diff --git a/apps/web/src/components/chat/ChatComposer.tsx b/apps/web/src/components/chat/ChatComposer.tsx
index e3ae139110360fa257a13e5a5a6b92975aeb89fd..fafdee59e04292cf093a30de5eadcfc33bf5ce96 100644
--- a/apps/web/src/components/chat/ChatComposer.tsx
+++ b/apps/web/src/components/chat/ChatComposer.tsx
@@ -242,6 +242,7 @@ import { ProviderModelPicker } from "./ProviderModelPicker";
 import { type ComposerCommandItem, ComposerCommandMenu } from "./ComposerCommandMenu";
 import { ComposerPendingApprovalActions } from "./ComposerPendingApprovalActions";
 import { CompactComposerControlsMenu } from "./CompactComposerControlsMenu";
+import { ComposerImageThumbnail } from "./ComposerImageThumbnail";
 import { ComposerPrimaryActions } from "./ComposerPrimaryActions";
 import { ComposerPendingApprovalPanel } from "./ComposerPendingApprovalPanel";
 import { ComposerPendingUserInputPanel } from "./ComposerPendingUserInputPanel";
@@ -4673,7 +4674,19 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
             }}
           >
             {image.previewUrl ? (
-              <img src={image.previewUrl} alt="" className="size-full object-cover" />
+              <ComposerImageThumbnail
+                file={image.file}
+                alt=""
+                className="size-full object-cover"
+                fallback={
+                  <PierreEntryIcon
+                    pathValue={image.name}
+                    kind="file"
+                    theme={resolvedTheme}
+                    className="m-auto size-3.5"
+                  />
+                }
+              />
             ) : (
               <PierreEntryIcon
                 pathValue={image.name}
@@ -6287,10 +6300,15 @@ export const ChatComposer = memo(function ChatComposer(props: ChatComposerProps)
                                   onExpandImage(preview);
                                 }}
                               >
-                                <img
-                                  src={image.previewUrl}
+                                <ComposerImageThumbnail
+                                  file={image.file}
                                   alt={image.name}
                                   className="h-full w-full object-cover"
+                                  fallback={
+                                    <span className="flex h-full items-center justify-center px-1 text-[10px] text-secondary-label">
+                                      {image.name}
+                                    </span>
+                                  }
                                 />
                               </button>
                             ) : (
diff --git a/apps/web/src/components/chat/ComposerImageThumbnail.tsx b/apps/web/src/components/chat/ComposerImageThumbnail.tsx
new file mode 100644
index 0000000000000000000000000000000000000000..c803d5693009f180231cd44d2358ce30fadfb4c9
--- /dev/null
+++ b/apps/web/src/components/chat/ComposerImageThumbnail.tsx
@@ -0,0 +1,29 @@
+import { memo, useEffect, useState, type ReactNode } from "react";
+
+import { createComposerImageThumbnail } from "../../lib/imageCompression";
+
+/** Keep full-resolution image decoding out of composer rerenders. */
+export const ComposerImageThumbnail = memo(function ComposerImageThumbnail({
+  file,
+  alt,
+  className,
+  fallback,
+}: {
+  file: File;
+  alt: string;
+  className: string;
+  fallback: ReactNode;
+}) {
+  const [preview, setPreview] = useState<{ file: File; src: string | null } | null>(null);
+  useEffect(() => {
+    let active = true;
+    void createComposerImageThumbnail(file).then((src) => {
+      if (active) setPreview({ file, src });
+    });
+    return () => {
+      active = false;
+    };
+  }, [file]);
+  const src = preview?.file === file ? preview.src : null;
+  return src ? <img src={src} alt={alt} className={className} /> : fallback;
+});
diff --git a/apps/web/src/lib/imageCompression.test.ts b/apps/web/src/lib/imageCompression.test.ts
index 5c8952144f5ab7caeba26073b0b8e0471ae64f89..d83bc1ef87c184bfad26be11f96a9d157029c6df 100644
--- a/apps/web/src/lib/imageCompression.test.ts
+++ b/apps/web/src/lib/imageCompression.test.ts
@@ -1,6 +1,7 @@
 import { afterEach, describe, expect, it, vi } from "vite-plus/test";
 
 import {
+  createComposerImageThumbnail,
   compressImageForStash,
   compressImageToByteLimit,
   dataUrlToFile,
@@ -123,6 +124,65 @@ afterEach(() => {
   globalThis.OffscreenCanvas = originalOffscreenCanvas;
 });
 
