diff --git a/Signal/src/ViewControllers/AppSettings/Donations/DonationSettingsViewController+MySupport.swift b/Signal/src/ViewControllers/AppSettings/Donations/DonationSettingsViewController+MySupport.swift
index 49cf3d18d6..22f3fa9918 100644
--- a/Signal/src/ViewControllers/AppSettings/Donations/DonationSettingsViewController+MySupport.swift
+++ b/Signal/src/ViewControllers/AppSettings/Donations/DonationSettingsViewController+MySupport.swift
@@ -471,10 +471,12 @@ extension DonationSettingsViewController {
             message: actionSheetMessage
         )
 
-        actionSheet.addAction(showDonateAndClearErrorAction(
-            title: .tryAgain,
-            preferredDonateMode: preferredDonateMode
-        ))
+        switch preferredDonateMode {
+        case .monthly:
+            actionSheet.addAction(showDonateAndCancelSubscriptionAction(title: .tryAgain))
+        case .oneTime:
+            actionSheet.addAction(showOneTimeDonateAndClearErrorAction(title: .tryAgain))
+        }
         actionSheet.addAction(OWSActionSheets.cancelAction)
 
         self.presentActionSheet(actionSheet, animated: true)
@@ -506,10 +508,7 @@ extension DonationSettingsViewController {
             message: actionSheetMessage
         )
 
-        actionSheet.addAction(showDonateAndClearErrorAction(
-            title: .renewSubscription,
-            preferredDonateMode: .monthly
-        ))
+        actionSheet.addAction(showDonateAndCancelSubscriptionAction(title: .renewSubscription))
         actionSheet.addAction(OWSActionSheets.cancelAction)
 
         self.presentActionSheet(actionSheet, animated: true)
@@ -535,20 +534,13 @@ extension DonationSettingsViewController {
         }
     }
 
-    private func showDonateAndClearErrorAction(
-        title: ShowDonateActionTitle,
-        preferredDonateMode: DonateViewController.DonateMode
+    private func showOneTimeDonateAndClearErrorAction(
+        title: ShowDonateActionTitle
     ) -> ActionSheetAction {
         return ActionSheetAction(title: title.localizedTitle) { _ in
             self.databaseStorage.write { tx in
-                switch preferredDonateMode {
-                case .oneTime:
-                    DependenciesBridge.shared.receiptCredentialResultStore
-                        .clearRequestError(errorMode: .oneTimeBoost, tx: tx.asV2Write)
-                case .monthly:
-                    DependenciesBridge.shared.receiptCredentialResultStore
-                        .clearRequestErrorForAnyRecurringSubscription(tx: tx.asV2Write)
-                }
+                DependenciesBridge.shared.receiptCredentialResultStore
+                    .clearRequestError(errorMode: .oneTimeBoost, tx: tx.asV2Write)
             }
 
             // Not ideal, because this makes network requests. However, this
@@ -556,11 +548,31 @@ extension DonationSettingsViewController {
             // methods for updating the state outside the normal loading flow.
             self.loadAndUpdateState().done(on: DispatchQueue.main) { [weak self] in
                 guard let self else { return }
-                self.showDonateViewController(preferredDonateMode: preferredDonateMode)
+                self.showDonateViewController(preferredDonateMode: .oneTime)
             }
         }
     }
 
