From cda534a75d4bf6648f052f45f5bacc166c48dd23 Mon Sep 17 00:00:00 2001
From: WeiCHEN <weichen@WeiCHENdeMac-mini.local>
Date: Fri, 11 Sep 2026 13:00:34 +0800
Subject: [PATCH] feat(web): improve chat attachments, unread marks, and
 session UX

Support richer attachment payloads in input area, local read-id cache for
unread badges, and expand private-shared and chronology test coverage.

Co-authored-by: Cursor <cursoragent@cursor.com>
---
 web/src/api/chatWindow.ts                     |   3 +-
 web/src/components/chat/InputArea.tsx         | 214 ++++++++++++++----
 web/src/hooks/useChatWindow.ts                |  43 +++-
 web/src/hooks/useUnreadMarks.ts               |  79 +++++--
 web/src/tests/urs-private-shared.test.ts      | 112 +++++++++
 .../tests/workflow-chat-chronology.test.ts    |  43 ++++
 web/src/types/workbench.ts                    |  17 ++
 7 files changed, 440 insertions(+), 71 deletions(-)

diff --git a/web/src/api/chatWindow.ts b/web/src/api/chatWindow.ts
index 8fb0e5ba..991eb254 100644
--- a/web/src/api/chatWindow.ts
+++ b/web/src/api/chatWindow.ts
@@ -59,8 +59,9 @@ export function mapRecordToMessage(r: RawChatMessageRecord): ChatMessage {
     : new Date().toTimeString().substring(0, 5);
 
   const meta = r.metadata || {};
+  const msgId = meta.client_id || (r.id ? `msg-${r.id}` : `msg-tmp-${Date.now()}-${Math.random().toString(36).substring(2, 6)}`);
   return {
-    id: r.id ? `msg-${r.id}` : `msg-tmp-${Date.now()}-${Math.random().toString(36).substring(2, 6)}`,
+    id: msgId,
     serverId: r.id,
     sessionId: r.session_id,
     role: r.role,
diff --git a/web/src/components/chat/InputArea.tsx b/web/src/components/chat/InputArea.tsx
index 498d6822..327dfe21 100644
--- a/web/src/components/chat/InputArea.tsx
+++ b/web/src/components/chat/InputArea.tsx
@@ -3,10 +3,19 @@ import { Send, Paperclip, Square, X, Loader2, Sparkles, Lock } from 'lucide-reac
 import { QuotedMessage } from '../../types/workbench';
 import { QuoteChip } from './QuoteChip';
 
+export interface InputAttachmentItem {
+  name: string;
+  size: string;
+  type: string;
+  docId?: string;
+  fileRaw?: File | Blob;
+  fileUrl?: string;
+}
+
 interface InputAreaProps {
   onSendMessage: (
     text: string,
-    attachments?: { name: string; size: string; type: string }[],
+    attachments?: InputAttachmentItem[],
     quotes?: QuotedMessage[]
   ) => void;
   isThinking: boolean;
@@ -18,6 +27,8 @@ interface InputAreaProps {
   disabledMessage?: string;
 }
 
+const MAX_ATTACHMENTS = 5;
+
 export const InputArea: React.FC<InputAreaProps> = ({
   onSendMessage,
   isThinking,
@@ -29,7 +40,8 @@ export const InputArea: React.FC<InputAreaProps> = ({
   disabledMessage,
 }) => {
   const [text, setText] = useState('');
-  const [attachments, setAttachments] = useState<{ name: string; size: string; type: string }[]>([]);
+  const [attachments, setAttachments] = useState<InputAttachmentItem[]>([]);
+  const [uploadWarning, setUploadWarning] = useState<string | null>(null);
   const textareaRef = useRef<HTMLTextAreaElement>(null);
   const fileInputRef = useRef<HTMLInputElement>(null);
 
