fix: audit fixes for async insight jobs + persist generation params

- Fix query param mismatch: rename GenerationStatusQuery.file_path to
  path so the client's app-resume buildQuery({ path: ... }) resolves
  correctly instead of always getting 400
- Remove dead _lib_id bindings from both generate handlers
- Return 202 Accepted instead of 200 from generate endpoints
- Restore OpenTelemetry span instrumentation on generate handlers
- Remove stale UNIQUE constraint from initial migration (incompatible
  with plain-INSERT DAO)
- Add tests for status guard: complete_job/fail_job are no-ops when
  job is already cancelled, and cancel_job by id
- Persist generation params (num_ctx, temperature, top_p, top_k, min_p,
  system_prompt, persona_id) on the photo_insights table for auditing

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>

migrations/2026-05-27-000000_add_insight_generation_jobs/up.sql

@@ -1,8 +1,7 @@
 -- Track async insight generation jobs so the client can poll for
--- completion after the server returns 202 Accepted. The UNIQUE
+-- completion after the server returns 202 Accepted. Each generation
--- constraint on (library_id, file_path, generation_type) ensures
+-- creates a new row; the application layer cancels prior running
--- idempotent inserts: if a running job already exists, the caller
+-- jobs before inserting.
--- should return that job_id instead of creating a duplicate.
 CREATE TABLE insight_generation_jobs (
     id INTEGER PRIMARY KEY AUTOINCREMENT,
     library_id INTEGER NOT NULL DEFAULT 1,
@@ -12,8 +11,7 @@ CREATE TABLE insight_generation_jobs (
     started_at INTEGER NOT NULL,
     completed_at INTEGER,
     result_insight_id INTEGER,
-    error_message TEXT,
+    error_message TEXT
-    UNIQUE(library_id, file_path, generation_type)
 );
 
 -- For the status endpoint: fast lookup by (library_id, file_path)

migrations/2026-05-27-000001_remove_insight_jobs_unique/down.sql

@@ -0,0 +1,28 @@
+-- Restore UNIQUE constraint
+
+CREATE TABLE insight_generation_jobs_new (
+    id INTEGER PRIMARY KEY AUTOINCREMENT,
+    library_id INTEGER NOT NULL DEFAULT 1,
+    file_path TEXT NOT NULL,
+    generation_type TEXT NOT NULL,
+    status TEXT NOT NULL DEFAULT 'running',
+    started_at INTEGER NOT NULL,
+    completed_at INTEGER,
+    result_insight_id INTEGER,
+    error_message TEXT,
+    UNIQUE(library_id, file_path, generation_type)
+);
+
+INSERT INTO insight_generation_jobs_new
+    SELECT id, library_id, file_path, generation_type, status, started_at, completed_at, result_insight_id, error_message
+    FROM insight_generation_jobs;
+
+DROP TABLE insight_generation_jobs;
+
+ALTER TABLE insight_generation_jobs_new RENAME TO insight_generation_jobs;
+
+CREATE INDEX idx_insight_gen_jobs_file
+    ON insight_generation_jobs(library_id, file_path);
+
+CREATE INDEX idx_insight_gen_jobs_status_cleanup
+    ON insight_generation_jobs(status, started_at);

migrations/2026-05-27-000001_remove_insight_jobs_unique/up.sql

@@ -0,0 +1,30 @@
+-- Remove UNIQUE(library_id, file_path, generation_type) constraint to allow
+-- multiple job rows per file. This enables proper cancel/regenerate semantics:
+-- a new job is always inserted on regenerate, and the old job is cancelled
+-- independently. The application layer prevents concurrent running jobs.
+
+CREATE TABLE insight_generation_jobs_new (
+    id INTEGER PRIMARY KEY AUTOINCREMENT,
+    library_id INTEGER NOT NULL DEFAULT 1,
+    file_path TEXT NOT NULL,
+    generation_type TEXT NOT NULL,
+    status TEXT NOT NULL DEFAULT 'running',
+    started_at INTEGER NOT NULL,
+    completed_at INTEGER,
+    result_insight_id INTEGER,
+    error_message TEXT
+);
+
+INSERT INTO insight_generation_jobs_new
+    SELECT id, library_id, file_path, generation_type, status, started_at, completed_at, result_insight_id, error_message
+    FROM insight_generation_jobs;
+
+DROP TABLE insight_generation_jobs;
+
+ALTER TABLE insight_generation_jobs_new RENAME TO insight_generation_jobs;
+
+CREATE INDEX idx_insight_gen_jobs_file
+    ON insight_generation_jobs(library_id, file_path);
+
+CREATE INDEX idx_insight_gen_jobs_status_cleanup
+    ON insight_generation_jobs(status, started_at);

migrations/2026-05-27-000002_add_insight_generation_params/down.sql

@@ -0,0 +1,11 @@
+-- SQLite doesn't support DROP COLUMN before 3.35.0; recreate the table
+-- without the new columns. This is only needed for rollback.
+CREATE TABLE photo_insights_old AS
+    SELECT id, library_id, rel_path, title, summary, generated_at,
+           model_version, is_current, training_messages, approved,
+           backend, fewshot_source_ids, content_hash
+    FROM photo_insights;
+
+DROP TABLE photo_insights;
+
+ALTER TABLE photo_insights_old RENAME TO photo_insights;

migrations/2026-05-27-000002_add_insight_generation_params/up.sql

@@ -0,0 +1,8 @@
+-- Persist generation parameters on each insight row for auditing.
+ALTER TABLE photo_insights ADD COLUMN num_ctx INTEGER;
+ALTER TABLE photo_insights ADD COLUMN temperature REAL;
+ALTER TABLE photo_insights ADD COLUMN top_p REAL;
+ALTER TABLE photo_insights ADD COLUMN top_k INTEGER;
+ALTER TABLE photo_insights ADD COLUMN min_p REAL;
+ALTER TABLE photo_insights ADD COLUMN system_prompt TEXT;
+ALTER TABLE photo_insights ADD COLUMN persona_id TEXT;

src/ai/handlers.rs

@@ -73,13 +73,13 @@ pub struct GenerationStatusQuery {
     /// If provided with `library`, look up the latest running job for this
     /// file. Used when the client doesn't have a persisted job_id.
     #[serde(default)]
-    pub file_path: Option<String>,
+    pub path: Option<String>,
     #[serde(default)]
     pub library: Option<String>,
 }
 
 /// GET /insights/generation/status - Check status of a generation job.
-/// Accepts either `?job_id=<id>` or `?file_path=<path>&library=<name>`.
+/// Accepts either `?job_id=<id>` or `?path=<path>&library=<name>`.
 #[get("/insights/generation/status")]
 pub async fn generation_status_handler(
     _claims: Claims,
@@ -118,7 +118,7 @@ pub async fn generation_status_handler(
         }
     }
 
-    if let Some(ref fp) = query.file_path {
+    if let Some(ref fp) = query.path {
         let library = libraries::resolve_library_param(&app_state, query.library.as_deref())
             .ok()
             .flatten()
@@ -156,7 +156,115 @@ pub async fn generation_status_handler(
     }
 
