chore: encrypt tenant NWC URL at rest and stop secret exposure in tenant APIs

Reviewed-on: coracle/caravel#54
Co-authored-by: userAdityaa <aditya.chaudhary1558@gmail.com>
Co-committed-by: userAdityaa <aditya.chaudhary1558@gmail.com>

backend/.env.template

@@ -28,5 +28,6 @@ LIVEKIT_API_SECRET=
 
 # Billing
 NWC_URL=                      # Nostr Wallet Connect URL for generating Lightning invoices
+ENCRYPTION_SECRET=            # Nostr secret key (hex or nsec) used to encrypt tenant NWC URLs at rest
 STRIPE_SECRET_KEY=            # Required Stripe API secret key (sk_...)
 STRIPE_WEBHOOK_SECRET=whsec_test_00000000000000000000000000  # Webhook signing secret (use real value in production)

backend/README.md

@@ -44,6 +44,7 @@ Environment variables:
 | `LIVEKIT_API_KEY`        | LiveKit API key sent to zooid                                           | _optional_                           |
 | `LIVEKIT_API_SECRET`     | LiveKit API secret sent to zooid                                        | _optional_                           |
 | `NWC_URL`                | Platform NWC URL used to generate BOLT11 invoices                       | _required for invoice generation_    |
+| `ENCRYPTION_SECRET`      | Nostr secret key (hex or nsec) used to encrypt tenant NWC URLs at rest  | _required_                           |
 | `STRIPE_SECRET_KEY`      | Stripe API secret key used for billing API operations                   | _required_                           |
 | `STRIPE_WEBHOOK_SECRET`  | Stripe webhook signing secret used to verify `Stripe-Signature` headers | _required_                           |
 | `ROBOT_SECRET`           | Robot Nostr secret key                                                  | _required_                           |

backend/migrations/0004_invoice_manual_lightning_payment.sql

@@ -0,0 +1,11 @@
+CREATE TABLE IF NOT EXISTS invoice_manual_lightning_payment (
+  invoice_id TEXT PRIMARY KEY,
+  tenant_pubkey TEXT NOT NULL,
+  bolt11 TEXT NOT NULL,
+  created_at INTEGER NOT NULL,
+  updated_at INTEGER NOT NULL,
+  FOREIGN KEY (tenant_pubkey) REFERENCES tenant(pubkey)
+);
+
+CREATE INDEX IF NOT EXISTS idx_invoice_manual_lightning_payment_tenant_pubkey
+ON invoice_manual_lightning_payment (tenant_pubkey);

backend/spec/api.md

@@ -57,7 +57,7 @@ Notes:
 
 - Serves `GET /tenants`
 - Authorizes admin only
-- Return `data` is a list of tenant structs from `query.list_tenants`
+- Return `data` is a list of `TenantResponse` structs (contains `nwc_is_set: bool` instead of `nwc_url`)
 
 ## `async fn create_tenant(...) -> Response`
 
@@ -69,20 +69,21 @@ Notes:
 - On unique-constraint race (`pubkey-exists`), re-fetch and return the existing tenant
 - If Stripe customer creation fails, return `code=stripe-customer-create-failed`
 - Always returns `200` (create-or-get is uniform)
-- Return `data` is a single `Tenant` struct
+- Return `data` is a single `TenantResponse` struct (contains `nwc_is_set: bool` instead of `nwc_url`)
 
 ## `async fn get_tenant(...) -> Response`
 
 - Serves `GET /tenants/:pubkey`
 - Authorizes admin or matching tenant
-- Return `data` is a single tenant struct from `query.get_tenant`
+- Return `data` is a single `TenantResponse` struct (contains `nwc_is_set: bool` instead of `nwc_url`)
 
 ## `async fn update_tenant(...) -> Response`
 
 - Serves `PUT /tenants/:pubkey`
 - Authorizes admin or matching tenant
+- Accepts `nwc_url` in the request body; encrypts it before storage using `cipher::encrypt`
 - Updates tenant using `command.update_tenant`
-- Return `data` is the updated tenant struct
+- Return `data` is the updated `TenantResponse` struct (contains `nwc_is_set: bool` instead of `nwc_url`)
 
 ## `async fn list_tenant_relays(...) -> Response`
 

backend/spec/models.md

@@ -52,7 +52,7 @@ There are three plans available:
 Tenants are customers of the service, identified by a nostr `pubkey`. Public metadata like name etc are pulled from the nostr network. They also have associated billing information.
 
