billing.rs

   1use anyhow::{Context as _, bail};
   2use axum::routing::put;
   3use axum::{
   4    Extension, Json, Router,
   5    extract::{self, Query},
   6    routing::{get, post},
   7};
   8use chrono::{DateTime, SecondsFormat, Utc};
   9use collections::{HashMap, HashSet};
  10use reqwest::StatusCode;
  11use sea_orm::ActiveValue;
  12use serde::{Deserialize, Serialize};
  13use serde_json::json;
  14use std::{str::FromStr, sync::Arc, time::Duration};
  15use stripe::{
  16    BillingPortalSession, CancellationDetailsReason, CreateBillingPortalSession,
  17    CreateBillingPortalSessionFlowData, CreateBillingPortalSessionFlowDataAfterCompletion,
  18    CreateBillingPortalSessionFlowDataAfterCompletionRedirect,
  19    CreateBillingPortalSessionFlowDataSubscriptionUpdateConfirm,
  20    CreateBillingPortalSessionFlowDataSubscriptionUpdateConfirmItems,
  21    CreateBillingPortalSessionFlowDataType, CustomerId, EventObject, EventType, ListEvents,
  22    PaymentMethod, Subscription, SubscriptionId, SubscriptionStatus,
  23};
  24use util::{ResultExt, maybe};
  25use zed_llm_client::LanguageModelProvider;
  26
  27use crate::api::events::SnowflakeRow;
  28use crate::db::billing_subscription::{
  29    StripeCancellationReason, StripeSubscriptionStatus, SubscriptionKind,
  30};
  31use crate::llm::AGENT_EXTENDED_TRIAL_FEATURE_FLAG;
  32use crate::llm::db::subscription_usage_meter::{self, CompletionMode};
  33use crate::rpc::{ResultExt as _, Server};
  34use crate::stripe_client::{
  35    StripeCancellationDetailsReason, StripeClient, StripeCustomerId, StripeSubscription,
  36    StripeSubscriptionId, UpdateCustomerParams,
  37};
  38use crate::{AppState, Error, Result};
  39use crate::{db::UserId, llm::db::LlmDatabase};
  40use crate::{
  41    db::{
  42        BillingSubscriptionId, CreateBillingCustomerParams, CreateBillingSubscriptionParams,
  43        CreateProcessedStripeEventParams, UpdateBillingCustomerParams,
  44        UpdateBillingPreferencesParams, UpdateBillingSubscriptionParams, billing_customer,
  45    },
  46    stripe_billing::StripeBilling,
  47};
  48
  49pub fn router() -> Router {
  50    Router::new()
  51        .route("/billing/preferences", put(update_billing_preferences))
  52        .route(
  53            "/billing/subscriptions",
  54            get(list_billing_subscriptions).post(create_billing_subscription),
  55        )
  56        .route(
  57            "/billing/subscriptions/manage",
  58            post(manage_billing_subscription),
  59        )
  60        .route(
  61            "/billing/subscriptions/sync",
  62            post(sync_billing_subscription),
  63        )
  64        .route("/billing/usage", get(get_current_usage))
  65}
  66
  67#[derive(Debug, Serialize)]
  68struct BillingPreferencesResponse {
  69    trial_started_at: Option<String>,
  70    max_monthly_llm_usage_spending_in_cents: i32,
  71    model_request_overages_enabled: bool,
  72    model_request_overages_spend_limit_in_cents: i32,
  73}
  74
  75#[derive(Debug, Deserialize)]
  76struct UpdateBillingPreferencesBody {
  77    github_user_id: i32,
  78    #[serde(default)]
  79    max_monthly_llm_usage_spending_in_cents: i32,
  80    #[serde(default)]
  81    model_request_overages_enabled: bool,
  82    #[serde(default)]
  83    model_request_overages_spend_limit_in_cents: i32,
  84}
  85
  86async fn update_billing_preferences(
  87    Extension(app): Extension<Arc<AppState>>,
  88    Extension(rpc_server): Extension<Arc<crate::rpc::Server>>,
  89    extract::Json(body): extract::Json<UpdateBillingPreferencesBody>,
  90) -> Result<Json<BillingPreferencesResponse>> {
  91    let user = app
  92        .db
  93        .get_user_by_github_user_id(body.github_user_id)
  94        .await?
  95        .context("user not found")?;
  96
  97    let billing_customer = app.db.get_billing_customer_by_user_id(user.id).await?;
  98
  99    let max_monthly_llm_usage_spending_in_cents =
 100        body.max_monthly_llm_usage_spending_in_cents.max(0);
 101    let model_request_overages_spend_limit_in_cents =
 102        body.model_request_overages_spend_limit_in_cents.max(0);
 103
 104    let billing_preferences =
 105        if let Some(_billing_preferences) = app.db.get_billing_preferences(user.id).await? {
 106            app.db
 107                .update_billing_preferences(
 108                    user.id,
 109                    &UpdateBillingPreferencesParams {
 110                        max_monthly_llm_usage_spending_in_cents: ActiveValue::set(
 111                            max_monthly_llm_usage_spending_in_cents,
 112                        ),
 113                        model_request_overages_enabled: ActiveValue::set(
 114                            body.model_request_overages_enabled,
 115                        ),
 116                        model_request_overages_spend_limit_in_cents: ActiveValue::set(
 117                            model_request_overages_spend_limit_in_cents,
 118                        ),
 119                    },
 120                )
 121                .await?
 122        } else {
 123            app.db
 124                .create_billing_preferences(
 125                    user.id,
 126                    &crate::db::CreateBillingPreferencesParams {
 127                        max_monthly_llm_usage_spending_in_cents,
 128                        model_request_overages_enabled: body.model_request_overages_enabled,
 129                        model_request_overages_spend_limit_in_cents,
 130                    },
 131                )
 132                .await?
 133        };
 134
 135    SnowflakeRow::new(
 136        "Billing Preferences Updated",
 137        Some(user.metrics_id),
 138        user.admin,
 139        None,
 140        json!({
 141            "user_id": user.id,
 142            "model_request_overages_enabled": billing_preferences.model_request_overages_enabled,
 143            "model_request_overages_spend_limit_in_cents": billing_preferences.model_request_overages_spend_limit_in_cents,
 144            "max_monthly_llm_usage_spending_in_cents": billing_preferences.max_monthly_llm_usage_spending_in_cents,
 145        }),
 146    )
 147    .write(&app.kinesis_client, &app.config.kinesis_stream)
 148    .await
 149    .log_err();
 150
 151    rpc_server.refresh_llm_tokens_for_user(user.id).await;
 152
 153    Ok(Json(BillingPreferencesResponse {
 154        trial_started_at: billing_customer
 155            .and_then(|billing_customer| billing_customer.trial_started_at)
 156            .map(|trial_started_at| {
 157                trial_started_at
 158                    .and_utc()
 159                    .to_rfc3339_opts(SecondsFormat::Millis, true)
 160            }),
 161        max_monthly_llm_usage_spending_in_cents: billing_preferences
 162            .max_monthly_llm_usage_spending_in_cents,
 163        model_request_overages_enabled: billing_preferences.model_request_overages_enabled,
 164        model_request_overages_spend_limit_in_cents: billing_preferences
 165            .model_request_overages_spend_limit_in_cents,
 166    }))
 167}
 168
 169#[derive(Debug, Deserialize)]
 170struct ListBillingSubscriptionsParams {
 171    github_user_id: i32,
 172}
 173
 174#[derive(Debug, Serialize)]
 175struct BillingSubscriptionJson {
 176    id: BillingSubscriptionId,
 177    name: String,
 178    status: StripeSubscriptionStatus,
 179    period: Option<BillingSubscriptionPeriodJson>,
 180    trial_end_at: Option<String>,
 181    cancel_at: Option<String>,
 182    /// Whether this subscription can be canceled.