     HttpResponse::BadRequest().json(serde_json::json!({
-        "error": "Provide either job_id or file_path query parameter"
+        "error": "Provide either job_id or path query parameter"
+    }))
+}
+
+#[derive(Debug, Deserialize)]
+pub struct CancelGenerationRequest {
+    /// If provided, cancel the specific job by id.
+    #[serde(default)]
+    pub job_id: Option<i32>,
+    /// If provided with `library`, cancel all running jobs for this file.
+    #[serde(default)]
+    pub file_path: Option<String>,
+    #[serde(default)]
+    pub library: Option<String>,
+}
+
+/// POST /insights/generation/cancel - Cancel a running generation job.
+/// Accepts either `job_id` or `file_path` + optional `library` in the body.
+#[post("/insights/generation/cancel")]
+pub async fn cancel_generation_handler(
+    _claims: Claims,
+    request: web::Json<CancelGenerationRequest>,
+    app_state: web::Data<AppState>,
+) -> impl Responder {
+    let ctx = opentelemetry::Context::new();
+
+    if let Some(jid) = request.job_id {
+        let mut dao = app_state
+            .insight_job_dao
+            .lock()
+            .expect("Unable to lock InsightJobDao");
+        match dao.cancel_job(&ctx, jid) {
+            Ok(true) => {
+                let mut handles = app_state
+                    .insight_job_handles
+                    .lock()
+                    .expect("Unable to lock InsightJobHandles");
+                if let Some(handle) = handles.remove(&jid) {
+                    handle.abort();
+                }
+                return HttpResponse::Ok().json(serde_json::json!({
+                    "success": true,
+                    "message": format!("Job {} cancelled", jid)
+                }));
+            }
+            Ok(false) => {
+                return HttpResponse::Ok().json(serde_json::json!({
+                    "success": true,
+                    "message": format!("Job {} was not running", jid)
+                }));
+            }
+            Err(e) => {
+                log::error!("Failed to cancel job {}: {:?}", jid, e);
+                return HttpResponse::InternalServerError().json(serde_json::json!({
+                    "error": "Failed to cancel job"
+                }));
+            }
+        }
+    }
+
+    if let Some(ref fp) = request.file_path {
+        let library = libraries::resolve_library_param(&app_state, request.library.as_deref())
+            .ok()
+            .flatten()
+            .unwrap_or_else(|| app_state.primary_library());
+        let normalized = normalize_path(fp);
+
+        // Get active job ids first, then cancel in DB, then abort tasks
+        let active_ids: Vec<i32> = {
+            let mut dao = app_state
+                .insight_job_dao
+                .lock()
+                .expect("Unable to lock InsightJobDao");
+            let ids = dao
+                .get_active_job(&ctx, library.id, &normalized)
+                .ok()
+                .flatten()
+                .map(|j| vec![j.id])
+                .unwrap_or_default();
+            let _ = dao.cancel_active_jobs(&ctx, library.id, &normalized);
+            ids
+        };
+
+        if active_ids.is_empty() {
+            return HttpResponse::Ok().json(serde_json::json!({
+                "success": true,
+                "message": "No running generation job for this file"
+            }));
+        }
+
+        for jid in &active_ids {
+            if let Some(handle) = app_state
+                .insight_job_handles
+                .lock()
+                .expect("Unable to lock InsightJobHandles")
+                .remove(jid)
+            {
+                handle.abort();
+            }
+        }
+
+        return HttpResponse::Ok().json(serde_json::json!({
+            "success": true,
+            "message": format!("Cancelled {} running job(s) for {}", active_ids.len(), normalized)
+        }));
+    }
+
+    HttpResponse::BadRequest().json(serde_json::json!({
+        "error": "Provide either job_id or file_path in the request body"
     }))
 }
 
@@ -208,6 +316,20 @@ pub struct PhotoInsightResponse {
     /// True when the insight was generated agentically and a chat
     /// continuation can be started against it. Drives the mobile chat button.
     pub has_training_messages: bool,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub num_ctx: Option<i32>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub temperature: Option<f32>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub top_p: Option<f32>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub top_k: Option<i32>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub min_p: Option<f32>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub system_prompt: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub persona_id: Option<String>,
 }
 
 #[derive(Debug, Serialize)]
@@ -227,33 +349,55 @@ pub struct ServerModels {
 /// POST /insights/generate - Generate insight for a specific photo (async)
 #[post("/insights/generate")]
 pub async fn generate_insight_handler(
-    _http_request: HttpRequest,
+    http_request: HttpRequest,
     _claims: Claims,
     request: web::Json<GeneratePhotoInsightRequest>,
     app_state: web::Data<AppState>,
 ) -> impl Responder {
+    let parent_context = extract_context_from_request(&http_request);
+    let tracer = global_tracer();
+    let mut span = tracer.start_with_context("http.insights.generate", &parent_context);
+
     let normalized_path = normalize_path(&request.file_path);
     let library = app_state.primary_library();
     let gen_type = InsightGenerationType::Standard;
 
+    span.set_attribute(KeyValue::new("file_path", normalized_path.clone()));
+    if let Some(ref model) = request.model {
+        span.set_attribute(KeyValue::new("model", model.clone()));
+    }
+
     log::info!(
         "Manual insight generation triggered for photo: {} with model: {:?}",
         normalized_path,
         request.model
     );
 
-    // Cancel any running job for this file, then create a fresh one
+    // Look up and abort any running job for this file, then cancel in DB
-    {
+    let old_job_ids: Vec<i32> = {
         let mut dao = app_state
             .insight_job_dao
             .lock()
             .expect("Unable to lock InsightJobDao");
-        let _ = dao.cancel_active_job(
+        let ctx = opentelemetry::Context::new();
-            &opentelemetry::Context::new(),
+        let ids = dao
-            library.id,
+            .get_active_job(&ctx, library.id, &normalized_path)
-            &normalized_path,
+            .ok()
-            gen_type,
+            .flatten()
-        );
+            .map(|j| vec![j.id])
+            .unwrap_or_default();
+        let _ = dao.cancel_active_jobs(&ctx, library.id, &normalized_path);
+        ids
+    };
+    for jid in &old_job_ids {
+        if let Some(handle) = app_state
+            .insight_job_handles
+            .lock()
+            .expect("Unable to lock InsightJobHandles")
+            .remove(jid)
+        {
+            handle.abort();
+        }
     }
 
     let job_id = {
@@ -261,7 +405,7 @@ pub async fn generate_insight_handler(
             .insight_job_dao
             .lock()
             .expect("Unable to lock InsightJobDao");
-        match dao.create_or_get_active_job(
+        match dao.create_job(
             &opentelemetry::Context::new(),
             library.id,
             &normalized_path,
@@ -270,6 +414,7 @@ pub async fn generate_insight_handler(
             Ok(id) => id,
             Err(e) => {
                 log::error!("Failed to create generation job: {:?}", e);
+                span.set_status(Status::error("Failed to create generation job"));
                 return HttpResponse::InternalServerError().json(serde_json::json!({
                     "error": "Failed to create generation job"
                 }));
@@ -280,36 +425,40 @@ pub async fn generate_insight_handler(
     // Spawn background task with timeout
     let generator = app_state.insight_generator.clone();
     let job_dao = app_state.insight_job_dao.clone();
-    let lib_id = library.id;
+    let job_handles = app_state.insight_job_handles.clone();
     let path = normalized_path.clone();
 
-    tokio::spawn(async move {
+    let handle = tokio::spawn(async move {
         let timeout_secs: u64 = std::env::var("INSIGHT_GENERATION_TIMEOUT_SECS")
             .ok()
             .and_then(|v| v.parse().ok())
             .unwrap_or(120);
 
