diff --git a/libraries/matrix/impl/src/main/kotlin/io/element/android/libraries/matrix/impl/workmanager/VacuumDatabaseWorker.kt b/libraries/matrix/impl/src/main/kotlin/io/element/android/libraries/matrix/impl/workmanager/VacuumDatabaseWorker.kt
index 0602c2fdc2..c6f1b32405 100644
--- a/libraries/matrix/impl/src/main/kotlin/io/element/android/libraries/matrix/impl/workmanager/VacuumDatabaseWorker.kt
+++ b/libraries/matrix/impl/src/main/kotlin/io/element/android/libraries/matrix/impl/workmanager/VacuumDatabaseWorker.kt
@@ -15,6 +15,7 @@ import dev.zacsweers.metro.AssistedInject
 import io.element.android.libraries.di.annotations.ApplicationContext
 import io.element.android.libraries.matrix.api.MatrixClientProvider
 import io.element.android.libraries.matrix.api.core.SessionId
+import timber.log.Timber
 
 @AssistedInject
 class VacuumDatabaseWorker(
@@ -27,12 +28,19 @@ class VacuumDatabaseWorker(
     }
 
     override suspend fun doWork(): Result {
+        Timber.d("Starting database vacuuming...")
         val sessionId = inputData.getString(SESSION_ID_PARAM)?.let(::SessionId) ?: return Result.failure()
         val client = matrixClientProvider.getOrRestore(sessionId).getOrNull() ?: return Result.failure()
         return client.performDatabaseVacuum()
             .fold(
-                onSuccess = { Result.success() },
-                onFailure = { Result.failure() }
+                onSuccess = {
+                    Timber.d("Database vacuuming finished successfully")
+                    Result.success()
+                },
+                onFailure = {
+                    Timber.e(it, "Database vacuuming failed")
+                    Result.failure()
+                }
             )
     }
 }
diff --git a/libraries/workmanager/impl/src/main/kotlin/io/element/android/libraries/workmanager/impl/DefaultWorkManagerScheduler.kt b/libraries/workmanager/impl/src/main/kotlin/io/element/android/libraries/workmanager/impl/DefaultWorkManagerScheduler.kt
index 476e5995a8..ce16e323de 100644
--- a/libraries/workmanager/impl/src/main/kotlin/io/element/android/libraries/workmanager/impl/DefaultWorkManagerScheduler.kt
+++ b/libraries/workmanager/impl/src/main/kotlin/io/element/android/libraries/workmanager/impl/DefaultWorkManagerScheduler.kt
@@ -12,7 +12,6 @@ import androidx.work.WorkManager
 import dev.zacsweers.metro.AppScope
 import dev.zacsweers.metro.ContributesBinding
 import dev.zacsweers.metro.SingleIn
-import io.element.android.libraries.core.bool.orFalse
 import io.element.android.libraries.matrix.api.core.SessionId
 import io.element.android.libraries.sessionstorage.api.observer.SessionListener
 import io.element.android.libraries.sessionstorage.api.observer.SessionObserver
@@ -53,7 +52,9 @@ class DefaultWorkManagerScheduler(
     }
 
     override fun hasPendingWork(sessionId: SessionId, requestType: WorkManagerRequestType): Boolean {
-        return workManager.getWorkInfosByTag(workManagerTag(sessionId, requestType)).get()?.isNotEmpty().orFalse()
+        val workInfos = workManager.getWorkInfosByTag(workManagerTag(sessionId, requestType)).get().orEmpty()
+        // It has pending work if it's periodic or it isn't but it's not finished
+        return workInfos.any { it.periodicityInfo != null || !it.state.isFinished }
     }
 
     override fun cancel(sessionId: SessionId) {