diff --git a/apps/shared/OpenClawKit/Sources/OpenClawChatUI/ChatSessionSidebarModel.swift b/apps/shared/OpenClawKit/Sources/OpenClawChatUI/ChatSessionSidebarModel.swift
index a812058f9e1e..c511bae3da89 100644
--- a/apps/shared/OpenClawKit/Sources/OpenClawChatUI/ChatSessionSidebarModel.swift
+++ b/apps/shared/OpenClawKit/Sources/OpenClawChatUI/ChatSessionSidebarModel.swift
@@ -496,14 +496,11 @@ public enum ChatSessionSidebarModel {
             // active row selectable instead of showing an empty selection.
             entries.append(self.placeholder(key: currentSessionKey))
         }
-        entries.sort { (($0.updatedAt ?? $0.lastActivityAt) ?? 0) > (($1.updatedAt ?? $1.lastActivityAt) ?? 0) }
-
-        let needle = query.trimmingCharacters(in: .whitespacesAndNewlines).lowercased()
-        guard !needle.isEmpty else { return entries }
-        return entries.filter { entry in
-            self.displayName(for: entry).lowercased().contains(needle) ||
-                entry.key.lowercased().contains(needle)
-        }
+        // Gateway, cached lists, iOS, and macOS must share the same pin
+        // chronology, stable key ties, and searchable session fields.
+        return OpenClawChatSessionListOrganizer.filter(
+            OpenClawChatSessionListOrganizer.organize(entries),
+            search: query)
     }
 
     private static func placeholder(key: String) -> OpenClawChatSessionEntry {
diff --git a/apps/shared/OpenClawKit/Tests/OpenClawKitTests/ChatSessionSidebarModelTests.swift b/apps/shared/OpenClawKit/Tests/OpenClawKitTests/ChatSessionSidebarModelTests.swift
index 2861d03a88cc..2da94a64ef54 100644
--- a/apps/shared/OpenClawKit/Tests/OpenClawKitTests/ChatSessionSidebarModelTests.swift
+++ b/apps/shared/OpenClawKit/Tests/OpenClawKitTests/ChatSessionSidebarModelTests.swift
@@ -8,8 +8,12 @@ struct ChatSessionSidebarModelTests {
     private func entry(
         key: String,
         displayName: String? = nil,
+        label: String? = nil,
+        subject: String? = nil,
+        sessionId: String? = nil,
         updatedAt: Double? = nil,
         pinned: Bool? = nil,
+        pinnedAt: Double? = nil,
         archived: Bool? = nil,
         unread: Bool? = nil,
         lastReadAt: Double? = nil,
@@ -31,11 +35,11 @@ struct ChatSessionSidebarModelTests {
             kind: nil,
             displayName: displayName,
             surface: nil,
-            subject: nil,
+            subject: subject,
             room: nil,
             space: nil,
             updatedAt: updatedAt,
-            sessionId: nil,
+            sessionId: sessionId,
             systemSent: nil,
             abortedLastRun: nil,
             thinkingLevel: nil,
@@ -46,8 +50,10 @@ struct ChatSessionSidebarModelTests {
             modelProvider: nil,
             model: nil,
             contextTokens: nil,
+            label: label,
             category: category,
             pinned: pinned,
+            pinnedAt: pinnedAt,
             archived: archived,
             unread: unread,
             agentStatus: agentStatus,
@@ -80,6 +86,49 @@ struct ChatSessionSidebarModelTests {
         #expect(sections[1].title == "Recent")
     }
 
