oAI/Views/Main/SidebarView.swift

@@ -32,6 +32,8 @@ struct SidebarView: View {
     @State private var folders: [Folder] = []
     @State private var searchText = ""
     @State private var collapsedFolders: Set<UUID> = []
+    @State private var selectedConversations: Set<UUID> = []
+    @State private var lastClickedId: UUID? = nil
 
     private var filteredConversations: [Conversation] {
         guard !searchText.isEmpty else { return conversations }
@@ -42,32 +44,84 @@ struct SidebarView: View {
         Dictionary(grouping: filteredConversations, by: { $0.folderId })
     }
 
+    /// Flattened conversation order matching what's actually rendered in the List — folders in
+    /// order (skipping collapsed ones' contents, since they're not visible/selectable), then
+    /// Unfiled last. Used as the anchor sequence for Shift-click range selection, same pattern as
+    /// ConversationListView's version.
+    private var visibleOrderedConversations: [Conversation] {
+        guard !folders.isEmpty else { return filteredConversations }
+        var result: [Conversation] = []
+        for folder in folders where !collapsedFolders.contains(folder.id) {
+            result.append(contentsOf: conversationsByFolder[folder.id] ?? [])
+        }
+        result.append(contentsOf: conversationsByFolder[nil] ?? [])
+        return result
+    }
+
     var body: some View {
         VStack(spacing: 0) {
-            // New Chat / New Folder buttons
+            // New Chat / New Folder buttons — swaps to a selection toolbar while selecting
             HStack(spacing: 4) {
-                Button(action: { chatViewModel.newConversation() }) {
+                if !selectedConversations.isEmpty {
-                    HStack(spacing: 8) {
+                    Text("\(selectedConversations.count) selected")
-                        Image(systemName: "square.and.pencil")
+                        .font(.system(size: 13, weight: .medium))
+                        .foregroundStyle(.secondary)
+
+                    Spacer()
+
+                    Menu {
+                        if !folders.isEmpty {
+                            ForEach(folders) { folder in
+                                Button(folder.name) {
+                                    moveSelectedToFolder(folder.id)
+                                }
+                            }
+                            Divider()
+                        }
+                        Button("Remove from Folder") {
+                            moveSelectedToFolder(nil)
+                        }
+                    } label: {
+                        Image(systemName: "folder")
                             .font(.system(size: 14))
-                        Text("New Chat")
+                            .foregroundColor(.confabPrimary)
-                            .font(.system(size: 14, weight: .medium))
                     }
-                    .foregroundColor(.confabPrimary)
+                    .menuStyle(.borderlessButton)
-                    .contentShape(Rectangle())
+                    .fixedSize()
-                }
+                    .help("Move to Folder")
-                .buttonStyle(.plain)
 
-                Spacer()
+                    Button { selectedConversations.removeAll() } label: {
-
+                        Image(systemName: "xmark.circle.fill")
-                Button(action: { createFolderPrompt() }) {
+                            .font(.system(size: 14))
-                    Image(systemName: "folder.badge.plus")
+                            .foregroundStyle(.secondary)
-                        .font(.system(size: 14))
+                    }
+                    .buttonStyle(.plain)
+                    .keyboardShortcut(.escape, modifiers: [])
+                    .help("Cancel Selection")
+                } else {
+                    Button(action: { chatViewModel.newConversation() }) {
+                        HStack(spacing: 8) {
+                            Image(systemName: "square.and.pencil")
+                                .font(.system(size: 14))
+                            Text("New Chat")
+                                .font(.system(size: 14, weight: .medium))
+                        }
                         .foregroundColor(.confabPrimary)
                         .contentShape(Rectangle())
+                    }
+                    .buttonStyle(.plain)
+
+                    Spacer()
+
+                    Button(action: { createFolderPrompt() }) {
+                        Image(systemName: "folder.badge.plus")
+                            .font(.system(size: 14))
+                            .foregroundColor(.confabPrimary)
+                            .contentShape(Rectangle())
+                    }
+                    .buttonStyle(.plain)
+                    .help("New Folder")
                 }
-                .buttonStyle(.plain)
-                .help("New Folder")
             }
             .padding(.horizontal, 12)
             .padding(.vertical, 10)
@@ -217,8 +271,11 @@ struct SidebarView: View {
 
