diff --git a/packages/app/src/pages/session.tsx b/packages/app/src/pages/session.tsx
index 1c9391e0fdcf..5516d2ae13c6 100644
--- a/packages/app/src/pages/session.tsx
+++ b/packages/app/src/pages/session.tsx
@@ -62,6 +62,7 @@ import {
 import { MessageTimeline } from "@/pages/session/timeline/message-timeline"
 import { createTimelineModel } from "@/pages/session/timeline/model"
 import { type DiffStyle, SessionReviewTab, type SessionReviewTabProps } from "@/pages/session/review-tab"
+import { shouldFillLoad, shouldScrollLoad } from "@/pages/session/session-fill"
 import { useSessionLayout } from "@/pages/session/session-layout"
 import { syncSessionModel } from "@/pages/session/session-model-helpers"
 import { SessionSidePanel } from "@/pages/session/session-side-panel"
@@ -1229,13 +1230,40 @@ export default function Page() {
 
       const el = scroller
       if (!el) return
-      if (el.scrollHeight > el.clientHeight + 1) return
-      if (!historyMore()) return
+      if (
+        !shouldFillLoad({
+          historyMore: historyMore(),
+          scrollHeight: el.scrollHeight,
+          clientHeight: el.clientHeight,
+          messageCount: messages().length,
+        })
+      )
+        return
 
       void loadOlder()
     })
   }
 
+  makeEventListener(
+    () => scroller,
+    "scroll",
+    () => {
+      const el = scroller
+      if (!el) return
+      if (!params.id) return
+      if (
+        !shouldScrollLoad({
+          scrollTop: el.scrollTop,
+          historyMore: historyMore(),
+          historyLoading: historyLoading(),
+        })
+      )
+        return
+      void loadOlder()
+    },
+    { passive: true },
+  )
+
   createEffect(
     on(
       () =>
diff --git a/packages/app/src/pages/session/session-fill.test.ts b/packages/app/src/pages/session/session-fill.test.ts
new file mode 100644
index 000000000000..f1a2d5f4b292
--- /dev/null
+++ b/packages/app/src/pages/session/session-fill.test.ts
@@ -0,0 +1,56 @@
+import { describe, expect, test } from "bun:test"
+import { shouldFillLoad, shouldScrollLoad } from "./session-fill"
+
+describe("shouldFillLoad", () => {
+  test("returns false when historyMore is false, regardless of viewport state", () => {
+    expect(shouldFillLoad({ historyMore: false, scrollHeight: 100, clientHeight: 200, messageCount: 1 })).toBe(false)
+    expect(shouldFillLoad({ historyMore: false, scrollHeight: 300, clientHeight: 200, messageCount: 10 })).toBe(false)
+    expect(shouldFillLoad({ historyMore: false, scrollHeight: 200, clientHeight: 200, messageCount: 0 })).toBe(false)
+  })
+
+  test("returns true when viewport is not full (scrollHeight <= clientHeight + 1)", () => {
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 200, clientHeight: 200, messageCount: 0 })).toBe(true)
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 201, clientHeight: 200, messageCount: 0 })).toBe(true)
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 100, clientHeight: 200, messageCount: 5 })).toBe(true)
+  })
+
+  test("returns true when viewport is full but messageCount is <= 2 (fix: session switch with few messages)", () => {
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 300, clientHeight: 200, messageCount: 0 })).toBe(true)
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 300, clientHeight: 200, messageCount: 1 })).toBe(true)
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 300, clientHeight: 200, messageCount: 2 })).toBe(true)
+  })
+
+  test("returns false when viewport is full and messageCount > 2 (normal case, no fill needed)", () => {
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 300, clientHeight: 200, messageCount: 3 })).toBe(false)
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 300, clientHeight: 200, messageCount: 10 })).toBe(false)
+    expect(shouldFillLoad({ historyMore: true, scrollHeight: 500, clientHeight: 200, messageCount: 100 })).toBe(false)
+  })
+})
+
+describe("shouldScrollLoad", () => {
+  test("returns false when scrollTop >= 200", () => {
+    expect(shouldScrollLoad({ scrollTop: 200, historyMore: true, historyLoading: false })).toBe(false)
+    expect(shouldScrollLoad({ scrollTop: 500, historyMore: true, historyLoading: false })).toBe(false)
+    expect(shouldScrollLoad({ scrollTop: 200, historyMore: true, historyLoading: false })).toBe(false)
+  })
+
+  test("returns true when scrollTop < 200 and historyMore is true and not loading", () => {
+    expect(shouldScrollLoad({ scrollTop: 0, historyMore: true, historyLoading: false })).toBe(true)
+    expect(shouldScrollLoad({ scrollTop: 100, historyMore: true, historyLoading: false })).toBe(true)
+    expect(shouldScrollLoad({ scrollTop: 199, historyMore: true, historyLoading: false })).toBe(true)
+  })
+
+  test("returns false when historyMore is false, even at the top", () => {
+    expect(shouldScrollLoad({ scrollTop: 0, historyMore: false, historyLoading: false })).toBe(false)
+    expect(shouldScrollLoad({ scrollTop: 10, historyMore: false, historyLoading: false })).toBe(false)
+  })
+
+  test("returns false when historyLoading is true, even at the top", () => {
+    expect(shouldScrollLoad({ scrollTop: 0, historyMore: true, historyLoading: true })).toBe(false)
+    expect(shouldScrollLoad({ scrollTop: 50, historyMore: true, historyLoading: true })).toBe(false)
+  })
+
+  test("returns false when both historyMore is false and historyLoading is true", () => {
+    expect(shouldScrollLoad({ scrollTop: 0, historyMore: false, historyLoading: true })).toBe(false)
+  })
+})
\ No newline at end of file
diff --git a/packages/app/src/pages/session/session-fill.ts b/packages/app/src/pages/session/session-fill.ts
new file mode 100644
index 000000000000..5e6e7b6731e0
--- /dev/null
+++ b/packages/app/src/pages/session/session-fill.ts
@@ -0,0 +1,38 @@
+/**
+ * Determines whether the fill mechanism should trigger loading older messages.
+ * Used when the scroll viewport is not fully filled with content.
+ *
+ * Returns true when:
+ * - There is more history to load, AND
+ * - Either the viewport is not full (scrollHeight <= clientHeight + 1), OR
+ *   the message count is small (<= 2, to handle session switch scenarios)
+ */
+export function shouldFillLoad(input: {
+  historyMore: boolean
+  scrollHeight: number
+  clientHeight: number
+  messageCount: number
+}): boolean {
+  if (!input.historyMore) return false
+  if (input.scrollHeight > input.clientHeight + 1 && input.messageCount > 2) return false
+  return true
+}
+
+/**
+ * Determines whether scrolling near the top of the timeline should trigger
+ * loading older messages. Used as a guard in the scroll event handler.
+ *
+ * Returns true when:
+ * - The scroll position is near the top (scrollTop < 200), AND
+ * - There is more history to load, AND
+ * - History is not currently loading
+ */
+export function shouldScrollLoad(input: {
+  scrollTop: number
+  historyMore: boolean
+  historyLoading: boolean
+}): boolean {
+  if (input.scrollTop >= 200) return false
+  if (!input.historyMore || input.historyLoading) return false
+  return true
+}
\ No newline at end of file