 - `pubkey` is the nostr public key identifying the tenant
-- `nwc_url` (private) a nostr wallet connect URL used for **paying** invoices generated by the system on the tenant's behalf
+- `nwc_url` (private) a nostr wallet connect URL used for **paying** invoices generated by the system on the tenant's behalf; stored encrypted at rest using NIP-44 via `ENCRYPTION_SECRET`; never serialized to API responses — tenant API endpoints expose `nwc_is_set: bool` instead
 - `nwc_error` (private) a string indicating the most recent NWC payment error, if any. Cleared on successful NWC payment.
 - `created_at` unix timestamp identifying tenant creation time
 - `stripe_customer_id` a string identifying the associated stripe customer

backend/src/api.rs

@@ -445,6 +445,31 @@ struct IdentityResponse {
     is_admin: bool,
 }
 
+#[derive(Serialize)]
+struct TenantResponse {
+    pubkey: String,
+    nwc_is_set: bool,
+    nwc_error: Option<String>,
+    created_at: i64,
+    stripe_customer_id: String,
+    stripe_subscription_id: Option<String>,
+    past_due_at: Option<i64>,
+}
+
+impl From<Tenant> for TenantResponse {
+    fn from(t: Tenant) -> Self {
+        TenantResponse {
+            nwc_is_set: !t.nwc_url.is_empty(),
+            pubkey: t.pubkey,
+            nwc_error: t.nwc_error,
+            created_at: t.created_at,
+            stripe_customer_id: t.stripe_customer_id,
+            stripe_subscription_id: t.stripe_subscription_id,
+            past_due_at: t.past_due_at,
+        }
+    }
+}
+
 #[derive(Deserialize)]
 struct CreateRelayRequest {
     tenant: String,
@@ -486,7 +511,13 @@ async fn list_tenants(
     state.api.require_admin(&pubkey)?;
 
     match state.api.query.list_tenants().await {
-        Ok(tenants) => Ok(ok(StatusCode::OK, tenants)),
+        Ok(tenants) => Ok(ok(
+            StatusCode::OK,
+            tenants
+                .into_iter()
+                .map(TenantResponse::from)
+                .collect::<Vec<_>>(),
+        )),
         Err(e) => Ok(err(
             StatusCode::INTERNAL_SERVER_ERROR,
             "internal",
@@ -515,7 +546,7 @@ async fn create_tenant(
     let pubkey = state.api.extract_auth_pubkey(&headers)?;
 
     match state.api.query.get_tenant(&pubkey).await {
-        Ok(Some(t)) => Ok(ok(StatusCode::OK, t)),
+        Ok(Some(t)) => Ok(ok(StatusCode::OK, TenantResponse::from(t))),
         Ok(None) => {
             let stripe_customer_id = match state.api.billing.stripe_create_customer(&pubkey).await {
                 Ok(id) => id,
@@ -539,10 +570,10 @@ async fn create_tenant(
             };
 
             match state.api.command.create_tenant(&tenant).await {
-                Ok(()) => Ok(ok(StatusCode::OK, tenant)),
+                Ok(()) => Ok(ok(StatusCode::OK, TenantResponse::from(tenant))),
                 Err(e) if matches!(map_unique_error(&e), Some("pubkey-exists")) => {
                     match state.api.query.get_tenant(&pubkey).await {
-                        Ok(Some(t)) => Ok(ok(StatusCode::OK, t)),
+                        Ok(Some(t)) => Ok(ok(StatusCode::OK, TenantResponse::from(t))),
                         Ok(None) => Ok(err(
                             StatusCode::INTERNAL_SERVER_ERROR,
                             "internal",
@@ -585,7 +616,7 @@ async fn get_tenant(
     let auth = state.api.extract_auth_pubkey(&headers)?;
     state.api.require_admin_or_tenant(&auth, &pubkey)?;
     let tenant = state.api.get_tenant_or_404(&pubkey).await?;
-    Ok(ok(StatusCode::OK, tenant))
+    Ok(ok(StatusCode::OK, TenantResponse::from(tenant)))
 }
 
 async fn list_relays(
@@ -1009,6 +1040,13 @@ async fn get_invoice(
         .map_err(map_invoice_lookup_error)?;
     state.api.require_admin_or_tenant(&auth, &tenant.pubkey)?;
 
