;

        let pr_url_re = regex::Regex::new(r"https://github\.com/[^/\s]+/[^/\s]+/pull/\d+")?;

        // Search from most recent events backwards for the PR URL
        for event in events.iter().rev() {
            if let Some(ref data) = event.event_data {
                // Check the content field inside event_data JSON
                if let Some(content) = data.get("content").and_then(|c| c.as_str()) {
                    if let Some(m) = pr_url_re.find(content) {
                        return Ok(Some(m.as_str().to_string()));
                    }
                }
                // Also check the raw JSON string representation as fallback
                let data_str = data.to_string();
                if let Some(m) = pr_url_re.find(&data_str) {
                    return Ok(Some(m.as_str().to_string()));
                }
            }
        }

        Ok(None)
    }
}

/// Build the planning prompt for a directive.
fn build_planning_prompt(
    directive: &crate::db::models::Directive,
    existing_steps: &[crate::db::models::DirectiveStep],
    generation: i32,
    goal_history: &[crate::db::models::DirectiveGoalHistory],
) -> String {
    let mut prompt = String::new();

    if !existing_steps.is_empty() {
        // ── RE-PLANNING header ──────────────────────────────────────
        prompt.push_str(&format!(
            "⚠️  RE-PLANNING: The GOAL has been updated — you must re-evaluate ALL existing steps.\n\
             Previous steps were planned for an earlier version of the goal. Some may no longer be \
             relevant. Review each step below and act according to the instructions per status category.\n\n",
        ));

        // ── Goal changes section ──────────────────────────────────
        if !goal_history.is_empty() {
            prompt.push_str("-- GOAL CHANGES --\n");
            prompt.push_str("The goal has been updated. Compare the previous and current goals to understand what changed:\n\n");
            for (i, entry) in goal_history.iter().enumerate() {
                if i == 0 {
                    prompt.push_str(&format!(
                        "PREVIOUS GOAL (replaced at {}):\n{}\n\n",
                        entry.created_at.format("%Y-%m-%d %H:%M:%S UTC"),
                        entry.goal
                    ));
                } else {
                    prompt.push_str(&format!(
                        "OLDER GOAL (version from {}):\n{}\n\n",
                        entry.created_at.format("%Y-%m-%d %H:%M:%S UTC"),
                        entry.goal
                    ));
                }
            }
            prompt.push_str(&format!(
                "CURRENT GOAL (what you must plan for):\n{}\n\n",
                directive.goal
            ));
            prompt.push_str(
                "IMPORTANT: Analyze what CHANGED between the previous goal and the current goal.\n\
                 - If the change is minor (e.g., clarification, small addition), try to KEEP existing pending steps and only add/modify what is needed for the delta.\n\
                 - If the change is major (e.g., completely different objective), you may need to remove most pending steps and create a fresh plan.\n\
                 - Always preserve completed and running steps - they represent work already done.\n\n",
            );
        }

        prompt.push_str(&format!(
            "EXISTING STEPS (generation {}):\n",
            generation - 1
        ));

        // Categorise steps by status
        let mut completed: Vec<&crate::db::models::DirectiveStep> = Vec::new();
        let mut running: Vec<&crate::db::models::DirectiveStep> = Vec::new();
        let mut pending_ready: Vec<&crate::db::models::DirectiveStep> = Vec::new();
        let mut failed: Vec<&crate::db::models::DirectiveStep> = Vec::new();
        let mut skipped: Vec<&crate::db::models::DirectiveStep> = Vec::new();

        for step in existing_steps {
            match step.status.as_str() {
                "completed" => completed.push(step),
                "running" => running.push(step),
                "pending" | "ready" => pending_ready.push(step),
                "failed" => failed.push(step),
                "skipped" => skipped.push(step),
                _ => pending_ready.push(step),
            }
        }

        // ── Completed steps ─────────────────────────────────────────
        if !completed.is_empty() {
            prompt.push_str("\n── COMPLETED steps (KEEP — work already done) ──\n");
            prompt.push_str("These steps have finished. Their work is committed and available.\n");
            prompt.push_str("Do NOT remove them. New steps can depend on them to inherit their changes.\n");
            let mut last_completed_id: Option<Uuid> = None;
            for step in &completed {
                prompt.push_str(&format!(
                    "  ✅ {} (id: {}): {}\n",
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
                last_completed_id = Some(step.id);
            }
            if let Some(last_id) = last_completed_id {
                prompt.push_str(&format!(
                    "\nNew steps that build on previous work SHOULD use --depends-on \"{}\" (the last completed step) \
                     so their worktree inherits all prior changes. Without this dependency, new steps start from a \
                     fresh checkout and won't see any of the work done by previous steps.\n",
                    last_id
                ));
            }
        }

