diff --git a/packages/app/src/agent-stream/strategy-web.test.tsx b/packages/app/src/agent-stream/strategy-web.test.tsx
index 3ef54b1c91..0204db41eb 100644
--- a/packages/app/src/agent-stream/strategy-web.test.tsx
+++ b/packages/app/src/agent-stream/strategy-web.test.tsx
@@ -428,6 +428,60 @@ describe("createWebStreamStrategy", () => {
     expect(onNearHistoryStart).toHaveBeenCalledTimes(2);
   });
 
+  it("loads older history when the current page projects no anchor row", async () => {
+    const strategy = createWebStreamStrategy({ isMobileBreakpoint: true });
+    const viewportRef = React.createRef<StreamViewportHandle>();
+    const onNearHistoryStart = vi.fn().mockReturnValue(true);
+    const renderInput: StreamRenderInput = {
+      agentId: "agent",
+      segments: {
+        historyVirtualized: [],
+        historyMounted: [],
+        liveHead: [],
+      },
+      boundary: {
+        hasVirtualizedHistory: false,
+        hasMountedHistory: false,
+        hasLiveHead: false,
+      },
+      renderers: createRenderers(vi.fn()),
+      listEmptyComponent: null,
+      viewportRef,
+      routeBottomAnchorRequest: null,
+      isAuthoritativeHistoryReady: true,
+      onNearBottomChange: vi.fn(),
+      onNearHistoryStart,
+      isLoadingOlderHistory: false,
+      hasOlderHistory: true,
+      olderHistoryProgressKey: "epoch-1:20",
+      scrollEnabled: true,
+      listStyle: null,
+      baseListContentContainerStyle: null,
+      forwardListContentContainerStyle: null,
+    };
+    container = document.createElement("div");
+    document.body.appendChild(container);
+    root = createRoot(container);
+
+    act(() => {
+      root?.render(strategy.render(renderInput));
+    });
+    const scrollContainer = container.querySelector('[data-testid="agent-chat-scroll"]');
+    if (!(scrollContainer instanceof HTMLElement)) {
+      throw new Error("Expected agent chat scroll container");
+    }
+    Object.defineProperty(scrollContainer, "clientHeight", { configurable: true, value: 1000 });
+    Object.defineProperty(scrollContainer, "scrollHeight", { configurable: true, value: 500 });
+    Object.defineProperty(scrollContainer, "scrollTop", { configurable: true, value: 0 });
+
+    await act(async () => {
+      await new Promise((resolve) => requestAnimationFrame(resolve));
+      await Promise.resolve();
+    });
+
+    expect(onNearHistoryStart).toHaveBeenCalledTimes(1);
+  });
+
   it("anchors prepended history independently from live content growth below it", async () => {
     let anchorTop = 0;
     let measuredScrollTop = 0;
diff --git a/packages/app/src/agent-stream/strategy-web.tsx b/packages/app/src/agent-stream/strategy-web.tsx
index dd341543bd..bc6966b18a 100644
--- a/packages/app/src/agent-stream/strategy-web.tsx
+++ b/packages/app/src/agent-stream/strategy-web.tsx
@@ -256,15 +256,16 @@ function WebStreamViewport(props: StreamRenderInput & { isMobileBreakpoint: bool
       const anchorRow = segments.historyMounted.at(-1) ?? segments.historyVirtualized.at(-1);
       const anchorElement =
         contentNode && anchorRow ? findHistoryRowElement(contentNode, anchorRow.id) : null;
-      if (!scrollContainer || !anchorRow || !anchorElement) {
-        return;
+      if (scrollContainer && anchorRow && anchorElement) {
+        historyStartPrependAnchorRef.current = {
+          progressKey: olderHistoryProgressKey,
+          rowId: anchorRow.id,
+          viewportOffset:
+            anchorElement.getBoundingClientRect().top - scrollContainer.getBoundingClientRect().top,
+        };
+      } else {
+        historyStartPrependAnchorRef.current = null;
       }
-      historyStartPrependAnchorRef.current = {
-        progressKey: olderHistoryProgressKey,
-        rowId: anchorRow.id,
-        viewportOffset:
-          anchorElement.getBoundingClientRect().top - scrollContainer.getBoundingClientRect().top,
-      };
       historyStartPrependAnchorActiveRef.current = false;
       const requestedProgressKey = olderHistoryProgressKey;
       void (async () => {
diff --git a/packages/app/src/assistant-image/acquisition-cache.test.ts b/packages/app/src/assistant-image/acquisition-cache.test.ts
index 6de05bd1ef..9a245f91fd 100644
--- a/packages/app/src/assistant-image/acquisition-cache.test.ts
+++ b/packages/app/src/assistant-image/acquisition-cache.test.ts
@@ -140,4 +140,26 @@ describe("assistant image acquisition cache", () => {
       released: ["attachment-1"],
     });
   });
+
+  it("does not evict a value while an active consumer retains it", async () => {
+    const released: string[] = [];
+    const cache = createAssistantImageAcquisitionCache<string>({
+      capacity: 1,
+      onRetain: (value) => () => released.push(value),
+    });
+
+    const first = cache.acquireRetained("first", async () => "attachment-1");
+    await first.promise;
+    const second = cache.acquireRetained("second", async () => "attachment-2");
+    await second.promise;
+
+    expect({ released, size: cache.size() }).toEqual({ released: [], size: 2 });
+
+    first.release();
+    expect({ released, size: cache.size() }).toEqual({
+      released: ["attachment-1"],
+      size: 1,
+    });
+    second.release();
+  });
 });
diff --git a/packages/app/src/assistant-image/acquisition-cache.ts b/packages/app/src/assistant-image/acquisition-cache.ts
index cbe3ade702..f76f594b88 100644
--- a/packages/app/src/assistant-image/acquisition-cache.ts
+++ b/packages/app/src/assistant-image/acquisition-cache.ts
@@ -2,6 +2,10 @@ import { createPreviewAttachmentId } from "@/attachments/utils";
 