@@ -56,6 +68,7 @@ export const InputArea: React.FC<InputAreaProps> = ({
     onSendMessage(text.trim(), attachments, quotes);
     setText('');
     setAttachments([]);
+    setUploadWarning(null);
     if (textareaRef.current) {
       textareaRef.current.style.height = '42px';
     }
@@ -69,23 +82,65 @@ export const InputArea: React.FC<InputAreaProps> = ({
   };
 
   const handleFileChange = (e: React.ChangeEvent<HTMLInputElement>) => {
-    if (e.target.files && e.target.files.length > 0) {
-      const file = e.target.files[0];
-      const sizeStr = (file.size / 1024).toFixed(0) + ' KB';
-      setAttachments((prev) => [
-        ...prev,
-        {
-          name: file.name,
-          size: sizeStr,
-          type: file.type || 'document',
-        },
-      ]);
+    if (!e.target.files || e.target.files.length === 0) return;
+    const files = Array.from(e.target.files);
+    const currentCount = attachments.length;
+    const availableSlots = MAX_ATTACHMENTS - currentCount;
+
+    if (availableSlots <= 0) {
+      setUploadWarning(`单轮对话最多支持上传 ${MAX_ATTACHMENTS} 个文档`);
+      setTimeout(() => setUploadWarning(null), 3000);
       e.target.value = '';
+      return;
     }
+
+    let filesToAdd = files;
+    if (files.length > availableSlots) {
+      filesToAdd = files.slice(0, availableSlots);
+      setUploadWarning(
+        `单轮对话最多支持上传 ${MAX_ATTACHMENTS} 个文档，已为您选取前 ${availableSlots} 个`
+      );
+      setTimeout(() => setUploadWarning(null), 3500);
+    } else {
+      setUploadWarning(null);
+    }
+
+    const newAtts: InputAttachmentItem[] = filesToAdd.map((file) => {
+      let fileUrl = '';
+      try {
+        if (typeof window !== 'undefined' && window.URL && window.URL.createObjectURL) {
+          fileUrl = window.URL.createObjectURL(file);
+        }
+      } catch (err) {
+        console.warn('Failed to create object URL for file:', file.name, err);
+      }
+
+      return {
+        name: file.name,
+        size: (file.size / 1024).toFixed(0) + ' KB',
+        type: file.type || 'document',
+        fileRaw: file,
+        fileUrl,
+      };
+    });
+
+    setAttachments((prev) => [...prev, ...newAtts]);
+    e.target.value = '';
   };
 
   const removeAttachment = (index: number) => {
-    setAttachments((prev) => prev.filter((_, i) => i !== index));
+    setAttachments((prev) => {
+      const target = prev[index];
+      if (target?.fileUrl && target.fileUrl.startsWith('blob:') && typeof window !== 'undefined' && window.URL?.revokeObjectURL) {
+        try {
+          window.URL.revokeObjectURL(target.fileUrl);
+        } catch (e) {
+          // ignore
+        }
+      }
+      return prev.filter((_, i) => i !== index);
+    });
+    if (uploadWarning) setUploadWarning(null);
   };
 
   if (disabled) {
@@ -137,15 +192,50 @@ export const InputArea: React.FC<InputAreaProps> = ({
         position: 'relative',
       }}
     >
-      {/* 隐藏的原生文件上传 */}
+      {/* 隐藏的原生文件上传（支持单次多选，单轮累计最多 5 个） */}
       <input
         ref={fileInputRef}
         type="file"
+        multiple
         style={{ display: 'none' }}
         onChange={handleFileChange}
         accept=".pdf,.doc,.docx,.md,.txt,.xlsx"
       />
 
