diff --git a/plane-src/apps/web/core/components/issues/attachment/attachment-item-list.tsx b/plane-src/apps/web/core/components/issues/attachment/attachment-item-list.tsx
index 0ac4db8..e05096b 100644
--- a/plane-src/apps/web/core/components/issues/attachment/attachment-item-list.tsx
+++ b/plane-src/apps/web/core/components/issues/attachment/attachment-item-list.tsx
@@ -59,7 +59,8 @@ export const IssueAttachmentItemList = observer(function IssueAttachmentItemList
   // file size
   const { maxFileSize } = useFileSize();
   // derived values
-  const issueAttachments = getAttachmentsByIssueId(issueId);
+  const issueAttachments = getAttachmentsByIssueId(issueId) ?? [];
+  const hasAttachmentRows = issueAttachments.length > 0 || !!uploadStatus?.length;
 
   // handlers
   const handleFetchPropertyActivities = useCallback(() => {
@@ -68,80 +69,96 @@ export const IssueAttachmentItemList = observer(function IssueAttachmentItemList
 
   const onDrop = useCallback(
     (acceptedFiles: File[], rejectedFiles: FileRejection[]) => {
-      const totalAttachedFiles = acceptedFiles.length + rejectedFiles.length;
-
-      if (rejectedFiles.length === 0) {
-        const currentFile: File = acceptedFiles[0];
-        if (!currentFile || !workspaceSlug) return;
-
+      if (acceptedFiles.length > 0) {
+        if (!workspaceSlug) return;
         setIsUploading(true);
-        createAttachment(currentFile)
-          .catch(() => {
-            setToast({
-              type: TOAST_TYPE.ERROR,
-              title: t("toast.error"),
-              message: t("attachment.error"),
-            });
+
+        Promise.allSettled(acceptedFiles.map((file) => createAttachment(file)))
+          .then((results) => {
+            const failedUploads = results.filter((result) => result.status === "rejected").length;
+            if (failedUploads > 0)
+              setToast({
+                type: TOAST_TYPE.ERROR,
+                title: t("toast.error"),
+                message: t("attachment.error"),
+              });
+            return undefined;
           })
           .finally(() => {
             handleFetchPropertyActivities();
             setIsUploading(false);
           });
-        return;
       }
 
-      setToast({
-        type: TOAST_TYPE.ERROR,
-        title: t("toast.error"),
-        message:
-          totalAttachedFiles > 1
-            ? t("attachment.only_one_file_allowed")
-            : t("attachment.file_size_limit", { size: maxFileSize / 1024 / 1024 }),
-      });
+      if (rejectedFiles.length > 0)
+        setToast({
+          type: TOAST_TYPE.ERROR,
+          title: t("toast.error"),
+          message: t("attachment.file_size_limit", { size: maxFileSize / 1024 / 1024 }),
+        });
+
       return;
     },
-    [createAttachment, maxFileSize, workspaceSlug, handleFetchPropertyActivities]
+    [createAttachment, maxFileSize, workspaceSlug, handleFetchPropertyActivities, t]
   );
 
-  const { getRootProps, getInputProps, isDragActive } = useDropzone({
+  const { getRootProps, getInputProps, isDragActive, isDragReject } = useDropzone({
     onDrop,
     maxSize: maxFileSize,
-    multiple: false,
+    multiple: true,
     disabled: isUploading || disabled,
   });
 
