diff --git a/app/src/main/java/ru/risdeveau/pixeldragon/ui/layout/Room.kt b/app/src/main/java/ru/risdeveau/pixeldragon/ui/layout/Room.kt
index a14f83a..95b517d 100755
--- a/app/src/main/java/ru/risdeveau/pixeldragon/ui/layout/Room.kt
+++ b/app/src/main/java/ru/risdeveau/pixeldragon/ui/layout/Room.kt
@@ -25,19 +25,23 @@ import android.webkit.WebView
 import android.webkit.WebViewClient
 import android.widget.TextView
 import androidx.compose.foundation.background
+import androidx.compose.foundation.layout.Arrangement
 import androidx.compose.foundation.layout.Box
 import androidx.compose.foundation.layout.BoxWithConstraints
 import androidx.compose.foundation.layout.Column
 import androidx.compose.foundation.layout.Row
-import androidx.compose.foundation.layout.fillMaxHeight
+import androidx.compose.foundation.layout.Spacer
 import androidx.compose.foundation.layout.fillMaxWidth
 import androidx.compose.foundation.layout.height
-import androidx.compose.foundation.layout.heightIn
 import androidx.compose.foundation.layout.padding
+import androidx.compose.foundation.layout.size
+import androidx.compose.foundation.layout.width
+import androidx.compose.foundation.layout.widthIn
 import androidx.compose.foundation.lazy.LazyColumn
 import androidx.compose.foundation.lazy.items
 import androidx.compose.foundation.lazy.rememberLazyListState
-import androidx.compose.material3.ExperimentalMaterial3Api
+import androidx.compose.foundation.shape.CircleShape
+import androidx.compose.foundation.shape.RoundedCornerShape
 import androidx.compose.material3.Icon
 import androidx.compose.material3.IconButton
 import androidx.compose.material3.MaterialTheme
@@ -52,12 +56,14 @@ import androidx.compose.runtime.mutableStateOf
 import androidx.compose.runtime.remember
 import androidx.compose.runtime.rememberUpdatedState
 import androidx.compose.runtime.setValue
+import androidx.compose.ui.Alignment
 import androidx.compose.ui.Modifier
 import androidx.compose.ui.draw.alpha
 import androidx.compose.ui.graphics.Color
 import androidx.compose.ui.graphics.toArgb
 import androidx.compose.ui.platform.LocalContext
 import androidx.compose.ui.platform.LocalDensity
+import androidx.compose.ui.text.font.FontWeight
 import androidx.compose.ui.text.style.TextAlign
 import androidx.compose.ui.unit.dp
 import androidx.compose.ui.unit.sp
@@ -94,12 +100,17 @@ import org.jsoup.Jsoup
 import org.jsoup.nodes.Element
 import org.jsoup.safety.Safelist
 import ru.risdeveau.pixeldragon.client
+import java.text.SimpleDateFormat
+import java.util.Calendar
+import java.util.Date
+import java.util.Locale
 import kotlin.math.abs
 import kotlin.math.ceil
 import kotlin.math.max
 import kotlin.math.roundToInt
 
 private const val WEBVIEW_HEIGHT_TITLE_PREFIX = "pd-height:"
+private const val MESSAGE_GROUP_WINDOW_MS = 5 * 60 * 1000L
 
 private val simpleHtmlTags = setOf(
     "a", "b", "blockquote", "br", "code", "del", "div", "em", "h1", "h2",
@@ -175,6 +186,10 @@ fun Room(modifier: Modifier = Modifier, rid: String) {
             }
     }
     val events by eventsFlow.collectAsState(initial = emptyList())
+    val currentUserId = remember { client!!.userId.toString() }
+    val timelineItems = remember(events, currentUserId) {
+        buildTimelineItems(events = events, currentUserId = currentUserId)
+    }
 
     val listState = rememberLazyListState()
 
