6 files changed, 344 insertions, 3 deletions
diff --git a/makima/src/db/models.rs b/makima/src/db/models.rs
index 97657dc..c03b4ac 100644
--- a/makima/src/db/models.rs
+++ b/makima/src/db/models.rs
@@ -3050,4 +3050,31 @@ pub struct DirectiveOrderGroupListResponse {
     pub total: i64,
 }
 
+/// User setting record from the database (key-value per owner).
+#[derive(Debug, Clone, FromRow, Serialize, Deserialize, ToSchema)]
+#[serde(rename_all = "camelCase")]
+pub struct UserSetting {
+    pub id: Uuid,
+    pub owner_id: Uuid,
+    pub key: String,
+    pub value: serde_json::Value,
+    pub created_at: DateTime<Utc>,
+    pub updated_at: DateTime<Utc>,
+}
+
+/// Request body for upserting a user setting.
+#[derive(Debug, Deserialize, ToSchema)]
+#[serde(rename_all = "camelCase")]
+pub struct UpsertUserSettingRequest {
+    pub key: String,
+    pub value: serde_json::Value,
+}
+
+/// Response containing a list of user settings.
+#[derive(Debug, Serialize, ToSchema)]
+#[serde(rename_all = "camelCase")]
+pub struct UserSettingsResponse {
+    pub settings: Vec<UserSetting>,
+}
+
 
diff --git a/makima/src/db/repository.rs b/makima/src/db/repository.rs
index 57e8a78..401da94 100644
--- a/makima/src/db/repository.rs
+++ b/makima/src/db/repository.rs
@@ -21,6 +21,7 @@ use super::models::{
     PhaseDefinition, SupervisorHeartbeatRecord, SupervisorState,
     Task, TaskCheckpoint, TaskEvent, TaskSummary, UpdateContractRequest,
     UpdateFileRequest, UpdateTaskRequest, UpdateTemplateRequest,
+    UserSetting,
 };
 
 /// Repository error types.
@@ -6698,3 +6699,84 @@ pub async fn get_available_orders_for_dog_pickup(
     .await
 }
 
+// ─── User Settings ───────────────────────────────────────────────────────────
+
+/// Get all settings for a given owner.
+pub async fn get_user_settings(
+    pool: &PgPool,
+    owner_id: Uuid,
+) -> Result<Vec<UserSetting>, sqlx::Error> {
+    sqlx::query_as::<_, UserSetting>(
+        r#"
+        SELECT id, owner_id, key, value, created_at, updated_at
+        FROM user_settings
+        WHERE owner_id = $1
+        ORDER BY key ASC
+        "#,
+    )
+    .bind(owner_id)
+    .fetch_all(pool)
+    .await
+}
+
+/// Get a single setting by owner and key.
+pub async fn get_user_setting(
+    pool: &PgPool,
+    owner_id: Uuid,
+    key: &str,
+) -> Result<Option<UserSetting>, sqlx::Error> {
+    sqlx::query_as::<_, UserSetting>(
+        r#"
+        SELECT id, owner_id, key, value, created_at, updated_at
+        FROM user_settings
+        WHERE owner_id = $1 AND key = $2
+        "#,
+    )
+    .bind(owner_id)
+    .bind(key)
+    .fetch_optional(pool)
+    .await
+}
+
+/// Upsert a user setting (insert or update on conflict).
+pub async fn upsert_user_setting(
+    pool: &PgPool,
+    owner_id: Uuid,
+    key: &str,
+    value: &serde_json::Value,
+) -> Result<UserSetting, sqlx::Error> {
+    sqlx::query_as::<_, UserSetting>(
+        r#"
+        INSERT INTO user_settings (owner_id, key, value)
+        VALUES ($1, $2, $3)
+        ON CONFLICT (owner_id, key) DO UPDATE
+        SET value = EXCLUDED.value, updated_at = now()
+        RETURNING id, owner_id, key, value, created_at, updated_at
+        "#,
+    )
+    .bind(owner_id)
+    .bind(key)
+    .bind(value)
+    .fetch_one(pool)
+    .await
+}
+
+/// Delete a user setting. Returns true if a row was deleted.
+pub async fn delete_user_setting(
+    pool: &PgPool,
+    owner_id: Uuid,
+    key: &str,
+) -> Result<bool, sqlx::Error> {
+    let result = sqlx::query(
+        r#"
+        DELETE FROM user_settings
+        WHERE owner_id = $1 AND key = $2
+        "#,
+    )
+    .bind(owner_id)
+    .bind(key)
+    .execute(pool)
+    .await?;
+    Ok(result.rows_affected() > 0)
+}
+
diff --git a/makima/src/orchestration/directive.rs b/makima/src/orchestration/directive.rs
index 1e025c8..19077c9 100644
--- a/makima/src/orchestration/directive.rs
+++ b/makima/src/orchestration/directive.rs
@@ -442,8 +442,34 @@ impl DirectiveOrchestrator {
         let directives = repository::get_directives_needing_replanning(&self.pool).await?;
 