 export interface AssistantImageAcquisitionCache<T> {
   acquire(key: string, locate: () => Promise<T>): Promise<T>;
+  acquireRetained(
+    key: string,
+    locate: () => Promise<T>,
+  ): { promise: Promise<T>; value?: T; release: () => void };
   peek(key: string): T | undefined;
   size(): number;
 }
@@ -53,6 +57,7 @@ export function createAssistantImageAcquisitionCache<T>(input: {
     resolved: boolean;
     value?: T;
     release: (() => void) | null;
+    activeConsumers: number;
   }
   const entries = new Map<string, CacheEntry>();
 
@@ -64,42 +69,79 @@ export function createAssistantImageAcquisitionCache<T>(input: {
     entry.release = null;
   };
 
+  const enforceCapacity = () => {
+    while (entries.size > input.capacity) {
+      let evicted = false;
+      for (const [key, entry] of entries) {
+        if (entry.activeConsumers > 0) {
+          continue;
+        }
+        evict(key, entry);
+        evicted = true;
+        break;
+      }
+      if (!evicted) {
+        return;
+      }
+    }
+  };
+
+  const acquireEntry = (key: string, locate: () => Promise<T>, retain: boolean): CacheEntry => {
+    const cached = entries.get(key);
+    if (cached) {
+      entries.delete(key);
+      entries.set(key, cached);
+      if (retain) {
+        cached.activeConsumers += 1;
+      }
+      return cached;
+    }
+    const pending = locate();
+    const entry: CacheEntry = {
+      pending,
+      resolved: false,
+      release: null,
+      activeConsumers: retain ? 1 : 0,
+    };
+    entries.set(key, entry);
+    enforceCapacity();
+    void (async () => {
+      try {
+        const value = await pending;
+        const release = input.onRetain?.(value) ?? null;
+        if (entries.get(key) === entry) {
+          entry.value = value;
+          entry.resolved = true;
+          entry.release = release;
+        } else {
+          release?.();
+        }
+      } catch {
+        evict(key, entry);
+      }
+    })();
+    return entry;
+  };
+
   return {
     acquire(key, locate) {
-      const cached = entries.get(key);
-      if (cached) {
-        entries.delete(key);
-        entries.set(key, cached);
-        return cached.pending;
-      }
-      const pending = locate();
-      const entry: CacheEntry = { pending, resolved: false, release: null };
-      entries.set(key, entry);
-      if (entries.size > input.capacity) {
-        const leastRecentlyUsedKey = entries.keys().next().value;
-        if (leastRecentlyUsedKey !== undefined) {
-          const leastRecentlyUsedEntry = entries.get(leastRecentlyUsedKey);
-          if (leastRecentlyUsedEntry) {
-            evict(leastRecentlyUsedKey, leastRecentlyUsedEntry);
+      return acquireEntry(key, locate, false).pending;
+    },
+    acquireRetained(key, locate) {
+      const entry = acquireEntry(key, locate, true);
+      let released = false;
+      return {
+        promise: entry.pending,
+        ...(entry.resolved ? { value: entry.value } : {}),
+        release() {
+          if (released) {
+            return;
           }
-        }
-      }
-      void (async () => {
-        try {
-          const value = await pending;
-          const release = input.onRetain?.(value) ?? null;
-          if (entries.get(key) === entry) {
-            entry.value = value;
-            entry.resolved = true;
-            entry.release = release;
-          } else {
-            release?.();
-          }
-        } catch {
-          evict(key, entry);
-        }
-      })();
-      return pending;
+          released = true;
+          entry.activeConsumers = Math.max(0, entry.activeConsumers - 1);
+          enforceCapacity();
+        },
+      };
     },
     peek(key) {
       const entry = entries.get(key);
diff --git a/packages/app/src/assistant-image/use-assistant-image.ts b/packages/app/src/assistant-image/use-assistant-image.ts
index ecf3d2a8b7..6dc714e1ff 100644
--- a/packages/app/src/assistant-image/use-assistant-image.ts
+++ b/packages/app/src/assistant-image/use-assistant-image.ts
@@ -1,4 +1,12 @@
-import { useCallback, useEffect, useMemo, useReducer, useRef, useState } from "react";
+import {
+  useCallback,
+  useEffect,
+  useLayoutEffect,
+  useMemo,
+  useReducer,
+  useRef,
+  useState,
+} from "react";
 import type { ImageLoadEvent } from "react-native";
 import { useTranslation } from "react-i18next";
 import type { DaemonClient } from "@getpaseo/client/internal/daemon-client";
@@ -301,16 +309,16 @@ function usePreviewUrl(attachment: AttachmentMetadata | null | undefined): Previ
       ? `${id}:${storageType}:${storageKey}:${mimeType}`
       : null;
   const [entry, setEntry] = useState<{ key: string | null; state: PreviewUrlState }>(() => {
-    const cached = previewKey ? previewUrlCache.peek(previewKey) : undefined;
     return {
       key: previewKey,
-      state: cached ? { status: "loaded", uri: cached.uri } : { status: "waiting" },
+      state: { status: "waiting" },
     };
   });
   const getCurrentAttachment = useStableEvent(() => attachment ?? null);
 