@@ -182,11 +197,11 @@ fun Room(modifier: Modifier = Modifier, rid: String) {
         var message by remember { mutableStateOf("") }
 
         LazyColumn(Modifier.weight(1f), state = listState, reverseLayout = true) {
-            items(events, key = { it.eventId.full }) { event ->
-                EventItem(event)
+            items(timelineItems, key = { it.key }) { item ->
+                TimelineItem(item)
             }
 
-            if (events.isEmpty()) {
+            if (timelineItems.isEmpty()) {
                 item {
                     Text("Empty room", modifier = Modifier.padding(16.dp))
                 }
@@ -220,67 +235,386 @@ fun Room(modifier: Modifier = Modifier, rid: String) {
     }
 }
 
-@OptIn(ExperimentalMaterial3Api::class)
-@Composable
-fun EventItem(event: TimelineEvent) {
-    val content = event.content?.getOrNull()
-    Box(
-        Modifier
-            .fillMaxWidth()
-            .heightIn(min = 24.dp)
-    ) {
-        when {
-            content == null -> Text(
-                "Not decrypted",
-                Modifier
-                    .fillMaxHeight()
-                    .padding(4.dp)
-                    .background(MaterialTheme.colorScheme.errorContainer)
-                    .padding(4.dp)
+private sealed interface TimelineUiItem {
+    val key: String
+}
+
+private data class DateDividerItem(
+    override val key: String,
+    val label: String,
+) : TimelineUiItem
+
+private data class MessageTimelineItem(
+    override val key: String,
+    val content: RoomMessageEventContent,
+    val senderId: String?,
+    val senderLabel: String,
+    val timeLabel: String?,
+    val timestampMs: Long?,
+    val isOwn: Boolean,
+    val showSender: Boolean,
+    val showAvatar: Boolean,
+    val showTimestamp: Boolean,
+) : TimelineUiItem
+
+private data class SystemTimelineItem(
+    override val key: String,
+    val text: String,
+) : TimelineUiItem
+
+private fun buildTimelineItems(
+    events: List<TimelineEvent>,
+    currentUserId: String,
+): List<TimelineUiItem> {
+    if (events.isEmpty()) return emptyList()
+
+    val chronologicalEvents = events.asReversed()
+    val items = mutableListOf<TimelineUiItem>()
+
+    var previousDayStartMs: Long? = null
+    var lastMessageIndex: Int? = null
+
+    for (event in chronologicalEvents) {
+        val content = event.content?.getOrNull()
+        val timestampMs = event.extractTimestampMillis()
+        val dayStartMs = timestampMs?.let(::startOfDayMillis)
+
+        if (dayStartMs != null && dayStartMs != previousDayStartMs) {
+            items += DateDividerItem(
+                key = "date:$dayStartMs",
+                label = formatDateDividerLabel(dayStartMs),
             )
+            previousDayStartMs = dayStartMs
+            lastMessageIndex = null
+        }
+
+        when {
+            content == null -> {
+                items += SystemTimelineItem(
+                    key = "event:${event.eventId.full}",
+                    text = "Not decrypted",
+                )
+                lastMessageIndex = null
+            }
 