+      {/* 超出限制或操作提示条 */}
+      {uploadWarning && (
+        <div
+          style={{
+            padding: '6px 10px',
+            borderRadius: 'var(--r-sm, 6px)',
+            background: 'rgba(245, 158, 11, 0.1)',
+            border: '1px solid rgba(245, 158, 11, 0.3)',
+            color: '#d97706',
+            fontSize: '12px',
+            display: 'flex',
+            alignItems: 'center',
+            justifyContent: 'space-between',
+            animation: 'fadeIn 0.2s ease',
+          }}
+        >
+          <span>⚠️ {uploadWarning}</span>
+          <button
+            onClick={() => setUploadWarning(null)}
+            style={{
+              border: 'none',
+              background: 'transparent',
+              color: '#d97706',
+              cursor: 'pointer',
+              display: 'flex',
+              alignItems: 'center',
+              padding: '2px',
+            }}
+          >
+            <X size={12} />
+          </button>
+        </div>
+      )}
+
       {/* 已挂载引用卡片 */}
       {quotes.length > 0 && (
         <div style={{ display: 'flex', flexWrap: 'wrap', gap: '6px' }}>
@@ -157,31 +247,51 @@ export const InputArea: React.FC<InputAreaProps> = ({
 
       {/* 已挂载文件芯片 */}
       {attachments.length > 0 && (
-        <div style={{ display: 'flex', flexWrap: 'wrap', gap: '6px' }}>
-          {attachments.map((att, i) => (
-            <div
-              key={i}
-              style={{
-                display: 'flex',
-                alignItems: 'center',
-                gap: '5px',
-                padding: '3px 8px',
-                borderRadius: 'var(--r-sm)',
-                background: 'var(--bg-subtle)',
-                border: '1px solid var(--brand-100)',
-                fontSize: '11px',
-                color: 'var(--brand-600)',
-              }}
-            >
-              <span>📎 {att.name}</span>
-              <button
-                onClick={() => removeAttachment(i)}
-                style={{ display: 'flex', alignItems: 'center', color: 'var(--text-faint)' }}
+        <div style={{ display: 'flex', flexDirection: 'column', gap: '4px' }}>
+          <div
+            style={{
+              fontSize: '11px',
+              fontWeight: 600,
+              color: 'var(--text-muted, #64748b)',
+              display: 'flex',
+              alignItems: 'center',
+              justifyContent: 'space-between',
+            }}
+          >
+            <span>待上传文档 ({attachments.length}/{MAX_ATTACHMENTS})</span>
+            {attachments.length < MAX_ATTACHMENTS && (
+              <span style={{ fontSize: '10px', color: 'var(--text-faint, #94a3b8)' }}>
+                还可添加 {MAX_ATTACHMENTS - attachments.length} 个
+              </span>
+            )}
+          </div>
+          <div style={{ display: 'flex', flexWrap: 'wrap', gap: '6px' }}>
+            {attachments.map((att, i) => (
+              <div
+                key={i}
+                style={{
+                  display: 'flex',
+                  alignItems: 'center',
+                  gap: '5px',
+                  padding: '3px 8px',
+                  borderRadius: 'var(--r-sm)',
+                  background: 'var(--bg-subtle)',
+                  border: '1px solid var(--brand-100)',
+                  fontSize: '11px',
+                  color: 'var(--brand-600)',
+                }}
               >
-                <X size={12} />
-              </button>
-            </div>
-          ))}
+                <span>📎 {att.name} ({att.size})</span>
+                <button
+                  onClick={() => removeAttachment(i)}
+                  title="移除此文档"
+                  style={{ display: 'flex', alignItems: 'center', color: 'var(--text-faint)', cursor: 'pointer' }}
+                >
+                  <X size={12} />
+                </button>
+              </div>
+            ))}
+          </div>
         </div>
       )}
 
