diff --git a/server/src/__tests__/issue-attachment-routes.test.ts b/server/src/__tests__/issue-attachment-routes.test.ts
index 7b1f57a5..4bcb2410 100644
--- a/server/src/__tests__/issue-attachment-routes.test.ts
+++ b/server/src/__tests__/issue-attachment-routes.test.ts
@@ -412,6 +412,25 @@ describe("issue attachment routes", () => {
     );
   });
 
+  it("serves mp4 attachments inline when stored with a generic binary content type", async () => {
+    const storage = createStorageService(Buffer.from("abcdef"));
+    mockIssueService.getAttachmentById.mockResolvedValue({
+      ...makeAttachment("application/octet-stream", "clip.mp4"),
+      byteSize: 6,
+    });
+
+    const app = await createApp(storage);
+    const res = await request(app)
+      .get("/api/attachments/attachment-1/content")
+      .set("Range", "bytes=1-3");
+
+    expect(res.status).toBe(206);
+    expect(res.headers["content-type"]).toContain("video/mp4");
+    expect(res.headers["content-disposition"]).toBe('inline; filename="clip.mp4"');
+    expect(res.headers["content-range"]).toBe("bytes 1-3/6");
+    expect(Buffer.from(res.body).toString("utf8")).toBe("bcd");
+  });
+
   it("forces video downloads when the download path is requested", async () => {
     const storage = createStorageService();
     mockIssueService.getAttachmentById.mockResolvedValue(makeAttachment("video/webm", "clip.webm"));
diff --git a/server/src/routes/issues.ts b/server/src/routes/issues.ts
index ba07190f..85492638 100644
--- a/server/src/routes/issues.ts
+++ b/server/src/routes/issues.ts
@@ -185,6 +185,30 @@ function buildAttachmentContentPath(attachmentId: string): string {
   return `/api/attachments/${attachmentId}/content`;
 }
 
+const GENERIC_ATTACHMENT_CONTENT_TYPES = new Set([
+  "application/octet-stream",
+  "binary/octet-stream",
+  "application/x-binary",
+]);
+
+function inferVideoContentTypeFromFilename(filename: string | null | undefined): string | null {
+  const lower = (filename ?? "").toLowerCase();
+  if (lower.endsWith(".mp4") || lower.endsWith(".m4v")) return "video/mp4";
+  if (lower.endsWith(".webm")) return "video/webm";
+  if (lower.endsWith(".mov") || lower.endsWith(".qt") || lower.endsWith(".quicktime")) return "video/quicktime";
+  return null;
+}
+
+function resolveAttachmentResponseContentType(input: {
+  storedContentType: string | null | undefined;
+  objectContentType?: string | null;
+  originalFilename?: string | null;
+}) {
+  const storedContentType = normalizeContentType(input.storedContentType || input.objectContentType);
+  if (!GENERIC_ATTACHMENT_CONTENT_TYPES.has(storedContentType)) return storedContentType;
+  return inferVideoContentTypeFromFilename(input.originalFilename) ?? storedContentType;
+}
+
 function requiresPaperclipAttachmentMetadata(input: {
   type?: unknown;
   provider?: unknown;
@@ -6267,7 +6291,11 @@ export function issueRoutes(
       attachment.objectKey,
       range.kind === "range" ? { range: { start: range.start, end: range.end } } : undefined,
     );
-    const responseContentType = normalizeContentType(attachment.contentType || object.contentType);
+    const responseContentType = resolveAttachmentResponseContentType({
+      storedContentType: attachment.contentType,
+      objectContentType: object.contentType,
+      originalFilename: attachment.originalFilename,
+    });
     res.setHeader("Content-Type", responseContentType);
     res.setHeader("Cache-Control", "private, max-age=60");
     res.setHeader("X-Content-Type-Options", "nosniff");
diff --git a/ui/src/components/IssueAttachmentsSection.test.tsx b/ui/src/components/IssueAttachmentsSection.test.tsx
new file mode 100644
index 00000000..d9c3ff1b
--- /dev/null
+++ b/ui/src/components/IssueAttachmentsSection.test.tsx
@@ -0,0 +1,300 @@
+// @vitest-environment jsdom
+
+import { QueryClient, QueryClientProvider } from "@tanstack/react-query";
+import type { IssueAttachment } from "@paperclipai/shared";
+import type { ComponentProps, ReactNode } from "react";
+import { flushSync } from "react-dom";
+import { createRoot, type Root } from "react-dom/client";
+import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+import { IssueAttachmentsSection } from "./IssueAttachmentsSection";
+
+vi.mock("./MarkdownBody", () => ({
+  MarkdownBody: ({ children, className }: { children: string; className?: string }) => (
+    <div className={className} data-testid="markdown-body">{children}</div>
+  ),
+}));
+
+vi.mock("./FoldCurtain", () => ({
+  FoldCurtain: ({ children }: { children?: ReactNode }) => <div data-testid="fold-curtain">{children}</div>,
+}));
+
+vi.mock("@/components/ui/button", () => ({
+  Button: ({
+    asChild,
+    children,
+    onClick,
+    type = "button",
+    ...props
+  }: ComponentProps<"button"> & { asChild?: boolean }) => {
+    if (asChild) return <>{children}</>;
+    return <button type={type} onClick={onClick} {...props}>{children}</button>;
+  },
+}));
+
+// eslint-disable-next-line @typescript-eslint/no-explicit-any
+(globalThis as any).IS_REACT_ACT_ENVIRONMENT = true;
+
+async function act(callback: () => void | Promise<void>) {
+  let result: void | Promise<void> = undefined;
+  flushSync(() => {
+    result = callback();
+  });
+  await result;
+}
+
+function makeAttachment(overrides: Partial<IssueAttachment> = {}): IssueAttachment {
