diff --git a/src/services/sqlite/SessionStore.ts b/src/services/sqlite/SessionStore.ts
index c5ece703..d7d853a7 100644
--- a/src/services/sqlite/SessionStore.ts
+++ b/src/services/sqlite/SessionStore.ts
@@ -2615,6 +2615,23 @@ export class SessionStore {
     return { imported: true, id: result.lastInsertRowid as number };
   }
 
+  /**
+   * Rebuild the FTS5 index for observations.
+   * Should be called after bulk imports to ensure imported rows are searchable.
+   * No-op if observations_fts table does not exist.
+   */
+  rebuildObservationsFTSIndex(): void {
+    const hasFTS = (this.db.prepare(
+      "SELECT name FROM sqlite_master WHERE type='table' AND name='observations_fts'"
+    ).all() as { name: string }[]).length > 0;
+
+    if (!hasFTS) {
+      return;
+    }
+
+    this.db.run("INSERT INTO observations_fts(observations_fts) VALUES('rebuild')");
+  }
+
   /**
    * Import user prompt with duplicate checking
    * Duplicates are identified by content_session_id + prompt_number
diff --git a/src/services/worker/http/routes/DataRoutes.ts b/src/services/worker/http/routes/DataRoutes.ts
index 01013d5d..b476a3d9 100644
--- a/src/services/worker/http/routes/DataRoutes.ts
+++ b/src/services/worker/http/routes/DataRoutes.ts
@@ -391,6 +391,13 @@ export class DataRoutes extends BaseRouteHandler {
           stats.observationsSkipped++;
         }
       }
+
+      // Rebuild FTS index so imported observations are immediately searchable.
+      // The FTS5 content table relies on triggers for incremental updates, but
+      // those triggers may not have fired correctly for all import paths.
+      if (stats.observationsImported > 0) {
+        store.rebuildObservationsFTSIndex();
+      }
     }
 
     // Import prompts (depends on sessions)