diff --git a/ElementX/Resources/Localizations/en.lproj/Localizable.strings b/ElementX/Resources/Localizations/en.lproj/Localizable.strings
index 85fac299a..f81ac7c6d 100644
--- a/ElementX/Resources/Localizations/en.lproj/Localizable.strings
+++ b/ElementX/Resources/Localizations/en.lproj/Localizable.strings
@@ -36,8 +36,10 @@
 "action_confirm_password" = "Confirm password";
 "action_continue" = "Continue";
 "action_copy" = "Copy";
+"action_copy_caption" = "Copy caption";
 "action_copy_link" = "Copy link";
 "action_copy_link_to_message" = "Copy link to message";
+"action_copy_text" = "Copy text";
 "action_create" = "Create";
 "action_create_a_room" = "Create a room";
 "action_deactivate" = "Deactivate";
@@ -84,6 +86,7 @@
 "action_reject" = "Reject";
 "action_remove" = "Remove";
 "action_remove_caption" = "Remove caption";
+"action_remove_message" = "Remove message";
 "action_reply" = "Reply";
 "action_reply_in_thread" = "Reply in thread";
 "action_report_bug" = "Report bug";
diff --git a/ElementX/Sources/Generated/Strings.swift b/ElementX/Sources/Generated/Strings.swift
index db2328789..36ae30edd 100644
--- a/ElementX/Sources/Generated/Strings.swift
+++ b/ElementX/Sources/Generated/Strings.swift
@@ -104,10 +104,14 @@ internal enum L10n {
   internal static var actionContinue: String { return L10n.tr("Localizable", "action_continue") }
   /// Copy
   internal static var actionCopy: String { return L10n.tr("Localizable", "action_copy") }
+  /// Copy caption
+  internal static var actionCopyCaption: String { return L10n.tr("Localizable", "action_copy_caption") }
   /// Copy link
   internal static var actionCopyLink: String { return L10n.tr("Localizable", "action_copy_link") }
   /// Copy link to message
   internal static var actionCopyLinkToMessage: String { return L10n.tr("Localizable", "action_copy_link_to_message") }
+  /// Copy text
+  internal static var actionCopyText: String { return L10n.tr("Localizable", "action_copy_text") }
   /// Create
   internal static var actionCreate: String { return L10n.tr("Localizable", "action_create") }
   /// Create a room
@@ -204,6 +208,8 @@ internal enum L10n {
   internal static var actionRemove: String { return L10n.tr("Localizable", "action_remove") }
   /// Remove caption
   internal static var actionRemoveCaption: String { return L10n.tr("Localizable", "action_remove_caption") }
+  /// Remove message
+  internal static var actionRemoveMessage: String { return L10n.tr("Localizable", "action_remove_message") }
   /// Reply
   internal static var actionReply: String { return L10n.tr("Localizable", "action_reply") }
   /// Reply in thread
diff --git a/ElementX/Sources/Other/SwiftUI/Layout/MenuSheetLabelStyle.swift b/ElementX/Sources/Other/SwiftUI/Layout/MenuSheetLabelStyle.swift
index 0ea17f68e..12f701be9 100644
--- a/ElementX/Sources/Other/SwiftUI/Layout/MenuSheetLabelStyle.swift
+++ b/ElementX/Sources/Other/SwiftUI/Layout/MenuSheetLabelStyle.swift
@@ -7,14 +7,34 @@
 
 import SwiftUI
 
-extension LabelStyle where Self == MenuSheetLabelStyle {
-    /// A label style for labels that are within a menu that is being presented as a sheet.
-    static var menuSheet: Self { MenuSheetLabelStyle() }
+extension ButtonStyle where Self == MenuSheetButtonStyle {
+    /// A button style for buttons that are within a menu that is being presented as a sheet.
+    static var menuSheet: Self { MenuSheetButtonStyle() }
 }
 
-/// The style used for labels that are part of a menu that's presented as
-/// a sheet as `TimelineItemMenu` and `RoomAttachmentPicker`.
-struct MenuSheetLabelStyle: LabelStyle {
+/// The style used for buttons that are part of a menu that's presented as
+/// a sheet such as `TimelineItemMenu`.
+struct MenuSheetButtonStyle: ButtonStyle {
+    @Environment(\.accessibilityShowButtonShapes) private var accessibilityShowButtonShapes
+    
+    func makeBody(configuration: Configuration) -> some View {
+        configuration.label
+            .labelStyle(MenuSheetLabelStyle())
+            .foregroundStyle(configuration.role == .destructive ? .compound.textCriticalPrimary : .compound.textActionPrimary)
+            .contentShape(.rect)
+            .opacity(configuration.isPressed ? 0.3 : 1)
+            .background {
+                if accessibilityShowButtonShapes {
+                    RoundedRectangle(cornerRadius: 12)
+                        .fill(Color(uiColor: .secondarySystemFill))
+                        .opacity(configuration.isPressed ? 0.8 : 1)
+                        .padding(4)
+                }
+            }
+    }
+}
+
+private struct MenuSheetLabelStyle: LabelStyle {
     var spacing: CGFloat = 16
     