   return (
-    <>
-      {uploadStatus?.map((uploadStatus) => (
-        <IssueAttachmentsUploadItem key={uploadStatus.id} uploadStatus={uploadStatus} />
-      ))}
-      {issueAttachments && (
-        <>
-          {attachmentDeleteModalId && (
-            <IssueAttachmentDeleteModal
-              isOpen={Boolean(attachmentDeleteModalId)}
-              onClose={() => toggleDeleteAttachmentModal(null)}
-              attachmentOperations={attachmentOperations}
-              attachmentId={attachmentDeleteModalId}
-              issueServiceType={issueServiceType}
-            />
-          )}
-          <div
-            {...getRootProps()}
-            className={`relative flex flex-col ${isDragActive && issueAttachments.length < 3 ? "min-h-[200px]" : ""} ${disabled ? "cursor-not-allowed" : "cursor-pointer"}`}
-          >
-            <input {...getInputProps()} />
-            {isDragActive && (
-              <div className="absolute top-0 left-0 z-30 flex h-full w-full items-center justify-center bg-surface-2/75">
-                <div className="flex items-center justify-center rounded-md bg-surface-1 p-1">
-                  <div className="flex flex-col items-center justify-center rounded-md border border-dashed border-strong px-5 py-6">
-                    <UploadCloud className="size-7" />
-                    <span className="text-13 text-tertiary">{t("attachment.drag_and_drop")}</span>
-                  </div>
-                </div>
-              </div>
-            )}
-            {issueAttachments?.map((attachmentId) => (
+    <div className="space-y-3">
+      {attachmentDeleteModalId && (
+        <IssueAttachmentDeleteModal
+          isOpen={Boolean(attachmentDeleteModalId)}
+          onClose={() => toggleDeleteAttachmentModal(null)}
+          attachmentOperations={attachmentOperations}
+          attachmentId={attachmentDeleteModalId}
+          issueServiceType={issueServiceType}
+        />
+      )}
+
+      <div
+        {...getRootProps()}
+        data-drag-active={isDragActive ? "true" : "false"}
+        data-drag-reject={isDragReject ? "true" : "false"}
+        className={`nodedc-attachment-upload flex w-full items-center justify-between gap-4 px-5 py-4 ${
+          disabled ? "cursor-not-allowed opacity-70" : "cursor-pointer"
+        }`}
+      >
+        <input {...getInputProps()} />
+        <div className="flex min-w-0 items-center gap-4">
+          <div className="grid size-11 flex-shrink-0 place-items-center rounded-2xl bg-[rgba(var(--nodedc-accent-rgb),0.14)] text-[rgb(var(--nodedc-accent-rgb))]">
+            <UploadCloud className="size-5" />
+          </div>
+          <div className="min-w-0">
+            <div className="truncate text-14 font-semibold text-primary">
+              {isDragActive ? "Отпустите файлы здесь" : "Перетащите файлы сюда или нажмите для выбора"}
+            </div>
+            <div className="mt-1 truncate text-12 text-tertiary">
+              Любой формат, несколько файлов за раз, до {maxFileSize / 1024 / 1024} МБ на файл
+            </div>
+          </div>
+        </div>
+        <div className="hidden flex-shrink-0 rounded-full bg-[rgba(var(--nodedc-accent-rgb),0.12)] px-3 py-1 text-12 font-semibold text-[rgb(var(--nodedc-accent-rgb))] sm:block">
+          Выбрать
+        </div>
+      </div>
+
+      {hasAttachmentRows && (
+        <div className="rounded-[1.35rem] border border-subtle bg-surface-1/60 p-3 shadow-[0_12px_28px_rgba(0,0,0,0.08)]">
+          <div className="mb-2 flex items-center justify-between gap-3 px-1">
+            <div className="text-12 font-semibold uppercase tracking-[0.08em] text-tertiary">Вложения</div>
+            <div className="text-12 text-tertiary">{issueAttachments.length}</div>
+          </div>
+          <div className="flex gap-3 overflow-x-auto pb-1">
+            {uploadStatus?.map((status) => (
+              <IssueAttachmentsUploadItem key={status.id} uploadStatus={status} />
+            ))}
+            {issueAttachments.map((attachmentId) => (
               <IssueAttachmentsListItem
                 key={attachmentId}
                 attachmentId={attachmentId}
@@ -150,8 +167,8 @@ export const IssueAttachmentItemList = observer(function IssueAttachmentItemList
               />
             ))}
           </div>
-        </>
+        </div>
       )}
-    </>
+    </div>
   );
 });
diff --git a/plane-src/apps/web/core/components/issues/attachment/attachment-list-item.tsx b/plane-src/apps/web/core/components/issues/attachment/attachment-list-item.tsx
index ca396aa..2b467fe 100644
--- a/plane-src/apps/web/core/components/issues/attachment/attachment-list-item.tsx
+++ b/plane-src/apps/web/core/components/issues/attachment/attachment-list-item.tsx
@@ -5,6 +5,7 @@
  */
 