+    let invoice = state
+        .api
+        .billing
+        .reconcile_manual_lightning_invoice(&id, &invoice)
+        .await
+        .map_err(map_invoice_lookup_error)?;
+
     Ok(ok(StatusCode::OK, invoice))
 }
 
@@ -1026,6 +1064,13 @@ async fn get_invoice_bolt11(
         .map_err(map_invoice_lookup_error)?;
     state.api.require_admin_or_tenant(&auth, &tenant.pubkey)?;
 
+    let invoice = state
+        .api
+        .billing
+        .reconcile_manual_lightning_invoice(&id, &invoice)
+        .await
+        .map_err(map_invoice_lookup_error)?;
+
     let status = invoice["status"].as_str().unwrap_or_default();
     if status != "open" {
         return Ok(err(
@@ -1038,7 +1083,12 @@ async fn get_invoice_bolt11(
     let amount_due = invoice["amount_due"].as_i64().unwrap_or(0);
     let currency = invoice["currency"].as_str().unwrap_or("usd");
 
-    match state.api.billing.create_bolt11(amount_due, currency).await {
+    match state
+        .api
+        .billing
+        .get_or_create_manual_lightning_bolt11(&id, &tenant.pubkey, amount_due, currency)
+        .await
+    {
         Ok(bolt11) => Ok(ok(StatusCode::OK, serde_json::json!({ "bolt11": bolt11 }))),
         Err(e) => Ok(err(
             StatusCode::INTERNAL_SERVER_ERROR,
@@ -1084,7 +1134,12 @@ async fn update_tenant(
 
     let nwc_previously_empty = tenant.nwc_url.is_empty();
     if let Some(nwc_url) = payload.nwc_url {
-        tenant.nwc_url = nwc_url;
+        if nwc_url.is_empty() {
+            tenant.nwc_url = String::new();
+        } else {
+            tenant.nwc_url =
+                crate::cipher::encrypt(&nwc_url).map_err(|e| ApiError::Internal(e.to_string()))?;
+        }
     }
 
     match state.api.command.update_tenant(&tenant).await {
@@ -1103,7 +1158,7 @@ async fn update_tenant(
                     }
                 });
             }
-            Ok(ok(StatusCode::OK, tenant))
+            Ok(ok(StatusCode::OK, TenantResponse::from(tenant)))
         }
         Err(e) => Ok(err(
             StatusCode::INTERNAL_SERVER_ERROR,

backend/src/billing.rs

@@ -1,7 +1,8 @@
 use anyhow::{Result, anyhow};
 use hmac::{Hmac, Mac};
 use nwc::prelude::{
-    MakeInvoiceRequest, NWC, NostrWalletConnectURI, PayInvoiceRequest as NwcPayInvoiceRequest,
+    LookupInvoiceRequest, LookupInvoiceResponse, MakeInvoiceRequest, NWC, NostrWalletConnectURI,
+    PayInvoiceRequest as NwcPayInvoiceRequest, TransactionState,
 };
 use sha2::Sha256;
 
@@ -120,6 +121,10 @@ impl Billing {
     pub async fn start(self) {
         let mut rx = self.command.notify.subscribe();
 
+        if let Err(error) = self.reconcile_relay_subscriptions("startup").await {
+            tracing::error!(error = %error, "failed to reconcile relay billing state on startup");
+        }
+
         loop {
             match rx.recv().await {
                 Ok(activity) => {
@@ -129,12 +134,39 @@ impl Billing {
                 }
                 Err(tokio::sync::broadcast::error::RecvError::Lagged(n)) => {
                     tracing::warn!(missed = n, "billing lagged");
+
+                    if let Err(error) = self.reconcile_relay_subscriptions("lagged").await {
+                        tracing::error!(error = %error, "failed to reconcile relay billing state after lag");
+                    }
                 }
                 Err(tokio::sync::broadcast::error::RecvError::Closed) => break,
             }
         }
     }
 
