diff --git a/src/databases/officer_db/src/chat-session-cleanup.ts b/src/databases/officer_db/src/chat-session-cleanup.ts
index b287a4b1..a181c2aa 100644
--- a/src/databases/officer_db/src/chat-session-cleanup.ts
+++ b/src/databases/officer_db/src/chat-session-cleanup.ts
@@ -1,4 +1,4 @@
-import { inArray } from 'drizzle-orm';
+import { inArray, sql } from 'drizzle-orm';
 import { db } from './db';
 import { chatSessionEvents } from './chat-events/schema';
 import { chatNotificationPrefs } from './chat-notification-prefs/schema';
@@ -66,7 +66,27 @@ export async function forgetChatSessions({ transcriptIds, sessionKeys = [] }: Fo
     await db.delete(chatSessionModels).where(inArray(chatSessionModels.sessionId, transcriptIds));
     await db.delete(chatNotificationPrefs).where(inArray(chatNotificationPrefs.sessionId, transcriptIds));
   }
-  if (sessionKeys.length) {
+  /*
+    Events, resolved from the table's OWN data rather than from the caller's key.
+
+    `sessionKeys` is a fast path and not a reliable one: the caller gets it from an in-memory map that is
+    empty for any session created before the last restart, so the first real test of this deleted everything
+    except the events — the key came back null and the list was empty. A cleanup that only works for
+    conversations younger than the process is not a cleanup.
+
+    So ask the rows. Every event carries `claudeSessionId` in its payload, which is durable, survives any
+    restart, and is the one place the two id spaces are written down together. One id inside the JSON is
+    enough to resolve the key for all of that session's rows, including the events that carry no id of their
+    own — which is most of them.
+  */
+  if (transcriptIds.length) {
+    const keysFromEvents = await db
+      .selectDistinct({ sessionId: chatSessionEvents.sessionId })
+      .from(chatSessionEvents)
+      .where(inArray(sql`${chatSessionEvents.event}->>'claudeSessionId'`, transcriptIds));
+    const keys = [...new Set([...sessionKeys, ...keysFromEvents.map((r) => r.sessionId)])];
+    if (keys.length) await db.delete(chatSessionEvents).where(inArray(chatSessionEvents.sessionId, keys));
+  } else if (sessionKeys.length) {
     await db.delete(chatSessionEvents).where(inArray(chatSessionEvents.sessionId, sessionKeys));
   }
 }