diff --git a/src/nostr/lifecycle/deletion/runtime.rs b/src/nostr/lifecycle/deletion/runtime.rs
index 6d162b5..4d6783a 100644
--- a/src/nostr/lifecycle/deletion/runtime.rs
+++ b/src/nostr/lifecycle/deletion/runtime.rs
@@ -63,14 +63,6 @@ impl DeletionRuntime {
     /// Run deletion-owned startup tasks before the relay begins serving traffic.
     pub async fn run_startup_tasks(&self) -> Result<()> {
         log_startup_reconciliation(self.service.run_startup_reconciliation().await?);
-        // Enumeration failure is fatal before serving traffic; individual record
-        // failures are conservatively retained and retried by the timer.
-        let request_stats = self
-            .service
-            .cleanup_expired_requests(Timestamp::now())
-            .await?;
-        log_request_cleanup("startup catch-up", request_stats);
-        self.run_holding_startup_cleanup().await;
         Ok(())
     }
 
@@ -84,16 +76,22 @@ impl DeletionRuntime {
         let (shutdown_tx, mut shutdown_rx) = watch::channel(false);
 
         let handle = tokio::spawn(async move {
-            let mut interval = tokio::time::interval_at(
-                tokio::time::Instant::now() + interval_duration,
-                interval_duration,
-            );
+            let mut first_pass = true;
+            let mut interval =
+                tokio::time::interval_at(tokio::time::Instant::now(), interval_duration);
 
             loop {
                 tokio::select! {
                     _ = interval.tick() => {
+                        // The first pass is the startup catch-up. It deliberately
+                        // runs here, after the relay and SyncManager are live:
+                        // large retained request sets can take minutes to scan,
+                        // but must not prevent fresh purgatory work from starting.
                         match service.cleanup_expired_requests(Timestamp::now()).await {
-                            Ok(stats) => log_request_cleanup("periodic pass", stats),
+                            Ok(stats) => log_request_cleanup(
+                                if first_pass { "startup catch-up" } else { "periodic pass" },
+                                stats,
+                            ),
                             Err(error) => tracing::warn!(error = %error, "Deletion-request cleanup periodic pass failed"),
                         }
                         match holding.cleanup_expired_with_lifecycle(&lifecycle, Timestamp::now(), retention).await {
@@ -112,6 +110,7 @@ impl DeletionRuntime {
                                 tracing::warn!(error = %e, "Holding cleanup periodic pass failed");
                             }
                         }
+                        first_pass = false;
                     }
                     changed = shutdown_rx.changed() => {
                         if changed.is_ok() && *shutdown_rx.borrow() {
@@ -134,33 +133,6 @@ impl DeletionRuntime {
             handle,
         }
     }
-
-    async fn run_holding_startup_cleanup(&self) {
-        match self
-            .holding
-            .cleanup_expired_with_lifecycle(
-                &self.lifecycle,
-                Timestamp::now(),
-                self.holding_retention,
-            )
-            .await
-        {
-            Ok(stats) => {
-                if stats.expired_records > 0 {
-                    tracing::info!(
-                        examined = stats.metadata_examined,
-                        expired = stats.expired_records,
-                        metadata_deleted = stats.metadata_deleted,
-                        archived_events_deleted = stats.archived_events_deleted,
-                        "Holding cleanup startup catch-up completed"
-                    );
-                }
-            }
-            Err(e) => {
-                tracing::warn!(error = %e, "Holding cleanup startup catch-up failed");
-            }
-        }
-    }
 }
 
 pub struct DeletionCleanupTask {
@@ -284,3 +256,101 @@ fn log_whitelist_restore(stats: WhitelistRestoreStats) {
         );
     }
 }
+
+#[cfg(test)]
+mod tests {
+    use std::path::PathBuf;
+    use std::sync::Arc;
+
+    use nostr_memory::MemoryDatabase;
+    use nostr_relay_builder::prelude::{
+        EventBuilder, EventId, FinalizeEvent, Keys, Kind, NostrDatabase, Tag,
+    };
+
+    use super::*;
+    use crate::grasp06::receive::new_repo_init_locks;
+    use crate::nostr::lifecycle::{
+        DeletionContext, HoldingStore, ReplaceableHistoryStore, RepositoryLifecycle,
+        RequestClassification, Tombstones,
+    };
+    use crate::purgatory::Purgatory;
+
+    #[tokio::test]
+    async fn retained_request_cleanup_starts_after_blocking_startup_finishes() {
+        let database = Arc::new(MemoryDatabase::unbounded());
+        let tombstones = Tombstones::in_memory();
+        let holding = HoldingStore::in_memory();
+        let lifecycle = RepositoryLifecycle::in_memory();
+        let config = crate::config::Config {
+            deletion_request_retention_unused_served_secs: 1,
+            deletion_request_retention_unused_unserved_gating_additional_secs: 1,
+            ..crate::config::Config::for_testing()
+        };
+        let service = DeletionService::new(DeletionContext::new(
+            "test.example.com",
+            database.clone(),
+            tombstones.clone(),
+            holding.clone(),
+            lifecycle.clone(),
+            ReplaceableHistoryStore::in_memory(),
+            PathBuf::new(),
+            Arc::new(Purgatory::new(PathBuf::new())),
+            config,
+            new_repo_init_locks(),
+        ));
+        let runtime = DeletionRuntime::new(
+            service,
+            holding,
+            Duration::from_secs(60),
+            Duration::from_secs(60),
+        );
+        let request = EventBuilder::new(Kind::EventDeletion, "")
+            .tags(vec![Tag::event(EventId::all_zeros())])
+            .finalize(&Keys::generate())
+            .expect("deletion request should sign");
+
+        tombstones
+            .record_request(
+                &request,
+                Timestamp::from_secs(1),
+                RequestClassification::LocallyActionable,
+            )
+            .await
+            .expect("request lifecycle should be retained");
+        database
+            .save_event(&request)
+            .await
+            .expect("request payload should be served");
+
+        runtime
+            .run_startup_tasks()
+            .await
+            .expect("blocking startup reconciliation should complete");
+        assert!(
+            tombstones
+                .lifecycle_for_request_result(&request.id)
+                .await
+                .expect("lifecycle lookup should succeed")
+                .is_some(),
+            "retention cleanup must not delay relay and SyncManager startup"
+        );
+
+        let cleanup = runtime.spawn_cleanup_task();
+        tokio::time::timeout(Duration::from_secs(2), async {
+            loop {
+                if tombstones
+                    .lifecycle_for_request_result(&request.id)
+                    .await
+                    .expect("lifecycle lookup should succeed")
+                    .is_none()
+                {
+                    break;
+                }
+                tokio::time::sleep(Duration::from_millis(10)).await;
+            }
+        })
+        .await
+        .expect("background startup catch-up should run immediately");
+        cleanup.shutdown().await;
+    }
+}