     func makeBody(configuration: Configuration) -> some View {
diff --git a/ElementX/Sources/Screens/RoomScreen/ComposerToolbar/View/RoomAttachmentPicker.swift b/ElementX/Sources/Screens/RoomScreen/ComposerToolbar/View/RoomAttachmentPicker.swift
index 0732bd15f..b789445a7 100644
--- a/ElementX/Sources/Screens/RoomScreen/ComposerToolbar/View/RoomAttachmentPicker.swift
+++ b/ElementX/Sources/Screens/RoomScreen/ComposerToolbar/View/RoomAttachmentPicker.swift
@@ -32,7 +32,6 @@ struct RoomAttachmentPicker: View {
                 context.send(viewAction: .enableTextFormatting)
             } label: {
                 Label(L10n.screenRoomAttachmentTextFormatting, icon: \.textFormatting)
-                    .labelStyle(.menuSheet)
             }
             .accessibilityIdentifier(A11yIdentifiers.roomScreen.attachmentPickerTextFormatting)
             
@@ -40,7 +39,6 @@ struct RoomAttachmentPicker: View {
                 context.send(viewAction: .attach(.poll))
             } label: {
                 Label(L10n.screenRoomAttachmentSourcePoll, icon: \.polls)
-                    .labelStyle(.menuSheet)
             }
             .accessibilityIdentifier(A11yIdentifiers.roomScreen.attachmentPickerPoll)
             
@@ -48,7 +46,6 @@ struct RoomAttachmentPicker: View {
                 context.send(viewAction: .attach(.location))
             } label: {
                 Label(L10n.screenRoomAttachmentSourceLocation, icon: \.locationPin)
-                    .labelStyle(.menuSheet)
             }
             .accessibilityIdentifier(A11yIdentifiers.roomScreen.attachmentPickerLocation)
             
@@ -56,7 +53,6 @@ struct RoomAttachmentPicker: View {
                 context.send(viewAction: .attach(.file))
             } label: {
                 Label(L10n.screenRoomAttachmentSourceFiles, icon: \.attachment)
-                    .labelStyle(.menuSheet)
             }
             .accessibilityIdentifier(A11yIdentifiers.roomScreen.attachmentPickerDocuments)
             
@@ -64,7 +60,6 @@ struct RoomAttachmentPicker: View {
                 context.send(viewAction: .attach(.photoLibrary))
             } label: {
                 Label(L10n.screenRoomAttachmentSourceGallery, icon: \.image)
-                    .labelStyle(.menuSheet)
             }
             .accessibilityIdentifier(A11yIdentifiers.roomScreen.attachmentPickerPhotoLibrary)
             
@@ -72,7 +67,6 @@ struct RoomAttachmentPicker: View {
                 context.send(viewAction: .attach(.camera))
             } label: {
                 Label(L10n.screenRoomAttachmentSourceCamera, icon: \.takePhoto)
-                    .labelStyle(.menuSheet)
             }
             .accessibilityIdentifier(A11yIdentifiers.roomScreen.attachmentPickerCamera)
         }
diff --git a/ElementX/Sources/Screens/Timeline/TimelineInteractionHandler.swift b/ElementX/Sources/Screens/Timeline/TimelineInteractionHandler.swift
index c7d004df1..2e610569c 100644
--- a/ElementX/Sources/Screens/Timeline/TimelineInteractionHandler.swift
+++ b/ElementX/Sources/Screens/Timeline/TimelineInteractionHandler.swift
@@ -102,7 +102,13 @@ class TimelineInteractionHandler {
         case .copy:
             guard let messageTimelineItem = timelineItem as? EventBasedMessageTimelineItemProtocol else { return }
             UIPasteboard.general.string = messageTimelineItem.body
-        case .edit:
+        case .copyCaption:
+            guard let messageTimelineItem = timelineItem as? EventBasedMessageTimelineItemProtocol,
+                  let caption = messageTimelineItem.mediaCaption else {
+                return
+            }
+            UIPasteboard.general.string = caption
+        case .edit, .addCaption, .editCaption, .editPoll:
             switch timelineItem {
             case let messageTimelineItem as EventBasedMessageTimelineItemProtocol:
                 processEditMessageEvent(messageTimelineItem)
@@ -115,13 +121,6 @@ class TimelineInteractionHandler {
             default:
                 MXLog.error("Cannot edit item with id: \(timelineItem.id)")
             }
-        case .addCaption, .editCaption:
-            switch timelineItem {
-            case let messageTimelineItem as EventBasedMessageTimelineItemProtocol:
-                processEditMessageEvent(messageTimelineItem)
-            default:
-                MXLog.error("Cannot add/edit caption on item with id: \(timelineItem.id)")
-            }
         case .removeCaption:
             guard case let .event(_, eventOrTransactionID) = timelineItem.id else {
                 MXLog.error("Failed removing caption, missing event ID")
diff --git a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMacContextMenu.swift b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMacContextMenu.swift
index f97ae8011..8cb4264d4 100644
--- a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMacContextMenu.swift
+++ b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMacContextMenu.swift
@@ -51,7 +51,7 @@ struct TimelineItemMacContextMenu: View {
                 }
                 