         for directive in directives {
-            if let Err(e) = async {
-                tracing::info!(
+            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,
                     title = %directive.title,
                     "Directive goal updated — spawning re-planning task"
diff --git a/makima/src/server/handlers/mod.rs b/makima/src/server/handlers/mod.rs
index 4bdb424..b3c433b 100644
--- a/makima/src/server/handlers/mod.rs
+++ b/makima/src/server/handlers/mod.rs
@@ -20,6 +20,7 @@ pub mod mesh_merge;
 pub mod mesh_supervisor;
 pub mod mesh_ws;
 pub mod repository_history;
+pub mod settings;
 pub mod speak;
 pub mod templates;
 pub mod voice;
diff --git a/makima/src/server/handlers/settings.rs b/makima/src/server/handlers/settings.rs
new file mode 100644
index 0000000..ae52d5a
--- /dev/null
+++ b/makima/src/server/handlers/settings.rs
@@ -0,0 +1,196 @@
+//! HTTP handlers for user settings (feature flags / preferences).
+
+use axum::{
+    extract::{Path, State},
+    http::StatusCode,
+    response::IntoResponse,
+    Json,
+};
+
+use crate::db::models::{UpsertUserSettingRequest, UserSettingsResponse};
+use crate::db::repository;
+use crate::server::auth::Authenticated;
+use crate::server::messages::ApiError;
+use crate::server::state::SharedState;
+
+/// List all settings for the authenticated user.
+#[utoipa::path(
+    get,
+    path = "/api/v1/settings",
+    responses(
+        (status = 200, description = "User settings", body = UserSettingsResponse),
+        (status = 401, description = "Not authenticated", body = ApiError),
+        (status = 503, description = "Database not configured", body = ApiError),
+        (status = 500, description = "Internal server error", body = ApiError),
+    ),
+    security(
+        ("bearer_auth" = [])
+    ),
+    tag = "Settings"
+)]
+pub async fn list_settings(
+    State(state): State<SharedState>,
+    Authenticated(user): Authenticated,
+) -> impl IntoResponse {
+    let Some(ref pool) = state.db_pool else {
+        return (
+            StatusCode::SERVICE_UNAVAILABLE,
+            Json(ApiError::new("DB_UNAVAILABLE", "Database not configured")),
+        )
+            .into_response();
+    };
+
+    match repository::get_user_settings(pool, user.owner_id).await {
+        Ok(settings) => Json(UserSettingsResponse { settings }).into_response(),
+        Err(e) => {
+            tracing::error!("Failed to list user settings: {}", e);
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                Json(ApiError::new("DB_ERROR", e.to_string())),
+            )
+                .into_response()
+        }
+    }
+}
+
+/// Get a specific setting by key.
+#[utoipa::path(
+    get,
+    path = "/api/v1/settings/{key}",
+    params(
+        ("key" = String, Path, description = "Setting key")
+    ),
+    responses(
+        (status = 200, description = "User setting", body = crate::db::models::UserSetting),
+        (status = 401, description = "Not authenticated", body = ApiError),
+        (status = 404, description = "Setting not found", body = ApiError),
+        (status = 503, description = "Database not configured", body = ApiError),
+        (status = 500, description = "Internal server error", body = ApiError),
+    ),
+    security(
+        ("bearer_auth" = [])
+    ),
+    tag = "Settings"
+)]
+pub async fn get_setting(
+    State(state): State<SharedState>,
+    Authenticated(user): Authenticated,
+    Path(key): Path<String>,
+) -> impl IntoResponse {
+    let Some(ref pool) = state.db_pool else {
+        return (
+            StatusCode::SERVICE_UNAVAILABLE,
+            Json(ApiError::new("DB_UNAVAILABLE", "Database not configured")),
+        )
+            .into_response();
+    };
+
+    match repository::get_user_setting(pool, user.owner_id, &key).await {
+        Ok(Some(setting)) => Json(setting).into_response(),
+        Ok(None) => (
+            StatusCode::NOT_FOUND,
+            Json(ApiError::new("NOT_FOUND", format!("Setting '{}' not found", key))),
+        )
+            .into_response(),
+        Err(e) => {
+            tracing::error!("Failed to get user setting: {}", e);
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                Json(ApiError::new("DB_ERROR", e.to_string())),
+            )
+                .into_response()
+        }
+    }
+}
+
+/// Upsert a user setting (create or update).
+#[utoipa::path(
+    put,
+    path = "/api/v1/settings",
+    request_body = UpsertUserSettingRequest,
+    responses(
+        (status = 200, description = "Setting upserted", body = crate::db::models::UserSetting),
+        (status = 401, description = "Not authenticated", body = ApiError),
+        (status = 503, description = "Database not configured", body = ApiError),
+        (status = 500, description = "Internal server error", body = ApiError),
+    ),
+    security(
+        ("bearer_auth" = [])
+    ),
+    tag = "Settings"
+)]
+pub async fn upsert_setting(
+    State(state): State<SharedState>,
+    Authenticated(user): Authenticated,
+    Json(req): Json<UpsertUserSettingRequest>,
+) -> impl IntoResponse {
+    let Some(ref pool) = state.db_pool else {
+        return (
+            StatusCode::SERVICE_UNAVAILABLE,
+            Json(ApiError::new("DB_UNAVAILABLE", "Database not configured")),
+        )
+            .into_response();
+    };
+
+    match repository::upsert_user_setting(pool, user.owner_id, &req.key, &req.value).await {
+        Ok(setting) => Json(setting).into_response(),
+        Err(e) => {
+            tracing::error!("Failed to upsert user setting: {}", e);
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                Json(ApiError::new("DB_ERROR", e.to_string())),
+            )
+                .into_response()
+        }
+    }
+}
+
+/// Delete a user setting by key.
+#[utoipa::path(
+    delete,
+    path = "/api/v1/settings/{key}",
+    params(
+        ("key" = String, Path, description = "Setting key")
+    ),
+    responses(
+        (status = 200, description = "Setting deleted"),
+        (status = 401, description = "Not authenticated", body = ApiError),
+        (status = 404, description = "Setting not found", body = ApiError),
+        (status = 503, description = "Database not configured", body = ApiError),
+        (status = 500, description = "Internal server error", body = ApiError),
+    ),
+    security(
+        ("bearer_auth" = [])
+    ),
+    tag = "Settings"
+)]
+pub async fn delete_setting(
+    State(state): State<SharedState>,
+    Authenticated(user): Authenticated,
+    Path(key): Path<String>,
+) -> impl IntoResponse {
+    let Some(ref pool) = state.db_pool else {
+        return (
+            StatusCode::SERVICE_UNAVAILABLE,
+            Json(ApiError::new("DB_UNAVAILABLE", "Database not configured")),
+        )
+            .into_response();
+    };
+
+    match repository::delete_user_setting(pool, user.owner_id, &key).await {
+        Ok(true) => StatusCode::OK.into_response(),
+        Ok(false) => (
+            StatusCode::NOT_FOUND,
+            Json(ApiError::new("NOT_FOUND", format!("Setting '{}' not found", key))),
+        )
+            .into_response(),
+        Err(e) => {
+            tracing::error!("Failed to delete user setting: {}", e);
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                Json(ApiError::new("DB_ERROR", e.to_string())),
+            )
+                .into_response()
+        }
+    }
+}
diff --git a/makima/src/server/mod.rs b/makima/src/server/mod.rs
index b382f04..025ec85 100644
--- a/makima/src/server/mod.rs
+++ b/makima/src/server/mod.rs
@@ -18,7 +18,7 @@ use tower_http::trace::TraceLayer;
 use utoipa::OpenApi;
 use utoipa_swagger_ui::SwaggerUi;
 