@@ -216,8 +326,19 @@ export const InputArea: React.FC<InputAreaProps> = ({
       >
         {/* 附件按钮 */}
         <button
-          onClick={() => fileInputRef.current?.click()}
-          title="上传项目需求材料或参考文档"
+          onClick={() => {
+            if (attachments.length >= MAX_ATTACHMENTS) {
+              setUploadWarning(`单轮对话最多支持上传 ${MAX_ATTACHMENTS} 个文档（当前已达上限）`);
+              setTimeout(() => setUploadWarning(null), 3000);
+              return;
+            }
+            fileInputRef.current?.click();
+          }}
+          title={
+            attachments.length >= MAX_ATTACHMENTS
+              ? `已达上限 (最多 ${MAX_ATTACHMENTS} 个文档)`
+              : `上传项目需求材料或参考文档 (最多 ${MAX_ATTACHMENTS} 个，支持多选)`
+          }
           style={{
             width: '32px',
             height: '32px',
@@ -225,17 +346,20 @@ export const InputArea: React.FC<InputAreaProps> = ({
             display: 'flex',
             alignItems: 'center',
             justifyContent: 'center',
-            color: 'var(--text-muted)',
+            color: attachments.length >= MAX_ATTACHMENTS ? 'var(--text-faint)' : 'var(--text-muted)',
             flexShrink: 0,
             marginBottom: '4px',
             transition: 'all 0.15s ease',
           }}
           onMouseEnter={(e) => {
-            e.currentTarget.style.color = 'var(--brand-500)';
-            e.currentTarget.style.background = 'var(--bg-hover)';
+            if (attachments.length < MAX_ATTACHMENTS) {
+              e.currentTarget.style.color = 'var(--brand-500)';
+              e.currentTarget.style.background = 'var(--bg-hover)';
+            }
           }}
           onMouseLeave={(e) => {
-            e.currentTarget.style.color = 'var(--text-muted)';
+            e.currentTarget.style.color =
+              attachments.length >= MAX_ATTACHMENTS ? 'var(--text-faint)' : 'var(--text-muted)';
             e.currentTarget.style.background = 'transparent';
           }}
         >
diff --git a/web/src/hooks/useChatWindow.ts b/web/src/hooks/useChatWindow.ts
index 9b1109c7..ac409b2e 100644
--- a/web/src/hooks/useChatWindow.ts
+++ b/web/src/hooks/useChatWindow.ts
@@ -501,14 +501,45 @@ export function useChatWindow({
       todayBucket.loadedCount++;
     }
 
-    // 严谨保序：按照 liveMessages 中的自然发生时序排列，保证新追加的对话永远沉淀在最底部
-    const getMessageSortKey = (m: ChatMessage): number => {
-      if (m.id && liveIndexMap.has(m.id)) return liveIndexMap.get(m.id)!;
-      if (m.serverId && liveIndexMap.has(`msg-${m.serverId}`)) return liveIndexMap.get(`msg-${m.serverId}`)!;
-      if (m.serverId) return -1000000 + m.serverId;
+    // 严谨保序：按照真实时间与发生时序排列，保证新追加的对话永远沉淀在最底部
+    const getMessageSortTime = (m: ChatMessage): number => {
+      if (m.createdAt) {
+        const t = new Date(m.createdAt).getTime();
+        if (!isNaN(t)) return t;
+      }
+      if (m.timestamp && m.timestamp.includes(':')) {
+        const [hh, mm] = m.timestamp.split(':').map(Number);
+        if (!isNaN(hh) && !isNaN(mm)) {
+          const d = new Date();
+          d.setHours(hh, mm, 0, 0);
+          return d.getTime();
+        }
+      }
+      if (m.id && (m.id.startsWith('msg-') || m.id.startsWith('ast-'))) {
+        const numPart = m.id.replace(/^[a-z]+-/, '');
+        const parsed = parseInt(numPart, 10);
+        if (!isNaN(parsed) && parsed > 1000000000000) {
+          return parsed;
+        }
+      }
       return 0;
     };
-    todayBucket.messages.sort((a, b) => getMessageSortKey(a) - getMessageSortKey(b));
+
+    todayBucket.messages.sort((a, b) => {
+      const tA = getMessageSortTime(a);
+      const tB = getMessageSortTime(b);
+      if (tA !== 0 && tB !== 0 && tA !== tB) {
+        return tA - tB;
+      }
+      const idxA = liveIndexMap.get(a.id) ?? (a.serverId ? liveIndexMap.get(`msg-${a.serverId}`) : undefined);
+      const idxB = liveIndexMap.get(b.id) ?? (b.serverId ? liveIndexMap.get(`msg-${b.serverId}`) : undefined);
+      if (idxA !== undefined && idxB !== undefined) {
+        return idxA - idxB;
+      }
+      if (idxA !== undefined) return 1;
+      if (idxB !== undefined) return -1;
+      return (a.serverId || 0) - (b.serverId || 0);
+    });
 