+    async fn reconcile_relay_subscriptions(&self, source: &str) -> Result<()> {
+        let relays = self.query.list_relays().await?;
+
+        if relays.is_empty() {
+            return Ok(());
+        }
+
+        tracing::info!(source, relay_count = relays.len(), "reconciling relay billing state");
+
+        for relay in relays {
+            if let Err(error) = self.sync_relay_subscription_for_relay(&relay).await {
+                tracing::error!(
+                    source,
+                    relay = %relay.id,
+                    error = %error,
+                    "failed to reconcile relay billing state"
+                );
+            }
+        }
+
+        Ok(())
+    }
+
     async fn handle_activity(&self, activity: &Activity) -> Result<()> {
         let needs_billing_sync = matches!(
             activity.activity_type.as_str(),
@@ -158,6 +190,10 @@ impl Billing {
             return Ok(());
         };
 
+        self.sync_relay_subscription_for_relay(&relay).await
+    }
+
+    async fn sync_relay_subscription_for_relay(&self, relay: &Relay) -> Result<()> {
         let Some(tenant) = self.query.get_tenant(&relay.tenant).await? else {
             return Ok(());
         };
@@ -386,13 +422,14 @@ impl Billing {
 
         // 1. NWC auto-pay: if the tenant has a nwc_url
         if !tenant.nwc_url.is_empty() {
+            let plain_nwc_url = crate::cipher::decrypt(&tenant.nwc_url)?;
             match self
                 .nwc_pay_invoice(
                     invoice_id,
                     &tenant.pubkey,
                     amount_due,
                     currency,
-                    &tenant.nwc_url,
+                    &plain_nwc_url,
                 )
                 .await?
             {
@@ -683,6 +720,50 @@ impl Billing {
         Ok((invoice, tenant))
     }
 
+    pub async fn reconcile_manual_lightning_invoice(
+        &self,
+        invoice_id: &str,
+        invoice: &serde_json::Value,
+    ) -> std::result::Result<serde_json::Value, InvoiceLookupError> {
+        self.reconcile_manual_lightning_invoice_if_settled(invoice_id, invoice)
+            .await
+    }
+
+    pub async fn get_or_create_manual_lightning_bolt11(
+        &self,
+        invoice_id: &str,
+        tenant_pubkey: &str,
+        amount_due_minor: i64,
+        currency: &str,
+    ) -> Result<String> {
+        if let Some(existing_bolt11) = self
+            .query
+            .get_invoice_manual_lightning_bolt11(invoice_id)
+            .await?
+        {
+            return Ok(existing_bolt11);
+        }
+
+        let bolt11 = self.create_bolt11(amount_due_minor, currency).await?;
+
+        if self
+            .command
+            .insert_manual_lightning_invoice_payment(invoice_id, tenant_pubkey, &bolt11)
+            .await?
+        {
+            return Ok(bolt11);
+        }
+
+        self.query
+            .get_invoice_manual_lightning_bolt11(invoice_id)
+            .await?
+            .ok_or_else(|| {
+                anyhow!(
+                    "manual lightning payment row missing after insert race for invoice {invoice_id}"
+                )
+            })
+    }
+
     pub async fn stripe_create_customer(&self, tenant_pubkey: &str) -> Result<String> {
         let short_pubkey: String = tenant_pubkey.chars().take(12).collect();
         let display_name = format!("Caravel tenant {short_pubkey}");
@@ -777,6 +858,8 @@ impl Billing {
             return Ok(());
         }
 
+        let plain_nwc_url = crate::cipher::decrypt(&tenant.nwc_url)?;
+
         let invoices = self
             .stripe_list_invoices(&tenant.stripe_customer_id)
             .await?;
@@ -798,7 +881,7 @@ impl Billing {
                     &tenant.pubkey,
                     amount_due,
                     currency,
-                    &tenant.nwc_url,
+                    &plain_nwc_url,
                 )
                 .await?
             {
@@ -1103,6 +1186,72 @@ impl Billing {
         Ok(())
     }
 