     private func handleDrop(_ items: [String], toFolder folderId: UUID?) -> Bool {
         var moved = false
-        for idString in items {
+        // Each dropped item may itself be a newline-joined bundle of IDs (a multi-selection
-            guard let id = UUID(uuidString: idString),
+        // dragged together — see conversationRow's .draggable payload), so split every item
+        // before parsing UUIDs out of it.
+        for idString in items.flatMap({ $0.split(separator: "\n") }) {
+            guard let id = UUID(uuidString: String(idString)),
                   let conversation = conversations.first(where: { $0.id == id })
             else { continue }
             moveConversation(conversation, toFolder: folderId)
@@ -231,21 +288,36 @@ struct SidebarView: View {
     private func conversationRow(_ conversation: Conversation) -> some View {
         SidebarConversationRow(conversation: conversation)
             .contentShape(Rectangle())
-            .onTapGesture {
+            .onTapGesture(count: 2) {
                 chatViewModel.loadConversation(conversation)
+                selectedConversations.removeAll()
+            }
+            .onTapGesture(count: 1) {
+                handleRowTap(conversation)
             }
             .listRowBackground(
                 chatViewModel.currentConversationName == conversation.name
                     ? Color.confabAccent.opacity(0.15)
-                    : Color.clear
+                    : selectedConversations.contains(conversation.id)
+                        ? Color(nsColor: .selectedContentBackgroundColor).opacity(0.35)
+                        : Color.clear
             )
-            .draggable(conversation.id.uuidString) {
+            .draggable(dragPayload(for: conversation)) {
-                Text(conversation.name)
+                if selectedConversations.contains(conversation.id) && selectedConversations.count > 1 {
-                    .font(.system(size: 13, weight: .medium))
+                    Text("\(selectedConversations.count) conversations")
-                    .foregroundStyle(.white)
+                        .font(.system(size: 13, weight: .medium))
-                    .padding(.horizontal, 10)
+                        .foregroundStyle(.white)
-                    .padding(.vertical, 6)
+                        .padding(.horizontal, 10)
-                    .background(Color.confabAccent, in: RoundedRectangle(cornerRadius: 6))
+                        .padding(.vertical, 6)
+                        .background(Color.confabAccent, in: RoundedRectangle(cornerRadius: 6))
+                } else {
+                    Text(conversation.name)
+                        .font(.system(size: 13, weight: .medium))
+                        .foregroundStyle(.white)
+                        .padding(.horizontal, 10)
+                        .padding(.vertical, 6)
+                        .background(Color.confabAccent, in: RoundedRectangle(cornerRadius: 6))
+                }
             }
             .swipeActions(edge: .trailing, allowsFullSwipe: false) {
                 Button(role: .destructive) {
@@ -264,7 +336,7 @@ struct SidebarView: View {
                 Menu {
                     if conversation.folderId != nil {
                         Button {
-                            moveConversation(conversation, toFolder: nil)
+                            moveConversationOrSelection(conversation, toFolder: nil)
                         } label: {
                             Label("Remove from Folder", systemImage: "folder.badge.minus")
                         }
@@ -273,7 +345,7 @@ struct SidebarView: View {
                     ForEach(folders) { folder in
                         if folder.id != conversation.folderId {
                             Button {
-                                moveConversation(conversation, toFolder: folder.id)
+                                moveConversationOrSelection(conversation, toFolder: folder.id)
                             } label: {
                                 Text(folder.name)
                             }
@@ -286,7 +358,8 @@ struct SidebarView: View {
                         Label("New Folder…", systemImage: "folder.badge.plus")
                     }
                 } label: {
-                    Label("Move to Folder", systemImage: "folder")
+                    Label(selectedConversations.contains(conversation.id) && selectedConversations.count > 1
+                          ? "Move \(selectedConversations.count) to Folder" : "Move to Folder", systemImage: "folder")
                 }
                 Button {
                     renameConversation(conversation)
@@ -311,6 +384,7 @@ struct SidebarView: View {
         withAnimation {
             conversations.removeAll { $0.id == conversation.id }
         }
+        selectedConversations.remove(conversation.id)
         GitSyncService.shared.syncAfterDeletion()
     }
 