-        let result = tokio::time::timeout(
+        let path_for_task = path.clone();
-            std::time::Duration::from_secs(timeout_secs),
+        let generator_for_task = generator.clone();
-            generator.generate_insight_for_photo_with_config(
+        let result = tokio::task::spawn(async move {
-                &path,
+            tokio::time::timeout(
-                request.model.clone(),
+                std::time::Duration::from_secs(timeout_secs),
-                request.system_prompt.clone(),
+                generator_for_task.generate_insight_for_photo_with_config(
-                request.num_ctx,
+                    &path_for_task,
-                request.temperature,
+                    request.model.clone(),
-                request.top_p,
+                    request.system_prompt.clone(),
-                request.top_k,
+                    request.num_ctx,
-                request.min_p,
+                    request.temperature,
-            ),
+                    request.top_p,
-        )
+                    request.top_k,
+                    request.min_p,
+                ),
+            )
+            .await
+        })
         .await;
 
         let ctx = opentelemetry::Context::new();
         let mut dao = job_dao.lock().expect("Unable to lock InsightJobDao");
 
         match result {
-            Ok(Ok(())) => {
+            Ok(Ok(Ok(()))) => {
-                // Look up the stored insight id to record on the job
                 let mut insight_dao = generator
                     .insight_dao()
                     .lock()
@@ -320,27 +469,60 @@ pub async fn generate_insight_handler(
                     .flatten()
                     .map(|i| i.id);
                 if let Some(id) = insight_id {
-                    let _ = dao.complete_job(&ctx, job_id, id);
+                    if let Err(e) = dao.complete_job(&ctx, job_id, id) {
+                        log::error!("Failed to mark job {} as completed: {:?}", job_id, e);
+                    }
                 } else {
-                    let _ = dao.fail_job(&ctx, job_id, "generation returned no insight");
+                    if let Err(e) = dao.fail_job(&ctx, job_id, "generation returned no insight") {
+                        log::error!("Failed to mark job {} as failed: {:?}", job_id, e);
+                    }
                 }
             }
-            Ok(Err(e)) => {
+            Ok(Ok(Err(e))) => {
                 log::error!("Insight generation failed for {}: {:?}", path, e);
-                let _ = dao.fail_job(&ctx, job_id, &format!("{:?}", e));
+                if let Err(err) = dao.fail_job(&ctx, job_id, &format!("{:?}", e)) {
+                    log::error!("Failed to mark job {} as failed: {:?}", job_id, err);
+                }
             }
-            Err(_) => {
+            Ok(Err(_)) => {
                 log::error!(
                     "Insight generation timed out for {} after {}s",
                     path,
                     timeout_secs
                 );
-                let _ = dao.fail_job(&ctx, job_id, &format!("timeout after {}s", timeout_secs));
+                if let Err(err) =
+                    dao.fail_job(&ctx, job_id, &format!("timeout after {}s", timeout_secs))
+                {
+                    log::error!("Failed to mark job {} as failed: {:?}", job_id, err);
+                }
+            }
+            Err(_) => {
+                log::error!("Insight generation task panicked for {}", path);
+                if let Err(err) = dao.fail_job(&ctx, job_id, "generation task panicked") {
+                    log::error!("Failed to mark job {} as failed: {:?}", job_id, err);
+                }
             }
         }
+
+        // Remove handle from map on completion
+        let mut handles = job_handles
+            .lock()
+            .expect("Unable to lock InsightJobHandles");
+        handles.remove(&job_id);
     });
 
-    HttpResponse::Ok().json(JobIdResponse { job_id })
+    // Store abort handle
+    {
+        let mut handles = app_state
+            .insight_job_handles
+            .lock()
+            .expect("Unable to lock InsightJobHandles");
+        handles.insert(job_id, handle.abort_handle());
+    }
+
+    span.set_attribute(KeyValue::new("job_id", job_id as i64));
+    span.set_status(Status::Ok);
+    HttpResponse::Accepted().json(JobIdResponse { job_id })
 }
 
 /// GET /insights?path=/path/to/photo.jpg - Fetch insight for specific photo
@@ -385,6 +567,13 @@ pub async fn get_insight_handler(
                 approved: insight.approved,
                 has_training_messages: insight.training_messages.is_some(),
                 backend: insight.backend,
+                num_ctx: insight.num_ctx,
+                temperature: insight.temperature,
+                top_p: insight.top_p,
+                top_k: insight.top_k,
+                min_p: insight.min_p,
+                system_prompt: insight.system_prompt,
+                persona_id: insight.persona_id,
             };
             HttpResponse::Ok().json(response)
         }
@@ -454,6 +643,13 @@ pub async fn get_all_insights_handler(
                     approved: insight.approved,
                     has_training_messages: insight.training_messages.is_some(),
                     backend: insight.backend,
+                    num_ctx: insight.num_ctx,
+                    temperature: insight.temperature,
+                    top_p: insight.top_p,
+                    top_k: insight.top_k,
+                    min_p: insight.min_p,
+                    system_prompt: insight.system_prompt,
+                    persona_id: insight.persona_id,
                 })
                 .collect();
 
@@ -471,33 +667,58 @@ pub async fn get_all_insights_handler(
 /// POST /insights/generate/agentic - Generate insight using agentic tool-calling loop (async)
 #[post("/insights/generate/agentic")]
 pub async fn generate_agentic_insight_handler(
-    _http_request: HttpRequest,
+    http_request: HttpRequest,
     claims: Claims,
     request: web::Json<GeneratePhotoInsightRequest>,
     app_state: web::Data<AppState>,
 ) -> impl Responder {
+    let parent_context = extract_context_from_request(&http_request);
+    let tracer = global_tracer();
+    let mut span = tracer.start_with_context("http.insights.generate_agentic", &parent_context);
+
     let normalized_path = normalize_path(&request.file_path);
     let library = app_state.primary_library();
     let gen_type = InsightGenerationType::Agentic;
 
+    span.set_attribute(KeyValue::new("file_path", normalized_path.clone()));
+    if let Some(ref model) = request.model {
+        span.set_attribute(KeyValue::new("model", model.clone()));
+    }
+    if let Some(ref backend) = request.backend {
+        span.set_attribute(KeyValue::new("backend", backend.clone()));
+    }
+
     log::info!(
         "Agentic insight generation triggered for photo: {} with model: {:?}",
         normalized_path,
         request.model
     );
 