+describe("composer image thumbnails", () => {
+  it("decodes a tall original once and caches a bounded center crop", async () => {
+    const close = vi.fn();
+    const bitmap = { width: 2304, height: 32766, close };
+    const decode = vi.fn(async () => bitmap);
+    const drawImage = vi.fn();
+    const dimensions: number[][] = [];
+    vi.stubGlobal("createImageBitmap", decode);
+    vi.stubGlobal(
+      "OffscreenCanvas",
+      class {
+        constructor(width: number, height: number) {
+          dimensions.push([width, height]);
+        }
+        getContext() {
+          return { drawImage };
+        }
+        async convertToBlob() {
+          return new Blob(["thumbnail"], { type: "image/png" });
+        }
+      },
+    );
+    const original = new File(["original bytes"], "tall.png", { type: "image/png" });
+    const [first, second] = await Promise.all([
+      createComposerImageThumbnail(original),
+      createComposerImageThumbnail(original),
+    ]);
+    expect(first).toBe("data:image/png;base64,dGh1bWJuYWls");
+    expect(second).toBe(first);
+    expect(await createComposerImageThumbnail(original)).toBe(first);
+    expect(decode).toHaveBeenCalledExactlyOnceWith(original);
+    expect(dimensions).toEqual([[256, 256]]);
+    expect(drawImage).toHaveBeenCalledWith(bitmap, 0, 15231, 2304, 2304, 0, 0, 256, 256);
+    expect(close).toHaveBeenCalledOnce();
+    expect(await original.text()).toBe("original bytes");
+  });
+
+  it("releases the decoded image when thumbnail encoding fails", async () => {
+    const close = vi.fn();
+    vi.stubGlobal(
+      "createImageBitmap",
+      vi.fn(async () => ({ width: 500, height: 500, close })),
+    );
+    vi.stubGlobal(
+      "OffscreenCanvas",
+      class {
+        getContext() {
+          return { drawImage: vi.fn() };
+        }
+        async convertToBlob() {
+          throw new Error("encoder unavailable");
+        }
+      },
+    );
+    expect(await createComposerImageThumbnail(makeFile(5))).toBeNull();
+    expect(close).toHaveBeenCalledOnce();
+  });
+});
+
 describe("dataUrlToFile", () => {
   it("decodes a captured image without a fetch request", async () => {
     const file = dataUrlToFile("data:image/png;base64,AAEC/w==", "window.png", "image/png");
diff --git a/apps/web/src/lib/imageCompression.ts b/apps/web/src/lib/imageCompression.ts
index af51001f7102edc867e993f29c048a7461b539a0..8414f190d5d9d64a913c51202919b3064b623963 100644
--- a/apps/web/src/lib/imageCompression.ts
+++ b/apps/web/src/lib/imageCompression.ts
@@ -247,6 +247,47 @@ async function encodeCanvas(
   return { dataUrl: await blobToDataUrl(blob, mimeType), mimeType };
 }
 
+const composerThumbnails = new WeakMap<File, Promise<string | null>>();
+
+/** Cache a centered square crop for the composer's object-cover image tiles. */
+export function createComposerImageThumbnail(file: File): Promise<string | null> {
+  const cached = composerThumbnails.get(file);
+  if (cached) return cached;
+  const thumbnail = (async () => {
+    if (!canRecompress()) return null;
+    let bitmap: ImageBitmap | undefined;
+    try {
+      bitmap = await createImageBitmap(file);
+      const side = Math.min(bitmap.width, bitmap.height);
+      if (side <= 0) return null;
+      const dimension = Math.min(256, side);
+      const surface = createCanvas(dimension, dimension);
+      if (!surface) return null;
+      surface.context.drawImage(
+        bitmap,
+        (bitmap.width - side) / 2,
+        (bitmap.height - side) / 2,
+        side,
+        side,
+        0,
+        0,
+        dimension,
+        dimension,
+      );
+      return (
+        (await encodeCanvas(surface.canvas, 1, "image/png", Number.POSITIVE_INFINITY))?.dataUrl ??
+        null
+      );
+    } catch {
+      return null;
+    } finally {
+      bitmap?.close();
+    }
+  })();
+  composerThumbnails.set(file, thumbnail);
+  return thumbnail;
+}
+
 /**
  * Draws `bitmap` scaled to fit `maxDimension` and encodes it, stepping
  * quality down until the data URL fits `budgetChars`.