diff --git a/matrix-sdk-android/src/androidTest/java/org/matrix/android/sdk/common/CommonTestHelper.kt b/matrix-sdk-android/src/androidTest/java/org/matrix/android/sdk/common/CommonTestHelper.kt
index 7dcf43ba0f..cb49ee8818 100644
--- a/matrix-sdk-android/src/androidTest/java/org/matrix/android/sdk/common/CommonTestHelper.kt
+++ b/matrix-sdk-android/src/androidTest/java/org/matrix/android/sdk/common/CommonTestHelper.kt
@@ -86,7 +86,7 @@ class CommonTestHelper(context: Context) {
      *
      * @param session    the session to sync
      */
-    fun syncSession(session: Session) {
+    fun syncSession(session: Session, timeout: Long = TestConstants.timeOutMillis) {
         val lock = CountDownLatch(1)
 
         val job = GlobalScope.launch(Dispatchers.Main) {
@@ -109,7 +109,7 @@ class CommonTestHelper(context: Context) {
         }
         GlobalScope.launch(Dispatchers.Main) { syncLiveData.observeForever(syncObserver) }
 
-        await(lock)
+        await(lock, timeout)
     }
 
     /**
@@ -215,14 +215,14 @@ class CommonTestHelper(context: Context) {
                     .getLoginFlow(hs, it)
         }
 
-        doSync<RegistrationResult> {
+        doSync<RegistrationResult>(timeout = 60_000) {
             matrix.authenticationService
                     .getRegistrationWizard()
                     .createAccount(userName, password, null, it)
         }
 
         // Perform dummy step
-        val registrationResult = doSync<RegistrationResult> {
+        val registrationResult = doSync<RegistrationResult>(timeout = 60_000) {
             matrix.authenticationService
                     .getRegistrationWizard()
                     .dummy(it)
@@ -231,7 +231,7 @@ class CommonTestHelper(context: Context) {
         assertTrue(registrationResult is RegistrationResult.Success)
         val session = (registrationResult as RegistrationResult.Success).session
         if (sessionTestParams.withInitialSync) {
-            syncSession(session)
+            syncSession(session, 60_000)
         }
 
         return session
diff --git a/matrix-sdk-android/src/androidTest/java/org/matrix/android/sdk/session/room/timeline/TimelineWithManyMembersTest.kt b/matrix-sdk-android/src/androidTest/java/org/matrix/android/sdk/session/room/timeline/TimelineWithManyMembersTest.kt
index dacde121b3..ca74acdee7 100644
--- a/matrix-sdk-android/src/androidTest/java/org/matrix/android/sdk/session/room/timeline/TimelineWithManyMembersTest.kt
+++ b/matrix-sdk-android/src/androidTest/java/org/matrix/android/sdk/session/room/timeline/TimelineWithManyMembersTest.kt
@@ -35,66 +35,11 @@ import kotlin.test.fail
 @FixMethodOrder(MethodSorters.JVM)
 class TimelineWithManyMembersTest : InstrumentedTest {
 
-    private val NUMBER_OF_MEMBERS = 5
+    private val NUMBER_OF_MEMBERS = 6
 
     private val commonTestHelper = CommonTestHelper(context())
     private val cryptoTestHelper = CryptoTestHelper(commonTestHelper)
 