 183    is_cancelable: bool,
 184}
 185
 186#[derive(Debug, Serialize)]
 187struct BillingSubscriptionPeriodJson {
 188    start_at: String,
 189    end_at: String,
 190}
 191
 192#[derive(Debug, Serialize)]
 193struct ListBillingSubscriptionsResponse {
 194    subscriptions: Vec<BillingSubscriptionJson>,
 195}
 196
 197async fn list_billing_subscriptions(
 198    Extension(app): Extension<Arc<AppState>>,
 199    Query(params): Query<ListBillingSubscriptionsParams>,
 200) -> Result<Json<ListBillingSubscriptionsResponse>> {
 201    let user = app
 202        .db
 203        .get_user_by_github_user_id(params.github_user_id)
 204        .await?
 205        .context("user not found")?;
 206
 207    let subscriptions = app.db.get_billing_subscriptions(user.id).await?;
 208
 209    Ok(Json(ListBillingSubscriptionsResponse {
 210        subscriptions: subscriptions
 211            .into_iter()
 212            .map(|subscription| BillingSubscriptionJson {
 213                id: subscription.id,
 214                name: match subscription.kind {
 215                    Some(SubscriptionKind::ZedPro) => "Zed Pro".to_string(),
 216                    Some(SubscriptionKind::ZedProTrial) => "Zed Pro (Trial)".to_string(),
 217                    Some(SubscriptionKind::ZedFree) => "Zed Free".to_string(),
 218                    None => "Zed LLM Usage".to_string(),
 219                },
 220                status: subscription.stripe_subscription_status,
 221                period: maybe!({
 222                    let start_at = subscription.current_period_start_at()?;
 223                    let end_at = subscription.current_period_end_at()?;
 224
 225                    Some(BillingSubscriptionPeriodJson {
 226                        start_at: start_at.to_rfc3339_opts(SecondsFormat::Millis, true),
 227                        end_at: end_at.to_rfc3339_opts(SecondsFormat::Millis, true),
 228                    })
 229                }),
 230                trial_end_at: if subscription.kind == Some(SubscriptionKind::ZedProTrial) {
 231                    maybe!({
 232                        let end_at = subscription.stripe_current_period_end?;
 233                        let end_at = DateTime::from_timestamp(end_at, 0)?;
 234
 235                        Some(end_at.to_rfc3339_opts(SecondsFormat::Millis, true))
 236                    })
 237                } else {
 238                    None
 239                },
 240                cancel_at: subscription.stripe_cancel_at.map(|cancel_at| {
 241                    cancel_at
 242                        .and_utc()
 243                        .to_rfc3339_opts(SecondsFormat::Millis, true)
 244                }),
 245                is_cancelable: subscription.kind != Some(SubscriptionKind::ZedFree)
 246                    && subscription.stripe_subscription_status.is_cancelable()
 247                    && subscription.stripe_cancel_at.is_none(),
 248            })
 249            .collect(),
 250    }))
 251}
 252
 253#[derive(Debug, PartialEq, Clone, Copy, Deserialize)]
 254#[serde(rename_all = "snake_case")]
 255enum ProductCode {
 256    ZedPro,
 257    ZedProTrial,
 258}
 259
 260#[derive(Debug, Deserialize)]
 261struct CreateBillingSubscriptionBody {
 262    github_user_id: i32,
 263    product: ProductCode,
 264}
 265
 266#[derive(Debug, Serialize)]
 267struct CreateBillingSubscriptionResponse {
 268    checkout_session_url: String,
 269}
 270
 271/// Initiates a Stripe Checkout session for creating a billing subscription.
 272async fn create_billing_subscription(
 273    Extension(app): Extension<Arc<AppState>>,
 274    extract::Json(body): extract::Json<CreateBillingSubscriptionBody>,
 275) -> Result<Json<CreateBillingSubscriptionResponse>> {
 276    let user = app
 277        .db
 278        .get_user_by_github_user_id(body.github_user_id)
 279        .await?
 280        .context("user not found")?;
 281
 282    let Some(stripe_billing) = app.stripe_billing.clone() else {
 283        log::error!("failed to retrieve Stripe billing object");
 284        Err(Error::http(
 285            StatusCode::NOT_IMPLEMENTED,
 286            "not supported".into(),
 287        ))?
 288    };
 289
 290    if let Some(existing_subscription) = app.db.get_active_billing_subscription(user.id).await? {
 291        let is_checkout_allowed = body.product == ProductCode::ZedProTrial
 292            && existing_subscription.kind == Some(SubscriptionKind::ZedFree);
 293
 294        if !is_checkout_allowed {
 295            return Err(Error::http(
 296                StatusCode::CONFLICT,
 297                "user already has an active subscription".into(),
 298            ));
 299        }
 300    }
 301
 302    let existing_billing_customer = app.db.get_billing_customer_by_user_id(user.id).await?;
 303    if let Some(existing_billing_customer) = &existing_billing_customer {
 304        if existing_billing_customer.has_overdue_invoices {
 305            return Err(Error::http(
 306                StatusCode::PAYMENT_REQUIRED,
 307                "user has overdue invoices".into(),
 308            ));
 309        }
 310    }
 311
 312    let customer_id = if let Some(existing_customer) = &existing_billing_customer {
 313        let customer_id = StripeCustomerId(existing_customer.stripe_customer_id.clone().into());
 314        if let Some(email) = user.email_address.as_deref() {
 315            stripe_billing
 316                .client()
 317                .update_customer(&customer_id, UpdateCustomerParams { email: Some(email) })
 318                .await
 319                // Update of email address is best-effort - continue checkout even if it fails
 320                .context("error updating stripe customer email address")
 321                .log_err();
 322        }
 323        customer_id
 324    } else {
 325        stripe_billing
 326            .find_or_create_customer_by_email(user.email_address.as_deref())
 327            .await?
 328    };
 329
 330    let success_url = format!(
 331        "{}/account?checkout_complete=1",
 332        app.config.zed_dot_dev_url()
 333    );
 334
 335    let checkout_session_url = match body.product {
 336        ProductCode::ZedPro => {
 337            stripe_billing
 338                .checkout_with_zed_pro(&customer_id, &user.github_login, &success_url)
 339                .await?
 340        }
 341        ProductCode::ZedProTrial => {
 342            if let Some(existing_billing_customer) = &existing_billing_customer {
 343                if existing_billing_customer.trial_started_at.is_some() {
 344                    return Err(Error::http(
 345                        StatusCode::FORBIDDEN,
 346                        "user already used free trial".into(),
 347                    ));
 348                }
 349            }
 350
 351            let feature_flags = app.db.get_user_flags(user.id).await?;
 352
 353            stripe_billing
 354                .checkout_with_zed_pro_trial(
 355                    &customer_id,
 356                    &user.github_login,
 357                    feature_flags,
 358                    &success_url,
 359                )
 360                .await?