                 Section {
-                    ForEach(menuActions.debugActions) { action in
+                    ForEach(menuActions.secondaryActions) { action in
                         Button(role: action.isDestructive ? .destructive : nil) {
                             send(action)
                         } label: {
diff --git a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenu.swift b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenu.swift
index 43e7144ac..e7448035c 100644
--- a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenu.swift
+++ b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenu.swift
@@ -47,7 +47,7 @@ struct TimelineItemMenu: View {
                             .background(Color.compound.bgSubtlePrimary)
                     }
                     
-                    viewsForActions(actions.debugActions)
+                    viewsForActions(actions.secondaryActions)
                 }
             }
         }
@@ -179,8 +179,8 @@ struct TimelineItemMenu: View {
                 send(action)
             } label: {
                 action.label
-                    .labelStyle(.menuSheet)
             }
+            .buttonStyle(.menuSheet)
         }
     }
     
@@ -261,21 +261,28 @@ private extension View {
 // MARK: - Previews
 
 struct TimelineItemMenu_Previews: PreviewProvider, TestablePreview {
+    enum ItemType { case incomingText, outgoingMedia, outgoingMediaWithCaption }
+    
     static let viewModel = TimelineViewModel.mock
-    static let (item, actions) = makeItem()
-    static let (backupItem, _) = makeItem(authenticity: .notGuaranteed(color: .gray))
-    static let (unsignedItem, _) = makeItem(authenticity: .unsignedDevice(color: .red))
-    static let (unencryptedItem, _) = makeItem(authenticity: .sentInClear(color: .red))
-    static let (unknownFailureItem, _) = makeItem(deliveryStatus: .sendingFailed(.unknown))
-    static let (identityChangedItem, _) = makeItem(deliveryStatus: .sendingFailed(.verifiedUser(.changedIdentity(users: [
+    static let (item, actions) = makeActions()
+    static let (backupItem, _) = makeActions(authenticity: .notGuaranteed(color: .gray))
+    static let (unsignedItem, _) = makeActions(authenticity: .unsignedDevice(color: .red))
+    static let (unencryptedItem, _) = makeActions(authenticity: .sentInClear(color: .red))
+    static let (unknownFailureItem, _) = makeActions(deliveryStatus: .sendingFailed(.unknown))
+    static let (identityChangedItem, _) = makeActions(deliveryStatus: .sendingFailed(.verifiedUser(.changedIdentity(users: [
         "@alice:matrix.org"
     ]))))
-    static let (unsignedDevicesItem, _) = makeItem(deliveryStatus: .sendingFailed(.verifiedUser(.hasUnsignedDevice(devices: [
+    static let (unsignedDevicesItem, _) = makeActions(deliveryStatus: .sendingFailed(.verifiedUser(.hasUnsignedDevice(devices: [
         "@alice:matrix.org": ["DEVICE1", "DEVICE2"]
     ]))))
-    static let (ownUnsignedDevicesItem, _) = makeItem(deliveryStatus: .sendingFailed(.verifiedUser(.hasUnsignedDevice(devices: [
+    static let (ownUnsignedDevicesItem, _) = makeActions(deliveryStatus: .sendingFailed(.verifiedUser(.hasUnsignedDevice(devices: [
         RoomMemberProxyMock.mockMe.userID: ["DEVICE1"]
     ]))))
+    
+    // Media
+    
+    static let (mediaItem, mediaItemActions) = makeActions(itemType: .outgoingMedia)
+    static let (mediaItemWithCaption, mediaItemWithCaptionActions) = makeActions(itemType: .outgoingMediaWithCaption)
 