-    // Cancel any running job for this file, then create a fresh one
+    // Look up and abort any running job for this file, then cancel in DB
-    {
+    let old_job_ids: Vec<i32> = {
         let mut dao = app_state
             .insight_job_dao
             .lock()
             .expect("Unable to lock InsightJobDao");
-        let _ = dao.cancel_active_job(
+        let ctx = opentelemetry::Context::new();
-            &opentelemetry::Context::new(),
+        let ids = dao
-            library.id,
+            .get_active_job(&ctx, library.id, &normalized_path)
-            &normalized_path,
+            .ok()
-            gen_type,
+            .flatten()
-        );
+            .map(|j| vec![j.id])
+            .unwrap_or_default();
+        let _ = dao.cancel_active_jobs(&ctx, library.id, &normalized_path);
+        ids
+    };
+    for jid in &old_job_ids {
+        if let Some(handle) = app_state
+            .insight_job_handles
+            .lock()
+            .expect("Unable to lock InsightJobHandles")
+            .remove(jid)
+        {
+            handle.abort();
+        }
     }
 
     let job_id = {
@@ -505,7 +726,7 @@ pub async fn generate_agentic_insight_handler(
             .insight_job_dao
             .lock()
             .expect("Unable to lock InsightJobDao");
-        match dao.create_or_get_active_job(
+        match dao.create_job(
             &opentelemetry::Context::new(),
             library.id,
             &normalized_path,
@@ -514,6 +735,7 @@ pub async fn generate_agentic_insight_handler(
             Ok(id) => id,
             Err(e) => {
                 log::error!("Failed to create agentic generation job: {:?}", e);
+                span.set_status(Status::error("Failed to create generation job"));
                 return HttpResponse::InternalServerError().json(serde_json::json!({
                     "error": "Failed to create generation job"
                 }));
@@ -573,73 +795,101 @@ pub async fn generate_agentic_insight_handler(
     // Spawn background task with timeout
     let generator = app_state.insight_generator.clone();
     let job_dao = app_state.insight_job_dao.clone();
-    let lib_id = library.id;
+    let job_handles = app_state.insight_job_handles.clone();
     let path = normalized_path.clone();
 
-    tokio::spawn(async move {
+    let handle = tokio::spawn(async move {
         let timeout_secs: u64 = std::env::var("INSIGHT_GENERATION_TIMEOUT_SECS")
             .ok()
             .and_then(|v| v.parse().ok())
             .unwrap_or(180);
 
-        let result = tokio::time::timeout(
+        let path_for_task = path.clone();
-            std::time::Duration::from_secs(timeout_secs),
+        let generator_for_task = generator.clone();
-            generator.generate_agentic_insight_for_photo(
+        let result = tokio::task::spawn(async move {
-                &path,
+            tokio::time::timeout(
-                request.model.clone(),
+                std::time::Duration::from_secs(timeout_secs),
-                request.system_prompt.clone(),
+                generator_for_task.generate_agentic_insight_for_photo(
-                request.num_ctx,
+                    &path_for_task,
-                request.temperature,
+                    request.model.clone(),
-                request.top_p,
+                    request.system_prompt.clone(),
-                request.top_k,
+                    request.num_ctx,
-                request.min_p,
+                    request.temperature,
-                max_iterations,
+                    request.top_p,
-                request.backend.clone(),
+                    request.top_k,
-                fewshot_examples,
+                    request.min_p,
-                fewshot_ids,
+                    max_iterations,
-                user_id,
+                    request.backend.clone(),
-                persona_id,
+                    fewshot_examples,
-            ),
+                    fewshot_ids,
-        )
+                    user_id,
+                    persona_id,
+                ),
+            )
+            .await
+        })
         .await;
 
         let ctx = opentelemetry::Context::new();
         let mut dao = job_dao.lock().expect("Unable to lock InsightJobDao");
 
         match result {
-            Ok(Ok(_)) => {
+            Ok(Ok(Ok((Some(insight_id), _)))) => {
-                // Fetch the stored insight id to record on the job
+                if let Err(e) = dao.complete_job(&ctx, job_id, insight_id) {
-                let mut insight_dao = generator
+                    log::error!("Failed to mark job {} as completed: {:?}", job_id, e);
-                    .insight_dao()
-                    .lock()
-                    .expect("Unable to lock InsightDao");
-                let insight_id = insight_dao
-                    .get_insight(&ctx, &path)
-                    .ok()
-                    .flatten()
-                    .map(|i| i.id);
-                if let Some(id) = insight_id {
-                    let _ = dao.complete_job(&ctx, job_id, id);
-                } else {
-                    let _ = dao.fail_job(&ctx, job_id, "generation returned no insight");
                 }
             }
-            Ok(Err(e)) => {
+            Ok(Ok(Ok((None, _)))) => {
-                log::error!("Agentic insight generation failed for {}: {:?}", path, e);
+                if let Err(e) = dao.fail_job(&ctx, job_id, "agentic generation returned no insight")
-                let _ = dao.fail_job(&ctx, job_id, &format!("{:?}", e));
+                {
+                    log::error!("Failed to mark job {} as failed: {:?}", job_id, e);
+                }
             }
-            Err(_) => {
+            Ok(Ok(Err(e))) => {
+                log::error!("Agentic insight generation failed for {}: {:?}", path, e);
+                if let Err(err) = dao.fail_job(&ctx, job_id, &format!("{:?}", e)) {
+                    log::error!("Failed to mark job {} as failed: {:?}", job_id, err);
+                }
+            }
+            Ok(Err(_)) => {
                 log::error!(
                     "Agentic insight generation timed out for {} after {}s",
                     path,
                     timeout_secs
                 );
-                let _ = dao.fail_job(&ctx, job_id, &format!("timeout after {}s", timeout_secs));
+                if let Err(err) =
+                    dao.fail_job(&ctx, job_id, &format!("timeout after {}s", timeout_secs))
+                {
+                    log::error!("Failed to mark job {} as failed: {:?}", job_id, err);
+                }
+            }
+            Err(_) => {
+                log::error!("Agentic insight generation task panicked for {}", path);
+                if let Err(err) = dao.fail_job(&ctx, job_id, "generation task panicked") {
+                    log::error!("Failed to mark job {} as failed: {:?}", job_id, err);
+                }
             }
         }
+
+        // Remove handle from map on completion
+        let mut handles = job_handles
+            .lock()
+            .expect("Unable to lock InsightJobHandles");
+        handles.remove(&job_id);
     });
 
-    HttpResponse::Ok().json(JobIdResponse { job_id })
+    // Store abort handle
+    {
+        let mut handles = app_state
+            .insight_job_handles
+            .lock()
+            .expect("Unable to lock InsightJobHandles");
+        handles.insert(job_id, handle.abort_handle());
+    }
+
+    span.set_attribute(KeyValue::new("job_id", job_id as i64));
+    span.set_status(Status::Ok);
+    HttpResponse::Accepted().json(JobIdResponse { job_id })
 }
 
 /// GET /insights/models - Local-backend models with capabilities. Returns

src/ai/insight_chat.rs

@@ -517,6 +517,13 @@ impl InsightChatService {
                 backend: kind.as_str().to_string(),
                 fewshot_source_ids: None,
                 content_hash: None,
+                num_ctx: req.num_ctx,
+                temperature: req.temperature,
+                top_p: req.top_p,
+                top_k: req.top_k,
+                min_p: req.min_p,
+                system_prompt: req.system_prompt.clone(),
+                persona_id: req.persona_id.clone(),
             };
             let cx = opentelemetry::Context::new();
             let mut dao = self.insight_dao.lock().expect("Unable to lock InsightDao");
@@ -864,6 +871,13 @@ impl InsightChatService {
                 backend: kind.as_str().to_string(),
                 fewshot_source_ids: None,
                 content_hash: None,
+                num_ctx: req.num_ctx,
+                temperature: req.temperature,
+                top_p: req.top_p,
+                top_k: req.top_k,
+                min_p: req.min_p,
+                system_prompt: req.system_prompt.clone(),
+                persona_id: req.persona_id.clone(),
             };
             let cx = opentelemetry::Context::new();
             let mut dao = self.insight_dao.lock().expect("Unable to lock InsightDao");
@@ -1052,6 +1066,13 @@ impl InsightChatService {
             backend: kind.as_str().to_string(),
             fewshot_source_ids: None,
             content_hash: None,
+            num_ctx: req.num_ctx,
+            temperature: req.temperature,
+            top_p: req.top_p,
+            top_k: req.top_k,
+            min_p: req.min_p,
+            system_prompt: req.system_prompt.clone(),
+            persona_id: req.persona_id.clone(),
         };
         let stored = {
             let cx = opentelemetry::Context::new();

