diff --git a/changelog.d/3542.bugfix b/changelog.d/3542.bugfix
new file mode 100644
index 0000000000..8e133e1e30
--- /dev/null
+++ b/changelog.d/3542.bugfix
@@ -0,0 +1 @@
+Fix some issues with timeline cache invalidation and visibility.
\ No newline at end of file
diff --git a/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/TimelineEventController.kt b/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/TimelineEventController.kt
index a0f87b9749..bbb1b7a06f 100644
--- a/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/TimelineEventController.kt
+++ b/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/TimelineEventController.kt
@@ -39,13 +39,13 @@ import im.vector.app.features.home.room.detail.UnreadState
 import im.vector.app.features.home.room.detail.timeline.factory.MergedHeaderItemFactory
 import im.vector.app.features.home.room.detail.timeline.factory.ReadReceiptsItemFactory
 import im.vector.app.features.home.room.detail.timeline.factory.TimelineItemFactory
+import im.vector.app.features.home.room.detail.timeline.factory.TimelineItemFactoryParams
 import im.vector.app.features.home.room.detail.timeline.helper.ContentDownloadStateTrackerBinder
 import im.vector.app.features.home.room.detail.timeline.helper.ContentUploadStateTrackerBinder
 import im.vector.app.features.home.room.detail.timeline.helper.TimelineControllerInterceptorHelper
 import im.vector.app.features.home.room.detail.timeline.helper.TimelineEventDiffUtilCallback
 import im.vector.app.features.home.room.detail.timeline.helper.TimelineEventVisibilityHelper
 import im.vector.app.features.home.room.detail.timeline.helper.TimelineEventVisibilityStateChangedListener
-import im.vector.app.features.home.room.detail.timeline.factory.TimelineItemFactoryParams
 import im.vector.app.features.home.room.detail.timeline.helper.TimelineMediaSizeProvider
 import im.vector.app.features.home.room.detail.timeline.item.AbsMessageItem
 import im.vector.app.features.home.room.detail.timeline.item.BasedMergedItem
@@ -163,10 +163,19 @@ class TimelineEventController @Inject constructor(private val dateFormatter: Vec
         override fun onChanged(position: Int, count: Int, payload: Any?) {
             synchronized(modelCache) {
                 assertUpdateCallbacksAllowed()
-                (position until (position + count)).forEach {
+                (position until position + count).forEach {
                     // Invalidate cache
                     modelCache[it] = null
                 }
+                // Also invalidate the first previous displayable event if
+                // it's sent by the same user so we are sure we have up to date information.
+                val invalidatedSenderId: String? = currentSnapshot.getOrNull(position)?.senderInfo?.userId
+                val prevDisplayableEventIndex = currentSnapshot.subList(0, position).indexOfLast {
+                    timelineEventVisibilityHelper.shouldShowEvent(it, eventIdToHighlight)
+                }
+                if (prevDisplayableEventIndex != -1 && currentSnapshot[prevDisplayableEventIndex].senderInfo.userId == invalidatedSenderId) {
+                    modelCache[prevDisplayableEventIndex] = null
+                }
                 requestModelBuild()
             }
         }
@@ -209,6 +218,7 @@ class TimelineEventController @Inject constructor(private val dateFormatter: Vec
     )
 
     init {
+        isDebugLoggingEnabled = true
         addInterceptor(this)
         requestModelBuild()
     }
@@ -340,10 +350,14 @@ class TimelineEventController @Inject constructor(private val dateFormatter: Vec
             val event = currentSnapshot[position]
             val nextEvent = currentSnapshot.nextOrNull(position)
             val prevEvent = currentSnapshot.prevOrNull(position)
+            val nextDisplayableEvent = currentSnapshot.subList(position + 1, currentSnapshot.size).firstOrNull {
+                timelineEventVisibilityHelper.shouldShowEvent(it, eventIdToHighlight)
+            }
             val params = TimelineItemFactoryParams(
                     event = event,
                     prevEvent = prevEvent,
                     nextEvent = nextEvent,
+                    nextDisplayableEvent = nextDisplayableEvent,
                     highlightedEventId = eventIdToHighlight,
                     lastSentEventIdWithoutReadReceipts = lastSentEventWithoutReadReceipts,
                     callback = callback
diff --git a/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/factory/TimelineItemFactoryParams.kt b/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/factory/TimelineItemFactoryParams.kt
index f92cd2800a..0e595ba30e 100644
--- a/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/factory/TimelineItemFactoryParams.kt
+++ b/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/factory/TimelineItemFactoryParams.kt
@@ -23,6 +23,7 @@ data class TimelineItemFactoryParams(
         val event: TimelineEvent,
         val prevEvent: TimelineEvent? = null,
         val nextEvent: TimelineEvent? = null,
+        val nextDisplayableEvent: TimelineEvent? = null,
         val highlightedEventId: String? = null,
         val lastSentEventIdWithoutReadReceipts: String? = null,
         val callback: TimelineEventController.Callback? = null
diff --git a/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/helper/MessageInformationDataFactory.kt b/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/helper/MessageInformationDataFactory.kt
index 124b196f72..221149aced 100644
--- a/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/helper/MessageInformationDataFactory.kt
+++ b/vector/src/main/java/im/vector/app/features/home/room/detail/timeline/helper/MessageInformationDataFactory.kt
@@ -50,27 +50,28 @@ import javax.inject.Inject
 class MessageInformationDataFactory @Inject constructor(private val session: Session,
                                                         private val roomSummariesHolder: RoomSummariesHolder,
                                                         private val dateFormatter: VectorDateFormatter,
+                                                        private val visibilityHelper: TimelineEventVisibilityHelper,
                                                         private val vectorPreferences: VectorPreferences) {
 
     fun create(params: TimelineItemFactoryParams): MessageInformationData {
         val event = params.event
-        val nextEvent = params.nextEvent
+        val nextDisplayableEvent = params.nextDisplayableEvent
         val eventId = event.eventId
 
         val date = event.root.localDateTime()
-        val nextDate = nextEvent?.root?.localDateTime()
+        val nextDate = nextDisplayableEvent?.root?.localDateTime()
         val addDaySeparator = date.toLocalDate() != nextDate?.toLocalDate()
         val isNextMessageReceivedMoreThanOneHourAgo = nextDate?.isBefore(date.minusMinutes(60))
                 ?: false
 
         val showInformation =
                 addDaySeparator
-                        || event.senderInfo.avatarUrl != nextEvent?.senderInfo?.avatarUrl
-                        || event.senderInfo.disambiguatedDisplayName != nextEvent?.senderInfo?.disambiguatedDisplayName
-                        || nextEvent.root.getClearType() !in listOf(EventType.MESSAGE, EventType.STICKER, EventType.ENCRYPTED)
+                        || event.senderInfo.avatarUrl != nextDisplayableEvent?.senderInfo?.avatarUrl
+                        || event.senderInfo.disambiguatedDisplayName != nextDisplayableEvent?.senderInfo?.disambiguatedDisplayName
+                        || nextDisplayableEvent.root.getClearType() !in listOf(EventType.MESSAGE, EventType.STICKER, EventType.ENCRYPTED)
                         || isNextMessageReceivedMoreThanOneHourAgo
-                        || isTileTypeMessage(nextEvent)
-                        || nextEvent.isEdition()
+                        || isTileTypeMessage(nextDisplayableEvent)
+                        || nextDisplayableEvent.isEdition()
 
         val time = dateFormatter.format(event.root.originServerTs, DateFormatKind.MESSAGE_SIMPLE)
         val e2eDecoration = getE2EDecoration(event)