     static var previews: some View {
         TimelineItemMenu(item: item, actions: actions)
@@ -314,26 +321,56 @@ struct TimelineItemMenu_Previews: PreviewProvider, TestablePreview {
         TimelineItemMenu(item: identityChangedItem, actions: actions)
             .environmentObject(viewModel.context)
             .previewDisplayName("Identity Changed")
+        
+        // Media
+        
+        TimelineItemMenu(item: mediaItem, actions: mediaItemActions)
+            .environmentObject(viewModel.context)
+            .previewDisplayName("Media")
+        
+        TimelineItemMenu(item: mediaItemWithCaption, actions: mediaItemWithCaptionActions)
+            .environmentObject(viewModel.context)
+            .previewDisplayName("Media with Caption")
     }
     
-    static func makeItem(authenticity: EncryptionAuthenticity? = nil,
-                         deliveryStatus: TimelineItemDeliveryStatus? = nil) -> (TextRoomTimelineItem, TimelineItemMenuActions)! {
-        guard var item = RoomTimelineItemFixtures.singleMessageChunk.first as? TextRoomTimelineItem,
-              let actions = TimelineItemMenuActions(isReactable: true,
-                                                    actions: [.copy, .edit, .reply(isThread: false), .pin, .redact],
-                                                    debugActions: [.viewSource],
-                                                    emojiProvider: EmojiProvider(appSettings: ServiceLocator.shared.settings)) else {
-            return nil
-        }
+    static func makeActions(itemType: ItemType = .incomingText,
+                            authenticity: EncryptionAuthenticity? = nil,
+                            deliveryStatus: TimelineItemDeliveryStatus? = nil) -> (EventBasedTimelineItemProtocol, TimelineItemMenuActions)! {
+        guard var item = makeItem(itemType: itemType) else { return nil }
+        let provider = TimelineItemMenuActionProvider(timelineItem: item,
+                                                      canCurrentUserRedactSelf: true,
+                                                      canCurrentUserRedactOthers: false,
+                                                      canCurrentUserPin: true,
+                                                      pinnedEventIDs: [],
+                                                      isDM: true,
+                                                      isViewSourceEnabled: true,
+                                                      isCreateMediaCaptionsEnabled: true,
+                                                      isPinnedEventsTimeline: false,
+                                                      emojiProvider: EmojiProvider(appSettings: ServiceLocator.shared.settings))
+        guard let actions = provider.makeActions() else { return nil }
         
-        if let authenticity {
-            item.properties.encryptionAuthenticity = authenticity
-        }
-        
-        if let deliveryStatus {
-            item.properties.deliveryStatus = deliveryStatus
+        if var textItem = item as? TextRoomTimelineItem {
+            if let authenticity {
+                textItem.properties.encryptionAuthenticity = authenticity
+            }
+            
+            if let deliveryStatus {
+                textItem.properties.deliveryStatus = deliveryStatus
+            }
+            item = textItem
         }
         
         return (item, actions)
     }
+    
+    static func makeItem(itemType: ItemType) -> EventBasedTimelineItemProtocol? {
+        switch itemType {
+        case .incomingText:
+            RoomTimelineItemFixtures.singleMessageChunk.first as? EventBasedTimelineItemProtocol
+        case .outgoingMedia:
+            RoomTimelineItemFixtures.mediaChunk[1] as? EventBasedTimelineItemProtocol
+        case .outgoingMediaWithCaption:
+            RoomTimelineItemFixtures.mediaChunk[5] as? EventBasedTimelineItemProtocol
+        }
+    }
 }
diff --git a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenuAction.swift b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenuAction.swift
index 38f824622..3a0e88b79 100644
--- a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenuAction.swift
+++ b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenuAction.swift
@@ -13,18 +13,18 @@ import SwiftUI
 struct TimelineItemMenuActions {
     let reactions: [TimelineItemMenuReaction]
     let actions: [TimelineItemMenuAction]
-    let debugActions: [TimelineItemMenuAction]
+    let secondaryActions: [TimelineItemMenuAction]
     
     init?(isReactable: Bool,
           actions: [TimelineItemMenuAction],
-          debugActions: [TimelineItemMenuAction],
+          secondaryActions: [TimelineItemMenuAction],
           emojiProvider: EmojiProviderProtocol) {
-        if !isReactable, actions.isEmpty, debugActions.isEmpty {
+        if !isReactable, actions.isEmpty, secondaryActions.isEmpty {
             return nil
         }
         
         self.actions = actions
-        self.debugActions = debugActions
+        self.secondaryActions = secondaryActions
         