+    async fn reconcile_manual_lightning_invoice_if_settled(
+        &self,
+        invoice_id: &str,
+        invoice: &serde_json::Value,
+    ) -> std::result::Result<serde_json::Value, InvoiceLookupError> {
+        if invoice["status"].as_str().unwrap_or_default() != "open" {
+            return Ok(invoice.clone());
+        }
+
+        let Some(bolt11) = self
+            .query
+            .get_invoice_manual_lightning_bolt11(invoice_id)
+            .await?
+        else {
+            return Ok(invoice.clone());
+        };
+
+        let settled = match self.is_manual_lightning_invoice_settled(&bolt11).await {
+            Ok(settled) => settled,
+            Err(error) => {
+                tracing::warn!(
+                    error = %error,
+                    invoice_id,
+                    "failed to lookup manual lightning invoice settlement"
+                );
+                return Ok(invoice.clone());
+            }
+        };
+
+        if !settled {
+            return Ok(invoice.clone());
+        }
+
+        if let Err(error) = self.stripe_pay_invoice_out_of_band(invoice_id).await {
+            tracing::warn!(
+                error = %error,
+                invoice_id,
+                "failed to mark settled manual lightning invoice as paid_out_of_band"
+            );
+        }
+
+        self.stripe_get_invoice(invoice_id).await
+    }
+
+    async fn is_manual_lightning_invoice_settled(&self, bolt11: &str) -> Result<bool> {
+        let system_uri = Self::parse_nwc_uri(&self.nwc_url, "system")?;
+        let system_nwc = NWC::new(system_uri);
+
+        let lookup_req = LookupInvoiceRequest {
+            payment_hash: None,
+            invoice: Some(bolt11.to_string()),
+        };
+
+        let lookup_result = system_nwc.lookup_invoice(lookup_req).await;
+        system_nwc.shutdown().await;
+
+        let lookup_response =
+            lookup_result.map_err(|error| anyhow!("failed to lookup invoice: {error}"))?;
+
+        Ok(Self::lookup_invoice_response_is_settled(&lookup_response))
+    }
+
+    fn lookup_invoice_response_is_settled(response: &LookupInvoiceResponse) -> bool {
+        response.state == Some(TransactionState::Settled) || response.settled_at.is_some()
+    }
+
     fn parse_nwc_uri(nwc_url: &str, role: &str) -> Result<NostrWalletConnectURI> {
         nwc_url
             .parse::<NostrWalletConnectURI>()

backend/src/cipher.rs

@@ -0,0 +1,28 @@
+use anyhow::{Result, anyhow};
+use nostr_sdk::prelude::*;
+
+pub fn encrypt(plaintext: &str) -> Result<String> {
+    let keys = load_key()?;
+    nip44::encrypt(
+        keys.secret_key(),
+        &keys.public_key(),
+        plaintext,
+        nip44::Version::V2,
+    )
+    .map_err(|e| anyhow!("encryption failed: {e}"))
+}
+
+pub fn decrypt(ciphertext: &str) -> Result<String> {
+    let keys = load_key()?;
+    nip44::decrypt(keys.secret_key(), &keys.public_key(), ciphertext)
+        .map_err(|e| anyhow!("decryption failed: {e}"))
+}
+
+fn load_key() -> Result<Keys> {
+    let secret = std::env::var("ENCRYPTION_SECRET")
+        .map_err(|_| anyhow!("missing ENCRYPTION_SECRET environment variable"))?;
+    if secret.trim().is_empty() {
+        return Err(anyhow!("ENCRYPTION_SECRET is empty"));
+    }
+    Keys::parse(&secret).map_err(|e| anyhow!("invalid ENCRYPTION_SECRET: {e}"))
+}

backend/src/command.rs

@@ -113,12 +113,12 @@ impl Command {
 
         sqlx::query(
             "INSERT INTO relay (
-                id, tenant, schema, subdomain, plan, status, sync_error,
+                id, tenant, schema, subdomain, plan, status, synced, sync_error,
                 info_name, info_icon, info_description,
                 policy_public_join, policy_strip_signatures,
                 groups_enabled, management_enabled, blossom_enabled,
                 livekit_enabled, push_enabled
-            ) VALUES (?, ?, ?, ?, ?, 'active', ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)",
+            ) VALUES (?, ?, ?, ?, ?, 'active', 0, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?, ?)",
         )
         .bind(&relay.id)
         .bind(&relay.tenant)
@@ -151,7 +151,7 @@ impl Command {
 