     return result;
   }, [dayStack, liveMessages])();
diff --git a/web/src/hooks/useUnreadMarks.ts b/web/src/hooks/useUnreadMarks.ts
index be8ae8df..3085340d 100644
--- a/web/src/hooks/useUnreadMarks.ts
+++ b/web/src/hooks/useUnreadMarks.ts
@@ -44,6 +44,22 @@ export interface UseUnreadMarksReturn {
   refresh: () => void;
 }
 
+function getLocalReadIds(sessionId: string): Set<number> {
+  try {
+    const raw = localStorage.getItem(`smdf_read_ids_${sessionId}`);
+    if (raw) return new Set(JSON.parse(raw));
+  } catch {}
+  return new Set();
+}
+
+function saveLocalReadId(sessionId: string, msgId: number) {
+  try {
+    const ids = getLocalReadIds(sessionId);
+    ids.add(msgId);
+    localStorage.setItem(`smdf_read_ids_${sessionId}`, JSON.stringify(Array.from(ids).slice(-200)));
+  } catch {}
+}
+
 export function useUnreadMarks(
   sessionId: string | null,
   userId?: number,
@@ -78,34 +94,52 @@ export function useUnreadMarks(
       if (!res.ok) return;
 
       const data = await res.json();
+      const localReadSet = getLocalReadIds(sessionId);
 
       // 兼容老格式 (Array) 与新格式 (UnreadSummaryResponse)
       if (Array.isArray(data)) {
-        const items: UnreadMark[] = data.map((item: UnreadDayApiItem) => ({
-          sessionId: sessionId,
-          date: item.date,
-          count: item.count,
-          lastMessageId: item.last_message_id,
-          senders: item.senders,
-        }));
+        const rawItems: UnreadDayApiItem[] = data;
+        const items: UnreadMark[] = rawItems
+          .map((item) => {
+            const isReadLocally = localReadSet.has(item.last_message_id);
+            const count = isReadLocally ? Math.max(0, item.count - 1) : item.count;
+            return {
+              sessionId: sessionId,
+              date: item.date,
+              count,
+              lastMessageId: item.last_message_id,
+              senders: item.senders,
+            };
+          })
+          .filter((item) => item.count > 0);
+
         setUnreadMarks(items);
         const total = items.reduce((sum, item) => sum + item.count, 0);
         setUnreadTotal(total);
-        setNextMessageId(items.length > 0 ? items[0].lastMessageId : null);
-        setUnreadMessageIds(items.map((i) => i.lastMessageId));
+        const validIds = items.map((i) => i.lastMessageId).filter((id) => !localReadSet.has(id));
+        setNextMessageId(validIds.length > 0 ? validIds[0] : null);
+        setUnreadMessageIds(validIds);
       } else {
         const summary = data as UnreadSummaryResponse;
-        const items: UnreadMark[] = (summary.items || []).map((item) => ({
-          sessionId: sessionId,
-          date: item.date,
-          count: item.count,
-          lastMessageId: item.last_message_id,
-          senders: item.senders,
-        }));
+        const unreadIds = (summary.unread_message_ids || []).filter((id) => !localReadSet.has(id));
+        const items: UnreadMark[] = (summary.items || [])
+          .map((item) => {
+            const isReadLocally = localReadSet.has(item.last_message_id);
+            const count = isReadLocally ? Math.max(0, item.count - 1) : item.count;
+            return {
+              sessionId: sessionId,
+              date: item.date,
+              count,
+              lastMessageId: item.last_message_id,
+              senders: item.senders,
+            };
+          })
+          .filter((item) => item.count > 0);
+
         setUnreadMarks(items);
-        setUnreadTotal(summary.total || 0);
-        setNextMessageId(summary.next_message_id > 0 ? summary.next_message_id : null);
-        setUnreadMessageIds(summary.unread_message_ids || []);
+        setUnreadTotal(unreadIds.length);
+        setNextMessageId(unreadIds.length > 0 ? unreadIds[0] : null);
+        setUnreadMessageIds(unreadIds);
       }
     } catch {
       // 网络错误静默处理，不中断协同
@@ -137,6 +171,9 @@ export function useUnreadMarks(
     }
     if (!targetId) return null;
 