+    private func showDonateAndCancelSubscriptionAction(
+        title: ShowDonateActionTitle
+    ) -> ActionSheetAction {
+        return ActionSheetAction(title: title.localizedTitle) { _ in
+            firstly(on: DispatchQueue.global()) {
+                self.databaseStorage.read { tx in
+                    SubscriptionManagerImpl.getSubscriberID(transaction: tx)
+                }
+            }.then(on: DispatchQueue.global()) { subscriberID in
+                guard let subscriberID else { return Promise.value(())}
+                return SubscriptionManagerImpl.cancelSubscription(for: subscriberID)
+            }.then(on: DispatchQueue.main) {
+                self.loadAndUpdateState()
+            }.done(on: DispatchQueue.main) { [weak self] in
+                guard let self else { return }
+                self.showDonateViewController(preferredDonateMode: .monthly)
+            }.cauterize()
+        }
+    }
+
     private func mySupportErrorIconView() -> UIView {
         let imageView = UIImageView.withTemplateImageName(
             "error-circle",
diff --git a/Signal/src/ViewControllers/Donations/DonateViewController.swift b/Signal/src/ViewControllers/Donations/DonateViewController.swift
index aac13a0e84..4f252bf939 100644
--- a/Signal/src/ViewControllers/Donations/DonateViewController.swift
+++ b/Signal/src/ViewControllers/Donations/DonateViewController.swift
@@ -1414,11 +1414,11 @@ class DonateViewController: OWSViewController, OWSNavigationChildController {
                 isEnabled: isDifferentSubscriptionLevelSelected(monthly.currentSubscription)
             )
             buttons.append(doomedContinueButton)
-        } else if
-            let currentSubscription = monthly.currentSubscription,
-            currentSubscription.active
-        {
-            if Self.canMakeNewDonations(forDonateMode: .monthly) {
+        } else if let currentSubscription = monthly.currentSubscription {
+            if
+                currentSubscription.active,
+                Self.canMakeNewDonations(forDonateMode: .monthly)
+            {
                 let updateTitle = OWSLocalizedString(
                     "DONATE_SCREEN_UPDATE_MONTHLY_SUBSCRIPTION_BUTTON",
                     comment: "On the donation screen, if you already have a subscription, you'll see a button to update your subscription. This is the text on that button."
diff --git a/SignalMessaging/Subscriptions/SubscriptionManagerImpl.swift b/SignalMessaging/Subscriptions/SubscriptionManagerImpl.swift
index 6490be77eb..21668e4e4e 100644
--- a/SignalMessaging/Subscriptions/SubscriptionManagerImpl.swift
+++ b/SignalMessaging/Subscriptions/SubscriptionManagerImpl.swift
@@ -404,17 +404,39 @@ public class SubscriptionManagerImpl: NSObject {
     public class func cancelSubscription(for subscriberID: Data) -> Promise<Void> {
         Logger.info("[Donations] Cancelling subscription")
 
-        let request = OWSRequestFactory.deleteSubscriberID(subscriberID)
-        return firstly {
-            networkManager.makePromise(request: request)
-        }.map(on: DispatchQueue.global()) { response in
-            switch response.responseStatusCode {
-            case 200, 404:
-                break
-            default:
-                throw OWSAssertionError("Got bad response code \(response.responseStatusCode).")
+        return firstly(on: DispatchQueue.global())  {
+            // Fetch the latest subscription state
+            self.getCurrentSubscriptionStatus(for: subscriberID)
+        }.then(on: DispatchQueue.global()) { subscription in
+            guard let subscription else {
+                return Promise.value(())
             }
 
+            // Check the subscription is in a state that can be cancelled
+            // If the state isn't in active or pastDue, skip deleting the
+            // subscription on the backend, and continue to clearing out the
+            // local subscription information.
+            switch subscription.status {
+            case .active, .pastDue:
+                break
+            case .canceled, .incomplete, .incompleteExpired, .trialing, .unpaid, .unknown:
+                return Promise.value(())
+            }
+
+            let request = OWSRequestFactory.deleteSubscriberID(subscriberID)
+            return firstly(on: DispatchQueue.global()) {
+                networkManager.makePromise(request: request)
+            }.map(on: DispatchQueue.global()) { response in
+                switch response.responseStatusCode {
+                case 200, 404:
+                    break
+                default:
+                    throw OWSAssertionError("Got bad response code \(response.responseStatusCode).")
+                }
+            }.done(on: DispatchQueue.global()) {
+                Logger.info("[Donations] Deleted remote subscription.")
+            }
+        }.done(on: DispatchQueue.global()) {
             databaseStorage.write { transaction in
                 self.setSubscriberID(nil, transaction: transaction)
                 self.setSubscriberCurrencyCode(nil, transaction: transaction)
@@ -429,6 +451,7 @@ public class SubscriptionManagerImpl: NSObject {
             }
 
             self.storageServiceManager.recordPendingLocalAccountUpdates()
+            Logger.info("[Donations] Deleted local subscription.")
         }
     }