         sqlx::query(
             "UPDATE relay
-             SET tenant = ?, schema = ?, subdomain = ?, plan = ?, status = ?, sync_error = ?,
+             SET tenant = ?, schema = ?, subdomain = ?, plan = ?, status = ?, sync_error = ?, synced = 0,
                  info_name = ?, info_icon = ?, info_description = ?,
                  policy_public_join = ?, policy_strip_signatures = ?,
                  groups_enabled = ?, management_enabled = ?, blossom_enabled = ?,
@@ -203,7 +203,7 @@ impl Command {
     ) -> Result<()> {
         let mut tx = self.pool.begin().await?;
 
-        sqlx::query("UPDATE relay SET status = ? WHERE id = ?")
+        sqlx::query("UPDATE relay SET status = ?, synced = 0 WHERE id = ?")
             .bind(status)
             .bind(relay_id)
             .execute(&mut *tx)
@@ -224,7 +224,7 @@ impl Command {
     pub async fn fail_relay_sync(&self, relay: &Relay, sync_error: String) -> Result<()> {
         let mut tx = self.pool.begin().await?;
 
-        sqlx::query("UPDATE relay SET sync_error = ? WHERE id = ?")
+        sqlx::query("UPDATE relay SET synced = 0, sync_error = ? WHERE id = ?")
             .bind(&sync_error)
             .bind(&relay.id)
             .execute(&mut *tx)
@@ -353,6 +353,30 @@ impl Command {
         Ok(())
     }
 
+    pub async fn insert_manual_lightning_invoice_payment(
+        &self,
+        invoice_id: &str,
+        tenant_pubkey: &str,
+        bolt11: &str,
+    ) -> Result<bool> {
+        let now = chrono::Utc::now().timestamp();
+        let result = sqlx::query(
+            "INSERT INTO invoice_manual_lightning_payment
+             (invoice_id, tenant_pubkey, bolt11, created_at, updated_at)
+             VALUES (?, ?, ?, ?, ?)
+             ON CONFLICT(invoice_id) DO NOTHING",
+        )
+        .bind(invoice_id)
+        .bind(tenant_pubkey)
+        .bind(bolt11)
+        .bind(now)
+        .bind(now)
+        .execute(&self.pool)
+        .await?;
+
+        Ok(result.rows_affected() > 0)
+    }
+
     pub async fn set_tenant_past_due(&self, pubkey: &str) -> Result<()> {
         let now = chrono::Utc::now().timestamp();
         sqlx::query("UPDATE tenant SET past_due_at = ? WHERE pubkey = ?")

backend/src/infra.rs

@@ -53,8 +53,8 @@ impl Infra {
     pub async fn start(self) {
         let mut rx = self.command.notify.subscribe();
 
-        if let Err(e) = self.schedule_startup_retries().await {
-            tracing::error!(error = %e, "failed to schedule relay sync retries on startup");
+        if let Err(error) = self.reconcile_relay_state("startup").await {
+            tracing::error!(error = %error, "failed to reconcile relay state on startup");
         }
 
         loop {
@@ -66,6 +66,10 @@ impl Infra {
                 }
                 Err(tokio::sync::broadcast::error::RecvError::Lagged(n)) => {
                     tracing::warn!(missed = n, "infra lagged");
+
+                    if let Err(error) = self.reconcile_relay_state("lagged").await {
+                        tracing::error!(error = %error, "failed to reconcile relay state after lag");
+                    }
                 }
                 Err(tokio::sync::broadcast::error::RecvError::Closed) => break,
             }
@@ -89,17 +93,28 @@ impl Infra {
             return Ok(());
         };
 
-        let is_new = relay.synced == 0;
+        let is_new = self.relay_sync_is_new(&relay).await?;
         self.sync_and_report(&relay, is_new).await;
 