 361        }
 362    };
 363
 364    Ok(Json(CreateBillingSubscriptionResponse {
 365        checkout_session_url,
 366    }))
 367}
 368
 369#[derive(Debug, PartialEq, Deserialize)]
 370#[serde(rename_all = "snake_case")]
 371enum ManageSubscriptionIntent {
 372    /// The user intends to manage their subscription.
 373    ///
 374    /// This will open the Stripe billing portal without putting the user in a specific flow.
 375    ManageSubscription,
 376    /// The user intends to update their payment method.
 377    UpdatePaymentMethod,
 378    /// The user intends to upgrade to Zed Pro.
 379    UpgradeToPro,
 380    /// The user intends to cancel their subscription.
 381    Cancel,
 382    /// The user intends to stop the cancellation of their subscription.
 383    StopCancellation,
 384}
 385
 386#[derive(Debug, Deserialize)]
 387struct ManageBillingSubscriptionBody {
 388    github_user_id: i32,
 389    intent: ManageSubscriptionIntent,
 390    /// The ID of the subscription to manage.
 391    subscription_id: BillingSubscriptionId,
 392    redirect_to: Option<String>,
 393}
 394
 395#[derive(Debug, Serialize)]
 396struct ManageBillingSubscriptionResponse {
 397    billing_portal_session_url: Option<String>,
 398}
 399
 400/// Initiates a Stripe customer portal session for managing a billing subscription.
 401async fn manage_billing_subscription(
 402    Extension(app): Extension<Arc<AppState>>,
 403    extract::Json(body): extract::Json<ManageBillingSubscriptionBody>,
 404) -> Result<Json<ManageBillingSubscriptionResponse>> {
 405    let user = app
 406        .db
 407        .get_user_by_github_user_id(body.github_user_id)
 408        .await?
 409        .context("user not found")?;
 410
 411    let Some(stripe_client) = app.real_stripe_client.clone() else {
 412        log::error!("failed to retrieve Stripe client");
 413        Err(Error::http(
 414            StatusCode::NOT_IMPLEMENTED,
 415            "not supported".into(),
 416        ))?
 417    };
 418
 419    let Some(stripe_billing) = app.stripe_billing.clone() else {
 420        log::error!("failed to retrieve Stripe billing object");
 421        Err(Error::http(
 422            StatusCode::NOT_IMPLEMENTED,
 423            "not supported".into(),
 424        ))?
 425    };
 426
 427    let customer = app
 428        .db
 429        .get_billing_customer_by_user_id(user.id)
 430        .await?
 431        .context("billing customer not found")?;
 432    let customer_id = CustomerId::from_str(&customer.stripe_customer_id)
 433        .context("failed to parse customer ID")?;
 434
 435    let subscription = app
 436        .db
 437        .get_billing_subscription_by_id(body.subscription_id)
 438        .await?
 439        .context("subscription not found")?;
 440    let subscription_id = SubscriptionId::from_str(&subscription.stripe_subscription_id)
 441        .context("failed to parse subscription ID")?;
 442
 443    if body.intent == ManageSubscriptionIntent::StopCancellation {
 444        let updated_stripe_subscription = Subscription::update(
 445            &stripe_client,
 446            &subscription_id,
 447            stripe::UpdateSubscription {
 448                cancel_at_period_end: Some(false),
 449                ..Default::default()
 450            },
 451        )
 452        .await?;
 453
 454        app.db
 455            .update_billing_subscription(
 456                subscription.id,
 457                &UpdateBillingSubscriptionParams {
 458                    stripe_cancel_at: ActiveValue::set(
 459                        updated_stripe_subscription
 460                            .cancel_at
 461                            .and_then(|cancel_at| DateTime::from_timestamp(cancel_at, 0))
 462                            .map(|time| time.naive_utc()),
 463                    ),
 464                    ..Default::default()
 465                },
 466            )
 467            .await?;
 468
 469        return Ok(Json(ManageBillingSubscriptionResponse {
 470            billing_portal_session_url: None,
 471        }));
 472    }
 473
 474    let flow = match body.intent {
 475        ManageSubscriptionIntent::ManageSubscription => None,
 476        ManageSubscriptionIntent::UpgradeToPro => {
 477            let zed_pro_price_id: stripe::PriceId =
 478                stripe_billing.zed_pro_price_id().await?.try_into()?;
 479            let zed_free_price_id: stripe::PriceId =
 480                stripe_billing.zed_free_price_id().await?.try_into()?;
 481
 482            let stripe_subscription =
 483                Subscription::retrieve(&stripe_client, &subscription_id, &[]).await?;
 484
 485            let is_on_zed_pro_trial = stripe_subscription.status == SubscriptionStatus::Trialing
 486                && stripe_subscription.items.data.iter().any(|item| {
 487                    item.price
 488                        .as_ref()
 489                        .map_or(false, |price| price.id == zed_pro_price_id)
 490                });
 491            if is_on_zed_pro_trial {
 492                let payment_methods = PaymentMethod::list(
 493                    &stripe_client,
 494                    &stripe::ListPaymentMethods {
 495                        customer: Some(stripe_subscription.customer.id()),
 496                        ..Default::default()
 497                    },
 498                )
 499                .await?;
 500
 501                let has_payment_method = !payment_methods.data.is_empty();
 502                if !has_payment_method {
 503                    return Err(Error::http(
 504                        StatusCode::BAD_REQUEST,
 505                        "missing payment method".into(),
 506                    ));
 507                }
 508
 509                // If the user is already on a Zed Pro trial and wants to upgrade to Pro, we just need to end their trial early.
