diff --git a/libraries/push/impl/src/main/kotlin/io/element/android/libraries/push/impl/workmanager/SyncNotificationWorkManagerRequest.kt b/libraries/push/impl/src/main/kotlin/io/element/android/libraries/push/impl/workmanager/SyncNotificationWorkManagerRequest.kt
index 9492977c3d..cff12cc17d 100644
--- a/libraries/push/impl/src/main/kotlin/io/element/android/libraries/push/impl/workmanager/SyncNotificationWorkManagerRequest.kt
+++ b/libraries/push/impl/src/main/kotlin/io/element/android/libraries/push/impl/workmanager/SyncNotificationWorkManagerRequest.kt
@@ -29,30 +29,29 @@ class SyncNotificationWorkManagerRequest(
     private val workerDataConverter: WorkerDataConverter,
     private val buildVersionSdkIntProvider: BuildVersionSdkIntProvider,
 ) : WorkManagerRequest {
-    override fun build(): Result<WorkRequest> {
+    override fun build(): List<Result<WorkRequest>> {
         if (notificationEventRequests.isEmpty()) {
-            return Result.failure(InvalidParameterException("notificationEventRequests cannot be empty"))
-        }
-        val data = workerDataConverter.serialize(notificationEventRequests).getOrElse {
-            return Result.failure(it)
+            return listOf(Result.failure(InvalidParameterException("notificationEventRequests cannot be empty")))
         }
         Timber.d("Scheduling ${notificationEventRequests.size} notification requests with WorkManager for $sessionId")
-        return Result.success(
-            OneTimeWorkRequestBuilder<FetchNotificationsWorker>()
-                .setInputData(data)
-                .apply {
-                    // Expedited workers aren't needed on Android 12 or lower:
-                    // They force displaying a foreground sync notification for no good reason, since they sync almost immediately anyway
-                    // See https://developer.android.com/develop/background-work/background-tasks/persistent/getting-started/define-work#backwards-compat
-                    if (buildVersionSdkIntProvider.isAtLeast(Build.VERSION_CODES.TIRAMISU)) {
-                        setExpedited(OutOfQuotaPolicy.RUN_AS_NON_EXPEDITED_WORK_REQUEST)
+        return workerDataConverter.serialize(notificationEventRequests).map {
+            it.map { data ->
+                OneTimeWorkRequestBuilder<FetchNotificationsWorker>()
+                    .setInputData(data)
+                    .apply {
+                        // Expedited workers aren't needed on Android 12 or lower:
+                        // They force displaying a foreground sync notification for no good reason, since they sync almost immediately anyway
+                        // See https://developer.android.com/develop/background-work/background-tasks/persistent/getting-started/define-work#backwards-compat
+                        if (buildVersionSdkIntProvider.isAtLeast(Build.VERSION_CODES.TIRAMISU)) {
+                            setExpedited(OutOfQuotaPolicy.RUN_AS_NON_EXPEDITED_WORK_REQUEST)
+                        }
                     }
-                }
-                .setTraceTag(workManagerTag(sessionId, WorkManagerRequestType.NOTIFICATION_SYNC))
-                // TODO investigate using this instead of the resolver queue
-                // .setInputMerger()
-                .build()
-        )
+                    .setTraceTag(workManagerTag(sessionId, WorkManagerRequestType.NOTIFICATION_SYNC))
+                    // TODO investigate using this instead of the resolver queue
+                    // .setInputMerger()
+                    .build()
+            }
+        }
     }
 