         Ok(())
     }
 
-    async fn schedule_startup_retries(&self) -> Result<()> {
-        let relays = self.query.list_relays_with_sync_error().await?;
+    async fn reconcile_relay_state(&self, source: &str) -> Result<()> {
+        let relays = self.query.list_relays_pending_sync().await?;
+
+        if relays.is_empty() {
+            return Ok(());
+        }
+
+        tracing::info!(source, relay_count = relays.len(), "reconciling pending relay state");
 
         for relay in relays {
-            self.schedule_relay_sync_retry(&relay.id, "startup").await?;
+            if relay.sync_error.trim().is_empty() {
+                let is_new = self.relay_sync_is_new(&relay).await?;
+                self.sync_and_report(&relay, is_new).await;
+            } else {
+                self.schedule_relay_sync_retry(&relay.id, source).await?;
+            }
         }
 
         Ok(())
@@ -151,11 +166,20 @@ impl Infra {
             return Ok(());
         }
 
-        let is_new = relay.synced == 0;
+        let is_new = self.relay_sync_is_new(&relay).await?;
         self.sync_and_report(&relay, is_new).await;
         Ok(())
     }
 
+    async fn relay_sync_is_new(&self, relay: &Relay) -> Result<bool> {
+        if relay.synced == 1 {
+            return Ok(false);
+        }
+
+        let has_completed_sync = self.query.relay_has_completed_sync(&relay.id).await?;
+        Ok(!has_completed_sync)
+    }
+
     async fn sync_and_report(&self, relay: &Relay, is_new: bool) {
         match self.sync_relay(relay, is_new).await {
             Ok(()) => {

backend/src/lib.rs

@@ -1,5 +1,6 @@
 pub mod api;
 pub mod billing;
+pub mod cipher;
 pub mod command;
 pub mod infra;
 pub mod models;

backend/src/main.rs

@@ -1,5 +1,6 @@
 mod api;
 mod billing;
+mod cipher;
 mod command;
 mod infra;
 mod models;

backend/src/query.rs

@@ -94,7 +94,7 @@ impl Query {
         Ok(rows)
     }
 
-    pub async fn list_relays_with_sync_error(&self) -> Result<Vec<Relay>> {
+    pub async fn list_relays_pending_sync(&self) -> Result<Vec<Relay>> {
         let rows = sqlx::query_as::<_, Relay>(
             "SELECT id, tenant, schema, subdomain, plan, stripe_subscription_item_id,
                      status, sync_error,
@@ -103,7 +103,7 @@ impl Query {
                      groups_enabled, management_enabled, blossom_enabled,
                      livekit_enabled, push_enabled, synced
               FROM relay
-              WHERE TRIM(sync_error) != ''
+              WHERE synced = 0 OR TRIM(sync_error) != ''
               ORDER BY id",
         )
         .fetch_all(&self.pool)
@@ -171,6 +171,19 @@ impl Query {
         Ok(state)
     }
 
+    pub async fn get_invoice_manual_lightning_bolt11(
+        &self,
+        invoice_id: &str,
+    ) -> Result<Option<String>> {
+        let bolt11 = sqlx::query_scalar::<_, String>(
+            "SELECT bolt11 FROM invoice_manual_lightning_payment WHERE invoice_id = ?",
+        )
+        .bind(invoice_id)
+        .fetch_optional(&self.pool)
+        .await?;
+        Ok(bolt11)
+    }
+
     pub async fn has_active_paid_relays(&self, tenant_id: &str) -> Result<bool> {
         let plans = sqlx::query_scalar::<_, String>(
             "SELECT plan FROM relay WHERE tenant = ? AND status = 'active'",
@@ -194,4 +207,20 @@ impl Query {
         .await?;
         Ok(rows)
     }
+
+    pub async fn relay_has_completed_sync(&self, relay_id: &str) -> Result<bool> {
+        let found = sqlx::query_scalar::<_, i64>(
+            "SELECT 1
+             FROM activity
+             WHERE resource_type = 'relay'
+               AND resource_id = ?
+               AND activity_type = 'complete_relay_sync'
+             LIMIT 1",
+        )
+        .bind(relay_id)
+        .fetch_optional(&self.pool)
+        .await?;
+
+        Ok(found.is_some())
+    }
 }