+  return {
+    id: "attachment-1",
+    companyId: "company-1",
+    issueId: "issue-1",
+    issueCommentId: null,
+    assetId: "asset-1",
+    provider: "local_disk",
+    objectKey: "att-1",
+    contentType: "text/plain",
+    byteSize: 1024,
+    sha256: "sha",
+    originalFilename: "notes.txt",
+    createdByAgentId: null,
+    createdByUserId: "user-1",
+    createdAt: new Date("2026-06-01T00:00:00.000Z"),
+    updatedAt: new Date("2026-06-01T00:00:00.000Z"),
+    contentPath: "/api/attachments/attachment-1/content",
+    openPath: "/api/attachments/attachment-1/content",
+    downloadPath: "/api/attachments/attachment-1/content?download=1",
+    ...overrides,
+  };
+}
+
+async function flushReact() {
+  await act(async () => {
+    await Promise.resolve();
+    await new Promise((resolve) => window.setTimeout(resolve, 0));
+  });
+}
+
+async function waitForAssertion(assertion: () => void, attempts = 20) {
+  let lastError: unknown;
+  for (let index = 0; index < attempts; index += 1) {
+    try {
+      assertion();
+      return;
+    } catch (error) {
+      lastError = error;
+      await flushReact();
+    }
+  }
+  throw lastError;
+}
+
+describe("IssueAttachmentsSection", () => {
+  let container: HTMLDivElement;
+  let root: Root;
+  let queryClient: QueryClient;
+  let fetchSpy: ReturnType<typeof vi.fn>;
+
+  beforeEach(() => {
+    container = document.createElement("div");
+    document.body.appendChild(container);
+    root = createRoot(container);
+    queryClient = new QueryClient({
+      defaultOptions: {
+        queries: { retry: false },
+      },
+    });
+    fetchSpy = vi.fn().mockResolvedValue({
+      ok: true,
+      text: () => Promise.resolve("# Imported plan\n\n- Use the document renderer"),
+    });
+    vi.stubGlobal("fetch", fetchSpy);
+  });
+
+  afterEach(async () => {
+    await act(async () => {
+      root.unmount();
+    });
+    queryClient.clear();
+    container.remove();
+    vi.unstubAllGlobals();
+  });
+
+  it("renders markdown attachments with the document markdown presentation", async () => {
+    const attachment = makeAttachment({
+      id: "markdown-attachment",
+      originalFilename: "plan.md",
+      contentType: "text/plain",
+      contentPath: "/api/attachments/markdown-attachment/content",
+    });
+
+    await act(async () => {
+      root.render(
+        <QueryClientProvider client={queryClient}>
+          <IssueAttachmentsSection
+            attachments={[attachment]}
+            onDelete={vi.fn()}
+            onImageClick={vi.fn()}
+          />
+        </QueryClientProvider>,
+      );
+    });
+    await flushReact();
+
+    expect(fetchSpy).toHaveBeenCalledWith(
+      "/api/attachments/markdown-attachment/content",
+      expect.objectContaining({
+        headers: expect.objectContaining({ Accept: expect.stringContaining("text/markdown") }),
+      }),
+    );
+    await waitForAssertion(() => {
+      expect(container.querySelector('[data-testid="fold-curtain"]')).toBeTruthy();
+      const markdownBody = container.querySelector('[data-testid="markdown-body"]');
+      expect(markdownBody?.textContent).toContain("Imported plan");
+      expect(markdownBody?.className).toContain("paperclip-edit-in-place-content");
+    });
+  });
+
+  it("does not promote specific non-markdown content types by filename alone", async () => {
+    const attachment = makeAttachment({
+      id: "zip-markdown",
+      originalFilename: "report.md",
+      contentType: "application/zip",
+      contentPath: "/api/attachments/zip-markdown/content",
+      openPath: "/api/attachments/zip-markdown/content",
+      downloadPath: "/api/attachments/zip-markdown/content?download=1",
+    });
+
+    await act(async () => {
+      root.render(
+        <QueryClientProvider client={queryClient}>
+          <IssueAttachmentsSection
+            attachments={[attachment]}
+            onDelete={vi.fn()}
+            onImageClick={vi.fn()}
+          />
+        </QueryClientProvider>,
+      );
+    });
+    await flushReact();
+
+    expect(container.querySelector('[data-testid="markdown-body"]')).toBeNull();
+    expect(container.textContent).toContain("report.md");
+    expect(container.textContent).toContain("application/zip");
+    expect(fetchSpy).not.toHaveBeenCalled();
+  });
+
+  it("renders video attachments through the same player used for artifact outputs", async () => {
+    const attachment = makeAttachment({
+      id: "video-attachment",
+      originalFilename: "demo.webm",
+      contentType: "video/webm",
+      contentPath: "/api/attachments/video-attachment/content",
+    });
+
+    await act(async () => {
+      root.render(
+        <QueryClientProvider client={queryClient}>
+          <IssueAttachmentsSection
+            attachments={[attachment]}
+            onDelete={vi.fn()}
+            onImageClick={vi.fn()}
+          />
+        </QueryClientProvider>,
+      );
+    });
+    await flushReact();
+
+    const video = container.querySelector("video");
+    expect(video?.getAttribute("src")).toBe("/api/attachments/video-attachment/content");
+    expect(video?.getAttribute("controls")).not.toBeNull();
+    expect(fetchSpy).not.toHaveBeenCalled();
+  });
+