         var frequentlyUsed: OrderedSet<TimelineItemMenuReaction> = [
             .init(key: "👍️", symbol: .handThumbsup),
@@ -56,10 +56,12 @@ struct TimelineItemMenuReaction: Hashable {
 
 enum TimelineItemMenuAction: Identifiable, Hashable {
     case copy
+    case copyCaption
     case edit
     case addCaption
     case editCaption
     case removeCaption
+    case editPoll
     case copyPermalink
     case redact
     case reply(isThread: Bool)
@@ -79,7 +81,7 @@ enum TimelineItemMenuAction: Identifiable, Hashable {
     /// Whether the item should cancel a reply/edit occurring in the composer.
     var switchToDefaultComposer: Bool {
         switch self {
-        case .reply, .edit, .addCaption, .editCaption:
+        case .reply, .edit, .addCaption, .editCaption, .editPoll:
             return false
         default:
             return true
@@ -89,7 +91,7 @@ enum TimelineItemMenuAction: Identifiable, Hashable {
     /// Whether the action should be shown for an item that failed to send.
     var canAppearInFailedEcho: Bool {
         switch self {
-        case .copy, .edit, .redact, .viewSource:
+        case .copy, .edit, .redact, .viewSource, .editPoll:
             return true
         default:
             return false
@@ -130,7 +132,9 @@ enum TimelineItemMenuAction: Identifiable, Hashable {
     var label: some View {
         switch self {
         case .copy:
-            Label(L10n.actionCopy, icon: \.copy)
+            Label(L10n.actionCopyText, icon: \.copy)
+        case .copyCaption:
+            Label(L10n.actionCopyCaption, icon: \.copy)
         case .edit:
             Label(L10n.actionEdit, icon: \.edit)
         case .addCaption:
@@ -138,7 +142,9 @@ enum TimelineItemMenuAction: Identifiable, Hashable {
         case .editCaption:
             Label(L10n.actionEditCaption, icon: \.edit)
         case .removeCaption:
-            Label(L10n.actionRemoveCaption, icon: \.delete)
+            Label(L10n.actionRemoveCaption, icon: \.close)
+        case .editPoll:
+            Label(L10n.actionEditPoll, icon: \.edit)
         case .copyPermalink:
             Label(L10n.actionCopyLinkToMessage, icon: \.link)
         case .reply(let isThread):
@@ -146,7 +152,7 @@ enum TimelineItemMenuAction: Identifiable, Hashable {
         case .forward:
             Label(L10n.actionForward, icon: \.forward)
         case .redact:
-            Label(L10n.actionRemove, icon: \.delete)
+            Label(L10n.actionRemoveMessage, icon: \.delete)
         case .viewSource:
             Label(L10n.actionViewSource, icon: \.code)
         case .retryDecryption:
diff --git a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenuActionProvider.swift b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenuActionProvider.swift
index cad18009e..4d624fb3f 100644
--- a/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenuActionProvider.swift
+++ b/ElementX/Sources/Screens/Timeline/View/ItemMenu/TimelineItemMenuActionProvider.swift
@@ -32,26 +32,12 @@ struct TimelineItemMenuActionProvider {
             return nil
         }
 
-        var debugActions: [TimelineItemMenuAction] = []
-        if isViewSourceEnabled {
-            debugActions.append(.viewSource)
-        }
-
         if let encryptedItem = timelineItem as? EncryptedRoomTimelineItem {
-            switch encryptedItem.encryptionType {
-            case .megolmV1AesSha2(let sessionID, _):
-                debugActions.append(.retryDecryption(sessionID: sessionID))
-            default:
-                break
-            }
-            
-            return .init(isReactable: false,
-                         actions: [.copyPermalink],
-                         debugActions: debugActions,
-                         emojiProvider: emojiProvider)
+            return makeEncryptedItemActions(encryptedItem)
         }
         
         var actions: [TimelineItemMenuAction] = []
+        var secondaryActions: [TimelineItemMenuAction] = []
 
         if item.canBeRepliedTo {
             if let messageItem = item as? EventBasedMessageTimelineItemProtocol {
@@ -64,59 +50,95 @@ struct TimelineItemMenuActionProvider {
         if item.isForwardable {
             actions.append(.forward(itemID: item.id))
         }
-
-        if item.isEditable {
-            if let messageItem = item as? EventBasedMessageTimelineItemProtocol, messageItem.supportsMediaCaption {
-                if messageItem.hasMediaCaption {
-                    actions.append(contentsOf: [.editCaption, .removeCaption])
-                } else if isCreateMediaCaptionsEnabled {
-                    actions.append(.addCaption)
-                }
-            } else if !(item is VoiceMessageRoomTimelineItem) {
-                actions.append(.edit)
-            }
-        }
         