 510                Subscription::update(
 511                    &stripe_client,
 512                    &stripe_subscription.id,
 513                    stripe::UpdateSubscription {
 514                        trial_end: Some(stripe::Scheduled::now()),
 515                        ..Default::default()
 516                    },
 517                )
 518                .await?;
 519
 520                return Ok(Json(ManageBillingSubscriptionResponse {
 521                    billing_portal_session_url: None,
 522                }));
 523            }
 524
 525            let subscription_item_to_update = stripe_subscription
 526                .items
 527                .data
 528                .iter()
 529                .find_map(|item| {
 530                    let price = item.price.as_ref()?;
 531
 532                    if price.id == zed_free_price_id {
 533                        Some(item.id.clone())
 534                    } else {
 535                        None
 536                    }
 537                })
 538                .context("No subscription item to update")?;
 539
 540            Some(CreateBillingPortalSessionFlowData {
 541                type_: CreateBillingPortalSessionFlowDataType::SubscriptionUpdateConfirm,
 542                subscription_update_confirm: Some(
 543                    CreateBillingPortalSessionFlowDataSubscriptionUpdateConfirm {
 544                        subscription: subscription.stripe_subscription_id,
 545                        items: vec![
 546                            CreateBillingPortalSessionFlowDataSubscriptionUpdateConfirmItems {
 547                                id: subscription_item_to_update.to_string(),
 548                                price: Some(zed_pro_price_id.to_string()),
 549                                quantity: Some(1),
 550                            },
 551                        ],
 552                        discounts: None,
 553                    },
 554                ),
 555                ..Default::default()
 556            })
 557        }
 558        ManageSubscriptionIntent::UpdatePaymentMethod => Some(CreateBillingPortalSessionFlowData {
 559            type_: CreateBillingPortalSessionFlowDataType::PaymentMethodUpdate,
 560            after_completion: Some(CreateBillingPortalSessionFlowDataAfterCompletion {
 561                type_: stripe::CreateBillingPortalSessionFlowDataAfterCompletionType::Redirect,
 562                redirect: Some(CreateBillingPortalSessionFlowDataAfterCompletionRedirect {
 563                    return_url: format!(
 564                        "{}{path}",
 565                        app.config.zed_dot_dev_url(),
 566                        path = body.redirect_to.unwrap_or_else(|| "/account".to_string())
 567                    ),
 568                }),
 569                ..Default::default()
 570            }),
 571            ..Default::default()
 572        }),
 573        ManageSubscriptionIntent::Cancel => {
 574            if subscription.kind == Some(SubscriptionKind::ZedFree) {
 575                return Err(Error::http(
 576                    StatusCode::BAD_REQUEST,
 577                    "free subscription cannot be canceled".into(),
 578                ));
 579            }
 580
 581            Some(CreateBillingPortalSessionFlowData {
 582                type_: CreateBillingPortalSessionFlowDataType::SubscriptionCancel,
 583                after_completion: Some(CreateBillingPortalSessionFlowDataAfterCompletion {
 584                    type_: stripe::CreateBillingPortalSessionFlowDataAfterCompletionType::Redirect,
 585                    redirect: Some(CreateBillingPortalSessionFlowDataAfterCompletionRedirect {
 586                        return_url: format!("{}/account", app.config.zed_dot_dev_url()),
 587                    }),
 588                    ..Default::default()
 589                }),
 590                subscription_cancel: Some(
 591                    stripe::CreateBillingPortalSessionFlowDataSubscriptionCancel {
 592                        subscription: subscription.stripe_subscription_id,
 593                        retention: None,
 594                    },
 595                ),
 596                ..Default::default()
 597            })
 598        }
 599        ManageSubscriptionIntent::StopCancellation => unreachable!(),
 600    };
 601
 602    let mut params = CreateBillingPortalSession::new(customer_id);
 603    params.flow_data = flow;
 604    let return_url = format!("{}/account", app.config.zed_dot_dev_url());
 605    params.return_url = Some(&return_url);
 606
 607    let session = BillingPortalSession::create(&stripe_client, params).await?;
 608
 609    Ok(Json(ManageBillingSubscriptionResponse {
 610        billing_portal_session_url: Some(session.url),
 611    }))
 612}
 613
 614#[derive(Debug, Deserialize)]
 615struct SyncBillingSubscriptionBody {
 616    github_user_id: i32,
 617}
 618
 619#[derive(Debug, Serialize)]
 620struct SyncBillingSubscriptionResponse {
 621    stripe_customer_id: String,
 622}
 623
 624async fn sync_billing_subscription(
 625    Extension(app): Extension<Arc<AppState>>,
 626    extract::Json(body): extract::Json<SyncBillingSubscriptionBody>,
 627) -> Result<Json<SyncBillingSubscriptionResponse>> {
 628    let Some(stripe_client) = app.stripe_client.clone() else {
 629        log::error!("failed to retrieve Stripe client");
 630        Err(Error::http(
 631            StatusCode::NOT_IMPLEMENTED,
 632            "not supported".into(),
 633        ))?
 634    };
 635
 636    let user = app
 637        .db
 638        .get_user_by_github_user_id(body.github_user_id)
 639        .await?
 640        .context("user not found")?;
 641
 642    let billing_customer = app
 643        .db
 644        .get_billing_customer_by_user_id(user.id)
 645        .await?
 646        .context("billing customer not found")?;
 647    let stripe_customer_id = StripeCustomerId(billing_customer.stripe_customer_id.clone().into());
 648
 649    let subscriptions = stripe_client
 650        .list_subscriptions_for_customer(&stripe_customer_id)
 651        .await?;
 652
 653    for subscription in subscriptions {
 654        let subscription_id = subscription.id.clone();
 655
 656        sync_subscription(&app, &stripe_client, subscription)
 657            .await
 658            .with_context(|| {
 659                format!(
 660                    "failed to sync subscription {subscription_id} for user {}",
 661                    user.id,
 662                )
 663            })?;
 664    }
 665
 666    Ok(Json(SyncBillingSubscriptionResponse {
 667        stripe_customer_id: billing_customer.stripe_customer_id.clone(),
 668    }))
 669}
 670
 671/// The amount of time we wait in between each poll of Stripe events.
 672///
 673/// This value should strike a balance between:
 674///   1. Being short enough that we update quickly when something in Stripe changes
 675///   2. Being long enough that we don't eat into our rate limits.
 676///
 677/// As a point of reference, the Sequin folks say they have this at **500ms**:
 678///
 679/// > We poll the Stripe /events endpoint every 500ms per account
 680/// >
 681/// > — https://blog.sequinstream.com/events-not-webhooks/
 682const POLL_EVENTS_INTERVAL: Duration = Duration::from_secs(5);
 683
 684/// The maximum number of events to return per page.
 685///
 686/// We set this to 100 (the max) so we have to make fewer requests to Stripe.
 687///
 688/// > Limit can range between 1 and 100, and the default is 10.
 689const EVENTS_LIMIT_PER_PAGE: u64 = 100;
 690
 691/// The number of pages consisting entirely of already-processed events that we
 692/// will see before we stop retrieving events.
 693///
 694/// This is used to prevent over-fetching the Stripe events API for events we've
 695/// already seen and processed.
 696const NUMBER_OF_ALREADY_PROCESSED_PAGES_BEFORE_WE_STOP: usize = 4;
 697
 698/// Polls the Stripe events API periodically to reconcile the records in our
 699/// database with the data in Stripe.
 700pub fn poll_stripe_events_periodically(app: Arc<AppState>, rpc_server: Arc<Server>) {
 701    let Some(real_stripe_client) = app.real_stripe_client.clone() else {
 702        log::warn!("failed to retrieve Stripe client");
 703        return;
 704    };
 705    let Some(stripe_client) = app.stripe_client.clone() else {
 706        log::warn!("failed to retrieve Stripe client");
 707        return;
 708    };
 709
 710    let executor = app.executor.clone();
 711    executor.spawn_detached({
 712        let executor = executor.clone();
 713        async move {
 714            loop {
 715                poll_stripe_events(&app, &rpc_server, &stripe_client, &real_stripe_client)
 716                    .await
 717                    .log_err();
 718
 719                executor.sleep(POLL_EVENTS_INTERVAL).await;
 720            }
 721        }
 722    });
 723}
 724
 725async fn poll_stripe_events(
 726    app: &Arc<AppState>,
 727    rpc_server: &Arc<Server>,
 728    stripe_client: &Arc<dyn StripeClient>,
 729    real_stripe_client: &stripe::Client,
 730) -> anyhow::Result<()> {
 731    fn event_type_to_string(event_type: EventType) -> String {
 732        // Calling `to_string` on `stripe::EventType` members gives us a quoted string,
 733        // so we need to unquote it.
