diff --git a/Classes/Issues/IssueManagingContextController.swift b/Classes/Issues/IssueManagingContextController.swift
index 437c2d34f..2f9ea4eba 100644
--- a/Classes/Issues/IssueManagingContextController.swift
+++ b/Classes/Issues/IssueManagingContextController.swift
@@ -304,10 +304,23 @@ final class IssueManagingContextController: NSObject, ContextMenuDelegate {
         Haptic.triggerNotification(.success)
     }
 
-    func didDismiss(selected labels: [RepositoryLabel]) {
+    func didDismiss(controller: LabelsViewController) {
         guard let previous = result,
-            previous.labels.labels != labels
+            previous.labels.labels != controller.selected
             else { return }
+
+        if controller.wasDismissedByDone {
+            self.update(selected: controller.selected, previous: previous)
+        } else {
+            // Ask for confirmation
+            self.showCancelAlert { [weak self] keepChanges in
+                guard keepChanges else { return }
+                self?.update(selected: controller.selected, previous: previous)
+            }
+        }
+    }
+
+    private func update(selected labels: [RepositoryLabel], previous: IssueResult) {
         delegate?.willMutateModel(from: self)
         client.mutateLabels(
             previous: previous,
@@ -323,10 +336,23 @@ final class IssueManagingContextController: NSObject, ContextMenuDelegate {
 
         let selected = controller.selected
         guard controller.selectionChanged(newValues: selected) else { return }
+
+        if controller.wasDismissedByDone {
+            self.update(selected: selected, type: controller.type, previous: previous)
+        } else {
+            // Ask for confirmation
+            self.showCancelAlert { [weak self] keepChanges in
+                guard keepChanges else { return }
+                self?.update(selected: selected, type: controller.type, previous: previous)
+            }
+        }
+    }
+
+    private func update(selected assignees: [IssueAssigneeViewModel], type: PeopleViewController.PeopleType, previous: IssueResult) {
         delegate?.willMutateModel(from: self)
 
         let mutationType: V3AddPeopleRequest.PeopleType
-        switch controller.type {
+        switch type {
         case .assignee: mutationType = .assignees
         case .reviewer: mutationType = .reviewers
         }
@@ -337,7 +363,7 @@ final class IssueManagingContextController: NSObject, ContextMenuDelegate {
             owner: model.owner,
             repo: model.repo,
             number: model.number,
-            people: controller.selected
+            people: assignees
         )
     }
 
@@ -345,13 +371,26 @@ final class IssueManagingContextController: NSObject, ContextMenuDelegate {
         guard let previous = result,
             previous.milestone != controller.selected
             else { return }
+
+        if controller.wasDismissedByDone {
+            self.update(selected: controller.selected, previous: previous)
+        } else {
+            // Ask for confirmation
+            self.showCancelAlert { [weak self] keepChanges in
+                guard keepChanges else { return }
+                self?.update(selected: controller.selected, previous: previous)
+            }
+        }
+    }
+
+    private func update(selected milestone: Milestone?, previous: IssueResult) {
         delegate?.willMutateModel(from: self)
         client.setMilestone(
             previous: previous,
             owner: model.owner,
             repo: model.repo,
             number: model.number,
-            milestone: controller.selected
+            milestone: milestone
         )
     }
 
@@ -363,10 +402,24 @@ final class IssueManagingContextController: NSObject, ContextMenuDelegate {
         } else if let people = viewController as? PeopleViewController {
             didDismiss(controller: people)
         } else if let labels = viewController as? LabelsViewController {
-            didDismiss(selected: labels.selected)
+            didDismiss(controller: labels)
         }
     }
 