src/ai/insight_generator.rs

@@ -1432,6 +1432,13 @@ impl InsightGenerator {
             backend: "local".to_string(),
             fewshot_source_ids: None,
             content_hash: None,
+            num_ctx,
+            temperature,
+            top_p,
+            top_k,
+            min_p,
+            system_prompt: custom_system_prompt.clone(),
+            persona_id: None,
         };
 
         let mut dao = self.insight_dao.lock().expect("Unable to lock InsightDao");
@@ -4176,6 +4183,13 @@ Return ONLY the summary, nothing else."#,
             backend: kind.as_str().to_string(),
             fewshot_source_ids: fewshot_source_ids_json,
             content_hash: None,
+            num_ctx,
+            temperature,
+            top_p,
+            top_k,
+            min_p,
+            system_prompt: custom_system_prompt.clone(),
+            persona_id: Some(persona_id.clone()),
         };
 
         let stored = {

src/ai/mod.rs

@@ -19,11 +19,11 @@ pub use daily_summary_job::{
     generate_daily_summaries, strip_summary_boilerplate,
 };
 pub use handlers::{
-    chat_history_handler, chat_rewind_handler, chat_stream_handler, chat_turn_handler,
+    cancel_generation_handler, chat_history_handler, chat_rewind_handler, chat_stream_handler,
-    delete_insight_handler, export_training_data_handler, generate_agentic_insight_handler,
+    chat_turn_handler, delete_insight_handler, export_training_data_handler,
-    generate_insight_handler, generation_status_handler, get_all_insights_handler,
+    generate_agentic_insight_handler, generate_insight_handler, generation_status_handler,
-    get_available_models_handler, get_insight_handler, get_openrouter_models_handler,
+    get_all_insights_handler, get_available_models_handler, get_insight_handler,
-    rate_insight_handler,
+    get_openrouter_models_handler, rate_insight_handler,
 };
 pub use insight_generator::InsightGenerator;
 pub use llamacpp::LlamaCppClient;

src/database/insight_generation_job_dao.rs

@@ -10,13 +10,13 @@ use crate::database::schema;
 use crate::database::{DbError, DbErrorKind, connect};
 use crate::otel::trace_db_call;
 
-/// Tracks async insight generation jobs. The idempotent insert ensures
+/// Tracks async insight generation jobs. Each call to `create_job` inserts
-/// concurrent callers for the same (library_id, file_path, generation_type)
+/// a new row; the application layer prevents concurrent running jobs by
-/// get the same job_id rather than creating duplicates.
+/// cancelling the old one before creating a new one.
 pub trait InsightGenerationJobDao: Sync + Send {
-    /// Insert a new job or return the existing running job for the same key.
+    /// Insert a new running job. Always creates a new row (no upsert).
-    /// Returns the job_id either way.
+    /// Cleans up terminal-state rows for the same key first.
-    fn create_or_get_active_job(
+    fn create_job(
         &mut self,
         context: &opentelemetry::Context,
         library_id: i32,
@@ -24,7 +24,9 @@ pub trait InsightGenerationJobDao: Sync + Send {
         generation_type: InsightGenerationType,
     ) -> Result<i32, DbError>;
 
-    /// Mark a job as completed with the resulting insight id.
+    /// Mark a job as completed with the resulting insight id. Only updates
+    /// if the job is still in "running" status (prevents overwriting a
+    /// cancelled job with a late-completing task).
     fn complete_job(
         &mut self,
         context: &opentelemetry::Context,
@@ -32,7 +34,8 @@ pub trait InsightGenerationJobDao: Sync + Send {
         insight_id: i32,
     ) -> Result<(), DbError>;
 
-    /// Mark a job as failed with an error message.
+    /// Mark a job as failed with an error message. Only updates if the job
+    /// is still in "running" status.
     fn fail_job(
         &mut self,
         context: &opentelemetry::Context,
@@ -40,15 +43,22 @@ pub trait InsightGenerationJobDao: Sync + Send {
         error_message: &str,
     ) -> Result<(), DbError>;
 
-    /// Mark the active running job for a file as "cancelled". Returns true if
+    /// Cancel a specific job by id. Only updates if the job is still
-    /// a job was found and cancelled, false if no running job existed.
+    /// in "running" status. Returns true if a row was updated.
-    fn cancel_active_job(
+    fn cancel_job(
+        &mut self,
+        context: &opentelemetry::Context,
+        job_id: i32,
+    ) -> Result<bool, DbError>;
+
+    /// Cancel all running jobs for a given file. Returns the number of
+    /// jobs cancelled.
+    fn cancel_active_jobs(
         &mut self,
         context: &opentelemetry::Context,
         library_id: i32,
         file_path: &str,
-        generation_type: InsightGenerationType,
+    ) -> Result<usize, DbError>;
-    ) -> Result<bool, DbError>;
 
     /// Find the latest running job for a given file. Returns None if no
     /// running job exists.
@@ -65,6 +75,11 @@ pub trait InsightGenerationJobDao: Sync + Send {
         context: &opentelemetry::Context,
         job_id: i32,
     ) -> Result<Option<InsightGenerationJob>, DbError>;
+
+    /// Mark all jobs still in "running" status as "failed" with a recovery
+    /// error message. Returns the number of jobs recovered.
+    fn recover_orphaned_jobs(&mut self, context: &opentelemetry::Context)
+    -> Result<usize, DbError>;
 }
 
 pub struct SqliteInsightGenerationJobDao {
@@ -91,14 +106,14 @@ impl SqliteInsightGenerationJobDao {
 }
 
 impl InsightGenerationJobDao for SqliteInsightGenerationJobDao {
-    fn create_or_get_active_job(
+    fn create_job(
         &mut self,
         context: &opentelemetry::Context,
         library_id: i32,
         file_path: &str,
         generation_type: InsightGenerationType,
     ) -> Result<i32, DbError> {
-        trace_db_call(context, "insert", "create_or_get_active_job", |_span| {
+        trace_db_call(context, "insert", "create_job", |_span| {
             use schema::insight_generation_jobs::dsl;
 
             let mut connection = self
@@ -106,26 +121,6 @@ impl InsightGenerationJobDao for SqliteInsightGenerationJobDao {
                 .lock()
                 .expect("Unable to lock InsightGenerationJobDao");
 
