diff --git a/apps/web/src/app/api/cron/auth-anomaly-check/route.test.ts b/apps/web/src/app/api/cron/auth-anomaly-check/route.test.ts
index b93ae2a..c417e48 100644
--- a/apps/web/src/app/api/cron/auth-anomaly-check/route.test.ts
+++ b/apps/web/src/app/api/cron/auth-anomaly-check/route.test.ts
@@ -82,7 +82,7 @@ describe("GET /api/cron/auth-anomaly-check — cron secret enforcement", () => {
     const { GET } = await importRoute();
     const res = await GET(makeRequest());
     expect(res.status).toBe(401);
-  });
+  }, 15_000); // next/server cold-import can take >5s on the act runner
 
   it("proceeds when verifyCronSecret returns null (allowed)", async () => {
     verifyCronSecretMock.mockReturnValue(null);
diff --git a/apps/web/src/components/timeline/TimelineContext.tsx b/apps/web/src/components/timeline/TimelineContext.tsx
index 6c9db5a..69777c4 100644
--- a/apps/web/src/components/timeline/TimelineContext.tsx
+++ b/apps/web/src/components/timeline/TimelineContext.tsx
@@ -284,7 +284,7 @@ export function TimelineProvider({
       const d = new Date(sp);
       if (!isNaN(d.getTime())) return d;
     }
-    return addDays(today, -30);
+    return addDays(today, -90);
   });
   const [viewDays, setViewDays] = useState(() => {
     const sp = searchParams.get("days");
@@ -310,7 +310,7 @@ export function TimelineProvider({
         const d = new Date(spStart);
         if (!isNaN(d.getTime())) return d;
       }
-      return addDays(today, -30);
+      return addDays(today, -90);
     });
 
     const spDays = searchParams.get("days");
diff --git a/apps/web/src/components/timeline/TimelineView.tsx b/apps/web/src/components/timeline/TimelineView.tsx
index d515a11..8767b5b 100644
--- a/apps/web/src/components/timeline/TimelineView.tsx
+++ b/apps/web/src/components/timeline/TimelineView.tsx
@@ -2,7 +2,7 @@
 
 import { clsx } from "clsx";
 import { useSession } from "next-auth/react";
-import { useCallback, useEffect, useMemo, useRef, useState } from "react";
+import { useCallback, useEffect, useLayoutEffect, useMemo, useRef, useState } from "react";
 import { useAllocationHistory } from "~/hooks/useAllocationHistory.js";
 import { useProjectDragContext } from "~/hooks/useProjectDragContext.js";
 import { useTimelineDrag } from "~/hooks/useTimelineDrag.js";
@@ -685,15 +685,70 @@ function TimelineViewContent({
   const scrollRafRef = useRef<number | null>(null);
   const [scrollLeft, setScrollLeft] = useState(0);
 