 import { observer } from "mobx-react";
+import { useState } from "react";
 
 import { useTranslation } from "@plane/i18n";
 import { getIconButtonStyling } from "@plane/propel/icon-button";
@@ -14,8 +15,9 @@ import type { TIssueServiceType } from "@plane/types";
 import { EIssueServiceType } from "@plane/types";
 // ui
 import type { TContextMenuItem } from "@plane/ui";
-import { ActionDropdown } from "@plane/ui";
+import { ActionDropdown, EModalPosition, EModalWidth, ModalCore } from "@plane/ui";
 import { convertBytesToSize, getFileExtension, getFileName, getFileURL, renderFormattedDate } from "@plane/utils";
+import { Download, FileText, ImageIcon, Play, X } from "lucide-react";
 // components
 //
 import { ButtonAvatars } from "@/components/dropdowns/member/avatar";
@@ -32,6 +34,18 @@ type TIssueAttachmentsListItem = {
   issueServiceType?: TIssueServiceType;
 };
 
+const IMAGE_EXTENSIONS = new Set(["apng", "avif", "bmp", "gif", "jpg", "jpeg", "png", "svg", "webp"]);
+const VIDEO_EXTENSIONS = new Set(["avi", "m4v", "mov", "mp4", "mpeg", "mpg", "ogv", "webm"]);
+const PDF_EXTENSIONS = new Set(["pdf"]);
+
+const getPreviewType = (extension: string) => {
+  const normalizedExtension = extension.toLowerCase();
+  if (IMAGE_EXTENSIONS.has(normalizedExtension)) return "image";
+  if (VIDEO_EXTENSIONS.has(normalizedExtension)) return "video";
+  if (PDF_EXTENSIONS.has(normalizedExtension)) return "pdf";
+  return "file";
+};
+
 export const IssueAttachmentsListItem = observer(function IssueAttachmentsListItem(props: TIssueAttachmentsListItem) {
   const { t } = useTranslation();
   // props
@@ -46,8 +60,11 @@ export const IssueAttachmentsListItem = observer(function IssueAttachmentsListIt
   const attachment = attachmentId ? getAttachmentById(attachmentId) : undefined;
   const fileName = getFileName(attachment?.attributes.name ?? "");
   const fileExtension = getFileExtension(attachment?.attributes.name ?? "");
-  const fileIcon = getFileIcon(fileExtension, 18);
+  const fullFileName = fileExtension ? `${fileName}.${fileExtension}` : fileName;
+  const previewType = getPreviewType(fileExtension);
+  const fileIcon = getFileIcon(fileExtension, 32);
   const fileURL = getFileURL(attachment?.asset_url ?? "");
+  const [isPreviewOpen, setIsPreviewOpen] = useState(false);
   const menuItems: TContextMenuItem[] = [
     {
       key: "delete",
@@ -64,56 +81,135 @@ export const IssueAttachmentsListItem = observer(function IssueAttachmentsListIt
   if (!attachment) return <></>;
 
