diff --git a/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/subscription/InAppPaymentsRepository.kt b/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/subscription/InAppPaymentsRepository.kt
index dab6d69a4c..698599f2c8 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/subscription/InAppPaymentsRepository.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/components/settings/app/subscription/InAppPaymentsRepository.kt
@@ -44,6 +44,7 @@ import org.thoughtcrime.securesms.database.model.InAppPaymentSubscriberRecord
 import org.thoughtcrime.securesms.database.model.databaseprotos.InAppPaymentData
 import org.thoughtcrime.securesms.database.model.databaseprotos.PendingOneTimeDonation
 import org.thoughtcrime.securesms.dependencies.AppDependencies
+import org.thoughtcrime.securesms.jobmanager.Job
 import org.thoughtcrime.securesms.keyvalue.SignalStore
 import org.thoughtcrime.securesms.recipients.Recipient
 import org.thoughtcrime.securesms.storage.StorageSyncHelper
@@ -223,10 +224,14 @@ object InAppPaymentsRepository {
    * Returns a duration to utilize for jobs tied to different payment methods. For long running bank transfers, we need to
    * allow extra time for completion.
    */
-  fun resolveContextJobLifespan(inAppPayment: InAppPaymentTable.InAppPayment): Duration {
-    return when (inAppPayment.data.paymentMethodType) {
-      InAppPaymentData.PaymentMethodType.SEPA_DEBIT, InAppPaymentData.PaymentMethodType.IDEAL -> 30.days
-      else -> 1.days
+  fun resolveContextJobLifespanMillis(inAppPayment: InAppPaymentTable.InAppPayment): Long {
+    return if (inAppPayment.type == InAppPaymentType.RECURRING_BACKUP) {
+      Job.Parameters.IMMORTAL
+    } else {
+      when (inAppPayment.data.paymentMethodType) {
+        InAppPaymentData.PaymentMethodType.SEPA_DEBIT, InAppPaymentData.PaymentMethodType.IDEAL -> 30.days.inWholeMilliseconds
+        else -> 1.days.inWholeMilliseconds
+      }
     }
   }
 
diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/InAppPaymentTable.kt b/app/src/main/java/org/thoughtcrime/securesms/database/InAppPaymentTable.kt
index e01bd09c59..b480339d5c 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/InAppPaymentTable.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/InAppPaymentTable.kt
@@ -38,6 +38,7 @@ import org.thoughtcrime.securesms.util.parcelers.MillisecondDurationParceler
 import org.thoughtcrime.securesms.util.parcelers.NullableSubscriberIdParceler
 import org.whispersystems.signalservice.api.subscriptions.SubscriberId
 import kotlin.time.Duration
+import kotlin.time.Duration.Companion.hours
 import kotlin.time.Duration.Companion.milliseconds
 import kotlin.time.Duration.Companion.seconds
 
@@ -184,6 +185,20 @@ class InAppPaymentTable(context: Context, databaseHelper: SignalDatabase) : Data
     AppDependencies.databaseObserver.notifyInAppPaymentsObservers(inAppPayment)
   }
 
+  fun getOldPendingPayments(type: InAppPaymentType): List<InAppPayment> {
+    val oneDayAgo = System.currentTimeMillis().milliseconds - 24.hours
+    return readableDatabase
+      .select()
+      .from(TABLE_NAME)
+      .where(
+        "$STATE = ? AND $TYPE = ? AND $UPDATED_AT <= ${oneDayAgo.inWholeSeconds}",
+        State.serialize(State.PENDING),
+        InAppPaymentType.serialize(type)
+      )
+      .run()
+      .readToList(mapper = InAppPayment::deserialize)
+  }
+
   /**
    * Returns true if the user has submitted a pre-pending recurring donation.
    * In this state, the user would have had to cancel their subscription or be in the process of trying
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 fc49b9c1a3..5792de127b 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/BackupSubscriptionCheckJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/BackupSubscriptionCheckJob.kt
@@ -174,7 +174,11 @@ class BackupSubscriptionCheckJob private constructor(parameters: Parameters) : C
           val isGooglePlayBillingCanceled = purchase is BillingPurchaseResult.Success && !purchase.isAutoRenewing
 
           if (isGooglePlayBillingCanceled && (!hasActiveSignalSubscription || isSignalSubscriptionFailedOrCanceled)) {
-            Log.i(TAG, "Valid cancel state. Clearing mismatch. (isGooglePlayBillingCanceled: true, hasActiveSignalSubscription: $hasActiveSignalSubscription, isSignalSubscriptionFailedOrCanceled: $isSignalSubscriptionFailedOrCanceled", true)
+            Log.i(
+              TAG,
+              "Valid cancel state. Clearing mismatch. (isGooglePlayBillingCanceled: true, hasActiveSignalSubscription: $hasActiveSignalSubscription, isSignalSubscriptionFailedOrCanceled: $isSignalSubscriptionFailedOrCanceled",
+              true
+            )
             SignalStore.backup.subscriptionStateMismatchDetected = false
             return Result.success()
           } else {
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentKeepAliveJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentKeepAliveJob.kt
index efe4e5674e..338d0d4c73 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentKeepAliveJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentKeepAliveJob.kt
@@ -151,6 +151,8 @@ class InAppPaymentKeepAliveJob private constructor(
       return
     }
 