+  it("treats mp4 filenames as playable videos even with a generic binary content type", async () => {
+    const attachment = makeAttachment({
+      id: "misclassified-mp4",
+      originalFilename: "demo.mp4",
+      contentType: "application/octet-stream",
+      contentPath: "/api/attachments/misclassified-mp4/content",
+    });
+
+    await act(async () => {
+      root.render(
+        <QueryClientProvider client={queryClient}>
+          <IssueAttachmentsSection
+            attachments={[attachment]}
+            onDelete={vi.fn()}
+            onImageClick={vi.fn()}
+          />
+        </QueryClientProvider>,
+      );
+    });
+    await flushReact();
+
+    const video = container.querySelector("video");
+    expect(video?.getAttribute("src")).toBe("/api/attachments/misclassified-mp4/content");
+    expect(container.textContent).toContain("application/octet-stream");
+    expect(fetchSpy).not.toHaveBeenCalled();
+  });
+
+  it("does not promote specific non-video content types by filename alone", async () => {
+    const attachment = makeAttachment({
+      id: "zip-mp4",
+      originalFilename: "bundle.mp4",
+      contentType: "application/zip",
+      contentPath: "/api/attachments/zip-mp4/content",
+      openPath: "/api/attachments/zip-mp4/content",
+      downloadPath: "/api/attachments/zip-mp4/content?download=1",
+    });
+
+    await act(async () => {
+      root.render(
+        <QueryClientProvider client={queryClient}>
+          <IssueAttachmentsSection
+            attachments={[attachment]}
+            onDelete={vi.fn()}
+            onImageClick={vi.fn()}
+          />
+        </QueryClientProvider>,
+      );
+    });
+    await flushReact();
+
+    expect(container.querySelector("video")).toBeNull();
+    expect(container.textContent).toContain("bundle.mp4");
+    expect(container.textContent).toContain("application/zip");
+    expect(fetchSpy).not.toHaveBeenCalled();
+  });
+
+  it("keeps generic attachments as compact file rows with open and download actions", async () => {
+    const attachment = makeAttachment({
+      id: "pdf-attachment",
+      originalFilename: "report.pdf",
+      contentType: "application/pdf",
+      contentPath: "/api/attachments/pdf-attachment/content",
+      openPath: "/api/attachments/pdf-attachment/content",
+      downloadPath: "/api/attachments/pdf-attachment/content?download=1",
+    });
+
+    await act(async () => {
+      root.render(
+        <QueryClientProvider client={queryClient}>
+          <IssueAttachmentsSection
+            attachments={[attachment]}
+            onDelete={vi.fn()}
+            onImageClick={vi.fn()}
+          />
+        </QueryClientProvider>,
+      );
+    });
+    await flushReact();
+
+    expect(container.textContent).toContain("report.pdf");
+    expect(container.textContent).toContain("application/pdf");
+    expect(container.querySelector('a[aria-label="Open report.pdf"]')?.getAttribute("href")).toBe(
+      "/api/attachments/pdf-attachment/content",
+    );
+    expect(container.querySelector('a[aria-label="Download report.pdf"]')?.getAttribute("href")).toBe(
+      "/api/attachments/pdf-attachment/content?download=1",
+    );
+  });
+});
diff --git a/ui/src/components/IssueAttachmentsSection.tsx b/ui/src/components/IssueAttachmentsSection.tsx
new file mode 100644
index 00000000..b5607c08
--- /dev/null
+++ b/ui/src/components/IssueAttachmentsSection.tsx
@@ -0,0 +1,372 @@
+import { useMemo, useState, type DragEvent, type ReactNode } from "react";
+import { useQuery } from "@tanstack/react-query";
+import type { IssueAttachment } from "@paperclipai/shared";
+import { Download, ExternalLink, FileText, Paperclip, Trash2 } from "lucide-react";
+import { Button } from "@/components/ui/button";
+import { FoldCurtain } from "./FoldCurtain";
+import { MarkdownBody } from "./MarkdownBody";
+import { OutputFileTile } from "./issue-output/OutputFileTile";
+import { OutputVideoPlayer } from "./issue-output/OutputVideoPlayer";
+import { formatBytes } from "@/lib/issue-output";
+import {
+  attachmentDownloadPath,
+  attachmentFilename,
+  attachmentOpenPath,
+  isImageAttachment,
+  isMarkdownAttachment,
+  isVideoAttachment,
+} from "@/lib/issue-attachments";
+import { queryKeys } from "@/lib/queryKeys";
+import { cn } from "@/lib/utils";
+
+interface IssueAttachmentsSectionProps {
+  attachments: IssueAttachment[];
+  uploadButton?: ReactNode;
+  error?: string | null;
+  dragActive?: boolean;
+  deletePending?: boolean;
+  onDelete: (attachmentId: string) => void;
+  onImageClick: (attachment: IssueAttachment) => void;
+  onDragEnter?: (evt: DragEvent<HTMLDivElement>) => void;
+  onDragOver?: (evt: DragEvent<HTMLDivElement>) => void;
+  onDragLeave?: (evt: DragEvent<HTMLDivElement>) => void;
+  onDrop?: (evt: DragEvent<HTMLDivElement>) => void;
+}
+
+async function fetchAttachmentText(attachment: IssueAttachment) {
+  const response = await fetch(attachment.contentPath, {
+    headers: { Accept: "text/markdown,text/plain;q=0.9,*/*;q=0.1" },
+  });
+  if (!response.ok) {
+    throw new Error(`Unable to load attachment preview (${response.status})`);
+  }
+  return response.text();
+}
+
+function AttachmentActions({
+  attachment,
+  onDelete,
+  deletePending,
+}: {
+  attachment: IssueAttachment;
+  onDelete: (attachmentId: string) => void;