   return (
-    <div
-      role="button"
-      tabIndex={0}
-      onClick={(e) => {
-        e.preventDefault();
-        e.stopPropagation();
-        window.open(fileURL, "_blank");
-      }}
-      onKeyDown={(e) => {
-        if (e.key === "Enter" || e.key === " ") {
-          e.preventDefault();
-          e.stopPropagation();
-          window.open(fileURL, "_blank");
-        }
-      }}
-    >
-      <div className="group flex h-11 items-center justify-between gap-3 pr-2 pl-9 hover:bg-surface-2">
-          <div className="flex items-center gap-3 truncate text-13">
-            <div className="flex items-center gap-3">{fileIcon}</div>
-            <Tooltip tooltipContent={`${fileName}.${fileExtension}`} isMobile={isMobile}>
-              <p className="truncate font-medium text-secondary">{`${fileName}.${fileExtension}`}</p>
-            </Tooltip>
-            <span className="flex size-1.5 rounded-full bg-layer-1" />
-            <span className="flex-shrink-0 text-placeholder">{convertBytesToSize(attachment.attributes.size)}</span>
-          </div>
-
-          <div className="flex items-center gap-3">
-            {attachment?.created_by && (
+    <>
+      <div className="group flex h-32 w-72 flex-shrink-0 overflow-hidden rounded-2xl border border-subtle bg-surface-2/80 transition hover:border-[rgba(var(--nodedc-accent-rgb),0.45)] hover:bg-surface-2">
+        <button
+          type="button"
+          className="flex min-w-0 flex-1 items-stretch text-left"
+          onClick={(e) => {
+            e.preventDefault();
+            e.stopPropagation();
+            setIsPreviewOpen(true);
+          }}
+        >
+          <div className="relative h-full w-28 flex-shrink-0 overflow-hidden bg-surface-1">
+            {previewType === "image" && fileURL ? (
+              <img src={fileURL} alt={fullFileName} className="h-full w-full object-cover" loading="lazy" />
+            ) : previewType === "video" && fileURL ? (
               <>
-                <Tooltip
-                  isMobile={isMobile}
-                  tooltipContent={`${
-                    getUserDetails(attachment?.created_by)?.display_name ?? ""
-                  } uploaded on ${renderFormattedDate(attachment.updated_at)}`}
-                >
-                  <div className="flex items-center justify-center">
-                    <ButtonAvatars showTooltip userIds={attachment?.created_by} />
-                  </div>
-                </Tooltip>
+                <video src={fileURL} className="h-full w-full object-cover" muted playsInline preload="metadata" />
+                <div className="absolute inset-0 grid place-items-center bg-black/20 text-white">
+                  <Play className="size-6 fill-current" />
+                </div>
               </>
+            ) : previewType === "pdf" && fileURL ? (
+              <div className="flex h-full w-full items-center justify-center bg-white text-red-500">
+                <FileText className="size-9" />
+              </div>
+            ) : (
+              <div className="flex h-full w-full items-center justify-center">
+                {previewType === "file" ? fileIcon : <ImageIcon className="size-8 text-tertiary" />}
+              </div>
             )}
-
-            <ActionDropdown
-              items={menuItems}
-              buttonClassName={getIconButtonStyling("ghost", "sm")}
-              placement="bottom-end"
-              disabled={!!disabled}
-            />
           </div>
+
+          <div className="flex min-w-0 flex-1 flex-col justify-between p-3">
+            <div className="min-w-0">
+              <Tooltip tooltipContent={fullFileName} isMobile={isMobile}>
+                <p className="line-clamp-2 text-13 font-semibold text-secondary">{fullFileName}</p>
+              </Tooltip>
+              <div className="mt-2 flex items-center gap-2 text-11 text-tertiary">
+                <span>{fileExtension ? fileExtension.toUpperCase() : "FILE"}</span>
+                <span className="size-1 rounded-full bg-layer-1" />
+                <span>{convertBytesToSize(attachment.attributes.size)}</span>
+              </div>
+            </div>
+
+            {attachment?.created_by && (
+              <Tooltip
+                isMobile={isMobile}
+                tooltipContent={`${
+                  getUserDetails(attachment?.created_by)?.display_name ?? ""
+                } uploaded on ${renderFormattedDate(attachment.updated_at)}`}
+              >
+                <div className="flex w-fit items-center justify-center">
+                  <ButtonAvatars showTooltip userIds={attachment?.created_by} />
+                </div>
+              </Tooltip>
+            )}
+          </div>
+        </button>
+
+        <div className="flex w-10 flex-shrink-0 items-start justify-center pt-2">
+          <ActionDropdown
+            items={menuItems}
+            buttonClassName={getIconButtonStyling("ghost", "sm")}
+            placement="bottom-end"
+            disabled={!!disabled}
+          />
+        </div>
       </div>
-    </div>
+
+      <ModalCore
+        isOpen={isPreviewOpen}
+        handleClose={() => setIsPreviewOpen(false)}
+        position={EModalPosition.CENTER}
+        width={EModalWidth.VIXL}
+        className="overflow-hidden border border-subtle bg-surface-1"
+      >
+        <div className="relative min-h-[55vh] bg-surface-1 p-4">
+          <div className="absolute top-4 right-4 z-10 flex items-center gap-2">
+            {fileURL && (
+              <a
+                href={fileURL}
+                download={fullFileName}
+                target="_blank"
+                rel="noopener noreferrer"
+                className="grid size-10 place-items-center rounded-full bg-[rgb(var(--nodedc-accent-rgb))] text-[rgb(var(--nodedc-on-accent-rgb))] shadow-[0_14px_30px_rgba(0,0,0,0.3)] transition hover:brightness-110"
+                onClick={(e) => e.stopPropagation()}
+              >
+                <Download className="size-5" />
+              </a>
+            )}
+            <button
+              type="button"
+              className="grid size-10 place-items-center rounded-full bg-black/35 text-white backdrop-blur-md transition hover:bg-black/50"
+              onClick={() => setIsPreviewOpen(false)}
+            >
+              <X className="size-5" />
+            </button>
+          </div>
+
+          <div className="pr-24">
+            <div className="text-15 font-semibold text-primary">{fullFileName}</div>
+            <div className="mt-1 text-12 text-tertiary">{convertBytesToSize(attachment.attributes.size)}</div>
+          </div>
+
+          <div className="mt-4 flex h-[70vh] max-h-[70vh] items-center justify-center overflow-hidden rounded-2xl bg-black/20">
+            {previewType === "image" && fileURL ? (
+              <img src={fileURL} alt={fullFileName} className="max-h-full max-w-full object-contain" />
+            ) : previewType === "video" && fileURL ? (
+              <video src={fileURL} className="max-h-full max-w-full" controls autoPlay>
+                <track kind="captions" />
+              </video>
+            ) : previewType === "pdf" && fileURL ? (
+              <iframe
+                title={fullFileName}
+                src={fileURL}
+                sandbox="allow-downloads allow-same-origin"
+                className="h-full w-full rounded-2xl bg-white"
+              />
+            ) : (
+              <div className="flex flex-col items-center gap-4 p-8 text-center">
+                <div className="grid size-20 place-items-center rounded-3xl bg-surface-2">{fileIcon}</div>
+                <div className="max-w-md text-14 text-secondary">
+                  Предпросмотр для этого формата недоступен. Файл можно скачать или открыть в новой вкладке.
+                </div>
+              </div>
+            )}
+          </div>
+        </div>
+      </ModalCore>
+    </>
   );
 });
diff --git a/plane-src/apps/web/core/components/issues/attachment/attachment-list-upload-item.tsx b/plane-src/apps/web/core/components/issues/attachment/attachment-list-upload-item.tsx
index 4b16d8a..cbd6c2f 100644
--- a/plane-src/apps/web/core/components/issues/attachment/attachment-list-upload-item.tsx
+++ b/plane-src/apps/web/core/components/issues/attachment/attachment-list-upload-item.tsx
@@ -32,18 +32,21 @@ export const IssueAttachmentsUploadItem = observer(function IssueAttachmentsUplo
   const { isMobile } = usePlatformOS();
 