             content is RoomMessageEventContent -> {
-                val formatted = content.formattedBody
-                if (formatted != null) {
-                    FormattedMessageContent(
-                        htmlContent = formatted,
-                        plainText = content.body,
-                    )
+                val senderId = event.extractSenderId()
+                val isOwn = senderId != null && senderId == currentUserId
+                val senderLabel = event.extractSenderDisplayName().takeUnless { it.isNullOrBlank() }
+                    ?: senderId.toSenderLabel()
+                val timeLabel = timestampMs?.let(::formatTimeLabel)
+
+                val previousMessage = lastMessageIndex
+                    ?.let { items.getOrNull(it) as? MessageTimelineItem }
+                val groupedWithPrevious = previousMessage != null &&
+                    previousMessage.senderId != null &&
+                    previousMessage.senderId == senderId &&
+                    previousMessage.isOwn == isOwn &&
+                    previousMessage.timestampMs != null &&
+                    timestampMs != null &&
+                    timestampMs - previousMessage.timestampMs <= MESSAGE_GROUP_WINDOW_MS
+
+                if (groupedWithPrevious && previousMessage != null && lastMessageIndex != null) {
+                    items[lastMessageIndex] = previousMessage.copy(showTimestamp = false)
+                }
+
+                items += MessageTimelineItem(
+                    key = "event:${event.eventId.full}",
+                    content = content,
+                    senderId = senderId,
+                    senderLabel = senderLabel,
+                    timeLabel = timeLabel,
+                    timestampMs = timestampMs,
+                    isOwn = isOwn,
+                    showSender = !isOwn && !groupedWithPrevious,
+                    showAvatar = !isOwn && !groupedWithPrevious,
+                    showTimestamp = true,
+                )
+                lastMessageIndex = items.lastIndex
+            }
+
+            event.event is ClientEvent.RoomEvent.StateEvent -> {
+                items += SystemTimelineItem(
+                    key = "event:${event.eventId.full}",
+                    text = stateEventLabel(content),
+                )
+                lastMessageIndex = null
+            }
+
+            else -> {
+                items += SystemTimelineItem(
+                    key = "event:${event.eventId.full}",
+                    text = content.toString(),
+                )
+                lastMessageIndex = null
+            }
+        }
+    }
+
+    return items.asReversed()
+}
+
+@Composable
+private fun TimelineItem(item: TimelineUiItem) {
+    when (item) {
+        is DateDividerItem -> DateDivider(item)
+        is MessageTimelineItem -> MessageRow(item)
+        is SystemTimelineItem -> SystemEventRow(item)
+    }
+}
+
+@Composable
+private fun DateDivider(item: DateDividerItem) {
+    Text(
+        text = item.label,
+        modifier = Modifier
+            .fillMaxWidth()
+            .padding(vertical = 8.dp),
+        textAlign = TextAlign.Center,
+        style = MaterialTheme.typography.labelSmall,
+        color = MaterialTheme.colorScheme.onSurfaceVariant,
+    )
+}
+
+@Composable
+private fun SystemEventRow(item: SystemTimelineItem) {
+    Text(
+        text = item.text,
+        modifier = Modifier
+            .fillMaxWidth()
+            .padding(horizontal = 12.dp, vertical = 4.dp),