     func contextMenuDidDismiss(viewController: UIViewController, animated: Bool) {}
 
+    private func showCancelAlert(completion: @escaping (_ keepChanges: Bool) -> Void) {
+        guard let viewController = self.viewController else { return }
+
+        let title = NSLocalizedString("Are you sure?", comment: "")
+        let message = NSLocalizedString("Some changes have been made. Are you sure you want to discard them?", comment: "")
+        let alert = UIAlertController.configured(title: title, message: message, preferredStyle: .alert)
+
+        alert.addActions([
+            AlertAction.keep { _ in completion(true) },
+            AlertAction.discard { _ in completion(false) }
+        ])
+
+        viewController.present(alert, animated: trueUnlessReduceMotionEnabled)
+    }
 }
diff --git a/Classes/Labels/LabelsViewController.swift b/Classes/Labels/LabelsViewController.swift
index 0b6c0a0f6..4c3ef7fbf 100644
--- a/Classes/Labels/LabelsViewController.swift
+++ b/Classes/Labels/LabelsViewController.swift
@@ -19,6 +19,8 @@ LabelSectionControllerDelegate {
     private let client: GithubClient
     private let request: RepositoryLabelsQuery
 
+    var wasDismissedByDone = false
+
     init(
         selected: [RepositoryLabel],
         client: GithubClient,
@@ -102,6 +104,11 @@ LabelSectionControllerDelegate {
         })
     }
 
+    override func onMenuDone() {
+        self.wasDismissedByDone = true
+        super.onMenuDone()
+    }
+
     // MARK: BaseListViewControllerDataSource
 
     func models(adapter: ListSwiftAdapter) -> [ListSwiftPair] {
diff --git a/Classes/Milestones/MilestonesViewController.swift b/Classes/Milestones/MilestonesViewController.swift
index b621998ee..3ea587115 100644
--- a/Classes/Milestones/MilestonesViewController.swift
+++ b/Classes/Milestones/MilestonesViewController.swift
@@ -26,6 +26,8 @@ MilestoneSectionControllerDelegate {
     private let feedRefresh = FeedRefresh()
     private var milestones = [Milestone]()
 
+    var wasDismissedByDone = false
+
     private let dateFormatter: DateFormatter = {
         let formatter = DateFormatter()
         formatter.dateStyle = .long
@@ -96,6 +98,11 @@ MilestoneSectionControllerDelegate {
         }
     }
 
+    override func onMenuDone() {
+        self.wasDismissedByDone = true
+        super.onMenuDone()
+    }
+
     // MARK: BaseListViewControllerDataSource
 
     func models(adapter: ListSwiftAdapter) -> [ListSwiftPair] {
diff --git a/Classes/People/PeopleViewController.swift b/Classes/People/PeopleViewController.swift
index 7c56b81bc..538a118c8 100644
--- a/Classes/People/PeopleViewController.swift
+++ b/Classes/People/PeopleViewController.swift
@@ -30,6 +30,8 @@ PeopleSectionControllerDelegate {
     private var owner: String
     private var repo: String
 
+    var wasDismissedByDone = false
+
     init(
         selections: [String],
         exclusions: [String],
@@ -165,6 +167,11 @@ PeopleSectionControllerDelegate {
         }
     }
 
+    @objc override func onMenuDone() {
+        self.wasDismissedByDone = true
+        super.onMenuDone()
+    }
+
     // MARK: BaseListViewControllerDataSource
 
     func models(adapter: ListSwiftAdapter) -> [ListSwiftPair] {
diff --git a/Classes/Utility/AlertAction.swift b/Classes/Utility/AlertAction.swift
index c483b84a6..85c92f541 100644
--- a/Classes/Utility/AlertAction.swift
+++ b/Classes/Utility/AlertAction.swift
@@ -113,6 +113,10 @@ struct AlertAction {
         return UIAlertAction(title: NSLocalizedString("Discard", comment: ""), style: .destructive, handler: handler)
     }
 
+    static func keep(_ handler: AlertActionBlock? = nil) -> UIAlertAction {
+        return UIAlertAction(title: NSLocalizedString("Keep", comment: ""), style: .default, handler: handler)
+    }
+
     static func delete(_ handler: AlertActionBlock? = nil) -> UIAlertAction {
         return UIAlertAction(title: NSLocalizedString("Delete", comment: ""), style: .destructive, handler: handler)
     }