 734        event_type.to_string().trim_matches('"').to_string()
 735    }
 736
 737    let event_types = [
 738        EventType::CustomerCreated,
 739        EventType::CustomerUpdated,
 740        EventType::CustomerSubscriptionCreated,
 741        EventType::CustomerSubscriptionUpdated,
 742        EventType::CustomerSubscriptionPaused,
 743        EventType::CustomerSubscriptionResumed,
 744        EventType::CustomerSubscriptionDeleted,
 745    ]
 746    .into_iter()
 747    .map(event_type_to_string)
 748    .collect::<Vec<_>>();
 749
 750    let mut pages_of_already_processed_events = 0;
 751    let mut unprocessed_events = Vec::new();
 752
 753    log::info!(
 754        "Stripe events: starting retrieval for {}",
 755        event_types.join(", ")
 756    );
 757    let mut params = ListEvents::new();
 758    params.types = Some(event_types.clone());
 759    params.limit = Some(EVENTS_LIMIT_PER_PAGE);
 760
 761    let mut event_pages = stripe::Event::list(&real_stripe_client, &params)
 762        .await?
 763        .paginate(params);
 764
 765    loop {
 766        let processed_event_ids = {
 767            let event_ids = event_pages
 768                .page
 769                .data
 770                .iter()
 771                .map(|event| event.id.as_str())
 772                .collect::<Vec<_>>();
 773            app.db
 774                .get_processed_stripe_events_by_event_ids(&event_ids)
 775                .await?
 776                .into_iter()
 777                .map(|event| event.stripe_event_id)
 778                .collect::<Vec<_>>()
 779        };
 780
 781        let mut processed_events_in_page = 0;
 782        let events_in_page = event_pages.page.data.len();
 783        for event in &event_pages.page.data {
 784            if processed_event_ids.contains(&event.id.to_string()) {
 785                processed_events_in_page += 1;
 786                log::debug!("Stripe events: already processed '{}', skipping", event.id);
 787            } else {
 788                unprocessed_events.push(event.clone());
 789            }
 790        }
 791
 792        if processed_events_in_page == events_in_page {
 793            pages_of_already_processed_events += 1;
 794        }
 795
 796        if event_pages.page.has_more {
 797            if pages_of_already_processed_events >= NUMBER_OF_ALREADY_PROCESSED_PAGES_BEFORE_WE_STOP
 798            {
 799                log::info!(
 800                    "Stripe events: stopping, saw {pages_of_already_processed_events} pages of already-processed events"
 801                );
 802                break;
 803            } else {
 804                log::info!("Stripe events: retrieving next page");
 805                event_pages = event_pages.next(&real_stripe_client).await?;
 806            }
 807        } else {
 808            break;
 809        }
 810    }
 811
 812    log::info!("Stripe events: unprocessed {}", unprocessed_events.len());
 813
 814    // Sort all of the unprocessed events in ascending order, so we can handle them in the order they occurred.
 815    unprocessed_events.sort_by(|a, b| a.created.cmp(&b.created).then_with(|| a.id.cmp(&b.id)));
 816
 817    for event in unprocessed_events {
 818        let event_id = event.id.clone();
 819        let processed_event_params = CreateProcessedStripeEventParams {
 820            stripe_event_id: event.id.to_string(),
 821            stripe_event_type: event_type_to_string(event.type_),
 822            stripe_event_created_timestamp: event.created,
 823        };
 824
 825        // If the event has happened too far in the past, we don't want to
 826        // process it and risk overwriting other more-recent updates.
 827        //
 828        // 1 day was chosen arbitrarily. This could be made longer or shorter.
 829        let one_day = Duration::from_secs(24 * 60 * 60);
 830        let a_day_ago = Utc::now() - one_day;
 831        if a_day_ago.timestamp() > event.created {
 832            log::info!(
 833                "Stripe events: event '{}' is more than {one_day:?} old, marking as processed",
 834                event_id
 835            );
 836            app.db
 837                .create_processed_stripe_event(&processed_event_params)
 838                .await?;
 839
 840            continue;
 841        }
 842
 843        let process_result = match event.type_ {
 844            EventType::CustomerCreated | EventType::CustomerUpdated => {
 845                handle_customer_event(app, real_stripe_client, event).await
 846            }
 847            EventType::CustomerSubscriptionCreated
 848            | EventType::CustomerSubscriptionUpdated
 849            | EventType::CustomerSubscriptionPaused
 850            | EventType::CustomerSubscriptionResumed
 851            | EventType::CustomerSubscriptionDeleted => {
 852                handle_customer_subscription_event(app, rpc_server, stripe_client, event).await
 853            }
 854            _ => Ok(()),
 855        };
 856
 857        if let Some(()) = process_result
 858            .with_context(|| format!("failed to process event {event_id} successfully"))
 859            .log_err()
 860        {
 861            app.db
 862                .create_processed_stripe_event(&processed_event_params)
 863                .await?;
 864        }
 865    }
 866
 867    Ok(())
 868}
 869
 870async fn handle_customer_event(
 871    app: &Arc<AppState>,
 872    _stripe_client: &stripe::Client,
 873    event: stripe::Event,
 874) -> anyhow::Result<()> {
 875    let EventObject::Customer(customer) = event.data.object else {
 876        bail!("unexpected event payload for {}", event.id);
 877    };
 878
 879    log::info!("handling Stripe {} event: {}", event.type_, event.id);
 880
 881    let Some(email) = customer.email else {
 882        log::info!("Stripe customer has no email: skipping");
 883        return Ok(());
 884    };
 885
 886    let Some(user) = app.db.get_user_by_email(&email).await? else {
 887        log::info!("no user found for email: skipping");
 888        return Ok(());
 889    };
 890
 891    if let Some(existing_customer) = app
 892        .db
 893        .get_billing_customer_by_stripe_customer_id(&customer.id)
 894        .await?
 895    {
 896        app.db
 897            .update_billing_customer(
 898                existing_customer.id,
 899                &UpdateBillingCustomerParams {
 900                    // For now we just leave the information as-is, as it is not
 901                    // likely to change.
 902                    ..Default::default()
 903                },
 904            )
 905            .await?;
 906    } else {
 907        app.db
 908            .create_billing_customer(&CreateBillingCustomerParams {
 909                user_id: user.id,
 910                stripe_customer_id: customer.id.to_string(),
 911            })
 912            .await?;
 913    }
 914
 915    Ok(())
 916}
 917
 918async fn sync_subscription(
 919    app: &Arc<AppState>,
 920    stripe_client: &Arc<dyn StripeClient>,
 921    subscription: StripeSubscription,
 922) -> anyhow::Result<billing_customer::Model> {
 923    let subscription_kind = if let Some(stripe_billing) = &app.stripe_billing {
 924        stripe_billing
 925            .determine_subscription_kind(&subscription)
 926            .await
 927    } else {
 928        None
 929    };
 930
 931    let billing_customer =
 932        find_or_create_billing_customer(app, stripe_client.as_ref(), &subscription.customer)
 933            .await?