        // ── Running steps ───────────────────────────────────────────
        if !running.is_empty() {
            prompt.push_str("\n── RUNNING steps (cannot remove — note if obsolete) ──\n");
            prompt.push_str("These steps are currently executing and cannot be removed or skipped.\n");
            prompt.push_str("If a running step is no longer relevant to the NEW goal, note it but do not attempt to remove it.\n");
            for step in &running {
                prompt.push_str(&format!(
                    "  🔄 {} (id: {}): {}\n",
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
            }
        }

        // ── Pending / Ready steps ───────────────────────────────────
        if !pending_ready.is_empty() {
            prompt.push_str("\n── PENDING/READY steps (EVALUATE — remove if no longer relevant) ──\n");
            prompt.push_str("These steps have NOT started yet. Evaluate each against the NEW goal:\n");
            prompt.push_str("  • If still relevant → leave it in place (no action needed).\n");
            prompt.push_str("  • If NO LONGER relevant → remove it with: makima directive remove-step <step_id>\n");
            for step in &pending_ready {
                prompt.push_str(&format!(
                    "  ⏳ [{}] {} (id: {}): {}\n",
                    step.status,
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
            }
        }

        // ── Failed steps ────────────────────────────────────────────
        if !failed.is_empty() {
            prompt.push_str("\n── FAILED steps (EVALUATE — remove if no longer relevant) ──\n");
            prompt.push_str("These steps failed. Evaluate each against the NEW goal:\n");
            prompt.push_str("  • If still relevant → remove the failed step and re-add a corrected version.\n");
            prompt.push_str("  • If NO LONGER relevant → remove it with: makima directive remove-step <step_id>\n");
            for step in &failed {
                prompt.push_str(&format!(
                    "  ❌ {} (id: {}): {}\n",
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
            }
        }

        // ── Skipped steps ───────────────────────────────────────────
        if !skipped.is_empty() {
            prompt.push_str("\n── SKIPPED steps (remove if no longer relevant) ──\n");
            for step in &skipped {
                prompt.push_str(&format!(
                    "  ⏭️  {} (id: {}): {}\n",
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
            }
        }

        // ── Instructions ────────────────────────────────────────────
        prompt.push_str(&format!(
            "\n── ACTION PLAN ──\n\
             1. First, remove any pending/ready/failed/skipped steps that are NOT relevant to the NEW goal:\n\
             \x20  makima directive remove-step <step_id>\n\
             2. Then, add new steps for the updated goal. Use generation {}.\n\
             3. New steps that build on completed work MUST use --depends-on to inherit the worktree.\n\
             4. Ensure the new plan fully addresses the UPDATED goal.\n\n",
            generation
        ));
    }

    prompt.push_str(&format!(
        r#"You are planning the implementation of a directive.

DIRECTIVE: "{title}"
GOAL: {goal}
{repo_section}
Your job:
1. Explore the repository to understand the codebase
2. Decompose the goal into concrete, ordered steps
3. Each step = one task for a Claude Code instance to execute
4. Submit ALL steps using the batch command or individual add-step commands

For each step, define:
- name: Short imperative title (e.g., "Add user authentication middleware")
- description: What to do and acceptance criteria
- taskPlan: Full instructions for the Claude instance (include file paths, patterns to follow)
- dependsOn: UUIDs of steps this depends on (use IDs from previous add-step responses)
- orderIndex: Execution phase number. Steps only start after ALL steps with a lower orderIndex complete.
  Steps with the same orderIndex run in parallel. Use ascending values (0, 1, 2, ...) to create sequential phases.
  Use dependsOn for fine-grained control within the same phase.

Submit steps:
  makima directive add-step "Step Name" --description "..." --task-plan "..."
  (Use --depends-on "uuid1,uuid2" for dependencies, referencing IDs from earlier add-step outputs)

Or batch:
  makima directive batch-add-steps --json '[{{"name":"...","description":"...","taskPlan":"...","dependsOn":[],"orderIndex":0}}]'

DEPENDENCY WORKTREE CONTINUATION:
Each step runs in its own git worktree. How that worktree is initialised depends on dependsOn:
- With dependsOn: the step continues from the first dependency's worktree (inheriting all committed and
  uncommitted changes). Additional dependencies are merged in as branches before work starts.
- Without dependsOn: the step starts from a FRESH worktree based on the base branch (or the PR branch if
  a PR already exists from previous completions).