-use crate::server::handlers::{api_keys, chat, contract_chat, contract_daemon, contract_discuss, contracts, daemon_download, directives, file_ws, files, history, listen, mesh, mesh_chat, mesh_daemon, mesh_merge, mesh_supervisor, mesh_ws, orders, repository_history, speak, templates, transcript_analysis, users, versions};
+use crate::server::handlers::{api_keys, chat, contract_chat, contract_daemon, contract_discuss, contracts, daemon_download, directives, file_ws, files, history, listen, mesh, mesh_chat, mesh_daemon, mesh_merge, mesh_supervisor, mesh_ws, orders, repository_history, settings, speak, templates, transcript_analysis, users, versions};
 use crate::server::openapi::ApiDoc;
 use crate::server::state::SharedState;
 
@@ -281,6 +281,15 @@ pub fn make_router(state: SharedState) -> Router {
         .route("/timeline", get(history::get_timeline))
         // Contract type templates (built-in only)
         .route("/contract-types", get(templates::list_contract_types))
+        // User settings (feature flags) endpoints
+        .route(
+            "/user-settings",
+            get(settings::list_settings).put(settings::upsert_setting),
+        )
+        .route(
+            "/user-settings/{key}",
+            get(settings::get_setting).delete(settings::delete_setting),
+        )
         // Settings endpoints
         .route(
             "/settings/repository-history",