diff --git a/app/src/main/java/org/thoughtcrime/securesms/backup/v2/BackupRepository.kt b/app/src/main/java/org/thoughtcrime/securesms/backup/v2/BackupRepository.kt
index 81806eaa58..2314c3db1c 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/backup/v2/BackupRepository.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/backup/v2/BackupRepository.kt
@@ -1438,6 +1438,7 @@ object BackupRepository {
 
   fun enablePaidBackupTier() {
     Log.i(TAG, "Setting backup tier to PAID", true)
+    resetInitializedStateAndAuthCredentials()
     SignalStore.backup.backupTier = MessageBackupTier.PAID
     SignalStore.backup.lastCheckInMillis = System.currentTimeMillis()
     SignalStore.backup.lastCheckInSnoozeMillis = 0
diff --git a/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/BackupStateObserver.kt b/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/BackupStateObserver.kt
index b827e5b6ff..bcd3818b05 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/BackupStateObserver.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/BackupStateObserver.kt
@@ -63,9 +63,9 @@ class BackupStateObserver(
     private val backupTierChangedNotifier = MutableSharedFlow<Unit>()
 
     /**
-     * Called when the value returned by [SignalStore.backup.backupTier] changes.
+     * Called when the backup state likely changed.
      */
-    fun notifyBackupTierChanged(scope: CoroutineScope = staticScope) {
+    fun notifyBackupStateChanged(scope: CoroutineScope = staticScope) {
       Log.d(TAG, "Notifier got a change")
       scope.launch {
         backupTierChangedNotifier.emit(Unit)
diff --git a/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/BackupsSettingsViewModel.kt b/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/BackupsSettingsViewModel.kt
index a2ecf5159d..86b4363fc3 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/BackupsSettingsViewModel.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/backups/BackupsSettingsViewModel.kt
@@ -59,6 +59,6 @@ class BackupsSettingsViewModel : ViewModel() {
       StorageSyncHelper.scheduleSyncForDataChange()
     }
 
-    BackupStateObserver.notifyBackupTierChanged(scope = viewModelScope)
+    BackupStateObserver.notifyBackupStateChanged(scope = viewModelScope)
   }
 }
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/BackupSubscriptionCheckJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/BackupSubscriptionCheckJob.kt
index 29c5dcbecf..fc49b9c1a3 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/BackupSubscriptionCheckJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/BackupSubscriptionCheckJob.kt
@@ -14,6 +14,7 @@ import org.signal.donations.InAppPaymentType
 import org.thoughtcrime.securesms.backup.DeletionState
 import org.thoughtcrime.securesms.backup.v2.BackupRepository
 import org.thoughtcrime.securesms.backup.v2.MessageBackupTier
+import org.thoughtcrime.securesms.components.settings.app.backups.BackupStateObserver
 import org.thoughtcrime.securesms.components.settings.app.subscription.DonationSerializationHelper.toFiatValue
 import org.thoughtcrime.securesms.components.settings.app.subscription.InAppPaymentsRepository
 import org.thoughtcrime.securesms.components.settings.app.subscription.RecurringInAppPaymentRepository
@@ -225,6 +226,7 @@ class BackupSubscriptionCheckJob private constructor(parameters: Parameters) : C
         if (backupExpiration != null) {
           Log.i(TAG, "Marking subscription failed or canceled.")
           SignalStore.backup.setDownloadNotifierToTriggerAtHalfwayPoint(backupExpiration)
+          BackupStateObserver.notifyBackupStateChanged()
         } else {
           Log.w(TAG, "Failed to mark, no entitlement was found on WhoAmIResponse")
         }
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJob.kt
index 374be8dde7..b62a5d6a28 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJob.kt
@@ -106,7 +106,7 @@ class InAppPaymentRecurringContextJob private constructor(
     warning("A permanent failure occurred.")
 