 934            .context("billing customer not found")?;
 935
 936    if let Some(SubscriptionKind::ZedProTrial) = subscription_kind {
 937        if subscription.status == SubscriptionStatus::Trialing {
 938            let current_period_start =
 939                DateTime::from_timestamp(subscription.current_period_start, 0)
 940                    .context("No trial subscription period start")?;
 941
 942            app.db
 943                .update_billing_customer(
 944                    billing_customer.id,
 945                    &UpdateBillingCustomerParams {
 946                        trial_started_at: ActiveValue::set(Some(current_period_start.naive_utc())),
 947                        ..Default::default()
 948                    },
 949                )
 950                .await?;
 951        }
 952    }
 953
 954    let was_canceled_due_to_payment_failure = subscription.status == SubscriptionStatus::Canceled
 955        && subscription
 956            .cancellation_details
 957            .as_ref()
 958            .and_then(|details| details.reason)
 959            .map_or(false, |reason| {
 960                reason == StripeCancellationDetailsReason::PaymentFailed
 961            });
 962
 963    if was_canceled_due_to_payment_failure {
 964        app.db
 965            .update_billing_customer(
 966                billing_customer.id,
 967                &UpdateBillingCustomerParams {
 968                    has_overdue_invoices: ActiveValue::set(true),
 969                    ..Default::default()
 970                },
 971            )
 972            .await?;
 973    }
 974
 975    if let Some(existing_subscription) = app
 976        .db
 977        .get_billing_subscription_by_stripe_subscription_id(subscription.id.0.as_ref())
 978        .await?
 979    {
 980        app.db
 981            .update_billing_subscription(
 982                existing_subscription.id,
 983                &UpdateBillingSubscriptionParams {
 984                    billing_customer_id: ActiveValue::set(billing_customer.id),
 985                    kind: ActiveValue::set(subscription_kind),
 986                    stripe_subscription_id: ActiveValue::set(subscription.id.to_string()),
 987                    stripe_subscription_status: ActiveValue::set(subscription.status.into()),
 988                    stripe_cancel_at: ActiveValue::set(
 989                        subscription
 990                            .cancel_at
 991                            .and_then(|cancel_at| DateTime::from_timestamp(cancel_at, 0))
 992                            .map(|time| time.naive_utc()),
 993                    ),
 994                    stripe_cancellation_reason: ActiveValue::set(
 995                        subscription
 996                            .cancellation_details
 997                            .and_then(|details| details.reason)
 998                            .map(|reason| reason.into()),
 999                    ),
1000                    stripe_current_period_start: ActiveValue::set(Some(
1001                        subscription.current_period_start,
1002                    )),
1003                    stripe_current_period_end: ActiveValue::set(Some(
1004                        subscription.current_period_end,
1005                    )),
1006                },
1007            )
1008            .await?;
1009    } else {
1010        if let Some(existing_subscription) = app
1011            .db
1012            .get_active_billing_subscription(billing_customer.user_id)
1013            .await?
1014        {
1015            if existing_subscription.kind == Some(SubscriptionKind::ZedFree)
1016                && subscription_kind == Some(SubscriptionKind::ZedProTrial)
1017            {
1018                let stripe_subscription_id = StripeSubscriptionId(
1019                    existing_subscription.stripe_subscription_id.clone().into(),
1020                );
1021
1022                stripe_client
1023                    .cancel_subscription(&stripe_subscription_id)
1024                    .await?;
1025            } else {
1026                // If the user already has an active billing subscription, ignore the
1027                // event and return an `Ok` to signal that it was processed
1028                // successfully.
1029                //
1030                // There is the possibility that this could cause us to not create a
1031                // subscription in the following scenario:
1032                //
1033                //   1. User has an active subscription A
1034                //   2. User cancels subscription A
1035                //   3. User creates a new subscription B
1036                //   4. We process the new subscription B before the cancellation of subscription A
1037                //   5. User ends up with no subscriptions
1038                //
1039                // In theory this situation shouldn't arise as we try to process the events in the order they occur.
1040
1041                log::info!(
1042                    "user {user_id} already has an active subscription, skipping creation of subscription {subscription_id}",
1043                    user_id = billing_customer.user_id,
1044                    subscription_id = subscription.id
1045                );
1046                return Ok(billing_customer);
1047            }
1048        }
1049
1050        app.db
1051            .create_billing_subscription(&CreateBillingSubscriptionParams {
1052                billing_customer_id: billing_customer.id,
1053                kind: subscription_kind,
1054                stripe_subscription_id: subscription.id.to_string(),
1055                stripe_subscription_status: subscription.status.into(),
1056                stripe_cancellation_reason: subscription
1057                    .cancellation_details
1058                    .and_then(|details| details.reason)
1059                    .map(|reason| reason.into()),
1060                stripe_current_period_start: Some(subscription.current_period_start),
1061                stripe_current_period_end: Some(subscription.current_period_end),
1062            })
1063            .await?;
1064    }
1065
1066    if let Some(stripe_billing) = app.stripe_billing.as_ref() {
1067        if subscription.status == SubscriptionStatus::Canceled
1068            || subscription.status == SubscriptionStatus::Paused
1069        {
1070            let already_has_active_billing_subscription = app
1071                .db
1072                .has_active_billing_subscription(billing_customer.user_id)
1073                .await?;
1074            if !already_has_active_billing_subscription {
1075                let stripe_customer_id =
1076                    StripeCustomerId(billing_customer.stripe_customer_id.clone().into());
1077
1078                stripe_billing
1079                    .subscribe_to_zed_free(stripe_customer_id)
1080                    .await?;
1081            }
1082        }
1083    }
1084
1085    Ok(billing_customer)
1086}
1087
1088async fn handle_customer_subscription_event(
1089    app: &Arc<AppState>,
1090    rpc_server: &Arc<Server>,
1091    stripe_client: &Arc<dyn StripeClient>,
1092    event: stripe::Event,
1093) -> anyhow::Result<()> {
1094    let EventObject::Subscription(subscription) = event.data.object else {
1095        bail!("unexpected event payload for {}", event.id);
1096    };
1097
1098    log::info!("handling Stripe {} event: {}", event.type_, event.id);
1099
1100    let billing_customer = sync_subscription(app, stripe_client, subscription.into()).await?;
1101
1102    // When the user's subscription changes, push down any changes to their plan.
1103    rpc_server
1104        .update_plan_for_user(billing_customer.user_id)
1105        .await
1106        .trace_err();
1107
1108    // When the user's subscription changes, we want to refresh their LLM tokens
1109    // to either grant/revoke access.
1110    rpc_server
1111        .refresh_llm_tokens_for_user(billing_customer.user_id)
1112        .await;
1113
1114    Ok(())
1115}
1116
1117#[derive(Debug, Deserialize)]
1118struct GetCurrentUsageParams {
1119    github_user_id: i32,
1120}
1121
1122#[derive(Debug, Serialize)]
1123struct UsageCounts {
1124    pub used: i32,
1125    pub limit: Option<i32>,
1126    pub remaining: Option<i32>,
1127}
1128
1129#[derive(Debug, Serialize)]
1130struct ModelRequestUsage {
1131    pub model: String,
1132    pub mode: CompletionMode,
1133    pub requests: i32,
1134}
1135
1136#[derive(Debug, Serialize)]
1137struct CurrentUsage {
1138    pub model_requests: UsageCounts,
1139    pub model_request_usage: Vec<ModelRequestUsage>,
1140    pub edit_predictions: UsageCounts,
1141}
1142
1143#[derive(Debug, Default, Serialize)]
1144struct GetCurrentUsageResponse {
1145    pub plan: String,
1146    pub current_usage: Option<CurrentUsage>,
1147}
1148
1149async fn get_current_usage(
1150    Extension(app): Extension<Arc<AppState>>,
1151    Query(params): Query<GetCurrentUsageParams>,
1152) -> Result<Json<GetCurrentUsageResponse>> {
1153    let user = app
1154        .db
1155        .get_user_by_github_user_id(params.github_user_id)
1156        .await?