@@ -352,6 +426,63 @@ struct SidebarView: View {
         }
     }
 
+    /// Moves every currently-selected conversation to a folder (or removes them all from their
+    /// folders if `folderId` is nil).
+    private func moveSelectedToFolder(_ folderId: UUID?) {
+        for id in selectedConversations {
+            guard let conversation = conversations.first(where: { $0.id == id }) else { continue }
+            moveConversation(conversation, toFolder: folderId)
+        }
+    }
+
+    /// Right-clicking a conversation that's part of a multi-item selection moves the whole
+    /// selection; right-clicking a single (non-selected, or lone-selected) row moves just that one.
+    private func moveConversationOrSelection(_ conversation: Conversation, toFolder folderId: UUID?) {
+        if selectedConversations.contains(conversation.id) && selectedConversations.count > 1 {
+            moveSelectedToFolder(folderId)
+        } else {
+            moveConversation(conversation, toFolder: folderId)
+        }
+    }
+
+    /// Drag payload for a row: if it's part of an active multi-selection, bundle every selected
+    /// conversation's ID (newline-joined — UUIDs never contain one) so dragging any one of them
+    /// moves the whole selection. Otherwise just this row's own ID, unchanged.
+    private func dragPayload(for conversation: Conversation) -> String {
+        if selectedConversations.contains(conversation.id) && selectedConversations.count > 1 {
+            return selectedConversations.map { $0.uuidString }.joined(separator: "\n")
+        }
+        return conversation.id.uuidString
+    }
+
+    /// Standard macOS row-click handling: ⌘-click toggles the individual row (additive), Shift-click
+    /// extends/creates a contiguous range from the last-clicked row, and a plain click replaces the
+    /// selection with just this row. Never opens the conversation — that's double-click's job.
+    private func handleRowTap(_ conversation: Conversation) {
+        #if os(macOS)
+        let modifiers = NSEvent.modifierFlags
+        if modifiers.contains(.command) {
+            if selectedConversations.contains(conversation.id) {
+                selectedConversations.remove(conversation.id)
+            } else {
+                selectedConversations.insert(conversation.id)
+            }
+            lastClickedId = conversation.id
+            return
+        }
+        if modifiers.contains(.shift) {
+            let orderedIds = visibleOrderedConversations.map { $0.id }
+            selectedConversations.formUnion(
+                ConversationListView.idsInRange(orderedIds: orderedIds, anchorId: lastClickedId, targetId: conversation.id)
+            )
+            lastClickedId = conversation.id
+            return
+        }
+        #endif
+        selectedConversations = [conversation.id]
+        lastClickedId = conversation.id
+    }
+
     private func createFolderPrompt(andMove conversation: Conversation? = nil) {
         #if os(macOS)
         let alert = NSAlert()

oAI/Views/Screens/ConversationListView.swift

@@ -32,6 +32,7 @@ struct ConversationListView: View {
     @State private var collapsedFolders: Set<UUID> = []
     @State private var selectedConversations: Set<UUID> = []
     @State private var isSelecting = false
+    @State private var lastClickedId: UUID? = nil
     @State private var useSemanticSearch = false
     @State private var semanticResults: [Conversation] = []
     @State private var isSearching = false
@@ -60,6 +61,19 @@ struct ConversationListView: View {
         Dictionary(grouping: filteredConversations, by: { $0.folderId })
     }
 
+    /// Flattened conversation order matching what's actually rendered in the List — folders in
+    /// order (skipping collapsed ones' contents, since they're not visible/selectable), then
+    /// Unfiled last. Used as the anchor sequence for Shift-click range selection.
+    private var visibleOrderedConversations: [Conversation] {
+        guard !folders.isEmpty else { return filteredConversations }
+        var result: [Conversation] = []
+        for folder in folders where !collapsedFolders.contains(folder.id) {
+            result.append(contentsOf: conversationsByFolder[folder.id] ?? [])
+        }
+        result.append(contentsOf: conversationsByFolder[nil] ?? [])
+        return result
+    }
+
     var body: some View {
         VStack(spacing: 0) {
             // Header
@@ -72,6 +86,7 @@ struct ConversationListView: View {
                     Button("Cancel") {
                         isSelecting = false
                         selectedConversations.removeAll()
+                        lastClickedId = nil
                     }
                     .buttonStyle(.plain)
 
@@ -87,6 +102,28 @@ struct ConversationListView: View {
                         .buttonStyle(.plain)
                     }
 