+    // 0. 本地持久化记录已读
+    saveLocalReadId(sessionId, targetId);
+
     // 1. 乐观更新未读集合
     const remainingIds = unreadMessageIds.filter((id) => id !== targetId);
     setUnreadMessageIds(remainingIds);
@@ -190,6 +227,10 @@ export function useUnreadMarks(
     async (messageIds: number[]) => {
       if (!sessionId || messageIds.length === 0) return;
 
+      for (const id of messageIds) {
+        saveLocalReadId(sessionId, id);
+      }
+
       const idsToRead = new Set(messageIds);
       const remainingIds = unreadMessageIds.filter((id) => !idsToRead.has(id));
       setUnreadMessageIds(remainingIds);
diff --git a/web/src/tests/urs-private-shared.test.ts b/web/src/tests/urs-private-shared.test.ts
index 7b91450f..a72f71e8 100644
--- a/web/src/tests/urs-private-shared.test.ts
+++ b/web/src/tests/urs-private-shared.test.ts
@@ -148,4 +148,116 @@ describe('用户上传文档私密归档与共享流转测试', () => {
     assert.equal(newDeliverable.category, 'private');
     assert.equal(newDeliverable.space, 'my_private');
   });
+
+  it('单轮对话支持一次上传多个文档(上限5个)，批量生成私密交付物并遵循数量约束', () => {
+    const MAX_ATTACHMENTS = 5;
+
+    // 模拟用户一次性多选 6 个文件
+    const incomingFiles = [
+      { name: '1-临床需求规格书.docx', size: '120 KB', type: 'application/vnd.openxmlformats-officedocument.wordprocessingml.document' },
+      { name: '2-硬件设计草案.pdf', size: '350 KB', type: 'application/pdf' },
+      { name: '3-竞品比对表.xlsx', size: '80 KB', type: 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet' },
+      { name: '4-法规风险调研.md', size: '15 KB', type: 'text/markdown' },
+      { name: '5-型检预估预算.xlsx', size: '45 KB', type: 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet' },
+      { name: '6-超出限制的文件.pdf', size: '200 KB', type: 'application/pdf' },
+    ];
+
+    // 模拟 InputArea handleFileChange 截断逻辑
+    let currentAttachments: { name: string; size: string; type: string }[] = [];
+    const availableSlots = MAX_ATTACHMENTS - currentAttachments.length;
+    assert.equal(availableSlots, 5);
+
+    let filesToAdd = incomingFiles;
+    let warningTriggered = false;
+    if (incomingFiles.length > availableSlots) {
+      filesToAdd = incomingFiles.slice(0, availableSlots);
+      warningTriggered = true;
+    }
+    assert.equal(warningTriggered, true);
+    assert.equal(filesToAdd.length, 5);
+
+    currentAttachments = [...currentAttachments, ...filesToAdd];
+    assert.equal(currentAttachments.length, 5);
+
+    // 再次尝试添加：此时应无剩余槽位并拒绝
+    const nextAvailableSlots = MAX_ATTACHMENTS - currentAttachments.length;
+    assert.equal(nextAvailableSlots, 0);
+
+    // 模拟 App.tsx handleSendMessage 批量注册
+    const currentProjectId = 6001;
+    const currentUserId = 1;
+    const currentUserName = '张工';
+    const now = Date.now();
+
+    const newDeliverablesList: DeliverableItem[] = [];
+    const newDocCacheEntries: Record<string, any> = {};
+
+    const processedAttachments = currentAttachments.map((att, idx) => {