+    clearOldPendingPaymentsIfRequired()
+
     val activeInAppPayment = getActiveInAppPayment(subscriber, subscription)
     if (activeInAppPayment == null) {
       warn(type, "Failed to generate active in-app payment. Exiting")
@@ -227,6 +229,38 @@ class InAppPaymentKeepAliveJob private constructor(
     }
   }
 
+  /**
+   * If we have a pending payment that is at least 24 hours old AND we have no jobs
+   * enqueued that are associated with it, then something weird has happened. We should
+   * fail the job and let the keep-alive check create a new one as necessary.
+   */
+  private fun clearOldPendingPaymentsIfRequired() {
+    val inAppPayments = SignalDatabase.inAppPayments.getOldPendingPayments(type.inAppPaymentType)
+
+    inAppPayments.forEach { inAppPayment ->
+      val queue = InAppPaymentsRepository.resolveJobQueueKey(inAppPayment)
+
+      if (AppDependencies.jobManager.isQueueEmpty(queue)) {
+        Log.i(TAG, "User has an aged-out pending in-app payment [${inAppPayment.id}][${inAppPayment.type}]. Marking failed and proceeding with check.")
+        SignalDatabase.inAppPayments.update(
+          inAppPayment = inAppPayment.copy(
+            notified = true,
+            endOfPeriod = 0.seconds,
+            subscriberId = null,
+            state = InAppPaymentTable.State.END,
+            data = inAppPayment.data.newBuilder()
+              .error(
+                InAppPaymentData.Error(
+                  type = InAppPaymentData.Error.Type.REDEMPTION
+                )
+              )
+              .build()
+          )
+        )
+      }
+    }
+  }
+
   private fun getActiveInAppPayment(
     subscriber: InAppPaymentSubscriberRecord,
     subscription: ActiveSubscription.Subscription
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentOneTimeContextJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentOneTimeContextJob.kt
index d55264748d..2af6e49e15 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentOneTimeContextJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentOneTimeContextJob.kt
@@ -54,7 +54,7 @@ class InAppPaymentOneTimeContextJob private constructor(
         parameters = Parameters.Builder()
           .addConstraint(NetworkConstraint.KEY)
           .setQueue(InAppPaymentsRepository.resolveJobQueueKey(inAppPayment))
-          .setLifespan(InAppPaymentsRepository.resolveContextJobLifespan(inAppPayment).inWholeMilliseconds)
+          .setLifespan(InAppPaymentsRepository.resolveContextJobLifespanMillis(inAppPayment))
           .setMaxAttempts(Parameters.UNLIMITED)
           .build()
       )
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 b62a5d6a28..34efa73421 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentRecurringContextJob.kt
@@ -61,7 +61,7 @@ class InAppPaymentRecurringContextJob private constructor(
         parameters = Parameters.Builder()
           .addConstraint(NetworkConstraint.KEY)
           .setQueue(InAppPaymentsRepository.resolveJobQueueKey(inAppPayment))
-          .setLifespan(InAppPaymentsRepository.resolveContextJobLifespan(inAppPayment).inWholeMilliseconds)
+          .setLifespan(InAppPaymentsRepository.resolveContextJobLifespanMillis(inAppPayment))
           .setMaxAttempts(Parameters.UNLIMITED)
           .build()
       )
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentSetupJob.kt b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentSetupJob.kt
index a74b6a9d4d..61333e32fd 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentSetupJob.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/InAppPaymentSetupJob.kt
@@ -44,7 +44,7 @@ abstract class InAppPaymentSetupJob(
     protected fun getParameters(inAppPayment: InAppPaymentTable.InAppPayment): Parameters {
       return Parameters.Builder()
         .setQueue(InAppPaymentsRepository.resolveJobQueueKey(inAppPayment))
-        .setLifespan(InAppPaymentsRepository.resolveContextJobLifespan(inAppPayment).inWholeMilliseconds)
+        .setLifespan(InAppPaymentsRepository.resolveContextJobLifespanMillis(inAppPayment))
         .setMaxAttempts(Parameters.UNLIMITED)
         .build()
     }