+  // Pixels to add to scrollLeft after a left-extension re-render (prevents jump).
+  const pendingLeftCompensationPx = useRef(0);
+  // Flag: scroll viewport to today after the next viewStart-driven re-layout.
+  const pendingScrollToTodayRef = useRef(false);
+  // Guard reset on every real unmount (including Strict Mode fake-unmount) so the
+  // scroll-to-today fires correctly on remount.
+  const hasScrolledToTodayOnLoad = useRef(false);
+  useLayoutEffect(() => {
+    return () => {
+      hasScrolledToTodayOnLoad.current = false;
+    };
+  }, []);
+
+  // Scroll to today the first time the canvas is in the DOM (isInitialLoading → false).
+  // totalCanvasWidth is non-zero before data loads, so it can't be used as the trigger.
+  useLayoutEffect(() => {
+    if (isInitialLoading) return;
+    if (hasScrolledToTodayOnLoad.current) return;
+    const el = scrollContainerRef.current;
+    if (!el) return;
+    el.scrollLeft = toLeft(today);
+    hasScrolledToTodayOnLoad.current = true;
+  }, [isInitialLoading, toLeft, today]);
+
+  // Apply scroll compensation synchronously after the canvas grows (left-extend or Today button).
+  useLayoutEffect(() => {
+    const el = scrollContainerRef.current;
+    if (!el) return;
+    const px = pendingLeftCompensationPx.current;
+    if (px !== 0) {
+      el.scrollLeft += px;
+      pendingLeftCompensationPx.current = 0;
+    } else if (pendingScrollToTodayRef.current) {
+      el.scrollLeft = toLeft(today);
+      pendingScrollToTodayRef.current = false;
+    }
+  }, [viewStart, toLeft, today]);
+
+  // 5-year floor — no practical data exists further back; prevents runaway growth.
+  const minDate = useMemo(() => addDays(today, -(365 * 5)), [today]);
+
   // ─── Navigation callbacks for TimelineToolbar ────────────────────────────
   const handleNavigateBack = useCallback(
-    () => setViewStart((v) => addDays(v, -28)),
-    [setViewStart],
-  );
-  const handleNavigateToday = useCallback(
-    () => setViewStart(addDays(today, -30)),
-    [setViewStart, today],
+    () =>
+      setViewStart((v) => {
+        const candidate = addDays(v, -28);
+        return candidate < minDate ? minDate : candidate;
+      }),
+    [setViewStart, minDate],
   );
+  const handleNavigateToday = useCallback(() => {
+    const el = scrollContainerRef.current;
+    const todayMs = new Date(today).setHours(0, 0, 0, 0);
+    const vsMs = new Date(viewStart).setHours(0, 0, 0, 0);
+    const veMs = new Date(addDays(viewStart, viewDays)).setHours(0, 0, 0, 0);
+    if (todayMs >= vsMs && todayMs < veMs && el) {
+      // Today is in range — just scroll without touching state.
+      el.scrollLeft = toLeft(today);
+    } else {
+      // Today is out of range — reset the window and schedule a scroll.
+      pendingScrollToTodayRef.current = true;
+      setViewStart(addDays(today, -90));
+    }
+  }, [today, viewStart, viewDays, toLeft, setViewStart]);
   const handleNavigateForward = useCallback(
     () => setViewStart((v) => addDays(v, 28)),
     [setViewStart],
@@ -709,10 +764,31 @@ function TimelineViewContent({
   const handleContainerScroll = useCallback(() => {
     const el = scrollContainerRef.current;
     if (!el) return;
+
+    // Right-edge: extend future range
     const distanceFromRight = el.scrollWidth - el.scrollLeft - el.clientWidth;
     if (distanceFromRight < CELL_WIDTH * 40) {
       setViewDays((d) => d + 120);
     }
+
+    // Left-edge: prepend past range and compensate scroll position so viewport doesn't jump
+    if (el.scrollLeft < CELL_WIDTH * 40 && viewStart > minDate) {
+      const daysToPrepend = 120;
+      // Count the exact visible days (respecting showWeekends) being prepended
+      let prependedVisible = 0;
+      for (let i = 1; i <= daysToPrepend; i++) {
+        const d = addDays(viewStart, -i);
+        const dow = d.getDay();
+        if (filters.showWeekends || (dow !== 0 && dow !== 6)) prependedVisible++;
+      }
+      pendingLeftCompensationPx.current = prependedVisible * CELL_WIDTH;
+      setViewStart((v) => {
+        const candidate = addDays(v, -daysToPrepend);
+        return candidate < minDate ? minDate : candidate;
+      });
+      setViewDays((d) => d + daysToPrepend);
+    }
+
     scrollLeftRef.current = el.scrollLeft;
     if (scrollRafRef.current === null) {
       scrollRafRef.current = requestAnimationFrame(() => {
@@ -720,7 +796,7 @@ function TimelineViewContent({
         setScrollLeft(scrollLeftRef.current);
       });
     }
-  }, [CELL_WIDTH, setViewDays]);
+  }, [CELL_WIDTH, setViewDays, viewStart, minDate, setViewStart, filters.showWeekends]);
 
   // ─── Canvas mousemove — only forwards event when drag overlay is active ───
   const handleMouseMove = useCallback(