+        textAlign = TextAlign.Center,
+        style = MaterialTheme.typography.bodySmall,
+        color = MaterialTheme.colorScheme.onSurfaceVariant,
+    )
+}
+
+@Composable
+private fun MessageRow(item: MessageTimelineItem) {
+    val bubbleColor = MaterialTheme.colorScheme.surfaceVariant
+    val bubbleTextColor = MaterialTheme.colorScheme.onSurfaceVariant
+
+    Box(
+        modifier = Modifier
+            .fillMaxWidth()
+            .padding(horizontal = 8.dp, vertical = 2.dp),
+        contentAlignment = if (item.isOwn) Alignment.CenterEnd else Alignment.CenterStart,
+    ) {
+        Row(
+            horizontalArrangement = if (item.isOwn) Arrangement.End else Arrangement.Start,
+            verticalAlignment = Alignment.Bottom,
+        ) {
+            if (!item.isOwn) {
+                if (item.showAvatar) {
+                    AvatarPlaceholder(item.senderLabel)
                 } else {
+                    Spacer(Modifier.width(32.dp))
+                }
+                Spacer(Modifier.width(8.dp))
+            }
+
+            Column(
+                modifier = Modifier
+                    .widthIn(max = 320.dp)
+                    .background(bubbleColor, RoundedCornerShape(18.dp))
+                    .padding(horizontal = 10.dp, vertical = 8.dp),
+            ) {
+                if (item.showSender) {
                     Text(
-                        text = content.body,
-                        modifier = Modifier.padding(4.dp)
+                        text = item.senderLabel,
+                        style = MaterialTheme.typography.labelSmall,
+                        fontWeight = FontWeight.SemiBold,
+                        color = bubbleTextColor,
+                        modifier = Modifier.padding(bottom = 4.dp),
+                    )
+                }
+
+                MessageBody(
+                    content = item.content,
+                    textColor = bubbleTextColor,
+                )
+
+                if (item.showTimestamp && item.timeLabel != null) {
+                    Text(
+                        text = item.timeLabel,
+                        modifier = Modifier
+                            .align(Alignment.End)
+                            .padding(top = 4.dp),
+                        style = MaterialTheme.typography.labelSmall,
+                        color = bubbleTextColor.copy(alpha = 0.75f),
                     )
                 }
             }
-
-            event.event is ClientEvent.RoomEvent.StateEvent -> Text(
-                when (content) {
-                    is AvatarEventContent -> "Avatar changed"
-                    is PowerLevelsEventContent -> "Permissions changed"
-                    is MemberEventContent -> "Membership changed"
-                    is CanonicalAliasEventContent -> "Canonical alias changed"
-                    is TopicEventContent -> "Topic changed"
-                    is NameEventContent -> "Name changed"
-                    is HistoryVisibilityEventContent -> "History visibility changed"
-                    else -> content.toString()
-                },
-                Modifier.fillMaxWidth(),
-                textAlign = TextAlign.Center
-            )
-
-            else -> Text(
-                content.toString(),
-                Modifier
-                    .fillMaxHeight()
-                    .padding(4.dp)
-                    .background(MaterialTheme.colorScheme.errorContainer)
-                    .padding(4.dp)
-            )
         }
     }
 }
 