Because of this, you MUST chain steps using dependsOn whenever one step's work builds on another's.
If step B modifies files created/changed by step A, step B MUST list step A in its dependsOn — otherwise
step B will start from a blank worktree and won't see step A's changes at all.

Guidelines:
- For sequential work, create a linear chain: step1 → step2 → step3 (each depends on the previous).
- Only omit dependsOn for truly independent steps that can start from a fresh checkout.
- Parallel steps that share no files can omit mutual dependencies, but if they both build on a prior step
  they should BOTH list that prior step in dependsOn.

IMPORTANT: Each step's taskPlan must be self-contained. The executing instance won't have your planning context.
"#,
        title = directive.title,
        goal = directive.goal,
        repo_section = match &directive.repository_url {
            Some(url) => format!("REPOSITORY: {}\n", url),
            None => String::new(),
        },
    ));

    prompt
}

/// Build the prompt for a completion task that creates or updates a PR.
fn build_completion_prompt(
    directive: &crate::db::models::Directive,
    step_tasks: &[crate::db::repository::CompletedStepTask],
    step_branches: &[String],
    directive_branch: &str,
    base_branch: &str,
) -> String {
    let merge_commands: String = step_branches
        .iter()
        .map(|b| format!("git merge origin/{} --no-edit", b))
        .collect::<Vec<_>>()
        .join("\n");

    let step_summary: String = step_tasks
        .iter()
        .zip(step_branches.iter())
        .map(|(st, branch)| format!("- {} (branch: {})", st.step_name, branch))
        .collect::<Vec<_>>()
        .join("\n");

    if directive.pr_url.is_some() {
        // Re-completion: PR already exists, merge new branches into existing PR branch
        format!(
            r#"You are updating an existing PR for directive "{title}".

The PR branch `{directive_branch}` already exists. Merge any new step branches into it.

Steps completed:
{step_summary}

Run these commands:
```
git fetch origin
git checkout {directive_branch}
git pull origin {directive_branch}
{merge_commands}
git push origin {directive_branch}
```

Already-merged branches will be a no-op. If there are merge conflicts, resolve them sensibly.
"#,
            title = directive.title,
            directive_branch = directive_branch,
            step_summary = step_summary,
            merge_commands = merge_commands,
        )
    } else {
        // First completion: create new PR
        format!(
            r#"You are creating a PR for directive "{title}".

Goal: {goal}

Steps completed:
{step_summary}

Run these commands to create a combined branch and PR:
```
git fetch origin
git checkout -b {directive_branch} origin/{base_branch}
{merge_commands}
git push -u origin {directive_branch}
```

Then create the PR:
```
gh pr create --title "{title}" --body "{pr_body}" --head {directive_branch} --base {base_branch}
```

IMPORTANT: After creating the PR, you MUST store the PR URL so the directive system can track it.

1. Run `gh pr create` as shown above and capture its output
2. The output will contain the PR URL (e.g., https://github.com/owner/repo/pull/123)
3. Then run this command to store the URL:
```
makima directive update --pr-url "https://github.com/..."
```
Replace the URL with the actual PR URL from the `gh pr create` output. This step is CRITICAL — the PR will not be tracked by the directive system without it.

If there are merge conflicts, resolve them sensibly before pushing.
"#,
            title = directive.title,
            goal = directive.goal,
            directive_branch = directive_branch,
            base_branch = base_branch,
            step_summary = step_summary,
            merge_commands = merge_commands,
            pr_body = format!(
                "## Directive\\n\\n{}\\n\\n## Steps\\n\\n{}",
                directive.goal.replace('\n', "\\n").replace('"', "\\\""),
                step_summary.replace('\n', "\\n").replace('"', "\\\""),
            ),
        )
    }
}

/// Build a prompt for verifying whether a PR was created for a directive.
/// This is a one-shot task: if it can't find or create the PR, the directive
/// will be marked completed to avoid infinite retries.
fn build_verification_prompt(
    directive: &crate::db::models::Directive,
    pr_branch: &str,
    base_branch: &str,
) -> String {
    format!(
        r#"You are verifying whether a PR exists for directive "{title}".

The completion task already ran and pushed branch `{pr_branch}`, but the PR URL was not captured.