+    @Test func `pinned sidebar sessions follow gateway pin chronology`() {
+        let sections = ChatSessionSidebarModel.sections(
+            sessions: [
+                self.entry(key: "pinned-old", updatedAt: 300, pinned: true, pinnedAt: 100),
+                self.entry(key: "pinned-new", updatedAt: 100, pinned: true, pinnedAt: 300),
+                self.entry(key: "recent", updatedAt: 400),
+            ],
+            currentSessionKey: "recent",
+            query: "")
+
+        #expect(sections.map(\.id) == ["pinned", "recent"])
+        #expect(sections[0].nodes.map(\.session.key) == ["pinned-new", "pinned-old"])
+        #expect(sections[1].nodes.map(\.session.key) == ["recent"])
+    }
+
+    @Test func `sidebar sessions preserve deterministic gateway key ties`() {
+        let sections = ChatSessionSidebarModel.sections(
+            sessions: [
+                self.entry(key: "z-tie", updatedAt: 100),
+                self.entry(key: "a-tie", updatedAt: 100),
+                self.entry(key: "m-tie", updatedAt: 100),
+            ],
+            currentSessionKey: "a-tie",
+            query: "")
+
+        #expect(sections.flatMap(\.nodes).map(\.session.key) == ["a-tie", "m-tie", "z-tie"])
+    }
+
+    @Test func `gateway groups preserve canonical session order`() {
+        let sections = ChatSessionSidebarModel.sections(
+            sessions: [
+                self.entry(key: "project-z", updatedAt: 100, category: "Projects"),
+                self.entry(key: "project-a", updatedAt: 100, category: "Projects"),
+                self.entry(key: "recent", updatedAt: 50),
+            ],
+            currentSessionKey: "recent",
+            groups: [OpenClawChatSessionGroup(name: "Projects", position: 0)],
+            query: "")
+
+        #expect(sections.map(\.id) == ["group:Projects", "recent"])
+        #expect(sections[0].nodes.map(\.session.key) == ["project-a", "project-z"])
+    }
+
     @Test func `single unpinned section carries no title`() {
         let sections = ChatSessionSidebarModel.sections(
             sessions: [self.entry(key: "a", updatedAt: 100)],
@@ -258,6 +307,52 @@ struct ChatSessionSidebarModelTests {
         #expect(sections.flatMap(\.nodes).map(\.session.key) == ["agent:main:research"])
     }
 
+    @Test(arguments: ["holiday", "KYOTO", "session-123", "  HoLiDaY  "])
+    func `sidebar search matches every canonical gateway session field`(_ query: String) {
+        let matching = self.entry(
+            key: "agent:main:roadmap",
+            displayName: "Planning",
+            label: "Summer holiday",
+            subject: "Kyoto itinerary",
+            sessionId: "session-123",
+            updatedAt: 200)
+        let other = self.entry(
+            key: "agent:main:other",
+            displayName: "Unrelated",
+            updatedAt: 100)
+        let sections = ChatSessionSidebarModel.sections(
+            sessions: [other, matching],
+            currentSessionKey: other.key,
+            query: query)
+
+        #expect(sections.flatMap(\.nodes).map(\.session.key) == [matching.key])
+    }
+
+    @Test(arguments: ["holiday", "KYOTO", "session-123"])
+    func `canonical search never reveals hidden or archived sidebar sessions`(_ query: String) {
+        let archived = self.entry(
+            key: "agent:main:archived",
+            label: "Summer holiday",
+            subject: "Kyoto itinerary",
+            sessionId: "session-123",
+            updatedAt: 300,
+            archived: true)
+        let onboarding = self.entry(
+            key: "agent:main:onboarding",
+            label: "Summer holiday",
+            subject: "Kyoto itinerary",
+            sessionId: "session-123",
+            updatedAt: 200)
+        let active = self.entry(key: "agent:main:active", updatedAt: 100)
+
+        let sections = ChatSessionSidebarModel.sections(
+            sessions: [archived, onboarding, active],
+            currentSessionKey: active.key,
+            query: query)
+
+        #expect(sections.isEmpty)
+    }
+
     @Test func `session keys render as human names`() {
         #expect(ChatSessionSidebarModel.displayName(forKey: "agent:main:main") == "main")
         #expect(ChatSessionSidebarModel.displayName(forKey: "agent:ops:standup") == "standup (ops)")