+      const fileDocId = `doc-upload-${now}-${idx}`;
+      const baseTitle = att.name.replace(/\.[^/.]+$/, '');
+      const newDeliverable: DeliverableItem = {
+        docId: fileDocId,
+        projectId: currentProjectId,
+        taskKey: 'user_requirements',
+        title: baseTitle,
+        stage: 'V0.5',
+        category: 'private',
+        creatorId: currentUserId,
+        creatorName: currentUserName,
+        isFixedWorkflow: false,
+        isTemplateOnly: false,
+        lifecycleState: 'drafting',
+        isClaimed: true,
+        author: currentUserName,
+        reviewer: '李主管',
+        approver: '王总监',
+        updatedAt: '2026-09-11',
+        summary: `用户上传的私密需求文档《${att.name}》`,
+        space: 'my_private',
+        governanceMode: 'freeform',
+      };
+      const initialMd = `# ${baseTitle}\n\n> 上传人：${currentUserName} | 大小：${att.size}`;
+      const newAST = markdownToBlockAST(initialMd, {
+        docId: fileDocId,
+        title: baseTitle,
+        taskKey: 'user_requirements',
+        version: 'V1.0',
+        category: 'private',
+        creatorId: currentUserId,
+        creatorName: currentUserName,
+        lifecycleState: 'drafting',
+        isClaimed: true,
+        author: currentUserName,
+        reviewer: '李主管',
+        approver: '王总监',
+      });
+      newAST.governanceMode = 'freeform';
+      newAST.space = 'my_private';
+
+      newDeliverablesList.push(newDeliverable);
+      newDocCacheEntries[fileDocId] = newAST;
+
+      return {
+        ...att,
+        docId: fileDocId,
+      };
+    });
+
+    assert.equal(processedAttachments.length, 5);
+    assert.equal(newDeliverablesList.length, 5);
+    assert.equal(Object.keys(newDocCacheEntries).length, 5);
+
+    // 验证所有 5 份交付物均具有独立 docId 且为 private / my_private
+    const docIds = new Set(newDeliverablesList.map((d) => d.docId));
+    assert.equal(docIds.size, 5);
+    newDeliverablesList.forEach((d) => {
+      assert.equal(d.category, 'private');
+      assert.equal(d.space, 'my_private');
+      assert.equal(d.creatorName, '张工');
+    });
+
+    // 验证默认激活打开第 1 个文档
+    assert.equal(processedAttachments[0].docId, newDeliverablesList[0].docId);
+  });
 });
+
diff --git a/web/src/tests/workflow-chat-chronology.test.ts b/web/src/tests/workflow-chat-chronology.test.ts
index 0ba64afc..dc307616 100644
--- a/web/src/tests/workflow-chat-chronology.test.ts
+++ b/web/src/tests/workflow-chat-chronology.test.ts
@@ -98,4 +98,47 @@ describe('工作流切换与消息展示时序测试套件', () => {
     assert.equal(flat[4].id, 'msg-live-1');
     assert.equal(flat[5].id, 'ast-live-2');
   });
+
+  test('2. 页面刷新后，即使本地 liveMessages 未包含新消息，按时间戳与自增 ID 排序也绝对不倒挂在历史消息前', () => {
+    // 模拟服务端返回完整按时间排布的消息
+    const historicalMessages: ChatMessage[] = [
+      { id: 'm-jigu-1', sessionId: 'sess-jigu-u1', role: 'system', content: '助手就位', timestamp: '09:00', createdAt: '2026-09-11T09:00:00+08:00', serverId: 25217 },
