diff --git a/web/src/components/chat/ChatPaperclipButton.tsx b/web/src/components/chat/ChatPaperclipButton.tsx
new file mode 100644
index 0000000000..fac39f3c6b
--- /dev/null
+++ b/web/src/components/chat/ChatPaperclipButton.tsx
@@ -0,0 +1,114 @@
+import { useState } from "react";
+import { useTranslation } from "react-i18next";
+import { LuPaperclip } from "react-icons/lu";
+import { useApiHost } from "@/api";
+import { Button } from "@/components/ui/button";
+import { Input } from "@/components/ui/input";
+import {
+  Popover,
+  PopoverContent,
+  PopoverTrigger,
+} from "@/components/ui/popover";
+
+const EVENT_ID_RE = /^[A-Za-z0-9._-]+$/;
+
+type ChatPaperclipButtonProps = {
+  recentEventIds: string[];
+  onAttach: (eventId: string) => void;
+  disabled?: boolean;
+};
+
+/**
+ * Paperclip button with a popover for picking an event to attach.
+ * Shows a grid of recent thumbnails (from the latest assistant message) and a
+ * "paste event ID" fallback input.
+ */
+export function ChatPaperclipButton({
+  recentEventIds,
+  onAttach,
+  disabled = false,
+}: ChatPaperclipButtonProps) {
+  const apiHost = useApiHost();
+  const { t } = useTranslation(["views/chat"]);
+  const [open, setOpen] = useState(false);
+  const [pasteId, setPasteId] = useState("");
+
+  const handlePickThumbnail = (eventId: string) => {
+    onAttach(eventId);
+    setOpen(false);
+    setPasteId("");
+  };
+
+  const handlePasteSubmit = () => {
+    const trimmed = pasteId.trim();
+    if (!trimmed || !EVENT_ID_RE.test(trimmed)) return;
+    onAttach(trimmed);
+    setOpen(false);
+    setPasteId("");
+  };
+
+  const handlePasteKeyDown = (e: React.KeyboardEvent<HTMLInputElement>) => {
+    if (e.key === "Enter") {
+      e.preventDefault();
+      handlePasteSubmit();
+    }
+  };
+
+  return (
+    <Popover open={open} onOpenChange={setOpen}>
+      <PopoverTrigger asChild>
+        <Button
+          variant="ghost"
+          size="icon"
+          className="size-10 shrink-0 rounded-full"
+          disabled={disabled}
+          aria-label={t("attachment_picker_placeholder")}
+        >
+          <LuPaperclip className="size-4" />
+        </Button>
+      </PopoverTrigger>
+      <PopoverContent className="w-72" align="start">
+        <div className="flex flex-col gap-3">
+          {recentEventIds.length > 0 && (
+            <div className="grid grid-cols-4 gap-2">
+              {recentEventIds.slice(0, 8).map((id) => (
+                <button
+                  key={id}
+                  type="button"
+                  onClick={() => handlePickThumbnail(id)}
+                  className="relative aspect-square overflow-hidden rounded-md ring-offset-background hover:ring-2 hover:ring-primary"
+                  aria-label={t("attach_event_aria", { eventId: id })}
+                >
+                  <img
+                    className="size-full object-cover"
+                    src={`${apiHost}api/events/${id}/thumbnail.webp`}
+                    alt=""
+                    loading="lazy"
+                  />
+                </button>
+              ))}
+            </div>
+          )}
+          <div className="flex items-center gap-2">
+            <Input
+              placeholder={t("attachment_picker_paste_label")}
+              value={pasteId}
+              onChange={(e) => setPasteId(e.target.value)}
+              onKeyDown={handlePasteKeyDown}
+              className="h-8 text-xs"
+            />
+            <Button
+              size="sm"
+              variant="select"
+              className="h-8"
+              disabled={!pasteId.trim() || !EVENT_ID_RE.test(pasteId.trim())}
+              onClick={handlePasteSubmit}
+            >
+              {t("attachment_picker_attach")}
+            </Button>
+          </div>
+        </div>
+      </PopoverContent>
+    </Popover>
+  );
+}