     @Serializable
diff --git a/libraries/push/impl/src/main/kotlin/io/element/android/libraries/push/impl/workmanager/WorkerDataConverter.kt b/libraries/push/impl/src/main/kotlin/io/element/android/libraries/push/impl/workmanager/WorkerDataConverter.kt
index ac51c6c6a9..71d24cd62d 100644
--- a/libraries/push/impl/src/main/kotlin/io/element/android/libraries/push/impl/workmanager/WorkerDataConverter.kt
+++ b/libraries/push/impl/src/main/kotlin/io/element/android/libraries/push/impl/workmanager/WorkerDataConverter.kt
@@ -12,6 +12,7 @@ import androidx.work.Data
 import androidx.work.workDataOf
 import dev.zacsweers.metro.Inject
 import io.element.android.libraries.androidutils.json.JsonProvider
+import io.element.android.libraries.core.extensions.mapCatchingExceptions
 import io.element.android.libraries.core.extensions.runCatchingExceptions
 import io.element.android.libraries.matrix.api.core.EventId
 import io.element.android.libraries.matrix.api.core.RoomId
@@ -23,12 +24,29 @@ import timber.log.Timber
 class WorkerDataConverter(
     private val json: JsonProvider,
 ) {
-    fun serialize(notificationEventRequests: List<NotificationEventRequest>): Result<Data> {
+    fun serialize(notificationEventRequests: List<NotificationEventRequest>): List<Result<Data>> {
+        return serializeRequests(notificationEventRequests)
+            .fold(
+                onSuccess = {
+                    listOf(Result.success(it))
+                },
+                onFailure = {
+                    // Perform serialization on sublists, workDataOf may have failed because of size limit
+                    Timber.w(it, "Failed to serialize ${notificationEventRequests.size} notification requests, trying with chunks of $CHUNK_SIZE.")
+                    notificationEventRequests.chunked(CHUNK_SIZE).map { chunk ->
+                        serializeRequests(chunk)
+                    }
+                },
+            )
+    }
+
+    private fun serializeRequests(notificationEventRequests: List<NotificationEventRequest>): Result<Data> {
         return runCatchingExceptions { json().encodeToString(notificationEventRequests.map { it.toData() }) }
             .onFailure {
                 Timber.e(it, "Failed to serialize notification requests")
             }
-            .map { str ->
+            .mapCatchingExceptions { str ->
+                // Note: workDataOf can fail if the data is too large
                 workDataOf(REQUESTS_KEY to str)
             }
     }
@@ -51,6 +69,7 @@ class WorkerDataConverter(
 
     companion object {
         private const val REQUESTS_KEY = "requests"
+        private const val CHUNK_SIZE = 20
     }
 }
 
diff --git a/libraries/workmanager/api/src/main/kotlin/io/element/android/libraries/workmanager/api/WorkManagerRequest.kt b/libraries/workmanager/api/src/main/kotlin/io/element/android/libraries/workmanager/api/WorkManagerRequest.kt
index 7c3b165102..a6e4a26e3d 100644
--- a/libraries/workmanager/api/src/main/kotlin/io/element/android/libraries/workmanager/api/WorkManagerRequest.kt
+++ b/libraries/workmanager/api/src/main/kotlin/io/element/android/libraries/workmanager/api/WorkManagerRequest.kt
@@ -11,5 +11,5 @@ package io.element.android.libraries.workmanager.api
 import androidx.work.WorkRequest
 
 interface WorkManagerRequest {
-    fun build(): Result<WorkRequest>
+    fun build(): List<Result<WorkRequest>>
 }
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 70c9b719b2..6b19e48208 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
@@ -27,14 +27,16 @@ class DefaultWorkManagerScheduler(
     private val workManager by lazy { WorkManager.getInstance(context) }
 
     override fun submit(workManagerRequest: WorkManagerRequest) {
-        workManagerRequest.build().fold(
-            onSuccess = {
-                workManager.enqueue(it)
-            },
-            onFailure = {
-                Timber.e(it, "Failed to build WorkManager request $workManagerRequest")
-            }
-        )
+        workManagerRequest.build().forEach {
+            it.fold(
+                onSuccess = { workRequest ->
+                    workManager.enqueue(workRequest)
+                },
+                onFailure = {
+                    Timber.e(it, "Failed to build WorkManager request $workManagerRequest")
+                }
+            )
+        }
     }
 
     override fun cancel(sessionId: SessionId) {