diff --git a/internal/db/migrate.go b/internal/db/migrate.go
index 1314f0f..f1fe5a0 100644
--- a/internal/db/migrate.go
+++ b/internal/db/migrate.go
@@ -21,6 +21,7 @@ func Migrate(db *sql.DB) error {
 		createInvites,
 		createBuyerGroups,
 		createFolderAccess,
+		createFileComments,
 	}
 
 	for i, m := range migrations {
@@ -219,6 +220,16 @@ CREATE TABLE IF NOT EXISTS folder_access (
     PRIMARY KEY (folder_id, buyer_group)
 );`
 
+const createFileComments = `
+CREATE TABLE IF NOT EXISTS file_comments (
+    id TEXT PRIMARY KEY,
+    file_id TEXT NOT NULL,
+    deal_id TEXT NOT NULL,
+    user_id TEXT NOT NULL,
+    content TEXT NOT NULL,
+    created_at DATETIME DEFAULT CURRENT_TIMESTAMP
+);`
+
 // Additive migrations - each statement is run individually, errors ignored (for already-existing columns)
 var additiveMigrationStmts = []string{
 	// Section 1: org_type
diff --git a/internal/handler/files.go b/internal/handler/files.go
index 85c85f9..93a4434 100644
--- a/internal/handler/files.go
+++ b/internal/handler/files.go
@@ -158,6 +158,67 @@ func (h *Handler) logActivity(dealID, userID, orgID, actType, resourceType, reso
 		id, orgID, dealID, userID, actType, resourceType, resourceName, resourceID)
 }
 
+func (h *Handler) handleFileComments(w http.ResponseWriter, r *http.Request) {
+	profile := getProfile(r.Context())
+	// Parse: /deals/files/comments/{fileID}
+	fileID := strings.TrimPrefix(r.URL.Path, "/deals/files/comments/")
+
+	// Get deal_id for this file
+	var dealID string
+	h.db.QueryRow("SELECT deal_id FROM files WHERE id = ?", fileID).Scan(&dealID)
+
+	if r.Method == http.MethodPost {
+		content := strings.TrimSpace(r.FormValue("content"))
+		if content != "" {
+			id := generateID("cmt")
+			h.db.Exec("INSERT INTO file_comments (id, file_id, deal_id, user_id, content) VALUES (?, ?, ?, ?, ?)",
+				id, fileID, dealID, profile.ID, content)
+		}
+	}
+
+	// Get comments
+	rows, err := h.db.Query(`
+		SELECT c.id, c.content, c.created_at, COALESCE(p.full_name, 'Unknown')
+		FROM file_comments c LEFT JOIN profiles p ON c.user_id = p.id
+		WHERE c.file_id = ? ORDER BY c.created_at ASC`, fileID)
+	if err != nil {
+		http.Error(w, "Error loading comments", 500)
+		return
+	}
+	defer rows.Close()
+
+	w.Header().Set("Content-Type", "text/html")
+
+	// Build HTML response
+	html := `<div class="space-y-3 max-h-64 overflow-y-auto mb-4">`
+	hasComments := false
+	for rows.Next() {
+		hasComments = true
+		var id, content, userName string
+		var createdAt string
+		rows.Scan(&id, &content, &createdAt, &userName)
+		html += fmt.Sprintf(`<div class="bg-gray-800 rounded-lg p-3">
+			<div class="flex items-center gap-2 mb-1">
+				<span class="text-xs font-medium text-teal-400">%s</span>
+				<span class="text-xs text-gray-600">%s</span>
+			</div>
+			<p class="text-sm text-gray-300">%s</p>
+		</div>`, userName, createdAt, content)
+	}
+	if !hasComments {
+		html += `<p class="text-sm text-gray-500 italic">No comments yet.</p>`
+	}
+	html += `</div>`
+
+	// Add comment form
+	html += fmt.Sprintf(`<form hx-post="/deals/files/comments/%s" hx-target="#comments-%s" hx-swap="innerHTML" class="flex gap-2">
+		<input type="text" name="content" placeholder="Add a comment..." class="flex-1 px-3 py-2 bg-gray-800 border border-gray-700 rounded-lg text-sm text-gray-100 focus:border-teal-500 focus:outline-none"/>
+		<button type="submit" class="px-3 py-2 bg-teal-500 text-white text-sm rounded-lg hover:bg-teal-600 transition">Send</button>
+	</form>`, fileID, fileID)
+
+	w.Write([]byte(html))
+}
+
 func fileExists(path string) bool {
 	_, err := os.Stat(path)
 	return err == nil
diff --git a/internal/handler/handler.go b/internal/handler/handler.go
index 105ac8b..87f88fc 100644
--- a/internal/handler/handler.go
+++ b/internal/handler/handler.go
@@ -86,6 +86,7 @@ mux.HandleFunc("/auth/logout", h.handleLogout)
 	mux.HandleFunc("/deals/files/upload", h.requireAuth(h.handleFileUpload))
 	mux.HandleFunc("/deals/files/delete", h.requireAuth(h.handleFileDelete))
 	mux.HandleFunc("/deals/files/download/", h.requireAuth(h.handleFileDownload))
+	mux.HandleFunc("/deals/files/comments/", h.requireAuth(h.handleFileComments))
 