Follow these steps IN ORDER:

1. Check if a PR already exists for this branch:
```
gh pr list --head {pr_branch} --json url --jq '.[0].url'
```

2. If the command outputs a URL, store it:
```
makima directive update --pr-url "<URL_FROM_ABOVE>"
```
Done — the PR already exists.

3. If no PR was found, check if the branch exists on the remote:
```
git ls-remote --heads origin {pr_branch}
```

4. If the branch exists, create the PR:
```
gh pr create --title "{title}" --body "Directive PR verification — auto-created" --head {pr_branch} --base {base_branch}
```
Then store the resulting URL:
```
makima directive update --pr-url "<URL_FROM_GH_PR_CREATE>"
```

5. If the branch does NOT exist on the remote, the work was likely merged directly.
Mark the directive as completed:
```
makima directive update --status completed
```

IMPORTANT: You MUST run `makima directive update` with either `--pr-url` or `--status completed` before finishing.
"#,
        title = directive.title,
        pr_branch = pr_branch,
        base_branch = base_branch,
    )
}

/// Build a specialized planning prompt for picking up open orders.
///
/// This prompt instructs the planner to evaluate available orders, select an
/// adequate number based on priority and directive capacity, and create steps
/// to fulfil them.
pub fn build_order_pickup_prompt(
    directive: &crate::db::models::Directive,
    existing_steps: &[crate::db::models::DirectiveStep],
    orders: &[crate::db::models::Order],
    generation: i32,
    goal_history: &[crate::db::models::DirectiveGoalHistory],
) -> String {
    let mut prompt = String::new();

    // ── Directive context ──────────────────────────────────────────
    prompt.push_str(&format!(
        "You are planning work for directive \"{title}\".\n\n\
         GOAL: {goal}\n\
         {repo_section}\n",
        title = directive.title,
        goal = directive.goal,
        repo_section = match &directive.repository_url {
            Some(url) => format!("REPOSITORY: {}\n", url),
            None => String::new(),
        },
    ));

    // ── Goal history (if any) ─────────────────────────────────────
    if !goal_history.is_empty() {
        prompt.push_str("-- GOAL CHANGES --\n");
        for (i, entry) in goal_history.iter().enumerate() {
            if i == 0 {
                prompt.push_str(&format!(
                    "PREVIOUS GOAL (replaced at {}):\n{}\n\n",
                    entry.created_at.format("%Y-%m-%d %H:%M:%S UTC"),
                    entry.goal
                ));
            } else {
                prompt.push_str(&format!(
                    "OLDER GOAL (version from {}):\n{}\n\n",
                    entry.created_at.format("%Y-%m-%d %H:%M:%S UTC"),
                    entry.goal
                ));
            }
        }
    }

    // ── Orders being picked up ───────────────────────────────────
    prompt.push_str("== ORDERS AVAILABLE FOR PICKUP ==\n");
    prompt.push_str("The following open orders have been linked to this directive. \
                     Review them and create steps to fulfil them.\n\n");
    for (i, order) in orders.iter().enumerate() {
        prompt.push_str(&format!(
            "  {}. [{}] [{}] {} (id: {})\n",
            i + 1,
            order.priority,
            order.order_type,
            order.title,
            order.id,
        ));
        if let Some(ref desc) = order.description {
            prompt.push_str(&format!("     Description: {}\n", desc));
        }
    }
    prompt.push('\n');

    // ── Existing steps ───────────────────────────────────────────
    if !existing_steps.is_empty() {
        let mut completed: Vec<&crate::db::models::DirectiveStep> = Vec::new();
        let mut running: Vec<&crate::db::models::DirectiveStep> = Vec::new();
        let mut pending_ready: Vec<&crate::db::models::DirectiveStep> = Vec::new();
        let mut failed: Vec<&crate::db::models::DirectiveStep> = Vec::new();

        for step in existing_steps {
            match step.status.as_str() {
                "completed" => completed.push(step),
                "running" => running.push(step),
                "pending" | "ready" => pending_ready.push(step),
                "failed" => failed.push(step),
                _ => pending_ready.push(step),
            }
        }

        prompt.push_str("== EXISTING STEPS ==\n");

        if !completed.is_empty() {
            prompt.push_str("\n── COMPLETED steps (work already done) ──\n");
            let mut last_completed_id: Option<uuid::Uuid> = None;
            for step in &completed {
                prompt.push_str(&format!(
                    "  ✅ {} (id: {}): {}\n",
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
                last_completed_id = Some(step.id);
            }
            if let Some(last_id) = last_completed_id {
                prompt.push_str(&format!(
                    "\nNew steps that build on previous work SHOULD use --depends-on \"{}\" \
                     so their worktree inherits all prior changes.\n",
                    last_id
                ));
            }
        }

