diff --git a/Meshtastic/Persistence/UpdateCoreData.swift b/Meshtastic/Persistence/UpdateCoreData.swift
index 59fda031..3bc0e29b 100644
--- a/Meshtastic/Persistence/UpdateCoreData.swift
+++ b/Meshtastic/Persistence/UpdateCoreData.swift
@@ -75,6 +75,21 @@ public func deleteChannelMessages(channelIndex: Int32, context: NSManagedObjectC
 	}
 }
 
+public func deleteUserMessages(user: UserEntity, context: NSManagedObjectContext) {
+
+	let fetchUserMessagesRequest: NSFetchRequest<NSFetchRequestResult> = NSFetchRequest.init(entityName: "MessageEntity")
+	fetchUserMessagesRequest.predicate = NSPredicate(format: "((toUser.num == %lld) OR (fromUser.num == %lld)) AND toUser != nil AND fromUser != nil AND admin == false", Int64(user.num), Int64(user.num))
+	do {
+		let deleteRequest = NSBatchDeleteRequest(fetchRequest: fetchUserMessagesRequest)
+		try context.executeAndMergeChanges(using: deleteRequest)
+		try context.save()
+		
+	} catch let error as NSError {
+		print("Error: \(error.localizedDescription)")
+		abort()
+	}
+}
+
 public func clearCoreDataDatabase(context: NSManagedObjectContext) {
 	
 	let persistenceController = PersistenceController.shared.container
diff --git a/Meshtastic/Views/Messages/Contacts.swift b/Meshtastic/Views/Messages/Contacts.swift
index d8a34b40..8a2bf258 100644
--- a/Meshtastic/Views/Messages/Contacts.swift
+++ b/Meshtastic/Views/Messages/Contacts.swift
@@ -20,8 +20,9 @@ struct Contacts: View {
 	
 	private var users: FetchedResults<UserEntity>
 	@State var node: NodeInfoEntity? = nil
-	
 	@State private var selection: UserEntity? = nil // Nothing selected by default.
+	@State private var isPresentingDeleteChannelMessagesConfirm: Bool = false
+	@State private var isPresentingDeleteUserMessagesConfirm: Bool = false
 
     var body: some View {
 
@@ -83,11 +84,24 @@ struct Contacts: View {
 								}
 								.frame(maxWidth: .infinity, maxHeight: 80, alignment: .leading)
 								.contextMenu {
+									if channel.allPrivateMessages.count > 0 {
+										Button(role: .destructive) {
+											isPresentingDeleteChannelMessagesConfirm = true
+										} label: {
+											Label("Delete Messages", systemImage: "trash")
+										}
+									}
+								}
+								.confirmationDialog(
+									"This conversation will be deleted.",
+									isPresented: $isPresentingDeleteChannelMessagesConfirm,
+									titleVisibility: .visible
+								) {
+									
 									Button(role: .destructive) {
-										print("I want to delete all the messages for \(channel.name ?? String(channel.index))")
 										deleteChannelMessages(channelIndex: channel.index, context: context)
 									} label: {
-										Label("Delete Messages", systemImage: "trash")
+										Text("Delete")
 									}
 								}
 							}
@@ -143,6 +157,28 @@ struct Contacts: View {
 												}
 											}
 											.frame(maxWidth: .infinity, maxHeight: 80, alignment: .leading)
+											.contextMenu {
+												if user.messageList.count  > 0 {
+													Button(role: .destructive) {
+														print("I want to delete all the messages for \(user.longName)")
+														isPresentingDeleteUserMessagesConfirm = true
+													} label: {
+														Label("Delete Messages", systemImage: "trash")
+													}
+												}
+											}
+											.confirmationDialog(
+												"This conversation will be deleted.",
+												isPresented: $isPresentingDeleteUserMessagesConfirm,
+												titleVisibility: .visible
+											) {
+												
+												Button(role: .destructive) {
+													deleteUserMessages(user: user, context: context)
+												} label: {
+													Text("Delete")
+												}
+											}
 										}
 									}
 								}