-    /**
-     * Ensures when someone sends a message to a crowded room, everyone can decrypt the message.
-     */
-    @Test
-    fun everyoneShouldDecryptMessage3Members() {
-        val cryptoTestData = cryptoTestHelper.doE2ETestWithAliceAndBobAndSamInARoom()
-
-        val aliceSession = cryptoTestData.firstSession
-        val bobSession = cryptoTestData.secondSession!!
-        val samSession = cryptoTestData.thirdSession!!
-
-        val aliceRoomId = cryptoTestData.roomId
-
-        aliceSession.cryptoService().setWarnOnUnknownDevices(false)
-        bobSession.cryptoService().setWarnOnUnknownDevices(false)
-        samSession.cryptoService().setWarnOnUnknownDevices(false)
-
-        val roomFromAlicePOV = aliceSession.getRoom(aliceRoomId)!!
-        val roomFromBobPOV = bobSession.getRoom(aliceRoomId)!!
-        val roomFromSamPOV = samSession.getRoom(aliceRoomId)!!
-
-        val bobTimeline = roomFromBobPOV.createTimeline(null, TimelineSettings(30))
-        val samTimeline = roomFromSamPOV.createTimeline(null, TimelineSettings(30))
-        bobTimeline.start()
-        samTimeline.start()
-
-        val firstMessage = "First messages from Alice"
-        commonTestHelper.sendTextMessage(
-                roomFromAlicePOV,
-                firstMessage,
-                1)
-
-        bobSession.startSync(true)
-        run {
-            val lock = CountDownLatch(1)
-            val eventsListener = commonTestHelper.createEventListener(lock) { snapshot ->
-                snapshot.firstOrNull()?.root?.getClearContent()?.toModel<MessageContent>()?.body?.startsWith(firstMessage).orFalse()
-            }
-            bobTimeline.addListener(eventsListener)
-            commonTestHelper.await(lock)
-        }
-        bobSession.stopSync()
-
-        samSession.startSync(true)
-        run {
-            val lock = CountDownLatch(1)
-            val eventsListener = commonTestHelper.createEventListener(lock) { snapshot ->
-                snapshot.firstOrNull()?.root?.getClearContent()?.toModel<MessageContent>()?.body?.startsWith(firstMessage).orFalse()
-            }
-            samTimeline.addListener(eventsListener)
-            commonTestHelper.await(lock)
-        }
-        samSession.stopSync()
-    }
-
     /**
      * Ensures when someone sends a message to a crowded room, everyone can decrypt the message.
      */
@@ -129,6 +74,7 @@ class TimelineWithManyMembersTest : InstrumentedTest {
                             ?.let {
                                 val body = it.root.getClearContent()?.toModel<MessageContent>()?.body
                                 if (body?.startsWith(firstMessage).orFalse()) {
+                                    println("User " + session.myUserId + " decrypted as " + body)
                                     return@createEventListener true
                                 } else {
                                     fail("User " + session.myUserId + " decrypted as " + body + " CryptoError: " + it.root.mCryptoError)
diff --git a/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/tasks/SendEventTask.kt b/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/tasks/SendEventTask.kt
index 8b739c4b64..5c8c7dfb25 100644
--- a/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/tasks/SendEventTask.kt
+++ b/matrix-sdk-android/src/main/java/org/matrix/android/sdk/internal/crypto/tasks/SendEventTask.kt
@@ -20,6 +20,7 @@ import org.matrix.android.sdk.api.session.events.model.Event
 import org.matrix.android.sdk.api.session.room.send.SendState
 import org.matrix.android.sdk.internal.network.executeRequest
 import org.matrix.android.sdk.internal.session.room.RoomAPI
+import org.matrix.android.sdk.internal.session.room.membership.LoadRoomMembersTask
 import org.matrix.android.sdk.internal.session.room.send.LocalEchoRepository
 import org.matrix.android.sdk.internal.session.room.send.SendResponse
 import org.matrix.android.sdk.internal.task.Task
@@ -35,11 +36,19 @@ internal interface SendEventTask : Task<SendEventTask.Params, String> {
 internal class DefaultSendEventTask @Inject constructor(
         private val localEchoRepository: LocalEchoRepository,
         private val encryptEventTask: DefaultEncryptEventTask,
+        private val loadRoomMembersTask: LoadRoomMembersTask,
         private val roomAPI: RoomAPI,
         private val eventBus: EventBus) : SendEventTask {
 
     override suspend fun execute(params: SendEventTask.Params): String {
         try {
+            // Make sure to load all members in the room before sending the event.
+            params.event.roomId
+                    ?.takeIf { params.encrypt }
+                    ?.let { roomId ->
+                        loadRoomMembersTask.execute(LoadRoomMembersTask.Params(roomId))
+                    }
+
             val event = handleEncryption(params)
             val localId = event.eventId!!