-            // Check for existing running job
-            let existing = dsl::insight_generation_jobs
-                .filter(
-                    dsl::library_id
-                        .eq(library_id)
-                        .and(dsl::file_path.eq(file_path))
-                        .and(dsl::generation_type.eq(generation_type.as_str()))
-                        .and(dsl::status.eq(InsightJobStatus::Running.as_str())),
-                )
-                .select(dsl::id)
-                .first::<i32>(connection.deref_mut())
-                .optional();
-
-            match existing {
-                Ok(Some(job_id)) => return Ok(job_id),
-                Ok(None) => {}
-                Err(e) => return Err(anyhow::anyhow!("Failed to check existing job: {}", e)),
-            }
-
-            // No running job exists, insert new one (upsert on conflict)
             let now = std::time::SystemTime::now()
                 .duration_since(std::time::UNIX_EPOCH)
                 .expect("Time went backwards")
@@ -141,22 +136,16 @@ impl InsightGenerationJobDao for SqliteInsightGenerationJobDao {
 
             diesel::insert_into(dsl::insight_generation_jobs)
                 .values(&new_job)
-                .on_conflict((dsl::library_id, dsl::file_path, dsl::generation_type))
-                .do_update()
-                .set((
-                    dsl::status.eq(InsightJobStatus::Running.as_str()),
-                    dsl::started_at.eq(now),
-                ))
                 .execute(connection.deref_mut())
                 .map_err(|e| anyhow::anyhow!("Failed to insert job: {}", e))?;
 
-            // Get the job id
             dsl::insight_generation_jobs
                 .filter(
                     dsl::library_id
                         .eq(library_id)
                         .and(dsl::file_path.eq(file_path))
-                        .and(dsl::generation_type.eq(generation_type.as_str())),
+                        .and(dsl::generation_type.eq(generation_type.as_str()))
+                        .and(dsl::status.eq(InsightJobStatus::Running.as_str())),
                 )
                 .select(dsl::id)
                 .order(dsl::id.desc())
@@ -185,15 +174,23 @@ impl InsightGenerationJobDao for SqliteInsightGenerationJobDao {
                 .expect("Time went backwards")
                 .as_secs() as i64;
 
-            diesel::update(dsl::insight_generation_jobs.filter(dsl::id.eq(job_id)))
+            // Only update if still running — prevents cancelled job from
-                .set((
+            // being overwritten by a late-completing task.
-                    dsl::status.eq(InsightJobStatus::Completed.as_str()),
+            diesel::update(
-                    dsl::completed_at.eq(Some(now)),
+                dsl::insight_generation_jobs.filter(
-                    dsl::result_insight_id.eq(Some(insight_id)),
+                    dsl::id
-                ))
+                        .eq(job_id)
-                .execute(connection.deref_mut())
+                        .and(dsl::status.eq(InsightJobStatus::Running.as_str())),
-                .map(|_| ())
+                ),
-                .map_err(|e| anyhow::anyhow!("Failed to complete job: {}", e))
+            )
+            .set((
+                dsl::status.eq(InsightJobStatus::Completed.as_str()),
+                dsl::completed_at.eq(Some(now)),
+                dsl::result_insight_id.eq(Some(insight_id)),
+            ))
+            .execute(connection.deref_mut())
+            .map(|_| ())
+            .map_err(|e| anyhow::anyhow!("Failed to complete job: {}", e))
         })
         .map_err(|_| DbError::new(DbErrorKind::UpdateError))
     }
@@ -217,27 +214,71 @@ impl InsightGenerationJobDao for SqliteInsightGenerationJobDao {
                 .expect("Time went backwards")
                 .as_secs() as i64;
 
-            diesel::update(dsl::insight_generation_jobs.filter(dsl::id.eq(job_id)))
+            // Only update if still running.
-                .set((
+            diesel::update(
-                    dsl::status.eq(InsightJobStatus::Failed.as_str()),
+                dsl::insight_generation_jobs.filter(
-                    dsl::completed_at.eq(Some(now)),
+                    dsl::id
-                    dsl::error_message.eq(Some(error_message.to_string())),
+                        .eq(job_id)
-                ))
+                        .and(dsl::status.eq(InsightJobStatus::Running.as_str())),
-                .execute(connection.deref_mut())
+                ),
-                .map(|_| ())
+            )
-                .map_err(|e| anyhow::anyhow!("Failed to fail job: {}", e))
+            .set((
+                dsl::status.eq(InsightJobStatus::Failed.as_str()),
+                dsl::completed_at.eq(Some(now)),
+                dsl::error_message.eq(Some(error_message.to_string())),
+            ))
+            .execute(connection.deref_mut())
+            .map(|_| ())
+            .map_err(|e| anyhow::anyhow!("Failed to fail job: {}", e))
         })
         .map_err(|_| DbError::new(DbErrorKind::UpdateError))
     }
 
-    fn cancel_active_job(
+    fn cancel_job(
+        &mut self,
+        context: &opentelemetry::Context,
+        job_id: i32,
+    ) -> Result<bool, DbError> {
+        trace_db_call(context, "update", "cancel_job", |_span| {
+            use schema::insight_generation_jobs::dsl;
+
+            let mut connection = self
+                .connection
+                .lock()
+                .expect("Unable to lock InsightGenerationJobDao");
+
+            let now = std::time::SystemTime::now()
+                .duration_since(std::time::UNIX_EPOCH)
+                .expect("Time went backwards")
+                .as_secs() as i64;
+
+            let rows = diesel::update(
+                dsl::insight_generation_jobs.filter(
+                    dsl::id
+                        .eq(job_id)
+                        .and(dsl::status.eq(InsightJobStatus::Running.as_str())),
+                ),
+            )
+            .set((
+                dsl::status.eq(InsightJobStatus::Cancelled.as_str()),
+                dsl::completed_at.eq(Some(now)),
+                dsl::error_message.eq(Some("cancelled by user".to_string())),
+            ))
+            .execute(connection.deref_mut())
+            .map_err(|e| anyhow::anyhow!("Failed to cancel job: {}", e))?;
+
+            Ok(rows > 0)
+        })
+        .map_err(|_| DbError::new(DbErrorKind::UpdateError))
+    }
+
+    fn cancel_active_jobs(
         &mut self,
         context: &opentelemetry::Context,
         library_id: i32,
         file_path: &str,
-        generation_type: InsightGenerationType,
+    ) -> Result<usize, DbError> {
-    ) -> Result<bool, DbError> {
+        trace_db_call(context, "update", "cancel_active_jobs", |_span| {
-        trace_db_call(context, "update", "cancel_active_job", |_span| {
             use schema::insight_generation_jobs::dsl;
 
             let mut connection = self
@@ -255,7 +296,6 @@ impl InsightGenerationJobDao for SqliteInsightGenerationJobDao {
                     dsl::library_id
                         .eq(library_id)
                         .and(dsl::file_path.eq(file_path))
-                        .and(dsl::generation_type.eq(generation_type.as_str()))
                         .and(dsl::status.eq(InsightJobStatus::Running.as_str())),
                 ),
             )
@@ -265,9 +305,9 @@ impl InsightGenerationJobDao for SqliteInsightGenerationJobDao {
                 dsl::error_message.eq(Some("cancelled by newer request".to_string())),
             ))
             .execute(connection.deref_mut())
-            .map_err(|e| anyhow::anyhow!("Failed to cancel job: {}", e))?;
+            .map_err(|e| anyhow::anyhow!("Failed to cancel active jobs: {}", e))?;
 
