Add conversation pinning: pinned chats stay at top of sidebar

database/migrations/027_pin_conversations.sql

@@ -0,0 +1,2 @@
+-- Add pinned_at column to conversation_participants for pinning chats
+ALTER TABLE conversation_participants ADD COLUMN IF NOT EXISTS pinned_at TIMESTAMPTZ;

src/app/(dashboard)/chats/page.tsx

@@ -18,6 +18,7 @@ import {
   Search, Send, Phone, MoreHorizontal, Paperclip,
   Smile, Flag, Ban, Trash2, Image, FileIcon, X, Mic, Square, Play, Pause, Check, CheckCheck,
   CornerDownRight, Forward, Pencil, Download, Undo2, CalendarDays, Loader2, FolderOpen, Mail,
+  Pin, PinOff,
 } from "lucide-react"
 import { hasBlockedCodeExtension, filterBlockedFiles } from "@/lib/blocked-extensions"
 import {
@@ -211,8 +212,15 @@ const formatPreviewContent = (content: string) => {
   const messages = useMemo(() => conversationMessages.get(activeChat || "") || [], [conversationMessages, activeChat])
   const conversation = useMemo(() => conversations.find((c) => c.id === activeChat), [conversations, activeChat])
   const filteredConversations = useMemo(() => {
-    if (!searchQuery.trim()) return conversations
-    return conversations.filter((conv) => otherParticipant(conv).name.toLowerCase().includes(searchQuery.toLowerCase()))
+    let list = conversations
+    if (searchQuery.trim()) {
+      list = conversations.filter((conv) => otherParticipant(conv).name.toLowerCase().includes(searchQuery.toLowerCase()))
+    }
+    return [...list].sort((a, b) => {
+      if (a.pinned && !b.pinned) return -1
+      if (!a.pinned && b.pinned) return 1
+      return 0
+    })
   }, [conversations, searchQuery])
 
   // Fetch conversations from API
@@ -776,6 +784,23 @@ const formatPreviewContent = (content: string) => {
 
   const isImageFile = (file: File) => file.type.startsWith("image/")
 
+  const handleTogglePin = async (convId: string, pinned: boolean) => {
+    try {
+      const res = await fetch(`/api/conversations/${convId}/pin`, {
+        method: "PATCH",
+        headers: { "Content-Type": "application/json" },
+        body: JSON.stringify({ pin: !pinned }),
+      })
+      if (res.ok) {
+        setConversations((prev) =>
+          prev.map((c) => (c.id === convId ? { ...c, pinned: !pinned } : c))
+        )
+      }
+    } catch {
+      console.warn("Failed to toggle pin")
+    }
+  }
+
   const getDisplayContent = (content: string) => {
     try {
       const parsed = JSON.parse(content)
@@ -827,7 +852,7 @@ const formatPreviewContent = (content: string) => {
                     })
                   }}
                 className={cn(
-                  "w-full flex items-start gap-3 p-4 text-left transition-colors hover:bg-muted/50 relative",
+                  "w-full group flex items-start gap-3 p-4 text-left transition-colors hover:bg-muted/50 relative",
                   isActive && "bg-muted"
                 )}
               >
@@ -837,8 +862,21 @@ const formatPreviewContent = (content: string) => {
                 </Avatar>
                 <div className="flex-1 min-w-0">
                   <div className="flex items-center justify-between gap-2">
+                    <div className="flex items-center gap-1.5 min-w-0">
+                      {conv.pinned && <Pin className="h-3 w-3 shrink-0 text-muted-foreground rotate-45" />}
                       <span className="text-sm font-medium truncate">{person.name}</span>
-                    <span className="text-xs text-muted-foreground shrink-0">{conv.lastMessageTime}</span>
+                    </div>
+                    <div className="flex items-center gap-1 shrink-0">
+                      <button
+                        type="button"
+                        onClick={(e) => { e.stopPropagation(); handleTogglePin(conv.id, conv.pinned) }}
+                        className="h-5 w-5 flex items-center justify-center rounded hover:bg-muted-foreground/20 transition-colors opacity-0 group-hover:opacity-100"
+                        title={conv.pinned ? "Unpin" : "Pin"}
+                      >
+                        {conv.pinned ? <PinOff className="h-3 w-3 text-muted-foreground" /> : <Pin className="h-3 w-3 text-muted-foreground rotate-45" />}
+                      </button>
+                      <span className="text-xs text-muted-foreground">{conv.lastMessageTime}</span>
+                    </div>
                   </div>
                   <p className="text-xs text-muted-foreground truncate mt-0.5">{formatPreviewContent(conv.lastMessage)}</p>
                 </div>

src/app/api/conversations/[id]/pin/route.ts

@@ -0,0 +1,30 @@
+import { NextRequest, NextResponse } from "next/server"
+import { getSessionUser } from "@/lib/auth"
+import { query } from "@/lib/db"
+
+export async function PATCH(
+  request: NextRequest,
+  { params }: { params: Promise<{ id: string }> },
+) {
+  try {
+    const user = await getSessionUser()
+    if (!user) return NextResponse.json({ error: "Unauthorized" }, { status: 401 })
+
+    const { id } = await params
+    const body = await request.json()
+    const pin = body.pin === true
+
+    await query(
+      `UPDATE conversation_participants
+       SET pinned_at = $1
+       WHERE conversation_id = $2 AND user_id = $3`,
+      [pin ? new Date().toISOString() : null, id, user.id],
+    )
+
+    return NextResponse.json({ pinned: pin })
+  } catch (error) {
+    const message = error instanceof Error ? error.message : "Failed to toggle pin"
+    console.error("Pin conversation error:", message)
+    return NextResponse.json({ error: message }, { status: 500 })
+  }
+}

src/app/api/conversations/route.ts

@@ -13,6 +13,7 @@ export async function GET() {
          c.id,
          c.updated_at,
          cp_me.last_read_at,
+         cp_me.pinned_at,
           u.id AS other_user_id,
           u.first_name || ' ' || u.last_name AS other_user_name,
           u.email AS other_user_email,
@@ -28,7 +29,7 @@ export async function GET() {
        WHERE c.id IN (
          SELECT conversation_id FROM conversation_participants WHERE user_id = $1
        )
-        ORDER BY c.updated_at DESC
+        ORDER BY cp_me.pinned_at DESC NULLS LAST, c.updated_at DESC
         LIMIT 50`,
       [user.id],
     )
@@ -36,6 +37,7 @@ export async function GET() {
     const conversations = result.rows.map((row: any) => ({
       id: row.id,
       updatedAt: row.updated_at,
+      pinned: row.pinned_at !== null,
       otherUser: {
         id: row.other_user_id,
         name: row.other_user_name,