   return (
-    <div className="pointer-events-none flex h-11 items-center justify-between gap-3 bg-surface-2 pr-2 pl-9">
-      <div className="flex items-center gap-3 truncate text-13">
-        <div className="flex-shrink-0">{fileIcon}</div>
-        <Tooltip tooltipContent={fileName} isMobile={isMobile}>
-          <p className="truncate font-medium text-secondary">{fileName}</p>
-        </Tooltip>
+    <div className="pointer-events-none flex h-24 w-64 flex-shrink-0 items-center justify-between gap-3 rounded-2xl border border-subtle bg-surface-2 px-3 py-2">
+      <div className="flex min-w-0 items-center gap-3 text-13">
+        <div className="grid size-12 flex-shrink-0 place-items-center rounded-xl bg-surface-1">{fileIcon}</div>
+        <div className="min-w-0">
+          <Tooltip tooltipContent={fileName} isMobile={isMobile}>
+            <p className="truncate font-medium text-secondary">{fileName}</p>
+          </Tooltip>
+          <p className="mt-1 text-11 text-tertiary">Загрузка</p>
+        </div>
       </div>
-      <div className="flex flex-shrink-0 items-center gap-2">
+      <div className="flex flex-shrink-0 flex-col items-center gap-1">
         <span className="flex-shrink-0">
           <CircularProgressIndicator size={20} strokeWidth={3} percentage={uploadStatus.progress} />
         </span>
-        <div className="flex-shrink-0 text-13 font-medium">{uploadStatus.progress}% done</div>
+        <div className="flex-shrink-0 text-11 font-medium text-secondary">{uploadStatus.progress}%</div>
       </div>
     </div>
   );
diff --git a/plane-src/apps/web/core/components/issues/issue-detail-widgets/issue-detail-widget-collapsibles.tsx b/plane-src/apps/web/core/components/issues/issue-detail-widgets/issue-detail-widget-collapsibles.tsx
index 8f741ad..7fc036a 100644
--- a/plane-src/apps/web/core/components/issues/issue-detail-widgets/issue-detail-widget-collapsibles.tsx
+++ b/plane-src/apps/web/core/components/issues/issue-detail-widgets/issue-detail-widget-collapsibles.tsx
@@ -49,8 +49,8 @@ export const IssueDetailWidgetCollapsibles = observer(function IssueDetailWidget
   const attachmentUploads = getAttachmentsUploadStatusByIssueId(issueId);
   const attachmentsCount = getAttachmentsCountByIssueId(issueId);
   const shouldRenderAttachments =
-    attachmentsCount > 0 ||
-    (!!attachmentUploads && attachmentUploads.length > 0 && !hideWidgets?.includes("attachments"));
+    !hideWidgets?.includes("attachments") &&
+    (attachmentsCount > 0 || (!!attachmentUploads && attachmentUploads.length > 0));
 