-  useEffect(() => {
+  useLayoutEffect(() => {
     let disposed = false;
+    let releaseCurrent: (() => void) | null = null;
     const current = getCurrentAttachment();
 
     if (!current || !previewKey) {
@@ -318,21 +326,34 @@ function usePreviewUrl(attachment: AttachmentMetadata | null | undefined): Previ
       return;
     }
 
-    const cached = previewUrlCache.peek(previewKey);
-    if (cached) {
-      setEntry({ key: previewKey, state: { status: "loaded", uri: cached.uri } });
-      return;
+    const acquireCurrent = () => {
+      releaseCurrent?.();
+      const retained = previewUrlCache.acquireRetained(previewKey, async () => ({
+        attachment: current,
+        uri: await resolveAttachmentPreviewUrl(current),
+      }));
+      releaseCurrent = retained.release;
+      return retained;
+    };
+    const initial = acquireCurrent();
+    if (initial.value) {
+      setEntry({ key: previewKey, state: { status: "loaded", uri: initial.value.uri } });
+      return () => {
+        disposed = true;
+        releaseCurrent?.();
+      };
     }
 
     setEntry({ key: previewKey, state: { status: "loading" } });
     void (async () => {
+      let firstAttempt: ReturnType<typeof acquireCurrent> | null = initial;
       try {
         const preview = await runAssistantImageOperationWithRetry({
-          operation: async () =>
-            await previewUrlCache.acquire(previewKey, async () => ({
-              attachment: current,
-              uri: await resolveAttachmentPreviewUrl(current),
-            })),
+          operation: async () => {
+            const retained = firstAttempt ?? acquireCurrent();
+            firstAttempt = null;
+            return await retained.promise;
+          },
           shouldStop: () => disposed,
         });
         if (!disposed) {
@@ -347,16 +368,13 @@ function usePreviewUrl(attachment: AttachmentMetadata | null | undefined): Previ
 
     return () => {
       disposed = true;
+      releaseCurrent?.();
     };
   }, [getCurrentAttachment, previewKey]);
 
   if (!previewKey) {
     return { status: "waiting" };
   }
-  const cached = previewUrlCache.peek(previewKey);
-  if (cached) {
-    return { status: "loaded", uri: cached.uri };
-  }
   return entry.key === previewKey ? entry.state : { status: "waiting" };
 }