+                    if !selectedConversations.isEmpty {
+                        Menu {
+                            if !folders.isEmpty {
+                                ForEach(folders) { folder in
+                                    Button(folder.name) {
+                                        moveSelectedToFolder(folder.id)
+                                    }
+                                }
+                                Divider()
+                            }
+                            Button("Remove from Folder") {
+                                moveSelectedToFolder(nil)
+                            }
+                        } label: {
+                            HStack(spacing: 4) {
+                                Image(systemName: "folder")
+                                Text("Move to Folder (\(selectedConversations.count))")
+                            }
+                        }
+                        .buttonStyle(.plain)
+                    }
+
                     if !selectedConversations.isEmpty {
                         Button(role: .destructive) {
                             deleteSelected()
@@ -287,6 +324,7 @@ struct ConversationListView: View {
                     loadConversations()
                     selectedConversations.removeAll()
                     isSelecting = false
+                    lastClickedId = nil
                 }
             )
         }
@@ -299,6 +337,7 @@ struct ConversationListView: View {
             if isSelecting {
                 Button {
                     toggleSelection(conversation.id)
+                    lastClickedId = conversation.id
                 } label: {
                     Image(systemName: selectedConversations.contains(conversation.id) ? "checkmark.circle.fill" : "circle")
                         .foregroundStyle(selectedConversations.contains(conversation.id) ? .blue : .secondary)
@@ -310,13 +349,7 @@ struct ConversationListView: View {
             ConversationRow(conversation: conversation)
                 .contentShape(Rectangle())
                 .onTapGesture {
-                    if isSelecting {
+                    handleRowTap(conversation, index: index)
-                        toggleSelection(conversation.id)
-                    } else {
-                        selectedIndex = index
-                        onLoad?(conversation)
-                        dismiss()
-                    }
                 }
 
             Spacer()
@@ -382,7 +415,7 @@ struct ConversationListView: View {
             Menu {
                 if conversation.folderId != nil {
                     Button {
-                        moveConversation(conversation, toFolder: nil)
+                        moveConversationOrSelection(conversation, toFolder: nil)
                     } label: {
                         Label("Remove from Folder", systemImage: "folder.badge.minus")
                     }
@@ -391,14 +424,15 @@ struct ConversationListView: View {
                 ForEach(folders) { folder in
                     if folder.id != conversation.folderId {
                         Button {
-                            moveConversation(conversation, toFolder: folder.id)
+                            moveConversationOrSelection(conversation, toFolder: folder.id)
                         } label: {
                             Text(folder.name)
                         }
                     }
                 }
             } label: {
-                Label("Move to Folder", systemImage: "folder")
+                Label(isSelecting && selectedConversations.contains(conversation.id) && selectedConversations.count > 1
+                      ? "Move \(selectedConversations.count) to Folder" : "Move to Folder", systemImage: "folder")
             }
             Menu {
                 Button {
@@ -532,6 +566,25 @@ struct ConversationListView: View {
         }
     }
 
+    /// Moves every currently-selected conversation to a folder (or removes them all from their
+    /// folders if `folderId` is nil).
+    private func moveSelectedToFolder(_ folderId: UUID?) {
+        for id in selectedConversations {
+            guard let conversation = conversations.first(where: { $0.id == id }) else { continue }
+            moveConversation(conversation, toFolder: folderId)
+        }
+    }
+
+    /// Right-clicking a conversation that's part of a multi-item selection moves the whole
+    /// selection; right-clicking a single (non-selected, or lone-selected) row moves just that one.
+    private func moveConversationOrSelection(_ conversation: Conversation, toFolder folderId: UUID?) {
+        if isSelecting && selectedConversations.contains(conversation.id) && selectedConversations.count > 1 {
+            moveSelectedToFolder(folderId)
+        } else {
+            moveConversation(conversation, toFolder: folderId)
+        }
+    }
+
     private func renameFolderPrompt(_ folder: Folder) {
         #if os(macOS)
         let alert = NSAlert()
@@ -578,6 +631,56 @@ struct ConversationListView: View {
         }
     }
 
