diff --git a/CHANGES.md b/CHANGES.md
index a3eb4bfdf9..8692a2cff8 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -10,6 +10,7 @@ Improvements 🙌:
  - Improve initial sync performance (#983)
  - PIP support for Jitsi call (#2418)
  - Add tooltip for room quick actions
+ - Pre-share session keys when opening a room or start typing (#2771)
 
 Bugfix 🐛:
  - Try to fix crash about UrlPreview (#2640)
@@ -41,7 +42,6 @@ Improvements 🙌:
  - Improve room profile UX
  - Upgrade Jitsi library from 2.9.3 to 3.1.0
  - a11y improvements
- - Pre-share session keys when opening a room or start typing (#2771)
 
 Bugfix 🐛:
  - VoIP : fix audio devices output
diff --git a/matrix-sdk-android/src/main/java/org/matrix/android/sdk/api/session/room/crypto/RoomCryptoService.kt b/matrix-sdk-android/src/main/java/org/matrix/android/sdk/api/session/room/crypto/RoomCryptoService.kt
index d8bec878a1..6581247b90 100644
--- a/matrix-sdk-android/src/main/java/org/matrix/android/sdk/api/session/room/crypto/RoomCryptoService.kt
+++ b/matrix-sdk-android/src/main/java/org/matrix/android/sdk/api/session/room/crypto/RoomCryptoService.kt
@@ -33,7 +33,6 @@ interface RoomCryptoService {
 
     /**
      * Ensures all members of the room are loaded and outbound session keys are shared.
-     * Call this method according to [OutboundSessionKeySharingStrategy].
      * If this method is not called, CryptoService will ensure it before sending events.
      */
     suspend fun prepareToEncrypt()
diff --git a/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/algorithms/megolm/MXMegolmEncryption.kt b/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/algorithms/megolm/MXMegolmEncryption.kt
index bb75d014ff..6b91c0b859 100644
--- a/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/algorithms/megolm/MXMegolmEncryption.kt
+++ b/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/algorithms/megolm/MXMegolmEncryption.kt
@@ -18,8 +18,6 @@ package org.matrix.android.sdk.internal.crypto.algorithms.megolm
 
 import kotlinx.coroutines.CoroutineScope
 import kotlinx.coroutines.launch
-import org.matrix.android.sdk.api.MatrixCallback
-import org.matrix.android.sdk.api.auth.data.Credentials
 import org.matrix.android.sdk.api.session.crypto.MXCryptoError
 import org.matrix.android.sdk.api.session.events.model.Content
 import org.matrix.android.sdk.api.session.events.model.Event
@@ -40,8 +38,6 @@ import org.matrix.android.sdk.internal.crypto.model.forEach
 import org.matrix.android.sdk.internal.crypto.repository.WarnOnUnknownDeviceRepository
 import org.matrix.android.sdk.internal.crypto.store.IMXCryptoStore
 import org.matrix.android.sdk.internal.crypto.tasks.SendToDeviceTask
-import org.matrix.android.sdk.internal.task.TaskExecutor
-import org.matrix.android.sdk.internal.task.configureWith
 import org.matrix.android.sdk.internal.util.JsonCanonicalizer
 import org.matrix.android.sdk.internal.util.MatrixCoroutineDispatchers
 import org.matrix.android.sdk.internal.util.convertToUTF8
@@ -55,11 +51,11 @@ internal class MXMegolmEncryption(
         private val cryptoStore: IMXCryptoStore,
         private val deviceListManager: DeviceListManager,
         private val ensureOlmSessionsForDevicesAction: EnsureOlmSessionsForDevicesAction,
-        private val credentials: Credentials,
+        private val userId: String,
+        private val deviceId: String,
         private val sendToDeviceTask: SendToDeviceTask,
         private val messageEncrypter: MessageEncrypter,
         private val warnOnUnknownDevicesRepository: WarnOnUnknownDeviceRepository,
-        private val taskExecutor: TaskExecutor,
         private val coroutineDispatchers: MatrixCoroutineDispatchers,
         private val cryptoCoroutineScope: CoroutineScope
 ) : IMXEncrypting, IMXGroupEncryption {
@@ -282,7 +278,7 @@ internal class MXMegolmEncryption(
                 gossipingEventBuffer.add(
                         Event(
                         type = EventType.ROOM_KEY,
-                        senderId = credentials.userId,
+                        senderId = this.userId,
                         content = submap.apply {
                             this["session_key"] = ""
                             // we add a fake key for trail
@@ -310,8 +306,11 @@ internal class MXMegolmEncryption(
         }
     }
 
-    private fun notifyKeyWithHeld(targets: List<UserDevice>, sessionId: String, senderKey: String?, code: WithHeldCode) {
-        Timber.i("## CRYPTO | notifyKeyWithHeld() :sending withheld key for $targets session:$sessionId and code $code ")
+    private suspend fun notifyKeyWithHeld(targets: List<UserDevice>,
+                                          sessionId: String,
+                                          senderKey: String?,
+                                          code: WithHeldCode) {
+        Timber.i("## CRYPTO | notifyKeyWithHeld() :sending withheld key for $targets session:$sessionId and code $code")
         val withHeldContent = RoomKeyWithHeldContent(
                 roomId = roomId,
                 senderKey = senderKey,
@@ -327,13 +326,11 @@ internal class MXMegolmEncryption(
                     }
                 }
         )
-        sendToDeviceTask.configureWith(params) {
-            callback = object : MatrixCallback<Unit> {
-                override fun onFailure(failure: Throwable) {
-                    Timber.e("## CRYPTO | notifyKeyWithHeld() : Failed to notify withheld key for $targets session: $sessionId ")
-                }
-            }
-        }.executeBy(taskExecutor)
+        try {
+            sendToDeviceTask.execute(params)
+        } catch (failure: Throwable) {
+            Timber.e("## CRYPTO | notifyKeyWithHeld() : Failed to notify withheld key for $targets session: $sessionId ")
+        }
     }
 