         if canCurrentUserPin, let eventID = item.id.eventID {
             actions.append(pinnedEventIDs.contains(eventID) ? .unpin : .pin)
         }
-
-        if item.isCopyable {
-            actions.append(.copy)
-        }
         
         if item.isRemoteMessage {
             actions.append(.copyPermalink)
         }
+        
+        if item.isEditable {
+            if item.supportsMediaCaption {
+                if item.hasMediaCaption {
+                    actions.append(.editCaption)
+                } else if isCreateMediaCaptionsEnabled {
+                    actions.append(.addCaption)
+                }
+            } else if item is PollRoomTimelineItem {
+                actions.append(.editPoll)
+            } else if !(item is VoiceMessageRoomTimelineItem) {
+                actions.append(.edit)
+            }
+        }
 
+        if item.isCopyable {
+            actions.append(.copy)
+        } else if item.hasMediaCaption {
+            actions.append(.copyCaption)
+        }
+        
+        if item.hasMediaCaption {
+            actions.append(.removeCaption)
+        }
+        
         if canRedactItem(item), let poll = item.pollIfAvailable, !poll.hasEnded, let eventID = item.id.eventID {
             actions.append(.endPoll(pollStartID: eventID))
         }
         
-        if canRedactItem(item) {
-            actions.append(.redact)
+        if isViewSourceEnabled {
+            actions.append(.viewSource)
         }
-
+        
         if !item.isOutgoing {
-            actions.append(.report)
+            secondaryActions.append(.report)
         }
-
-        if item.hasFailedToSend {
-            actions = actions.filter(\.canAppearInFailedEcho)
-        }
-
-        if item.isRedacted {
-            actions = actions.filter(\.canAppearInRedacted)
+        
+        if canRedactItem(item) {
+            secondaryActions.append(.redact)
         }
         
         if isPinnedEventsTimeline {
             actions.insert(.viewInRoomTimeline, at: 0)
             actions = actions.filter(\.canAppearInPinnedEventsTimeline)
+            secondaryActions = secondaryActions.filter(\.canAppearInPinnedEventsTimeline)
+        }
+        
+        if item.hasFailedToSend {
+            actions = actions.filter(\.canAppearInFailedEcho)
+            secondaryActions = secondaryActions.filter(\.canAppearInFailedEcho)
+        }
+        
+        if item.isRedacted {
+            actions = actions.filter(\.canAppearInRedacted)
+            secondaryActions = secondaryActions.filter(\.canAppearInRedacted)
         }
 
         return .init(isReactable: isPinnedEventsTimeline ? false : item.isReactable,
                      actions: actions,
-                     debugActions: debugActions,
+                     secondaryActions: secondaryActions,
+                     emojiProvider: emojiProvider)
+    }
+    
+    private func makeEncryptedItemActions(_ encryptedItem: EncryptedRoomTimelineItem) -> TimelineItemMenuActions? {
+        var actions: [TimelineItemMenuAction] = [.copyPermalink]
+        var secondaryActions: [TimelineItemMenuAction] = []
+        
+        if isViewSourceEnabled {
+            actions.append(.viewSource)
+        }
+        
+        switch encryptedItem.encryptionType {
+        case .megolmV1AesSha2(let sessionID, _):
+            secondaryActions.append(.retryDecryption(sessionID: sessionID))
+        default:
+            break
+        }
+        
+        return .init(isReactable: false,
+                     actions: actions,
+                     secondaryActions: secondaryActions,
                      emojiProvider: emojiProvider)
     }
     
diff --git a/ElementX/Sources/Services/Timeline/Fixtures/RoomTimelineItemFixtures.swift b/ElementX/Sources/Services/Timeline/Fixtures/RoomTimelineItemFixtures.swift
index da67a49fc..716849af3 100644
--- a/ElementX/Sources/Services/Timeline/Fixtures/RoomTimelineItemFixtures.swift
+++ b/ElementX/Sources/Services/Timeline/Fixtures/RoomTimelineItemFixtures.swift
@@ -250,28 +250,16 @@ enum RoomTimelineItemFixtures {
     