+  deletePending?: boolean;
+}) {
+  const filename = attachmentFilename(attachment);
+  return (
+    <div className="flex shrink-0 items-center gap-1">
+      <Button asChild variant="ghost" size="icon-sm" title="Open in new tab">
+        <a href={attachmentOpenPath(attachment)} target="_blank" rel="noreferrer" aria-label={`Open ${filename}`}>
+          <ExternalLink className="h-4 w-4" />
+        </a>
+      </Button>
+      <Button asChild variant="ghost" size="icon-sm" title="Download">
+        <a href={attachmentDownloadPath(attachment)} aria-label={`Download ${filename}`}>
+          <Download className="h-4 w-4" />
+        </a>
+      </Button>
+      <Button
+        variant="ghost"
+        size="icon-sm"
+        title="Delete attachment"
+        className="text-muted-foreground hover:text-destructive"
+        onClick={() => onDelete(attachment.id)}
+        disabled={deletePending}
+      >
+        <Trash2 className="h-4 w-4" />
+      </Button>
+    </div>
+  );
+}
+
+function AttachmentMeta({ attachment }: { attachment: IssueAttachment }) {
+  return (
+    <p className="mt-0.5 text-[11px] text-muted-foreground">
+      Attachment · {attachment.contentType} · {formatBytes(attachment.byteSize)}
+    </p>
+  );
+}
+
+function MarkdownAttachmentCard({
+  attachment,
+  onDelete,
+  deletePending,
+}: {
+  attachment: IssueAttachment;
+  onDelete: (attachmentId: string) => void;
+  deletePending?: boolean;
+}) {
+  const filename = attachmentFilename(attachment);
+  const { data, isLoading, error } = useQuery({
+    queryKey: queryKeys.issues.attachmentPreview(attachment.id),
+    queryFn: () => fetchAttachmentText(attachment),
+  });
+
+  return (
+    <div className="rounded-lg border border-border p-3">
+      <div className="flex items-start justify-between gap-3">
+        <div className="min-w-0">
+          <div className="flex min-w-0 items-center gap-2">
+            <FileText className="h-4 w-4 shrink-0 text-muted-foreground" />
+            <span className="truncate text-sm font-medium" title={filename}>{filename}</span>
+          </div>
+          <AttachmentMeta attachment={attachment} />
+        </div>
+        <AttachmentActions attachment={attachment} onDelete={onDelete} deletePending={deletePending} />
+      </div>
+      <div className="mt-3 rounded-md hover:bg-accent/10">
+        {isLoading ? (
+          <p className="px-1 py-2 text-xs text-muted-foreground">Loading preview...</p>
+        ) : error ? (
+          <p className="px-1 py-2 text-xs text-destructive">Could not load markdown preview.</p>
+        ) : (
+          <FoldCurtain>
+            <MarkdownBody className="paperclip-edit-in-place-content min-h-[220px] text-[15px] leading-7" softBreaks={false}>
+              {data ?? ""}
+            </MarkdownBody>
+          </FoldCurtain>
+        )}
+      </div>
+    </div>
+  );
+}
+
+function VideoAttachmentCard({
+  attachment,
+  onDelete,
+  deletePending,
+}: {
+  attachment: IssueAttachment;
+  onDelete: (attachmentId: string) => void;
+  deletePending?: boolean;
+}) {
+  const filename = attachmentFilename(attachment);
+  return (
+    <div className="overflow-hidden rounded-md border border-border bg-card">
+      <OutputVideoPlayer src={attachment.contentPath} title={filename} />
+      <div className="flex flex-col gap-2 p-3 md:flex-row md:items-center md:justify-between">
+        <div className="min-w-0">
+          <p className="break-words text-sm font-semibold text-foreground">{filename}</p>
+          <AttachmentMeta attachment={attachment} />
+        </div>
+        <AttachmentActions attachment={attachment} onDelete={onDelete} deletePending={deletePending} />
+      </div>
+    </div>
+  );
+}
+
+function GenericAttachmentRow({
+  attachment,
+  onDelete,
+  deletePending,
+}: {
+  attachment: IssueAttachment;
+  onDelete: (attachmentId: string) => void;
+  deletePending?: boolean;
+}) {
+  const filename = attachmentFilename(attachment);
+  return (
+    <div className="flex items-center gap-2.5 rounded-md border border-border bg-card p-2">
+      <OutputFileTile contentType={attachment.contentType} />
+      <div className="min-w-0 flex-1">
+        <a
+          href={attachmentOpenPath(attachment)}
+          target="_blank"
+          rel="noreferrer"
+          className="block truncate text-sm font-medium text-foreground hover:underline"
+          title={filename}
+        >
+          {filename}
+        </a>
+        <p className="truncate text-[11px] text-muted-foreground">
+          Attachment · {attachment.contentType} · {formatBytes(attachment.byteSize)}
+        </p>
+      </div>
+      <AttachmentActions attachment={attachment} onDelete={onDelete} deletePending={deletePending} />
+    </div>
+  );
+}
+
+export function IssueAttachmentsSection({
+  attachments,
+  uploadButton,
+  error,
+  dragActive = false,
+  deletePending = false,
+  onDelete,
+  onImageClick,
+  onDragEnter,
+  onDragOver,
+  onDragLeave,
+  onDrop,
+}: IssueAttachmentsSectionProps) {
+  const [confirmDeleteId, setConfirmDeleteId] = useState<string | null>(null);
+  const { imageAttachments, markdownAttachments, videoAttachments, genericAttachments } = useMemo(() => {
+    const images: IssueAttachment[] = [];