        if !running.is_empty() {
            prompt.push_str("\n── RUNNING steps (in progress) ──\n");
            for step in &running {
                prompt.push_str(&format!(
                    "  🔄 {} (id: {}): {}\n",
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
            }
        }

        if !pending_ready.is_empty() {
            prompt.push_str("\n── PENDING/READY steps (not yet started) ──\n");
            for step in &pending_ready {
                prompt.push_str(&format!(
                    "  ⏳ [{}] {} (id: {}): {}\n",
                    step.status,
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
            }
        }

        if !failed.is_empty() {
            prompt.push_str("\n── FAILED steps ──\n");
            for step in &failed {
                prompt.push_str(&format!(
                    "  ❌ {} (id: {}): {}\n",
                    step.name,
                    step.id,
                    step.description.as_deref().unwrap_or("(no description)")
                ));
            }
        }

        // Determine whether to create fresh steps or combine with existing
        let all_terminal = existing_steps
            .iter()
            .all(|s| matches!(s.status.as_str(), "completed" | "failed" | "skipped"));

        if all_terminal {
            prompt.push_str(
                "\nAll existing steps are in terminal state (completed/failed/skipped). \
                 Create FRESH steps from the orders above.\n\n",
            );
        } else if !pending_ready.is_empty() || !running.is_empty() {
            prompt.push_str(
                "\nThere are existing active/pending steps. Evaluate whether to KEEP them \
                 and ADD new steps from the orders, creating a combined plan. \
                 Do not duplicate work already covered by existing steps.\n\n",
            );
        }
    }

    // ── Order selection guidance ─────────────────────────────────
    prompt.push_str(&format!(
        "== ORDER SELECTION GUIDANCE ==\n\
         You do NOT need to pick up ALL orders. Select an ADEQUATE number based on:\n\
         - Priority: prefer critical and high priority orders first\n\
         - Directive scope: consider the directive's current goal and capacity\n\
         - Avoid overloading: don't assign too many orders to a single directive\n\
         - The orders are already linked to this directive — focus on creating steps\n\n\
         If some orders are not relevant to this directive's goal or would overload it, \
         you may leave them for a future pickup cycle.\n\n"
    ));

    // ── Step creation instructions ───────────────────────────────
    prompt.push_str(&format!(
        r#"== STEP CREATION INSTRUCTIONS ==
For each order (or group of related orders), create one or more steps:
- name: Short imperative title (e.g., "Add user authentication middleware")
- description: What to do and acceptance criteria
- taskPlan: Full instructions for the Claude instance (include file paths, patterns to follow)
- dependsOn: UUIDs of steps this depends on (use IDs from previous add-step responses)
- orderIndex: Execution phase number. Steps only start after ALL steps with a lower orderIndex complete.
  Steps with the same orderIndex run in parallel. Use ascending values (0, 1, 2, ...) to create sequential phases.

Submit steps using generation {generation}:
  makima directive add-step "Step Name" --description "..." --task-plan "..." --generation {generation}
  (Use --depends-on "uuid1,uuid2" for dependencies)

Or batch:
  makima directive batch-add-steps --json '[{{"name":"...","description":"...","taskPlan":"...","dependsOn":[],"orderIndex":0,"generation":{generation}}}]'

DEPENDENCY WORKTREE CONTINUATION:
Each step runs in its own git worktree. How that worktree is initialised depends on dependsOn:
- With dependsOn: the step continues from the first dependency's worktree (inheriting all committed and
  uncommitted changes). Additional dependencies are merged in as branches before work starts.
- Without dependsOn: the step starts from a FRESH worktree based on the base branch (or the PR branch if
  a PR already exists from previous completions).

Because of this, you MUST chain steps using dependsOn whenever one step's work builds on another's.
If step B modifies files created/changed by step A, step B MUST list step A in its dependsOn — otherwise
step B will start from a blank worktree and won't see step A's changes at all.

Guidelines:
- For sequential work, create a linear chain: step1 → step2 → step3 (each depends on the previous).
- Only omit dependsOn for truly independent steps that can start from a fresh checkout.
- Parallel steps that share no files can omit mutual dependencies, but if they both build on a prior step
  they should BOTH list that prior step in dependsOn.

IMPORTANT: Each step's taskPlan must be self-contained. The executing instance won't have your planning context.
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        generation = generation,
    ));

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}