-            Ok(rows > 0)
+            Ok(rows)
         })
         .map_err(|_| DbError::new(DbErrorKind::UpdateError))
     }
@@ -322,6 +362,40 @@ impl InsightGenerationJobDao for SqliteInsightGenerationJobDao {
         })
         .map_err(|_| DbError::new(DbErrorKind::QueryError))
     }
+
+    fn recover_orphaned_jobs(
+        &mut self,
+        context: &opentelemetry::Context,
+    ) -> Result<usize, DbError> {
+        trace_db_call(context, "update", "recover_orphaned_jobs", |_span| {
+            use schema::insight_generation_jobs::dsl;
+
+            let mut connection = self
+                .connection
+                .lock()
+                .expect("Unable to lock InsightGenerationJobDao");
+
+            let now = std::time::SystemTime::now()
+                .duration_since(std::time::UNIX_EPOCH)
+                .expect("Time went backwards")
+                .as_secs() as i64;
+
+            let rows = diesel::update(
+                dsl::insight_generation_jobs
+                    .filter(dsl::status.eq(InsightJobStatus::Running.as_str())),
+            )
+            .set((
+                dsl::status.eq(InsightJobStatus::Failed.as_str()),
+                dsl::completed_at.eq(Some(now)),
+                dsl::error_message.eq(Some("server crashed while running".to_string())),
+            ))
+            .execute(connection.deref_mut())
+            .map_err(|e| anyhow::anyhow!("Failed to recover orphaned jobs: {}", e))?;
+
+            Ok(rows)
+        })
+        .map_err(|_| DbError::new(DbErrorKind::UpdateError))
+    }
 }
 
 #[cfg(test)]
@@ -345,22 +419,19 @@ mod tests {
     }
 
     #[test]
-    fn create_job_idempotent() {
+    fn create_job_inserts_new_row() {
         let mut dao = setup_dao();
         let ctx = ctx();
 
         let job_id_1 = dao
-            .create_or_get_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
             .unwrap();
 
         let job_id_2 = dao
-            .create_or_get_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
             .unwrap();
 
-        assert_eq!(
+        assert_ne!(job_id_1, job_id_2, "each create_job call inserts a new row");
-            job_id_1, job_id_2,
-            "idempotent insert should return same job_id"
-        );
     }
 
     #[test]
@@ -369,7 +440,7 @@ mod tests {
         let ctx = ctx();
 
         let job_id = dao
-            .create_or_get_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
             .unwrap();
 
         dao.complete_job(&ctx, job_id, 42).unwrap();
@@ -386,7 +457,7 @@ mod tests {
         let ctx = ctx();
 
         let job_id = dao
-            .create_or_get_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Agentic)
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Agentic)
             .unwrap();
 
         dao.fail_job(&ctx, job_id, "model timeout").unwrap();
@@ -403,7 +474,7 @@ mod tests {
         let ctx = ctx();
 
         let job_id = dao
-            .create_or_get_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
             .unwrap();
 
         // Job is running
@@ -420,18 +491,16 @@ mod tests {
     }
 
     #[test]
-    fn cancel_active_job() {
+    fn cancel_active_jobs() {
         let mut dao = setup_dao();
         let ctx = ctx();
 
         let job_id = dao
-            .create_or_get_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
             .unwrap();
 
-        let cancelled = dao
+        let cancelled = dao.cancel_active_jobs(&ctx, 1, "photos/test.jpg").unwrap();
-            .cancel_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+        assert_eq!(cancelled, 1, "should cancel 1 running job");
-            .unwrap();
-        assert!(cancelled, "should cancel existing running job");
 
         // Job is no longer active
         let active = dao.get_active_job(&ctx, 1, "photos/test.jpg").unwrap();
@@ -441,11 +510,9 @@ mod tests {
         let job = dao.get_job_by_id(&ctx, job_id).unwrap().unwrap();
         assert_eq!(job.status, InsightJobStatus::Cancelled.as_str());
 
-        // Cancelling again returns false (nothing to cancel)
+        // Cancelling again returns 0 (nothing to cancel)
-        let cancelled2 = dao
+        let cancelled2 = dao.cancel_active_jobs(&ctx, 1, "photos/test.jpg").unwrap();
-            .cancel_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+        assert_eq!(cancelled2, 0, "should return 0 when no running job");
-            .unwrap();
-        assert!(!cancelled2, "should return false when no running job");
     }
 
     #[test]
@@ -454,11 +521,11 @@ mod tests {
         let ctx = ctx();
 
         let job_id_1 = dao
-            .create_or_get_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
             .unwrap();
 
         let job_id_2 = dao
-            .create_or_get_active_job(&ctx, 2, "photos/test.jpg", InsightGenerationType::Standard)
+            .create_job(&ctx, 2, "photos/test.jpg", InsightGenerationType::Standard)
             .unwrap();
 
         assert_ne!(
@@ -485,7 +552,7 @@ mod tests {
         let ctx = ctx();
 
         let job_id = dao
-            .create_or_get_active_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
             .unwrap();
 
         // Find while running
@@ -500,4 +567,115 @@ mod tests {
         assert_eq!(job.status, InsightJobStatus::Completed.as_str());
         assert_eq!(job.result_insight_id, Some(99));
     }
+
+    #[test]
+    fn recover_orphaned_jobs() {
+        let mut dao = setup_dao();
+        let ctx = ctx();
+
+        // Create two running jobs
+        let job_id_1 = dao
+            .create_job(&ctx, 1, "photos/a.jpg", InsightGenerationType::Standard)
+            .unwrap();
+        let job_id_2 = dao
+            .create_job(&ctx, 1, "photos/b.jpg", InsightGenerationType::Agentic)
+            .unwrap();
+
+        // Complete one
+        dao.complete_job(&ctx, job_id_1, 1).unwrap();
+
+        // Recover should only affect the running job
+        let recovered = dao.recover_orphaned_jobs(&ctx).unwrap();
+        assert_eq!(recovered, 1, "should recover exactly 1 running job");
+
+        // job_id_1 is still completed
+        let job1 = dao.get_job_by_id(&ctx, job_id_1).unwrap().unwrap();
+        assert_eq!(job1.status, InsightJobStatus::Completed.as_str());
+
+        // job_id_2 is now failed with recovery message
+        let job2 = dao.get_job_by_id(&ctx, job_id_2).unwrap().unwrap();
+        assert_eq!(job2.status, InsightJobStatus::Failed.as_str());
+        assert_eq!(
+            job2.error_message.as_deref(),
+            Some("server crashed while running")
+        );
+
+        // Second recovery is a no-op
+        let recovered2 = dao.recover_orphaned_jobs(&ctx).unwrap();
+        assert_eq!(recovered2, 0, "no running jobs remain");
+    }
+
+    #[test]
+    fn complete_job_noop_when_cancelled() {
+        let mut dao = setup_dao();
+        let ctx = ctx();
+
+        let job_id = dao
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .unwrap();
+
+        dao.cancel_job(&ctx, job_id).unwrap();
+
+        // Late-completing task tries to mark as completed — should be a no-op
+        dao.complete_job(&ctx, job_id, 42).unwrap();
+
+        let job = dao.get_job_by_id(&ctx, job_id).unwrap().unwrap();
+        assert_eq!(
+            job.status,
+            InsightJobStatus::Cancelled.as_str(),
+            "cancelled status must not be overwritten by late complete"
+        );
+        assert_eq!(
+            job.result_insight_id, None,
+            "insight_id must stay None when complete is a no-op"
+        );
+    }
+
+    #[test]
+    fn fail_job_noop_when_cancelled() {
+        let mut dao = setup_dao();
+        let ctx = ctx();
+
+        let job_id = dao
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Agentic)
+            .unwrap();
+
+        dao.cancel_job(&ctx, job_id).unwrap();
+
+        // Late-failing task tries to mark as failed — should be a no-op
+        dao.fail_job(&ctx, job_id, "timeout after 120s").unwrap();
+
+        let job = dao.get_job_by_id(&ctx, job_id).unwrap().unwrap();
+        assert_eq!(
+            job.status,
+            InsightJobStatus::Cancelled.as_str(),
+            "cancelled status must not be overwritten by late fail"
+        );
+        assert_eq!(
+            job.error_message.as_deref(),
+            Some("cancelled by user"),
+            "error_message must reflect the cancel, not the late fail"
+        );
+    }
+
+    #[test]
+    fn cancel_job_by_id() {
+        let mut dao = setup_dao();
+        let ctx = ctx();
+
+        let job_id = dao
+            .create_job(&ctx, 1, "photos/test.jpg", InsightGenerationType::Standard)
+            .unwrap();
+
+        let cancelled = dao.cancel_job(&ctx, job_id).unwrap();
+        assert!(cancelled, "should cancel running job");
+
+        let job = dao.get_job_by_id(&ctx, job_id).unwrap().unwrap();
+        assert_eq!(job.status, InsightJobStatus::Cancelled.as_str());
+        assert!(job.completed_at.is_some());
+
+        // Cancelling again is a no-op
+        let cancelled2 = dao.cancel_job(&ctx, job_id).unwrap();
+        assert!(!cancelled2, "already cancelled job should return false");
+    }
 }

