diff --git a/ElementX/Sources/Screens/RoomScreen/RoomScreenInteractionHandler.swift b/ElementX/Sources/Screens/RoomScreen/RoomScreenInteractionHandler.swift
index e9dd8cbc1..cb2cf4050 100644
--- a/ElementX/Sources/Screens/RoomScreen/RoomScreenInteractionHandler.swift
+++ b/ElementX/Sources/Screens/RoomScreen/RoomScreenInteractionHandler.swift
@@ -257,6 +257,9 @@ class RoomScreenInteractionHandler {
             actionsSubject.send(.displayReportContent(itemID: itemID, senderID: eventTimelineItem.sender.id))
         case .react:
             showEmojiPicker(for: itemID)
+        case .toggleReaction(let key):
+            guard let eventID = itemID.eventID else { return }
+            Task { await roomProxy.timeline.toggleReaction(key, to: eventID) }
         case .endPoll(let pollStartID):
             endPoll(pollStartID: pollStartID)
         }
diff --git a/ElementX/Sources/Screens/RoomScreen/View/TimelineItemMacContextMenu.swift b/ElementX/Sources/Screens/RoomScreen/View/TimelineItemMacContextMenu.swift
index d6325b544..d0d6b0171 100644
--- a/ElementX/Sources/Screens/RoomScreen/View/TimelineItemMacContextMenu.swift
+++ b/ElementX/Sources/Screens/RoomScreen/View/TimelineItemMacContextMenu.swift
@@ -14,6 +14,8 @@
 // limitations under the License.
 //
 
+import Compound
+import SFSafeSymbols
 import SwiftUI
 
 /// The contents of the context menu shown when right clicking an item in the timeline on a Mac
@@ -27,8 +29,24 @@ struct TimelineItemMacContextMenu: View {
             if let menuActions = actionProvider?(item.id) {
                 Section {
                     if item.isReactable {
-                        Button { send(.react) } label: {
-                            TimelineItemMenuAction.react.label
+                        if #available(iOS 17.0, *) {
+                            let reactions = (item as? EventBasedTimelineItemProtocol)?.properties.reactions ?? []
+                            ControlGroup {
+                                ForEach(menuActions.reactions, id: \.key) {
+                                    ReactionToggle(reaction: $0, reactions: reactions) {
+                                        send(.toggleReaction(key: $0))
+                                    }
+                                }
+                                
+                                Button { send(.react) } label: {
+                                    CompoundIcon(\.reactionAdd)
+                                }
+                            }
+                            .controlGroupStyle(.palette)
+                        } else {
+                            Button { send(.react) } label: {
+                                TimelineItemMenuAction.react.label
+                            }
                         }
                     }
                     
@@ -54,3 +72,21 @@ struct TimelineItemMacContextMenu: View {
         }
     }
 }
+
+/// A button that acts as a toggle for reacting to a message.
+private struct ReactionToggle: View {
+    let reaction: TimelineItemMenuReaction
+    let reactions: [AggregatedReaction]
+    let action: (String) -> Void
+    
+    var isOn: Bool {
+        reactions.contains { $0.key == reaction.key && $0.isHighlighted }
+    }
+    
+    var body: some View {
+        Button { action(reaction.key) } label: {
+            Image(systemSymbol: reaction.symbol)
+                .symbolVariant(isOn ? .fill : .none)
+        }
+    }
+}
diff --git a/ElementX/Sources/Screens/RoomScreen/View/TimelineItemMenu.swift b/ElementX/Sources/Screens/RoomScreen/View/TimelineItemMenu.swift
index 9266ce024..7c20573b3 100644
--- a/ElementX/Sources/Screens/RoomScreen/View/TimelineItemMenu.swift
+++ b/ElementX/Sources/Screens/RoomScreen/View/TimelineItemMenu.swift
@@ -15,9 +15,11 @@
 //
 
 import Compound
+import SFSafeSymbols
 import SwiftUI
 
 struct TimelineItemMenuActions {
+    let reactions: [TimelineItemMenuReaction]
     let actions: [TimelineItemMenuAction]
     let debugActions: [TimelineItemMenuAction]
     
@@ -28,6 +30,13 @@ struct TimelineItemMenuActions {
         
         self.actions = actions
         self.debugActions = debugActions
+        reactions = [
+            .init(key: "👍️", symbol: .handThumbsup),
+            .init(key: "👎️", symbol: .handThumbsdown),
+            .init(key: "🔥", symbol: .flame),
+            .init(key: "❤️", symbol: .heart),
+            .init(key: "👏", symbol: .handsClap)
+        ]
     }
     
     var canReply: Bool {
@@ -41,6 +50,11 @@ struct TimelineItemMenuActions {
     }
 }
 
+struct TimelineItemMenuReaction {
+    let key: String
+    let symbol: SFSymbol
+}
+
 enum TimelineItemMenuAction: Identifiable, Hashable {
     case copy
     case edit
@@ -52,6 +66,7 @@ enum TimelineItemMenuAction: Identifiable, Hashable {
     case retryDecryption(sessionID: String)
     case report
     case react
+    case toggleReaction(key: String)
     case endPoll(pollStartID: String)
     
     var id: Self { self }
@@ -120,6 +135,9 @@ enum TimelineItemMenuAction: Identifiable, Hashable {
             Label(L10n.actionReportContent, icon: \.chatProblem)
         case .react:
             Label(L10n.actionReact, icon: \.reactionAdd)
+        case .toggleReaction:
+            // Unused label - manually created in TimelineItemMacContextMenu.
+            Label(L10n.actionReact, icon: \.reactionAdd)
         case .endPoll:
             Label(L10n.actionEndPoll, icon: \.pollsEnd)
         }
@@ -216,11 +234,9 @@ struct TimelineItemMenu: View {
     private var reactionsSection: some View {
         ScrollView(.horizontal) {
             HStack(alignment: .center, spacing: 8) {
-                reactionButton(for: "👍️")
-                reactionButton(for: "👎️")
-                reactionButton(for: "🔥")
-                reactionButton(for: "❤️")
-                reactionButton(for: "👏")
+                ForEach(actions.reactions, id: \.key) {
+                    reactionButton(for: $0.key)
+                }
                 
                 Button {
                     dismiss()