     static var mediaChunk: [RoomTimelineItemProtocol] {
         [
-            VideoRoomTimelineItem(id: .randomEvent,
-                                  timestamp: "10:47 am",
-                                  isOutgoing: false,
-                                  isEditable: false,
-                                  canBeRepliedTo: true,
-                                  isThreaded: false,
-                                  sender: .init(id: ""),
-                                  content: .init(filename: "video.mp4",
-                                                 videoInfo: .mockVideo,
-                                                 thumbnailInfo: .mockThumbnail,
-                                                 blurhash: "KtI~70X5V?yss9oyrYs:t6")),
-            ImageRoomTimelineItem(id: .randomEvent,
-                                  timestamp: "10:47 am",
-                                  isOutgoing: false,
-                                  isEditable: false,
-                                  canBeRepliedTo: true,
-                                  isThreaded: false,
-                                  sender: .init(id: ""),
-                                  content: .init(filename: "image.jpg",
-                                                 imageInfo: .mockImage,
-                                                 thumbnailInfo: nil,
-                                                 blurhash: "KpE4oyayR5|GbHb];3j@of"))
+            AudioRoomTimelineItem(isOutgoing: false, caption: "Listen to this!"),
+            AudioRoomTimelineItem(isOutgoing: true),
+            FileRoomTimelineItem(isOutgoing: false),
+            FileRoomTimelineItem(isOutgoing: true, caption: "Please check this ASAP!"),
+            ImageRoomTimelineItem(isOutgoing: false),
+            ImageRoomTimelineItem(isOutgoing: true, caption: "Isn't this pretty!"),
+            VideoRoomTimelineItem(isOutgoing: false, caption: "Woah, it was incredible!"),
+            VideoRoomTimelineItem(isOutgoing: true),
+            VoiceMessageRoomTimelineItem(isOutgoing: false),
+            VoiceMessageRoomTimelineItem(isOutgoing: true)
         ]
     }
 }
@@ -294,3 +282,92 @@ private extension TextRoomTimelineItem {
         return newSelf
     }
 }
+
+private extension AudioRoomTimelineItem {
+    init(isOutgoing: Bool, caption: String? = nil) {
+        self.init(id: .randomEvent,
+                  timestamp: "10:47 am",
+                  isOutgoing: isOutgoing,
+                  isEditable: isOutgoing,
+                  canBeRepliedTo: true,
+                  isThreaded: false,
+                  sender: .init(id: isOutgoing ? "@alice:matrix.org" : "@bob:matrix.org"),
+                  content: .init(filename: "audio.mp3",
+                                 caption: caption,
+                                 duration: 60,
+                                 waveform: nil,
+                                 source: .init(url: .mockMXCAudio, mimeType: nil),
+                                 fileSize: nil,
+                                 contentType: .mp3))
+    }
+}
+
+private extension FileRoomTimelineItem {
+    init(isOutgoing: Bool, caption: String? = nil) {
+        self.init(id: .randomEvent,
+                  timestamp: "10:47 am",
+                  isOutgoing: isOutgoing,
+                  isEditable: isOutgoing,
+                  canBeRepliedTo: true,
+                  isThreaded: false,
+                  sender: .init(id: isOutgoing ? "@alice:matrix.org" : "@bob:matrix.org"),
+                  content: .init(filename: "file.pdf",
+                                 caption: caption,
+                                 source: .init(url: .mockMXCFile, mimeType: nil),
+                                 fileSize: nil,
+                                 thumbnailSource: nil,
+                                 contentType: .pdf))
+    }
+}
+
+private extension ImageRoomTimelineItem {
+    init(isOutgoing: Bool, caption: String? = nil) {
+        self.init(id: .randomEvent,
+                  timestamp: "10:47 am",
+                  isOutgoing: isOutgoing,
+                  isEditable: isOutgoing,
+                  canBeRepliedTo: true,
+                  isThreaded: false,
+                  sender: .init(id: isOutgoing ? "@alice:matrix.org" : "@bob:matrix.org"),
+                  content: .init(filename: "image.jpg",
+                                 caption: caption,
+                                 imageInfo: .mockImage,
+                                 thumbnailInfo: nil,
+                                 blurhash: "KpE4oyayR5|GbHb];3j@of"))
+    }
+}
+
+private extension VideoRoomTimelineItem {
+    init(isOutgoing: Bool, caption: String? = nil) {
+        self.init(id: .randomEvent,
+                  timestamp: "10:47 am",
+                  isOutgoing: isOutgoing,
+                  isEditable: isOutgoing,
+                  canBeRepliedTo: true,
+                  isThreaded: false,
+                  sender: .init(id: isOutgoing ? "@alice:matrix.org" : "@bob:matrix.org"),
+                  content: .init(filename: "video.mp4",
+                                 caption: caption,
+                                 videoInfo: .mockVideo,
+                                 thumbnailInfo: .mockThumbnail,
+                                 blurhash: "KtI~70X5V?yss9oyrYs:t6"))
+    }
+}
+
+private extension VoiceMessageRoomTimelineItem {
+    init(isOutgoing: Bool) {
+        self.init(id: .randomEvent,
+                  timestamp: "10:47 am",
+                  isOutgoing: isOutgoing,
+                  isEditable: isOutgoing,
+                  canBeRepliedTo: true,
+                  isThreaded: false,
+                  sender: .init(id: isOutgoing ? "@alice:matrix.org" : "@bob:matrix.org"),
+                  content: .init(filename: "message.ogg",
+                                 duration: 10,
+                                 waveform: .mockWaveform,
+                                 source: .init(url: .mockMXCAudio, mimeType: nil),
+                                 fileSize: nil,
+                                 contentType: .audio))
+    }
+}
diff --git a/ElementX/Sources/Services/Timeline/TimelineItems/EventBasedMessageTimelineItemProtocol.swift b/ElementX/Sources/Services/Timeline/TimelineItems/EventBasedMessageTimelineItemProtocol.swift
index a0832abf5..734037766 100644
--- a/ElementX/Sources/Services/Timeline/TimelineItems/EventBasedMessageTimelineItemProtocol.swift
+++ b/ElementX/Sources/Services/Timeline/TimelineItems/EventBasedMessageTimelineItemProtocol.swift
@@ -35,18 +35,22 @@ extension EventBasedMessageTimelineItemProtocol {
         }
     }
     