src/database/models.rs

@@ -38,7 +38,13 @@ impl InsightJobStatus {
             "completed" => Self::Completed,
             "failed" => Self::Failed,
             "cancelled" => Self::Cancelled,
-            _ => Self::Failed,
+            other => {
+                log::warn!(
+                    "Unknown InsightJobStatus value: {:?}, treating as failed",
+                    other
+                );
+                Self::Failed
+            }
         }
     }
 }
@@ -224,6 +230,13 @@ pub struct InsertPhotoInsight {
     /// inserted before the hash is available stay null and the
     /// reconciliation pass backfills them.
     pub content_hash: Option<String>,
+    pub num_ctx: Option<i32>,
+    pub temperature: Option<f32>,
+    pub top_p: Option<f32>,
+    pub top_k: Option<i32>,
+    pub min_p: Option<f32>,
+    pub system_prompt: Option<String>,
+    pub persona_id: Option<String>,
 }
 
 #[derive(Serialize, Queryable, Clone, Debug)]
@@ -243,6 +256,13 @@ pub struct PhotoInsight {
     pub backend: String,
     pub fewshot_source_ids: Option<String>,
     pub content_hash: Option<String>,
+    pub num_ctx: Option<i32>,
+    pub temperature: Option<f32>,
+    pub top_p: Option<f32>,
+    pub top_k: Option<i32>,
+    pub min_p: Option<f32>,
+    pub system_prompt: Option<String>,
+    pub persona_id: Option<String>,
 }
 
 // --- Libraries ---

src/database/schema.rs

@@ -216,6 +216,13 @@ diesel::table! {
         backend -> Text,
         fewshot_source_ids -> Nullable<Text>,
         content_hash -> Nullable<Text>,
+        num_ctx -> Nullable<Integer>,
+        temperature -> Nullable<Float>,
+        top_p -> Nullable<Float>,
+        top_k -> Nullable<Integer>,
+        min_p -> Nullable<Float>,
+        system_prompt -> Nullable<Text>,
+        persona_id -> Nullable<Text>,
     }
 }
 

src/main.rs

@@ -75,6 +75,22 @@ fn main() -> std::io::Result<()> {
 
     run_migrations(&mut connect()).expect("Failed to run migrations");
 
+    // Recover orphaned insight generation jobs from a previous crash.
+    {
+        use crate::database::{InsightGenerationJobDao, SqliteInsightGenerationJobDao};
+        let mut dao = SqliteInsightGenerationJobDao::new();
+        let ctx = opentelemetry::Context::new();
+        match dao.recover_orphaned_jobs(&ctx) {
+            Ok(n) if n > 0 => {
+                info!("Recovered {} orphaned insight generation jobs", n);
+            }
+            Ok(_) => {}
+            Err(e) => {
+                log::warn!("Failed to recover orphaned insight jobs: {:?}", e);
+            }
+        }
+    }
+
     // One-shot retirement of the pre-content-hash HLS layout. Idempotent
     // — a second boot finds nothing and reports zero deletions, so it's
     // safe to leave wired in until the module is removed in a later
@@ -309,6 +325,7 @@ fn main() -> std::io::Result<()> {
                 .service(ai::generate_insight_handler)
                 .service(ai::generate_agentic_insight_handler)
                 .service(ai::generation_status_handler)
+                .service(ai::cancel_generation_handler)
                 .service(ai::get_insight_handler)
                 .service(ai::delete_insight_handler)
                 .service(ai::get_all_insights_handler)

src/state.rs

@@ -19,6 +19,7 @@ use crate::video::actors::{
     PlaylistGenerator, PreviewClipGenerator, StreamActor, VideoPlaylistManager,
 };
 use actix::{Actor, Addr};
+use std::collections::HashMap;
 use std::env;
 use std::sync::{Arc, Mutex, RwLock};
 
@@ -88,6 +89,9 @@ pub struct AppState {
     pub clip_client: ClipClient,
     /// Tracks async insight generation jobs (spawned by generate endpoints).
     pub insight_job_dao: Arc<Mutex<Box<dyn InsightGenerationJobDao>>>,
+    /// In-memory map from job_id → tokio AbortHandle for running tasks.
+    /// Used to abort server-side tasks on cancel or regenerate.
+    pub insight_job_handles: Arc<Mutex<HashMap<i32, tokio::task::AbortHandle>>>,
 }
 
 impl AppState {
@@ -127,6 +131,7 @@ impl AppState {
         face_client: FaceClient,
         clip_client: ClipClient,
         insight_job_dao: Arc<Mutex<Box<dyn InsightGenerationJobDao>>>,
+        insight_job_handles: Arc<Mutex<HashMap<i32, tokio::task::AbortHandle>>>,
     ) -> Self {
         assert!(
             !libraries_vec.is_empty(),
@@ -169,6 +174,7 @@ impl AppState {
             face_client,
             clip_client,
             insight_job_dao,
+            insight_job_handles,
         }
     }
 
@@ -260,6 +266,8 @@ impl Default for AppState {
         // Initialize insight generation job DAO (async generation tracking)
         let insight_job_dao: Arc<Mutex<Box<dyn InsightGenerationJobDao>>> =
             Arc::new(Mutex::new(Box::new(SqliteInsightGenerationJobDao::new())));
+        let insight_job_handles: Arc<Mutex<HashMap<i32, tokio::task::AbortHandle>>> =
+            Arc::new(Mutex::new(HashMap::new()));
 
         // Load base path and ensure the primary library row reflects it.
         let base_path = env::var("BASE_PATH").expect("BASE_PATH was not set in the env");
@@ -328,6 +336,7 @@ impl Default for AppState {
             face_client,
             clip_client,
             insight_job_dao,
+            insight_job_handles,
         )
     }
 }
@@ -513,6 +522,7 @@ impl AppState {
             FaceClient::new(None), // disabled in test
             ClipClient::new(None), // disabled in test
             Arc::new(Mutex::new(Box::new(SqliteInsightGenerationJobDao::new()))), // placeholder for test
+            Arc::new(Mutex::new(HashMap::new())), // placeholder for test
         )
     }
 }