     val inAppPayment = SignalDatabase.inAppPayments.getById(inAppPaymentId)
-    val isRedeemed = inAppPayment?.state == InAppPaymentTable.State.END && inAppPayment.data.redemption?.stage != InAppPaymentData.RedemptionState.Stage.REDEEMED
+    val isRedeemed = inAppPayment?.state == InAppPaymentTable.State.END && inAppPayment.data.redemption?.stage == InAppPaymentData.RedemptionState.Stage.REDEEMED
     if (isRedeemed) {
       info("Already redeemed. Exiting quietly.")
       return
@@ -116,11 +116,11 @@ class InAppPaymentRecurringContextJob private constructor(
         inAppPayment.copy(
           notified = false,
           state = InAppPaymentTable.State.END,
-          data = inAppPayment.data.copy(
+          data = inAppPayment.data.newBuilder().error(
             error = InAppPaymentData.Error(
               type = InAppPaymentData.Error.Type.REDEMPTION
             )
-          )
+          ).build()
         )
       )
     }
@@ -544,7 +544,9 @@ class InAppPaymentRecurringContextJob private constructor(
       409 -> {
         warning("Already redeemed this token during new subscription. Failing.", applicationError)
 
-        if (inAppPayment.type == InAppPaymentType.RECURRING_BACKUP) {
+        // During keep-alive processing, we don't alert the user about redemption failures.
+        if (inAppPayment.type == InAppPaymentType.RECURRING_BACKUP && inAppPayment.data.redemption?.keepAlive != true) {
+          info("Displaying redemption failure for non-keep-alive processing.")
           SignalStore.backup.hasBackupAlreadyRedeemedError = true
         }
 
@@ -633,12 +635,14 @@ class InAppPaymentRecurringContextJob private constructor(
     SignalDatabase.inAppPayments.update(
       inAppPayment = inAppPayment.copy(
         state = InAppPaymentTable.State.END,
-        data = inAppPayment.data.copy(
-          error = InAppPaymentData.Error(
-            type = InAppPaymentData.Error.Type.REDEMPTION,
-            data_ = "409"
+        data = inAppPayment.data.newBuilder()
+          .error(
+            InAppPaymentData.Error(
+              type = InAppPaymentData.Error.Type.REDEMPTION,
+              data_ = "409"
+            )
           )
-        )
+          .build()
       )
     )
   }
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRedemptionJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRedemptionJob.kt
index 90b41031f8..d42777e815 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRedemptionJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRedemptionJob.kt
@@ -130,11 +130,11 @@ class InAppPaymentRedemptionJob private constructor(
           inAppPayment.copy(
             notified = false,
             state = InAppPaymentTable.State.END,
-            data = inAppPayment.data.copy(
-              error = InAppPaymentData.Error(
+            data = inAppPayment.data.newBuilder().error(
+              InAppPaymentData.Error(
                 type = InAppPaymentData.Error.Type.REDEMPTION
               )
-            )
+            ).build()
           )
         )
       }
diff --git a/app/src/main/java/org/thoughtcrime/securesms/keyvalue/BackupValues.kt b/app/src/main/java/org/thoughtcrime/securesms/keyvalue/BackupValues.kt
index ab0c52bb0a..987ad00b80 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/keyvalue/BackupValues.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/keyvalue/BackupValues.kt
@@ -262,7 +262,7 @@ class BackupValues(store: KeyValueStore) : SignalStoreValues(store) {
         putLong(KEY_BACKUP_TIER, serializedValue)
       }
 
-      BackupStateObserver.notifyBackupTierChanged()
+      BackupStateObserver.notifyBackupStateChanged()
     }
 
   /** An internal setting that can override the backup tier for a user. */
diff --git a/app/src/test/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJobTest.kt b/app/src/test/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJobTest.kt
index 4faafc19e9..d998e54509 100644
--- a/app/src/test/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJobTest.kt
+++ b/app/src/test/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJobTest.kt
@@ -452,6 +452,7 @@ class InAppPaymentRecurringContextJobTest {
 
     mockkObject(BackupRepository)
     every { BackupRepository.getBackupTier() } returns NetworkResult.Success(MessageBackupTier.PAID)
+    every { BackupRepository.resetInitializedStateAndAuthCredentials() } returns Unit
 
     val iap = insertInAppPayment(
       type = InAppPaymentType.RECURRING_BACKUP