1157        .context("user not found")?;
1158
1159    let feature_flags = app.db.get_user_flags(user.id).await?;
1160    let has_extended_trial = feature_flags
1161        .iter()
1162        .any(|flag| flag == AGENT_EXTENDED_TRIAL_FEATURE_FLAG);
1163
1164    let Some(llm_db) = app.llm_db.clone() else {
1165        return Err(Error::http(
1166            StatusCode::NOT_IMPLEMENTED,
1167            "LLM database not available".into(),
1168        ));
1169    };
1170
1171    let Some(subscription) = app.db.get_active_billing_subscription(user.id).await? else {
1172        return Ok(Json(GetCurrentUsageResponse::default()));
1173    };
1174
1175    let subscription_period = maybe!({
1176        let period_start_at = subscription.current_period_start_at()?;
1177        let period_end_at = subscription.current_period_end_at()?;
1178
1179        Some((period_start_at, period_end_at))
1180    });
1181
1182    let Some((period_start_at, period_end_at)) = subscription_period else {
1183        return Ok(Json(GetCurrentUsageResponse::default()));
1184    };
1185
1186    let usage = llm_db
1187        .get_subscription_usage_for_period(user.id, period_start_at, period_end_at)
1188        .await?;
1189
1190    let plan = subscription
1191        .kind
1192        .map(Into::into)
1193        .unwrap_or(zed_llm_client::Plan::ZedFree);
1194
1195    let model_requests_limit = match plan.model_requests_limit() {
1196        zed_llm_client::UsageLimit::Limited(limit) => {
1197            let limit = if plan == zed_llm_client::Plan::ZedProTrial && has_extended_trial {
1198                1_000
1199            } else {
1200                limit
1201            };
1202
1203            Some(limit)
1204        }
1205        zed_llm_client::UsageLimit::Unlimited => None,
1206    };
1207
1208    let edit_predictions_limit = match plan.edit_predictions_limit() {
1209        zed_llm_client::UsageLimit::Limited(limit) => Some(limit),
1210        zed_llm_client::UsageLimit::Unlimited => None,
1211    };
1212
1213    let Some(usage) = usage else {
1214        return Ok(Json(GetCurrentUsageResponse {
1215            plan: plan.as_str().to_string(),
1216            current_usage: Some(CurrentUsage {
1217                model_requests: UsageCounts {
1218                    used: 0,
1219                    limit: model_requests_limit,
1220                    remaining: model_requests_limit,
1221                },
1222                model_request_usage: Vec::new(),
1223                edit_predictions: UsageCounts {
1224                    used: 0,
1225                    limit: edit_predictions_limit,
1226                    remaining: edit_predictions_limit,
1227                },
1228            }),
1229        }));
1230    };
1231
1232    let subscription_usage_meters = llm_db
1233        .get_current_subscription_usage_meters_for_user(user.id, Utc::now())
1234        .await?;
1235
1236    let model_request_usage = subscription_usage_meters
1237        .into_iter()
1238        .filter_map(|(usage_meter, _usage)| {
1239            let model = llm_db.model_by_id(usage_meter.model_id).ok()?;
1240
1241            Some(ModelRequestUsage {
1242                model: model.name.clone(),
1243                mode: usage_meter.mode,
1244                requests: usage_meter.requests,
1245            })
1246        })
1247        .collect::<Vec<_>>();
1248
1249    Ok(Json(GetCurrentUsageResponse {
1250        plan: plan.as_str().to_string(),
1251        current_usage: Some(CurrentUsage {
1252            model_requests: UsageCounts {
1253                used: usage.model_requests,
1254                limit: model_requests_limit,
1255                remaining: model_requests_limit.map(|limit| (limit - usage.model_requests).max(0)),
1256            },
1257            model_request_usage,
1258            edit_predictions: UsageCounts {
1259                used: usage.edit_predictions,
1260                limit: edit_predictions_limit,
1261                remaining: edit_predictions_limit
1262                    .map(|limit| (limit - usage.edit_predictions).max(0)),
1263            },
1264        }),
1265    }))
1266}
1267
1268impl From<SubscriptionStatus> for StripeSubscriptionStatus {
1269    fn from(value: SubscriptionStatus) -> Self {
1270        match value {
1271            SubscriptionStatus::Incomplete => Self::Incomplete,
1272            SubscriptionStatus::IncompleteExpired => Self::IncompleteExpired,
1273            SubscriptionStatus::Trialing => Self::Trialing,
1274            SubscriptionStatus::Active => Self::Active,
1275            SubscriptionStatus::PastDue => Self::PastDue,
1276            SubscriptionStatus::Canceled => Self::Canceled,
1277            SubscriptionStatus::Unpaid => Self::Unpaid,
1278            SubscriptionStatus::Paused => Self::Paused,
1279        }
1280    }
1281}
1282
1283impl From<CancellationDetailsReason> for StripeCancellationReason {
1284    fn from(value: CancellationDetailsReason) -> Self {
1285        match value {
1286            CancellationDetailsReason::CancellationRequested => Self::CancellationRequested,
1287            CancellationDetailsReason::PaymentDisputed => Self::PaymentDisputed,
1288            CancellationDetailsReason::PaymentFailed => Self::PaymentFailed,
1289        }
1290    }
1291}
1292
1293/// Finds or creates a billing customer using the provided customer.
1294pub async fn find_or_create_billing_customer(
1295    app: &Arc<AppState>,
1296    stripe_client: &dyn StripeClient,
1297    customer_id: &StripeCustomerId,
1298) -> anyhow::Result<Option<billing_customer::Model>> {
1299    // If we already have a billing customer record associated with the Stripe customer,
1300    // there's nothing more we need to do.
1301    if let Some(billing_customer) = app
1302        .db
1303        .get_billing_customer_by_stripe_customer_id(customer_id.0.as_ref())
1304        .await?
