diff --git a/apps/web/src/app/api/sse/timeline/route.ts b/apps/web/src/app/api/sse/timeline/route.ts
index 2b4e085..acaf4d4 100644
--- a/apps/web/src/app/api/sse/timeline/route.ts
+++ b/apps/web/src/app/api/sse/timeline/route.ts
@@ -5,13 +5,14 @@ import { prisma } from "@capakraken/db";
 import { SSE_EVENT_TYPES, SystemRole, type PermissionOverrides } from "@capakraken/shared";
 import { auth } from "~/server/auth.js";
 
-// Start the reminder scheduler (idempotent — only starts once)
-startReminderScheduler();
-
 export const dynamic = "force-dynamic";
 export const runtime = "nodejs";
 
 export async function GET() {
+  // Start lazily on the first real SSE request so builds/import-time evaluation
+  // never attempt reminder processing against a live database.
+  startReminderScheduler();
+
   const session = await auth();
 
   if (!session?.user) {
diff --git a/apps/web/src/hooks/useTimelineSSE.ts b/apps/web/src/hooks/useTimelineSSE.ts
index 7f7de54..ad0a785 100644
--- a/apps/web/src/hooks/useTimelineSSE.ts
+++ b/apps/web/src/hooks/useTimelineSSE.ts
@@ -15,10 +15,27 @@ export function useTimelineSSE() {
   useEffect(() => {
     let es: EventSource | null = null;
     let reconnectAttempts = 0;
+    let isDisposed = false;
+
+    function scheduleReconnect() {
+      if (isDisposed || reconnectTimeout.current) return;
+      reconnectAttempts++;
+      const delay = Math.min(1000 * Math.pow(2, reconnectAttempts), 30000);
+      reconnectTimeout.current = setTimeout(() => {
+        reconnectTimeout.current = null;
+        if (isDisposed) return;
+        connect();
+      }, delay);
+    }
 
     function connect() {
+      if (isDisposed) return;
       es = new EventSource("/api/sse/timeline");
 
+      es.onopen = () => {
+        reconnectAttempts = 0;
+      };
+
       es.onmessage = (event) => {
         try {
           const data = JSON.parse(event.data as string) as { type: string };
@@ -35,6 +52,7 @@ export function useTimelineSSE() {
               void queryClient.invalidateQueries({ queryKey: [["timeline", "getMyEntriesView"]] });
               void queryClient.invalidateQueries({ queryKey: [["timeline", "getHolidayOverlays"]] });
               void queryClient.invalidateQueries({ queryKey: [["timeline", "getMyHolidayOverlays"]] });
+              void queryClient.invalidateQueries({ queryKey: [["vacation", "list"]] });
               void queryClient.invalidateQueries({ queryKey: [["allocation", "list"]] });
               break;
 
@@ -82,18 +100,18 @@ export function useTimelineSSE() {
 
       es.onerror = () => {
         es?.close();
-        reconnectAttempts++;
-        const delay = Math.min(1000 * Math.pow(2, reconnectAttempts), 30000);
-        reconnectTimeout.current = setTimeout(connect, delay);
+        scheduleReconnect();
       };
     }
 
     connect();
 
     return () => {
+      isDisposed = true;
       es?.close();
       if (reconnectTimeout.current) {
         clearTimeout(reconnectTimeout.current);
+        reconnectTimeout.current = null;
       }
     };
   }, [queryClient]);