diff --git a/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/crypto/attachments/MXEncryptedAttachments.kt b/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/crypto/attachments/MXEncryptedAttachments.kt
index 7fe82421..02c8931f 100755
--- a/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/crypto/attachments/MXEncryptedAttachments.kt
+++ b/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/crypto/attachments/MXEncryptedAttachments.kt
@@ -18,6 +18,7 @@ package im.vector.matrix.android.internal.crypto.attachments
 
 import android.text.TextUtils
 import android.util.Base64
+import arrow.core.Try
 import im.vector.matrix.android.internal.crypto.model.rest.EncryptedFileInfo
 import im.vector.matrix.android.internal.crypto.model.rest.EncryptedFileKey
 import timber.log.Timber
@@ -51,7 +52,7 @@ object MXEncryptedAttachments {
      * @param mimetype the mime type
      * @return the encryption file info
      */
-    fun encryptAttachment(attachmentStream: InputStream, mimetype: String): EncryptionResult? {
+    fun encryptAttachment(attachmentStream: InputStream, mimetype: String): Try<EncryptionResult> {
         val t0 = System.currentTimeMillis()
         val secureRandom = SecureRandom()
 
@@ -115,23 +116,21 @@ object MXEncryptedAttachments {
                     encryptedByteArray = outStream.toByteArray()
             )
 
-            outStream.close()
-
             Timber.v("Encrypt in " + (System.currentTimeMillis() - t0) + " ms")
-            return result
+            return Try.just(result)
         } catch (oom: OutOfMemoryError) {
-            Timber.e(oom, "## encryptAttachment failed " + oom.message)
+            Timber.e(oom, "## encryptAttachment failed")
+            return Try.Failure(oom)
         } catch (e: Exception) {
-            Timber.e(e, "## encryptAttachment failed " + e.message)
+            Timber.e(e, "## encryptAttachment failed")
+            return Try.Failure(e)
+        } finally {
+            try {
+                outStream.close()
+            } catch (e: Exception) {
+                Timber.e(e, "## encryptAttachment() : fail to close outStream")
+            }
         }
-
-        try {
-            outStream.close()
-        } catch (e: Exception) {
-            Timber.e(e, "## encryptAttachment() : fail to close outStream")
-        }
-
-        return null
     }
 
     /**
diff --git a/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/session/content/UploadContentWorker.kt b/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/session/content/UploadContentWorker.kt
index 5a8688ee..fd6b15f3 100644
--- a/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/session/content/UploadContentWorker.kt
+++ b/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/session/content/UploadContentWorker.kt
@@ -69,24 +69,30 @@ internal class UploadContentWorker(context: Context, params: WorkerParameters) :
         val eventId = params.event.eventId ?: return Result.success()
         val attachment = params.attachment
 
-        val isRoomEncrypted = params.isRoomEncrypted
+        val attachmentFile = try {
+            File(attachment.path)
+        } catch (e: Exception) {
+            Timber.e(e)
+            return Result.success(
+                    WorkerParamsFactory.toData(params.copy(
+                            lastFailureMessage = e.localizedMessage
+                    ))
+            )
+        }
 
-
-        val thumbnailData = ThumbnailExtractor.extractThumbnail(params.attachment)
-        val attachmentFile = createAttachmentFile(attachment) ?: return Result.failure()
         var uploadedThumbnailUrl: String? = null
         var uploadedThumbnailEncryptedFileInfo: EncryptedFileInfo? = null
 
-        if (thumbnailData != null) {
-            val contentUploadResponse = if (isRoomEncrypted) {
+        ThumbnailExtractor.extractThumbnail(params.attachment)?.let { thumbnailData ->
+            val contentUploadResponse = if (params.isRoomEncrypted) {
                 Timber.v("Encrypt thumbnail")
-                val encryptionResult = MXEncryptedAttachments.encryptAttachment(ByteArrayInputStream(thumbnailData.bytes), thumbnailData.mimeType)
-                        ?: return Result.failure()
+                MXEncryptedAttachments.encryptAttachment(ByteArrayInputStream(thumbnailData.bytes), thumbnailData.mimeType)
+                        .flatMap { encryptionResult ->
+                            uploadedThumbnailEncryptedFileInfo = encryptionResult.encryptedFileInfo
 
-                uploadedThumbnailEncryptedFileInfo = encryptionResult.encryptedFileInfo
-
-                fileUploader
-                        .uploadByteArray(encryptionResult.encryptedByteArray, "thumb_${attachment.name}", "application/octet-stream")
+                            fileUploader
+                                    .uploadByteArray(encryptionResult.encryptedByteArray, "thumb_${attachment.name}", "application/octet-stream")
+                        }
             } else {
                 fileUploader
                         .uploadByteArray(thumbnailData.bytes, "thumb_${attachment.name}", thumbnailData.mimeType)
@@ -107,16 +113,16 @@ internal class UploadContentWorker(context: Context, params: WorkerParameters) :
 
         var uploadedFileEncryptedFileInfo: EncryptedFileInfo? = null
 
-        val contentUploadResponse = if (isRoomEncrypted) {
+        val contentUploadResponse = if (params.isRoomEncrypted) {
             Timber.v("Encrypt file")
 
-            val encryptionResult = MXEncryptedAttachments.encryptAttachment(FileInputStream(attachmentFile), attachment.mimeType)
-                    ?: return Result.failure()
+            MXEncryptedAttachments.encryptAttachment(FileInputStream(attachmentFile), attachment.mimeType)
+                    .flatMap { encryptionResult ->
+                        uploadedFileEncryptedFileInfo = encryptionResult.encryptedFileInfo
 
-            uploadedFileEncryptedFileInfo = encryptionResult.encryptedFileInfo
-
-            fileUploader
-                    .uploadByteArray(encryptionResult.encryptedByteArray, attachment.name, "application/octet-stream", progressListener)
+                        fileUploader
+                                .uploadByteArray(encryptionResult.encryptedByteArray, attachment.name, "application/octet-stream", progressListener)
+                    }
         } else {
             fileUploader
                     .uploadFile(attachmentFile, attachment.name, attachment.mimeType, progressListener)
@@ -129,15 +135,6 @@ internal class UploadContentWorker(context: Context, params: WorkerParameters) :
                 )
     }
 
-    private fun createAttachmentFile(attachment: ContentAttachmentData): File? {
-        return try {
-            File(attachment.path)
-        } catch (e: Exception) {
-            Timber.e(e)
-            null
-        }
-    }
-
     private fun handleFailure(params: Params, failure: Throwable): Result {
         contentUploadStateTracker.setFailure(params.event.eventId!!)
         return Result.success(