   return (
     <div className="flex flex-col">
diff --git a/plane-src/apps/web/core/components/issues/issue-detail-widgets/root.tsx b/plane-src/apps/web/core/components/issues/issue-detail-widgets/root.tsx
index b918945..8b091c5 100644
--- a/plane-src/apps/web/core/components/issues/issue-detail-widgets/root.tsx
+++ b/plane-src/apps/web/core/components/issues/issue-detail-widgets/root.tsx
@@ -8,6 +8,7 @@ import React from "react";
 // plane imports
 import type { TIssueServiceType, TWorkItemWidgets } from "@plane/types";
 // local imports
+import { IssueAttachmentsCollapsibleContent } from "./attachments/content";
 import { IssueDetailWidgetActionButtons } from "./action-buttons";
 import { IssueDetailWidgetCollapsibles } from "./issue-detail-widget-collapsibles";
 import { IssueDetailWidgetModals } from "./issue-detail-widget-modals";
@@ -34,6 +35,9 @@ export function IssueDetailWidgets(props: Props) {
     hideWidgets,
     compactView = false,
   } = props;
+  const hideWidgetsWithInlineAttachments = hideWidgets?.includes("attachments")
+    ? hideWidgets
+    : ([...(hideWidgets ?? []), "attachments"] as TWorkItemWidgets[]);
 
   return (
     <>
@@ -44,16 +48,25 @@ export function IssueDetailWidgets(props: Props) {
           issueId={issueId}
           disabled={disabled}
           issueServiceType={issueServiceType}
-          hideWidgets={hideWidgets}
+          hideWidgets={hideWidgetsWithInlineAttachments}
           compactView={compactView}
         />
+        {!hideWidgets?.includes("attachments") && (
+          <IssueAttachmentsCollapsibleContent
+            workspaceSlug={workspaceSlug}
+            projectId={projectId}
+            issueId={issueId}
+            disabled={disabled}
+            issueServiceType={issueServiceType}
+          />
+        )}
         <IssueDetailWidgetCollapsibles
           workspaceSlug={workspaceSlug}
           projectId={projectId}
           issueId={issueId}
           disabled={disabled}
           issueServiceType={issueServiceType}
-          hideWidgets={hideWidgets}
+          hideWidgets={hideWidgetsWithInlineAttachments}
         />
       </div>
       {renderWidgetModals && (