1305    {
1306        return Ok(Some(billing_customer));
1307    }
1308
1309    let customer = stripe_client.get_customer(customer_id).await?;
1310
1311    let Some(email) = customer.email else {
1312        return Ok(None);
1313    };
1314
1315    let Some(user) = app.db.get_user_by_email(&email).await? else {
1316        return Ok(None);
1317    };
1318
1319    let billing_customer = app
1320        .db
1321        .create_billing_customer(&CreateBillingCustomerParams {
1322            user_id: user.id,
1323            stripe_customer_id: customer.id.to_string(),
1324        })
1325        .await?;
1326
1327    Ok(Some(billing_customer))
1328}
1329
1330const SYNC_LLM_REQUEST_USAGE_WITH_STRIPE_INTERVAL: Duration = Duration::from_secs(60);
1331
1332pub fn sync_llm_request_usage_with_stripe_periodically(app: Arc<AppState>) {
1333    let Some(stripe_billing) = app.stripe_billing.clone() else {
1334        log::warn!("failed to retrieve Stripe billing object");
1335        return;
1336    };
1337    let Some(llm_db) = app.llm_db.clone() else {
1338        log::warn!("failed to retrieve LLM database");
1339        return;
1340    };
1341
1342    let executor = app.executor.clone();
1343    executor.spawn_detached({
1344        let executor = executor.clone();
1345        async move {
1346            loop {
1347                sync_model_request_usage_with_stripe(&app, &llm_db, &stripe_billing)
1348                    .await
1349                    .context("failed to sync LLM request usage to Stripe")
1350                    .trace_err();
1351                executor
1352                    .sleep(SYNC_LLM_REQUEST_USAGE_WITH_STRIPE_INTERVAL)
1353                    .await;
1354            }
1355        }
1356    });
1357}
1358
1359async fn sync_model_request_usage_with_stripe(
1360    app: &Arc<AppState>,
1361    llm_db: &Arc<LlmDatabase>,
1362    stripe_billing: &Arc<StripeBilling>,
1363) -> anyhow::Result<()> {
1364    log::info!("Stripe usage sync: Starting");
1365    let started_at = Utc::now();
1366
1367    let staff_users = app.db.get_staff_users().await?;
1368    let staff_user_ids = staff_users
1369        .iter()
1370        .map(|user| user.id)
1371        .collect::<HashSet<UserId>>();
1372
1373    let usage_meters = llm_db
1374        .get_current_subscription_usage_meters(Utc::now())
1375        .await?;
1376    let mut usage_meters_by_user_id =
1377        HashMap::<UserId, Vec<subscription_usage_meter::Model>>::default();
1378    for (usage_meter, usage) in usage_meters {
1379        let meters = usage_meters_by_user_id.entry(usage.user_id).or_default();
1380        meters.push(usage_meter);
1381    }
1382
1383    log::info!("Stripe usage sync: Retrieving Zed Pro subscriptions");
1384    let get_zed_pro_subscriptions_started_at = Utc::now();
1385    let billing_subscriptions = app.db.get_active_zed_pro_billing_subscriptions().await?;
1386    log::info!(
1387        "Stripe usage sync: Retrieved {} Zed Pro subscriptions in {}",
1388        billing_subscriptions.len(),
1389        Utc::now() - get_zed_pro_subscriptions_started_at
1390    );
1391
1392    let claude_sonnet_4 = stripe_billing
1393        .find_price_by_lookup_key("claude-sonnet-4-requests")
1394        .await?;
1395    let claude_sonnet_4_max = stripe_billing
1396        .find_price_by_lookup_key("claude-sonnet-4-requests-max")
1397        .await?;
1398    let claude_opus_4 = stripe_billing
1399        .find_price_by_lookup_key("claude-opus-4-requests")
1400        .await?;
1401    let claude_opus_4_max = stripe_billing
1402        .find_price_by_lookup_key("claude-opus-4-requests-max")
1403        .await?;
1404    let claude_3_5_sonnet = stripe_billing
1405        .find_price_by_lookup_key("claude-3-5-sonnet-requests")
1406        .await?;
1407    let claude_3_7_sonnet = stripe_billing
1408        .find_price_by_lookup_key("claude-3-7-sonnet-requests")
1409        .await?;
1410    let claude_3_7_sonnet_max = stripe_billing
1411        .find_price_by_lookup_key("claude-3-7-sonnet-requests-max")
1412        .await?;
1413
1414    let model_mode_combinations = [
1415        ("claude-opus-4", CompletionMode::Max),
1416        ("claude-opus-4", CompletionMode::Normal),
1417        ("claude-sonnet-4", CompletionMode::Max),
1418        ("claude-sonnet-4", CompletionMode::Normal),
1419        ("claude-3-7-sonnet", CompletionMode::Max),
1420        ("claude-3-7-sonnet", CompletionMode::Normal),
1421        ("claude-3-5-sonnet", CompletionMode::Normal),
1422    ];
1423
1424    let billing_subscription_count = billing_subscriptions.len();
1425
1426    log::info!("Stripe usage sync: Syncing {billing_subscription_count} Zed Pro subscriptions");
1427
1428    for (user_id, (billing_customer, billing_subscription)) in billing_subscriptions {
1429        maybe!(async {
1430            if staff_user_ids.contains(&user_id) {
1431                return anyhow::Ok(());
1432            }
1433
1434            let stripe_customer_id =
1435                StripeCustomerId(billing_customer.stripe_customer_id.clone().into());
1436            let stripe_subscription_id =
1437                StripeSubscriptionId(billing_subscription.stripe_subscription_id.clone().into());
1438
1439            let usage_meters = usage_meters_by_user_id.get(&user_id);
1440
1441            for (model, mode) in &model_mode_combinations {
1442                let Ok(model) =
1443                    llm_db.model(LanguageModelProvider::Anthropic, model)
1444                else {
1445                    log::warn!("Failed to load model for user {user_id}: {model}");
1446                    continue;
1447                };
1448
1449                let (price, meter_event_name) = match model.name.as_str() {
1450                    "claude-opus-4" => match mode {
1451                        CompletionMode::Normal => (&claude_opus_4, "claude_opus_4/requests"),
1452                        CompletionMode::Max => (&claude_opus_4_max, "claude_opus_4/requests/max"),
1453                    },
1454                    "claude-sonnet-4" => match mode {
1455                        CompletionMode::Normal => (&claude_sonnet_4, "claude_sonnet_4/requests"),
1456                        CompletionMode::Max => {
1457                            (&claude_sonnet_4_max, "claude_sonnet_4/requests/max")
1458                        }
1459                    },
1460                    "claude-3-5-sonnet" => (&claude_3_5_sonnet, "claude_3_5_sonnet/requests"),
1461                    "claude-3-7-sonnet" => match mode {
1462                        CompletionMode::Normal => {
1463                            (&claude_3_7_sonnet, "claude_3_7_sonnet/requests")
1464                        }
1465                        CompletionMode::Max => {
1466                            (&claude_3_7_sonnet_max, "claude_3_7_sonnet/requests/max")
1467                        }
1468                    },
1469                    model_name => {
1470                        bail!("Attempted to sync usage meter for unsupported model: {model_name:?}")
1471                    }
1472                };
1473
1474                let model_requests = usage_meters
1475                    .and_then(|usage_meters| {
1476                        usage_meters
1477                            .iter()
1478                            .find(|meter| meter.model_id == model.id && meter.mode == *mode)
1479                    })
1480                    .map(|usage_meter| usage_meter.requests)
1481                    .unwrap_or(0);
1482
1483                if model_requests > 0 {
1484                    stripe_billing
1485                        .subscribe_to_price(&stripe_subscription_id, price)
1486                        .await?;
1487                }
1488
1489                stripe_billing
1490                    .bill_model_request_usage(&stripe_customer_id, meter_event_name, model_requests)
1491                    .await
1492                    .with_context(|| {
1493                        format!(
1494                            "Failed to bill model request usage of {model_requests} for {stripe_customer_id}: {meter_event_name}",
1495                        )
1496                    })?;
1497            }
1498
1499            Ok(())
1500        })
1501        .await
1502        .log_err();
1503    }
1504
1505    log::info!(
1506        "Stripe usage sync: Synced {billing_subscription_count} Zed Pro subscriptions in {}",
1507        Utc::now() - started_at
1508    );
1509
1510    Ok(())
1511}