-    var hasMediaCaption: Bool {
+    var mediaCaption: String? {
         switch contentType {
         case .audio(let content):
-            content.caption != nil
+            content.caption
         case .file(let content):
-            content.caption != nil
+            content.caption
         case .image(let content):
-            content.caption != nil
+            content.caption
         case .video(let content):
-            content.caption != nil
+            content.caption
         case .emote, .notice, .text, .location, .voice:
-            false
+            nil
         }
     }
+    
+    var hasMediaCaption: Bool {
+        mediaCaption != nil
+    }
 }
diff --git a/ElementX/Sources/Services/Timeline/TimelineItems/EventBasedTimelineItemProtocol.swift b/ElementX/Sources/Services/Timeline/TimelineItems/EventBasedTimelineItemProtocol.swift
index aa99847b7..0150401ff 100644
--- a/ElementX/Sources/Services/Timeline/TimelineItems/EventBasedTimelineItemProtocol.swift
+++ b/ElementX/Sources/Services/Timeline/TimelineItems/EventBasedTimelineItemProtocol.swift
@@ -99,4 +99,14 @@ extension EventBasedTimelineItemProtocol {
             return true
         }
     }
+    
+    var supportsMediaCaption: Bool {
+        guard let messageBasedItem = self as? EventBasedMessageTimelineItemProtocol else { return false }
+        return messageBasedItem.supportsMediaCaption
+    }
+    
+    var hasMediaCaption: Bool {
+        guard let messageBasedItem = self as? EventBasedMessageTimelineItemProtocol else { return false }
+        return messageBasedItem.hasMediaCaption
+    }
 }
diff --git a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Authenticity.png b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Authenticity.png
index 5614e9125..c93414d20 100644
--- a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Authenticity.png
+++ b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Authenticity.png
@@ -1,3 +1,3 @@
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diff --git a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Button-shapes.png b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Button-shapes.png
index e6e1c3129..d3a797f89 100644
--- a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Button-shapes.png
+++ b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Button-shapes.png
@@ -1,3 +1,3 @@
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diff --git a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Identity-Changed.png b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Identity-Changed.png
index db49f1379..c4a29de51 100644
--- a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Identity-Changed.png
+++ b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Identity-Changed.png
@@ -1,3 +1,3 @@
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diff --git a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Media-with-Caption.png b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Media-with-Caption.png
new file mode 100644
index 000000000..d0b640996
--- /dev/null
+++ b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Media-with-Caption.png
@@ -0,0 +1,3 @@
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new file mode 100644
index 000000000..b34a3b3ca
--- /dev/null
+++ b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Media.png
@@ -0,0 +1,3 @@
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diff --git a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Normal.png b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Normal.png
index 6dc2b5e65..839ae5df7 100644
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+++ b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Normal.png
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index e1bddfabb..5cf9b34ab 100644
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+++ b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Own-Unsigned-Devices.png
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index 214c0a0e7..5df36e364 100644
--- a/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Unencrypted.png
+++ b/PreviewTests/Sources/__Snapshots__/PreviewTests/test_timelineItemMenu-iPad-en-GB.Unencrypted.png
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index 6dc2b5e65..839ae5df7 100644
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