+      { id: 'm-jigu-2', sessionId: 'sess-jigu-u1', role: 'user', content: '用户需求', timestamp: '09:14', createdAt: '2026-09-11T09:14:00+08:00', serverId: 25218 },
+    ];
+
+    const serverRecentMessages: ChatMessage[] = [
+      { id: 'msg-25227', sessionId: 'sess-jigu-u1', role: 'user', content: '分析一下测试方案中...', timestamp: '10:06', createdAt: '2026-09-11T10:06:46+08:00', serverId: 25227 },
+      { id: 'msg-25228', sessionId: 'sess-jigu-u1', role: 'assistant', content: '针对测试方案...', timestamp: '10:07', createdAt: '2026-09-11T10:07:26+08:00', serverId: 25228 },
+    ];
+
+    const allInBucket = [...serverRecentMessages, ...historicalMessages]; // 故意打乱测试排序算法鲁棒性
+
+    const getMessageSortTime = (m: ChatMessage): number => {
+      if (m.createdAt) {
+        const t = new Date(m.createdAt).getTime();
+        if (!isNaN(t)) return t;
+      }
+      if (m.timestamp && m.timestamp.includes(':')) {
+        const [hh, mm] = m.timestamp.split(':').map(Number);
+        if (!isNaN(hh) && !isNaN(mm)) {
+          const d = new Date();
+          d.setHours(hh, mm, 0, 0);
+          return d.getTime();
+        }
+      }
+      return 0;
+    };
+
+    allInBucket.sort((a, b) => {
+      const tA = getMessageSortTime(a);
+      const tB = getMessageSortTime(b);
+      if (tA !== 0 && tB !== 0 && tA !== tB) return tA - tB;
+      return (a.serverId || 0) - (b.serverId || 0);
+    });
+
+    assert.equal(allInBucket[0].id, 'm-jigu-1');
+    assert.equal(allInBucket[1].id, 'm-jigu-2');
+    assert.equal(allInBucket[2].id, 'msg-25227');
+    assert.equal(allInBucket[3].id, 'msg-25228');
+  });
 });
diff --git a/web/src/types/workbench.ts b/web/src/types/workbench.ts
index 414a4eec..bccaa367 100644
--- a/web/src/types/workbench.ts
+++ b/web/src/types/workbench.ts
@@ -144,6 +144,8 @@ export interface ChatMessage {
     size: string;
     type: string;
     docId?: string;
+    fileRaw?: File | Blob;
+    fileUrl?: string;
   }[];
   intentTag?: string;
   branchTag?: string;
@@ -228,6 +230,19 @@ export interface ChatCategoryStat {
 
 export type DeliverableCategory = 'workflow' | 'shared' | 'private';
 
+export type DeliverableSourceType = 'workflow' | 'chat_derived' | 'uploaded_file';
+
+export interface UploadedFileMetadata {
+  originalName: string;
+  size: string;
+  sizeBytes?: number;
+  mimeType: string;
+  extension: string;
+  fileRaw?: File | Blob;
+  fileUrl?: string;
+  uploadedAt: string;
+}
+
 export interface DeliverableItem {
   docId: string;
   projectId: number;
@@ -251,6 +266,8 @@ export interface DeliverableItem {
   visibilityRule?: DocVisibilityRule;
   governanceMode?: 'controlled' | 'freeform';
   space?: 'my_private' | 'project_shared' | 'trash';
+  sourceType?: DeliverableSourceType;
+  fileMeta?: UploadedFileMetadata;
 }
 
 export interface WorkbenchState {