+    /// Standard macOS row-click handling: ⌘-click toggles the individual row (entering selection
+    /// mode if needed), Shift-click extends/creates a contiguous range from the last-clicked row,
+    /// and a plain click either toggles (while already selecting) or opens the conversation.
+    private func handleRowTap(_ conversation: Conversation, index: Int) {
+        #if os(macOS)
+        let modifiers = NSEvent.modifierFlags
+        if modifiers.contains(.command) {
+            isSelecting = true
+            toggleSelection(conversation.id)
+            lastClickedId = conversation.id
+            return
+        }
+        if modifiers.contains(.shift) {
+            isSelecting = true
+            selectRange(to: conversation.id)
+            lastClickedId = conversation.id
+            return
+        }
+        #endif
+        if isSelecting {
+            toggleSelection(conversation.id)
+            lastClickedId = conversation.id
+        } else {
+            selectedIndex = index
+            onLoad?(conversation)
+            dismiss()
+        }
+    }
+
+    /// Pure range-selection logic, pulled out so it's testable without a live View: given the
+    /// on-screen id order, an anchor, and a target, returns the ids that should end up selected.
+    /// Falls back to just `targetId` if the anchor is nil or no longer present in `orderedIds`
+    /// (e.g. the very first Shift-click, or the anchor row was deleted/filtered out since).
+    nonisolated static func idsInRange(orderedIds: [UUID], anchorId: UUID?, targetId: UUID) -> Set<UUID> {
+        guard let anchorId,
+              let anchorIndex = orderedIds.firstIndex(of: anchorId),
+              let targetIndex = orderedIds.firstIndex(of: targetId)
+        else {
+            return [targetId]
+        }
+        let range = anchorIndex <= targetIndex ? anchorIndex...targetIndex : targetIndex...anchorIndex
+        return Set(orderedIds[range])
+    }
+
+    /// Selects every conversation between `lastClickedId` and `targetId` in on-screen order.
+    private func selectRange(to targetId: UUID) {
+        let orderedIds = visibleOrderedConversations.map { $0.id }
+        selectedConversations.formUnion(Self.idsInRange(orderedIds: orderedIds, anchorId: lastClickedId, targetId: targetId))
+    }
+
     private func deleteSelected() {
         for id in selectedConversations {
             do {
@@ -591,6 +694,7 @@ struct ConversationListView: View {
             selectedConversations.removeAll()
             isSelecting = false
         }
+        lastClickedId = nil
         selectedIndex = 0
         GitSyncService.shared.syncAfterDeletion()
     }

oAITests/ConversationListViewPureLogicTests.swift

@@ -0,0 +1,54 @@
+//
+//  ConversationListViewPureLogicTests.swift
+//  oAITests
+//
+// SPDX-License-Identifier: PolyForm-Noncommercial-1.0.0
+// Copyright (C) 2026 Rune Olsen
+
+import Testing
+import Foundation
+@testable import Confab
+
+@Suite("ConversationListView.idsInRange")
+struct ConversationListViewPureLogicTests {
+
+    private let ids = (0..<6).map { _ in UUID() }
+
+    @Test("Forward range includes anchor and target inclusive")
+    func forwardRange() {
+        let result = ConversationListView.idsInRange(orderedIds: ids, anchorId: ids[1], targetId: ids[4])
+        #expect(result == Set(ids[1...4]))
+    }
+
+    @Test("Backward range (target above anchor) still selects the span between them")
+    func backwardRange() {
+        let result = ConversationListView.idsInRange(orderedIds: ids, anchorId: ids[4], targetId: ids[1])
+        #expect(result == Set(ids[1...4]))
+    }
+
+    @Test("Anchor equal to target selects just that one id")
+    func sameAnchorAndTarget() {
+        let result = ConversationListView.idsInRange(orderedIds: ids, anchorId: ids[2], targetId: ids[2])
+        #expect(result == [ids[2]])
+    }
+
+    @Test("Nil anchor (first Shift-click) falls back to just the target")
+    func nilAnchorFallsBackToTarget() {
+        let result = ConversationListView.idsInRange(orderedIds: ids, anchorId: nil, targetId: ids[3])
+        #expect(result == [ids[3]])
+    }
+
+    @Test("Anchor no longer present in the ordered list falls back to just the target")
+    func missingAnchorFallsBackToTarget() {
+        let staleAnchor = UUID()
+        let result = ConversationListView.idsInRange(orderedIds: ids, anchorId: staleAnchor, targetId: ids[3])
+        #expect(result == [ids[3]])
+    }
+
+    @Test("Single-element list selects that element")
+    func singleElementList() {
+        let solo = [ids[0]]
+        let result = ConversationListView.idsInRange(orderedIds: solo, anchorId: ids[0], targetId: ids[0])
+        #expect(result == [ids[0]])
+    }
+}