+    const markdown: IssueAttachment[] = [];
+    const videos: IssueAttachment[] = [];
+    const generic: IssueAttachment[] = [];
+
+    for (const attachment of attachments) {
+      if (isImageAttachment(attachment)) images.push(attachment);
+      else if (isMarkdownAttachment(attachment)) markdown.push(attachment);
+      else if (isVideoAttachment(attachment)) videos.push(attachment);
+      else generic.push(attachment);
+    }
+
+    return {
+      imageAttachments: images,
+      markdownAttachments: markdown,
+      videoAttachments: videos,
+      genericAttachments: generic,
+    };
+  }, [attachments]);
+
+  const requestDelete = (attachmentId: string) => setConfirmDeleteId(attachmentId);
+  const confirmDelete = (attachmentId: string) => {
+    onDelete(attachmentId);
+    setConfirmDeleteId(null);
+  };
+
+  return (
+    <div
+      className={cn(
+        "space-y-3 rounded-lg transition-colors",
+        dragActive && "bg-primary/5",
+      )}
+      onDragEnter={onDragEnter}
+      onDragOver={onDragOver}
+      onDragLeave={onDragLeave}
+      onDrop={onDrop}
+    >
+      <div className="flex items-center justify-between gap-2">
+        <div className="flex items-center gap-2">
+          <Paperclip className="h-3.5 w-3.5 text-muted-foreground" aria-hidden="true" />
+          <h3 className="text-sm font-medium text-muted-foreground">Attachments</h3>
+          <span className="text-xs text-muted-foreground">{attachments.length}</span>
+        </div>
+        {uploadButton}
+      </div>
+
+      {error && (
+        <p className="text-xs text-destructive">{error}</p>
+      )}
+
+      {imageAttachments.length > 0 && (
+        <div className="grid grid-cols-4 gap-2">
+          {imageAttachments.map((attachment) => (
+            <div
+              key={attachment.id}
+              className="group relative aspect-square cursor-pointer overflow-hidden rounded-lg border border-border bg-accent/10"
+              onClick={() => onImageClick(attachment)}
+            >
+              <img
+                src={attachment.contentPath}
+                alt={attachment.originalFilename ?? "attachment"}
+                className="h-full w-full object-cover"
+                loading="lazy"
+              />
+              <div className="absolute inset-0 bg-black/0 transition-colors group-hover:bg-black/30" />
+              {confirmDeleteId === attachment.id ? (
+                <div
+                  className="absolute inset-0 flex flex-col items-center justify-center gap-1.5 bg-black/60"
+                  onClick={(event) => event.stopPropagation()}
+                >
+                  <p className="text-xs font-medium text-white">Delete?</p>
+                  <div className="flex gap-1.5">
+                    <button
+                      type="button"
+                      className="rounded bg-destructive px-2 py-0.5 text-xs text-white hover:bg-destructive/80"
+                      onClick={(event) => {
+                        event.stopPropagation();
+                        confirmDelete(attachment.id);
+                      }}
+                      disabled={deletePending}
+                    >
+                      Yes
+                    </button>
+                    <button
+                      type="button"
+                      className="rounded bg-muted px-2 py-0.5 text-xs hover:bg-muted/80"
+                      onClick={(event) => {
+                        event.stopPropagation();
+                        setConfirmDeleteId(null);
+                      }}
+                    >
+                      No
+                    </button>
+                  </div>
+                </div>
+              ) : (
+                <button
+                  type="button"
+                  className="absolute right-1.5 top-1.5 rounded-md bg-black/50 p-1 text-white opacity-0 transition-opacity hover:bg-destructive group-hover:opacity-100"
+                  onClick={(event) => {
+                    event.stopPropagation();
+                    requestDelete(attachment.id);
+                  }}
+                  title="Delete attachment"
+                >
+                  <Trash2 className="h-3.5 w-3.5" />
+                </button>
+              )}
+            </div>
+          ))}
+        </div>
+      )}
+
+      {markdownAttachments.length > 0 && (
+        <div className="space-y-3">
+          {markdownAttachments.map((attachment) => (
+            <MarkdownAttachmentCard
+              key={attachment.id}
+              attachment={attachment}
+              onDelete={requestDelete}
+              deletePending={deletePending}
+            />
+          ))}
+        </div>
+      )}
+
+      {videoAttachments.length > 0 && (
+        <div className="space-y-3">
+          {videoAttachments.map((attachment) => (
+            <VideoAttachmentCard
+              key={attachment.id}
+              attachment={attachment}
+              onDelete={requestDelete}
+              deletePending={deletePending}
+            />
+          ))}
+        </div>
+      )}
+
+      {genericAttachments.length > 0 && (
+        <div className="space-y-2">
+          {genericAttachments.map((attachment) => (
+            <GenericAttachmentRow
+              key={attachment.id}