     /**
@@ -359,7 +356,7 @@ internal class MXMegolmEncryption(
 
         // Include our device ID so that recipients can send us a
         // m.new_device message if they don't have our session key.
-        map["device_id"] = credentials.deviceId!!
+        map["device_id"] = deviceId
         session.useCount++
         return map
     }
diff --git a/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/algorithms/megolm/MXMegolmEncryptionFactory.kt b/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/algorithms/megolm/MXMegolmEncryptionFactory.kt
index f0cc15fb63..9f6312ea97 100644
--- a/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/algorithms/megolm/MXMegolmEncryptionFactory.kt
+++ b/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/algorithms/megolm/MXMegolmEncryptionFactory.kt
@@ -17,7 +17,6 @@
 package org.matrix.android.sdk.internal.crypto.algorithms.megolm
 
 import kotlinx.coroutines.CoroutineScope
-import org.matrix.android.sdk.api.auth.data.Credentials
 import org.matrix.android.sdk.internal.crypto.DeviceListManager
 import org.matrix.android.sdk.internal.crypto.MXOlmDevice
 import org.matrix.android.sdk.internal.crypto.actions.EnsureOlmSessionsForDevicesAction
@@ -26,7 +25,8 @@ import org.matrix.android.sdk.internal.crypto.keysbackup.DefaultKeysBackupServic
 import org.matrix.android.sdk.internal.crypto.repository.WarnOnUnknownDeviceRepository
 import org.matrix.android.sdk.internal.crypto.store.IMXCryptoStore
 import org.matrix.android.sdk.internal.crypto.tasks.SendToDeviceTask
-import org.matrix.android.sdk.internal.task.TaskExecutor
+import org.matrix.android.sdk.internal.di.DeviceId
+import org.matrix.android.sdk.internal.di.UserId
 import org.matrix.android.sdk.internal.util.MatrixCoroutineDispatchers
 import javax.inject.Inject
 
@@ -36,29 +36,29 @@ internal class MXMegolmEncryptionFactory @Inject constructor(
         private val cryptoStore: IMXCryptoStore,
         private val deviceListManager: DeviceListManager,
         private val ensureOlmSessionsForDevicesAction: EnsureOlmSessionsForDevicesAction,
-        private val credentials: Credentials,
+        @UserId private val userId: String,
+        @DeviceId private val deviceId: String?,
         private val sendToDeviceTask: SendToDeviceTask,
         private val messageEncrypter: MessageEncrypter,
         private val warnOnUnknownDevicesRepository: WarnOnUnknownDeviceRepository,
-        private val taskExecutor: TaskExecutor,
         private val coroutineDispatchers: MatrixCoroutineDispatchers,
         private val cryptoCoroutineScope: CoroutineScope) {
 
     fun create(roomId: String): MXMegolmEncryption {
         return MXMegolmEncryption(
-                roomId,
-                olmDevice,
-                defaultKeysBackupService,
-                cryptoStore,
-                deviceListManager,
-                ensureOlmSessionsForDevicesAction,
-                credentials,
-                sendToDeviceTask,
-                messageEncrypter,
-                warnOnUnknownDevicesRepository,
-                taskExecutor,
-                coroutineDispatchers,
-                cryptoCoroutineScope
+                roomId = roomId,
+                olmDevice = olmDevice,
+                defaultKeysBackupService = defaultKeysBackupService,
+                cryptoStore = cryptoStore,
+                deviceListManager = deviceListManager,
+                ensureOlmSessionsForDevicesAction = ensureOlmSessionsForDevicesAction,
+                userId = userId,
+                deviceId = deviceId!!,
+                sendToDeviceTask = sendToDeviceTask,
+                messageEncrypter = messageEncrypter,
+                warnOnUnknownDevicesRepository = warnOnUnknownDevicesRepository,
+                coroutineDispatchers = coroutineDispatchers,
+                cryptoCoroutineScope = cryptoCoroutineScope
         )
     }
 }
diff --git a/vector/src/main/java/im/vector/app/features/home/room/detail/RoomDetailViewModel.kt b/vector/src/main/java/im/vector/app/features/home/room/detail/RoomDetailViewModel.kt
index 7365801589..935b4ca2f8 100644
--- a/vector/src/main/java/im/vector/app/features/home/room/detail/RoomDetailViewModel.kt
+++ b/vector/src/main/java/im/vector/app/features/home/room/detail/RoomDetailViewModel.kt
@@ -195,11 +195,11 @@ class RoomDetailViewModel @AssistedInject constructor(
     }
 
     private fun prepareForEncryption() {
-        // check if there is not already a call made
-        if (prepareToEncrypt !is Loading) {
+        // check if there is not already a call made, or if there has been an error
+        if (prepareToEncrypt.shouldLoad) {
             prepareToEncrypt = Loading()
             viewModelScope.launch {
-                kotlin.runCatching {
+                runCatching {
                     room.prepareToEncrypt()
                 }.fold({
                     prepareToEncrypt = Success(Unit)
@@ -629,8 +629,6 @@ class RoomDetailViewModel @AssistedInject constructor(
             if (action.focused) {
                 // Should we add some rate limit here, or do it only once per model lifecycle?
                 prepareForEncryption()
-            } else {
-                // we could eventually cancel here :/
             }
         }
     }