+@Composable
+private fun AvatarPlaceholder(senderLabel: String) {
+    val initial = senderLabel.trim().firstOrNull()?.uppercaseChar()?.toString() ?: "?"
+
+    Box(
+        modifier = Modifier
+            .size(32.dp)
+            .background(
+                color = MaterialTheme.colorScheme.secondaryContainer,
+                shape = CircleShape,
+            ),
+        contentAlignment = Alignment.Center,
+    ) {
+        Text(
+            text = initial,
+            style = MaterialTheme.typography.labelMedium,
+            color = MaterialTheme.colorScheme.onSecondaryContainer,
+        )
+    }
+}
+
+@Composable
+private fun MessageBody(
+    content: RoomMessageEventContent,
+    textColor: Color,
+) {
+    val formatted = content.formattedBody
+    if (formatted != null) {
+        FormattedMessageContent(
+            htmlContent = formatted,
+            plainText = content.body,
+        )
+    } else {
+        Text(
+            text = content.body,
+            color = textColor,
+            style = MaterialTheme.typography.bodyMedium,
+        )
+    }
+}
+
+private fun stateEventLabel(content: Any): String {
+    return when (content) {
+        is AvatarEventContent -> "Avatar changed"
+        is PowerLevelsEventContent -> "Permissions changed"
+        is MemberEventContent -> "Membership changed"
+        is CanonicalAliasEventContent -> "Canonical alias changed"
+        is TopicEventContent -> "Topic changed"
+        is NameEventContent -> "Name changed"
+        is HistoryVisibilityEventContent -> "History visibility changed"
+        else -> content.toString()
+    }
+}
+
+private fun TimelineEvent.extractSenderId(): String? {
+    return readPropertyValue(this, "sender")?.toString()?.takeIf { it.isNotBlank() }
+        ?: readPropertyValue(event, "sender")?.toString()?.takeIf { it.isNotBlank() }
+}
+
+private fun TimelineEvent.extractSenderDisplayName(): String? {
+    return listOf(this, event).firstNotNullOfOrNull { holder ->
+        readPropertyValue(holder, "senderDisplayName")?.toString()?.takeIf { it.isNotBlank() }
+            ?: readPropertyValue(holder, "displayName")?.toString()?.takeIf { it.isNotBlank() }
+            ?: readPropertyValue(holder, "senderName")?.toString()?.takeIf { it.isNotBlank() }
+    }
+}
+
+private fun TimelineEvent.extractTimestampMillis(): Long? {
+    val rawValue = listOf(this, event).firstNotNullOfOrNull { holder ->
+        readPropertyValue(holder, "originTimestamp")
+            ?: readPropertyValue(holder, "originServerTs")
+            ?: readPropertyValue(holder, "timestamp")
+    }
+    return rawValue.toEpochMillisOrNull()
+}
+
+private fun readPropertyValue(target: Any?, propertyName: String): Any? {
+    if (target == null) return null
+
+    val getterName = buildString {
+        append("get")
+        append(propertyName.replaceFirstChar { if (it.isLowerCase()) it.titlecase() else it.toString() })
+    }
+
+    val methodsToTry = listOf(propertyName, getterName)
+    for (methodName in methodsToTry) {
+        val value = runCatching {
+            target.javaClass.methods.firstOrNull {
+                it.name == methodName && it.parameterCount == 0
+            }?.invoke(target)
+        }.getOrNull()
+        if (value != null) return value
+    }
+
+    return runCatching {
+        target.javaClass.declaredFields.firstOrNull { it.name == propertyName }?.let { field ->
+            field.isAccessible = true
+            field.get(target)
+        }
+    }.getOrNull()
+}
+
+private fun Any?.toEpochMillisOrNull(): Long? {
+    return when (this) {
+        null -> null
+        is Number -> toLong()
+        is Date -> time
+        else -> {
+            val directString = toString().toLongOrNull()
+            if (directString != null) {
+                directString
+            } else {
+                val methodNames = listOf(
+                    "toEpochMilliseconds",
+                    "toEpochMilli",
+                    "getEpochMilliseconds",
+                    "getTime",
+                )
+                methodNames.firstNotNullOfOrNull { methodName ->
+                    runCatching {
+                        javaClass.methods.firstOrNull {
+                            it.name == methodName && it.parameterCount == 0
+                        }?.invoke(this)
+                    }.getOrNull().let { value ->
+                        when (value) {
+                            is Number -> value.toLong()
+                            else -> value?.toString()?.toLongOrNull()
+                        }
+                    }
+                }
+            }
+        }
+    }
+}
+
+private fun String?.toSenderLabel(): String {
+    if (this.isNullOrBlank()) return "Unknown"
+    val withoutSigil = removePrefix("@")
+    return withoutSigil.substringBefore(':').ifBlank { this }
+}
+
+private fun startOfDayMillis(timestampMs: Long): Long {
+    val calendar = Calendar.getInstance().apply {
+        timeInMillis = timestampMs
+        set(Calendar.HOUR_OF_DAY, 0)
+        set(Calendar.MINUTE, 0)
+        set(Calendar.SECOND, 0)
+        set(Calendar.MILLISECOND, 0)
+    }
+    return calendar.timeInMillis
+}
+
+private fun formatDateDividerLabel(dayStartMs: Long): String {
+    val todayStart = startOfDayMillis(System.currentTimeMillis())
+    val yesterdayStart = todayStart - 24L * 60L * 60L * 1000L
+    return when (dayStartMs) {
+        todayStart -> "Today"
+        yesterdayStart -> "Yesterday"
+        else -> SimpleDateFormat("d MMM", Locale.getDefault()).format(Date(dayStartMs))
+    }
+}
+
+private fun formatTimeLabel(timestampMs: Long): String {
+    return SimpleDateFormat("HH:mm", Locale.getDefault()).format(Date(timestampMs))
+}
+
 @Composable
 private fun FormattedMessageContent(
     htmlContent: String,