 	// HTMX partials
 	mux.HandleFunc("/htmx/request-comment", h.requireAuth(h.handleUpdateComment))
diff --git a/internal/model/models.go b/internal/model/models.go
index 37f690a..179611e 100644
--- a/internal/model/models.go
+++ b/internal/model/models.go
@@ -144,6 +144,16 @@ type Session struct {
 	CreatedAt time.Time
 }
 
+type FileComment struct {
+	ID        string
+	FileID    string
+	DealID    string
+	UserID    string
+	Content   string
+	CreatedAt time.Time
+	UserName  string // computed
+}
+
 type Invite struct {
 	Token     string
 	OrgID     string
diff --git a/templates/dealroom.templ b/templates/dealroom.templ
index a36c317..c20f8a4 100644
--- a/templates/dealroom.templ
+++ b/templates/dealroom.templ
@@ -152,6 +152,9 @@ templ DealRoomDetail(profile *model.Profile, deal *model.Deal, folders []*model.
 												</td>
 												<td class="px-4 py-2.5 text-right">
 													<div class="flex items-center justify-end gap-2">
+														<button hx-get={ fmt.Sprintf("/deals/files/comments/%s", file.ID) } hx-target={ fmt.Sprintf("#comments-%s", file.ID) } hx-swap="innerHTML" onclick={ templ.ComponentScript{Call: fmt.Sprintf("document.getElementById('commentPanel-%s').classList.toggle('hidden')", file.ID)} } class="text-xs text-gray-500 hover:text-teal-400 transition" title="Comments">
+															<svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M8 12h.01M12 12h.01M16 12h.01M21 12c0 4.418-4.03 8-9 8a9.863 9.863 0 01-4.255-.949L3 20l1.395-3.72C3.512 15.042 3 13.574 3 12c0-4.418 4.03-8 9-8s9 3.582 9 8z"></path></svg>
+														</button>
 														<a href={ templ.SafeURL(fmt.Sprintf("/deals/files/download/%s", file.ID)) } class="text-xs text-gray-500 hover:text-teal-400 transition" title="Download">
 															<svg class="w-4 h-4" fill="none" stroke="currentColor" viewBox="0 0 24 24"><path stroke-linecap="round" stroke-linejoin="round" stroke-width="2" d="M4 16v1a3 3 0 003 3h10a3 3 0 003-3v-1m-4-4l-4 4m0 0l-4-4m4 4V4"></path></svg>
 														</a>
@@ -167,6 +170,13 @@ templ DealRoomDetail(profile *model.Profile, deal *model.Deal, folders []*model.
 													</div>
 												</td>
 											</tr>
+											<tr id={ fmt.Sprintf("commentPanel-%s", file.ID) } class="hidden">
+												<td colspan="6" class="px-4 py-3 bg-gray-800/30">
+													<div id={ fmt.Sprintf("comments-%s", file.ID) }>
+														<p class="text-xs text-gray-500 italic">Click the comment icon to load comments.</p>
+													</div>
+												</td>
+											</tr>
 										}
 									}
 								</tbody>