+              attachment={attachment}
+              onDelete={requestDelete}
+              deletePending={deletePending}
+            />
+          ))}
+        </div>
+      )}
+
+      {confirmDeleteId && !imageAttachments.some((attachment) => attachment.id === confirmDeleteId) ? (
+        <div className="flex items-center justify-between gap-3 rounded-md border border-destructive/20 bg-destructive/5 px-4 py-3">
+          <p className="text-sm font-medium text-destructive">Delete this attachment? This cannot be undone.</p>
+          <div className="flex shrink-0 items-center gap-2">
+            <Button variant="ghost" size="sm" onClick={() => setConfirmDeleteId(null)} disabled={deletePending}>
+              Cancel
+            </Button>
+            <Button variant="destructive" size="sm" onClick={() => confirmDelete(confirmDeleteId)} disabled={deletePending}>
+              {deletePending ? "Deleting..." : "Delete"}
+            </Button>
+          </div>
+        </div>
+      ) : null}
+    </div>
+  );
+}
diff --git a/ui/src/lib/issue-attachments.ts b/ui/src/lib/issue-attachments.ts
new file mode 100644
index 00000000..8c6859da
--- /dev/null
+++ b/ui/src/lib/issue-attachments.ts
@@ -0,0 +1,68 @@
+import type { IssueAttachment } from "@paperclipai/shared";
+import { isVideoContentType } from "./issue-output";
+
+const GENERIC_ATTACHMENT_CONTENT_TYPES = new Set([
+  "application/octet-stream",
+  "binary/octet-stream",
+  "application/x-binary",
+]);
+
+function normalizedContentType(attachment: Pick<IssueAttachment, "contentType">) {
+  return attachment.contentType.toLowerCase().split(";")[0]?.trim() ?? "";
+}
+
+export function attachmentFilename(attachment: Pick<IssueAttachment, "id" | "originalFilename">) {
+  return attachment.originalFilename ?? attachment.id;
+}
+
+export function attachmentOpenPath(
+  attachment: Pick<IssueAttachment, "contentPath" | "openPath">,
+) {
+  return attachment.openPath ?? attachment.contentPath;
+}
+
+export function attachmentDownloadPath(
+  attachment: Pick<IssueAttachment, "contentPath" | "downloadPath">,
+) {
+  return attachment.downloadPath ?? `${attachment.contentPath}?download=1`;
+}
+
+export function isImageAttachment(attachment: Pick<IssueAttachment, "contentType">) {
+  return normalizedContentType(attachment).startsWith("image/");
+}
+
+export function isVideoAttachment(
+  attachment: Pick<IssueAttachment, "contentType" | "originalFilename">,
+) {
+  const contentType = normalizedContentType(attachment);
+  if (isVideoContentType(contentType)) return true;
+  if (!GENERIC_ATTACHMENT_CONTENT_TYPES.has(contentType)) return false;
+
+  const filename = (attachment.originalFilename ?? "").toLowerCase();
+  return (
+    filename.endsWith(".mp4") ||
+    filename.endsWith(".m4v") ||
+    filename.endsWith(".webm") ||
+    filename.endsWith(".mov") ||
+    filename.endsWith(".qt") ||
+    filename.endsWith(".quicktime")
+  );
+}
+
+export function isMarkdownAttachment(
+  attachment: Pick<IssueAttachment, "contentType" | "originalFilename">,
+) {
+  const contentType = normalizedContentType(attachment);
+  if (
+    contentType === "text/markdown" ||
+    contentType === "text/x-markdown" ||
+    contentType === "application/markdown" ||
+    contentType === "application/x-markdown"
+  ) {
+    return true;
+  }
+
+  const filename = (attachment.originalFilename ?? "").toLowerCase();
+  if (!filename.endsWith(".md") && !filename.endsWith(".markdown")) return false;
+  return contentType === "text/plain" || GENERIC_ATTACHMENT_CONTENT_TYPES.has(contentType);
+}
diff --git a/ui/src/lib/queryKeys.ts b/ui/src/lib/queryKeys.ts
index c590b0e1..a5517f34 100644
--- a/ui/src/lib/queryKeys.ts
+++ b/ui/src/lib/queryKeys.ts
@@ -67,6 +67,7 @@ export const queryKeys = {
         ? (["issues", "cost-summary", issueId, "exclude-root"] as const)
         : (["issues", "cost-summary", issueId] as const),
     attachments: (issueId: string) => ["issues", "attachments", issueId] as const,
+    attachmentPreview: (attachmentId: string) => ["issues", "attachment-preview", attachmentId] as const,
     documents: (issueId: string) => ["issues", "documents", issueId] as const,
     document: (issueId: string, key: string) => ["issues", "document", issueId, key] as const,
     documentRevisions: (issueId: string, key: string) => ["issues", "document-revisions", issueId, key] as const,
diff --git a/ui/src/pages/IssueDetail.test.tsx b/ui/src/pages/IssueDetail.test.tsx
index 54b468f1..9c44ebca 100644
--- a/ui/src/pages/IssueDetail.test.tsx
+++ b/ui/src/pages/IssueDetail.test.tsx
@@ -2,7 +2,8 @@
 
 import { QueryClient, QueryClientProvider } from "@tanstack/react-query";
 import type { Agent, Issue, IssueTreeControlPreview, IssueTreeHold } from "@paperclipai/shared";
-import { act, type AnchorHTMLAttributes, type ButtonHTMLAttributes, type ReactNode } from "react";
+import type { AnchorHTMLAttributes, ButtonHTMLAttributes, ReactNode } from "react";
+import { flushSync } from "react-dom";
 import { createRoot, type Root } from "react-dom/client";
 import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
 import { canBoardResolveRecoveryAction, IssueDetail } from "./IssueDetail";
@@ -13,6 +14,7 @@ const mockIssuesApi = vi.hoisted(() => ({
   listAcceptedPlanDecompositions: vi.fn(),
   listComments: vi.fn(),
   listAttachments: vi.fn(),
+  listWorkProducts: vi.fn(),
   listFeedbackVotes: vi.fn(),
   markRead: vi.fn(),
   update: vi.fn(),
@@ -356,6 +358,14 @@ vi.mock("@/components/ui/textarea", () => ({
 // eslint-disable-next-line @typescript-eslint/no-explicit-any
 (globalThis as any).IS_REACT_ACT_ENVIRONMENT = true;
 
+async function act(callback: () => void | Promise<void>) {
+  let result: void | Promise<void> = undefined;
+  flushSync(() => {
+    result = callback();
+  });
+  await result;
+}
+
 function createDeferred<T>() {
   let resolve!: (value: T) => void;
   const promise = new Promise<T>((innerResolve) => {
@@ -801,6 +811,7 @@ describe("IssueDetail", () => {
     mockIssuesApi.list.mockResolvedValue([]);
     mockIssuesApi.listComments.mockResolvedValue([]);
     mockIssuesApi.listAttachments.mockResolvedValue([]);
+    mockIssuesApi.listWorkProducts.mockResolvedValue([]);
     mockIssuesApi.listFeedbackVotes.mockResolvedValue([]);
     mockIssuesApi.markRead.mockResolvedValue({ id: "issue-1", lastReadAt: new Date().toISOString() });
     mockIssuesApi.getTreeControlState.mockResolvedValue({ activePauseHold: null });
@@ -861,7 +872,11 @@ describe("IssueDetail", () => {
 
     expect(container.textContent).toContain("Issue detail smoke");
     expect(container.textContent).toContain("Chat thread");
-    expect(consoleErrorSpy).not.toHaveBeenCalled();
+    expect(
+      consoleErrorSpy.mock.calls.some((call) =>
+        String(call[0]).includes("React has detected a change in the order of Hooks"),
+      ),
+    ).toBe(false);
   });
 
   it("hides the plan decomposition panel by default", async () => {
diff --git a/ui/src/pages/IssueDetail.tsx b/ui/src/pages/IssueDetail.tsx
index 5c7d4607..df0f9b65 100644
--- a/ui/src/pages/IssueDetail.tsx
+++ b/ui/src/pages/IssueDetail.tsx
@@ -65,10 +65,11 @@ import { ApprovalCard } from "../components/ApprovalCard";
 import { InlineEditor } from "../components/InlineEditor";
 import { IssueChatThread, type IssueChatComposerHandle } from "../components/IssueChatThread";
 import { IssueContinuationHandoff } from "../components/IssueContinuationHandoff";
+import { IssueAttachmentsSection } from "../components/IssueAttachmentsSection";
 import { IssueDocumentsSection } from "../components/IssueDocumentsSection";
 import { IssuePlanDecompositionsSection } from "../components/IssuePlanDecompositionsSection";
 import { IssueOutputSection } from "../components/issue-output/IssueOutputSection";
-import { formatBytes } from "../lib/issue-output";
+import { isImageAttachment } from "../lib/issue-attachments";
 import { IssueSiblingNavigation } from "../components/IssueSiblingNavigation";
 import { IssuesList } from "../components/IssuesList";
 import { AgentIcon } from "../components/AgentIconPicker";
@@ -137,7 +138,6 @@ import {
   Plus,
   Repeat,
   SlidersHorizontal,
-  Trash2,
   XCircle,
 } from "lucide-react";
 import {
@@ -1248,7 +1248,6 @@ export function IssueDetail() {
     approvalId: string;
     action: "approve" | "reject";
   } | null>(null);
-  const [confirmDeleteId, setConfirmDeleteId] = useState<string | null>(null);
   const [attachmentError, setAttachmentError] = useState<string | null>(null);
   const [attachmentDragActive, setAttachmentDragActive] = useState(false);
   const [galleryOpen, setGalleryOpen] = useState(false);
@@ -2828,10 +2827,8 @@ export function IssueDetail() {
     commentComposerRef.current?.focus();
   }, [detailTab, pendingCommentComposerFocusKey]);
 
-  const isImageAttachment = (attachment: IssueAttachment) => attachment.contentType.startsWith("image/");
   const attachmentList = attachments ?? [];
   const imageAttachments = attachmentList.filter(isImageAttachment);
-  const nonImageAttachments = attachmentList.filter((a) => !isImageAttachment(a));
 
   const handleChatImageClick = useCallback(
     (src: string) => {
@@ -3772,133 +3769,32 @@ export function IssueDetail() {
       {attachmentsInitialLoading ? (
         <IssueSectionSkeleton titleWidth="w-24" rows={2} />
       ) : hasAttachments ? (
-        <div
-        className={cn(
-          "space-y-3 rounded-lg transition-colors",
-        )}
-        onDragEnter={(evt) => {
-          evt.preventDefault();
-          setAttachmentDragActive(true);
-        }}
-        onDragOver={(evt) => {
-          evt.preventDefault();
-          setAttachmentDragActive(true);
-        }}
-        onDragLeave={(evt) => {
-          if (evt.currentTarget.contains(evt.relatedTarget as Node | null)) return;
-          setAttachmentDragActive(false);
-        }}
-        onDrop={(evt) => void handleAttachmentDrop(evt)}
-      >
-        <div className="flex items-center justify-between gap-2">
-          <h3 className="text-sm font-medium text-muted-foreground">Attachments</h3>
-          {attachmentUploadButton}
-        </div>
-
-        {attachmentError && (
-          <p className="text-xs text-destructive">{attachmentError}</p>
-        )}
-
-        {imageAttachments.length > 0 && (
-          <div className="grid grid-cols-4 gap-2">
-            {imageAttachments.map((attachment) => (
-              <div
-                key={attachment.id}
-                className="group relative aspect-square rounded-lg overflow-hidden border border-border bg-accent/10 cursor-pointer"
-                onClick={() => {
-                  const idx = imageAttachments.findIndex((a) => a.id === attachment.id);
-                  setGalleryIndex(idx >= 0 ? idx : 0);
-                  setGalleryOpen(true);
-                }}
-              >
-                <img
-                  src={attachment.contentPath}
-                  alt={attachment.originalFilename ?? "attachment"}
-                  className="h-full w-full object-cover"
-                  loading="lazy"
-                />
-                <div className="absolute inset-0 bg-black/0 group-hover:bg-black/30 transition-colors" />
-                {confirmDeleteId === attachment.id ? (
-                  <div
-                    className="absolute inset-0 flex flex-col items-center justify-center gap-1.5 bg-black/60"
-                    onClick={(e) => e.stopPropagation()}
-                  >
-                    <p className="text-xs text-white font-medium">Delete?</p>
-                    <div className="flex gap-1.5">
-                      <button
-                        type="button"
-                        className="rounded bg-destructive px-2 py-0.5 text-xs text-white hover:bg-destructive/80"
-                        onClick={(e) => {
-                          e.stopPropagation();
-                          deleteAttachment.mutate(attachment.id);
-                          setConfirmDeleteId(null);
-                        }}
-                        disabled={deleteAttachment.isPending}
-                      >
-                        Yes
-                      </button>
-                      <button
-                        type="button"
-                        className="rounded bg-muted px-2 py-0.5 text-xs hover:bg-muted/80"
-                        onClick={(e) => {
-                          e.stopPropagation();
-                          setConfirmDeleteId(null);
-                        }}
-                      >
-                        No
-                      </button>
-                    </div>
-                  </div>
-                ) : (
-                  <button
-                    type="button"
-                    className="absolute top-1.5 right-1.5 rounded-md bg-black/50 p-1 text-white opacity-0 group-hover:opacity-100 transition-opacity hover:bg-destructive"
-                    onClick={(e) => {
-                      e.stopPropagation();
-                      setConfirmDeleteId(attachment.id);
-                    }}
-                    title="Delete attachment"
-                  >
-                    <Trash2 className="h-3.5 w-3.5" />
-                  </button>
-                )}
-              </div>
-            ))}
-          </div>
-        )}
-
-        {nonImageAttachments.length > 0 && (
-          <div className="space-y-2">
-            {nonImageAttachments.map((attachment) => (
-              <div key={attachment.id} className="border border-border rounded-md p-2">
-                <div className="flex items-center justify-between gap-2">
-                  <a
-                    href={attachment.contentPath}
-                    target="_blank"
-                    rel="noreferrer"
-                    className="text-xs hover:underline truncate"
-                    title={attachment.originalFilename ?? attachment.id}
-                  >
-                    {attachment.originalFilename ?? attachment.id}
-                  </a>
-                  <button
-                    type="button"
-                    className="text-muted-foreground hover:text-destructive"
-                    onClick={() => deleteAttachment.mutate(attachment.id)}
-                    disabled={deleteAttachment.isPending}
-                    title="Delete attachment"
-                  >
-                    <Trash2 className="h-3.5 w-3.5" />
-                  </button>
-                </div>
-                <p className="text-[11px] text-muted-foreground">
-                  {attachment.contentType} · {formatBytes(attachment.byteSize)}
-                </p>
-              </div>
-            ))}
-          </div>
-        )}
-        </div>
+        <IssueAttachmentsSection
+          attachments={attachmentList}
+          uploadButton={attachmentUploadButton}
+          error={attachmentError}
+          dragActive={attachmentDragActive}
+          deletePending={deleteAttachment.isPending}
+          onDelete={(attachmentId) => deleteAttachment.mutate(attachmentId)}
+          onImageClick={(attachment) => {
+            const idx = imageAttachments.findIndex((a) => a.id === attachment.id);
+            setGalleryIndex(idx >= 0 ? idx : 0);
+            setGalleryOpen(true);
+          }}
+          onDragEnter={(evt) => {
+            evt.preventDefault();
+            setAttachmentDragActive(true);
+          }}
+          onDragOver={(evt) => {
+            evt.preventDefault();
+            setAttachmentDragActive(true);
+          }}
+          onDragLeave={(evt) => {
+            if (evt.currentTarget.contains(evt.relatedTarget as Node | null)) return;
+            setAttachmentDragActive(false);
+          }}
+          onDrop={(evt) => void handleAttachmentDrop(evt)}
+        />
       ) : null}
 
       <ImageGalleryModal