diff --git a/app/src/main/java/com/geeksville/mesh/service/MeshDataHandler.kt b/app/src/main/java/com/geeksville/mesh/service/MeshDataHandler.kt
index a973888b3..a53500e64 100644
--- a/app/src/main/java/com/geeksville/mesh/service/MeshDataHandler.kt
+++ b/app/src/main/java/com/geeksville/mesh/service/MeshDataHandler.kt
@@ -27,6 +27,7 @@ import kotlinx.coroutines.CoroutineScope
 import kotlinx.coroutines.Dispatchers
 import kotlinx.coroutines.Job
 import kotlinx.coroutines.SupervisorJob
+import kotlinx.coroutines.delay
 import kotlinx.coroutines.flow.first
 import org.meshtastic.core.analytics.DataPair
 import org.meshtastic.core.analytics.platform.PlatformAnalytics
@@ -326,6 +327,37 @@ constructor(
         scope.handledLaunch {
             val isAck = routingError == MeshProtos.Routing.Error.NONE_VALUE
             val p = packetRepository.get().getPacketById(requestId)
+            val isMaxRetransmit = routingError == MeshProtos.Routing.Error.MAX_RETRANSMIT_VALUE
+            val shouldRetry =
+                isMaxRetransmit &&
+                    p != null &&
+                    p.port_num == Portnums.PortNum.TEXT_MESSAGE_APP_VALUE &&
+                    p.data.from == DataPacket.ID_LOCAL &&
+                    p.data.retryCount < MAX_RETRY_ATTEMPTS
+
+            Logger.d {
+                val retryInfo = "packetId=${p?.packetId} dataId=${p?.data?.id} retry=${p?.data?.retryCount}"
+                val statusInfo = "status=${p?.data?.status}"
+                "[ackNak] req=$requestId routeErr=$routingError isAck=$isAck " +
+                    "maxRetransmit=$isMaxRetransmit shouldRetry=$shouldRetry $retryInfo $statusInfo"
+            }
+
+            if (shouldRetry && p != null) {
+                val newRetryCount = p.data.retryCount + 1
+                val newId = commandSender.generatePacketId()
+                val updatedData =
+                    p.data.copy(id = newId, status = MessageStatus.QUEUED, retryCount = newRetryCount, relayNode = null)
+                val updatedPacket =
+                    p.copy(packetId = newId, data = updatedData, routingError = MeshProtos.Routing.Error.NONE_VALUE)
+                packetRepository.get().update(updatedPacket)
+
+                Logger.w { "[ackNak] retrying req=$requestId newId=$newId retry=$newRetryCount" }
+
+                delay(RETRY_DELAY_MS)
+                commandSender.sendData(updatedData)
+                return@handledLaunch
+            }
+
             val m =
                 when {
                     isAck && fromId == p?.data?.to -> MessageStatus.RECEIVED
@@ -528,6 +560,8 @@ constructor(
     }
 
     companion object {
+        private const val MAX_RETRY_ATTEMPTS = 5
+        private const val RETRY_DELAY_MS = 5_000L
         private const val MILLISECONDS_IN_SECOND = 1000L
         private const val HOPS_AWAY_UNAVAILABLE = -1
 
diff --git a/core/database/src/main/kotlin/org/meshtastic/core/database/entity/Packet.kt b/core/database/src/main/kotlin/org/meshtastic/core/database/entity/Packet.kt
index 986359359..3c4bdfa51 100644
--- a/core/database/src/main/kotlin/org/meshtastic/core/database/entity/Packet.kt
+++ b/core/database/src/main/kotlin/org/meshtastic/core/database/entity/Packet.kt
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2025 Meshtastic LLC
+ * Copyright (c) 2025-2026 Meshtastic LLC
  *
  * This program is free software: you can redistribute it and/or modify
  * it under the terms of the GNU General Public License as published by
@@ -14,7 +14,6 @@
  * You should have received a copy of the GNU General Public License
  * along with this program.  If not, see <https://www.gnu.org/licenses/>.
  */
-
 package org.meshtastic.core.database.entity
 
 import androidx.room.ColumnInfo
@@ -55,6 +54,7 @@ data class PacketEntity(
             viaMqtt = data.viaMqtt,
             relayNode = data.relayNode,
             relays = data.relays,
+            retryCount = data.retryCount,
         )
     }
 }
diff --git a/core/database/src/main/kotlin/org/meshtastic/core/database/model/Message.kt b/core/database/src/main/kotlin/org/meshtastic/core/database/model/Message.kt
index 0d5610fd7..06faca24a 100644
--- a/core/database/src/main/kotlin/org/meshtastic/core/database/model/Message.kt
+++ b/core/database/src/main/kotlin/org/meshtastic/core/database/model/Message.kt
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2025 Meshtastic LLC
+ * Copyright (c) 2025-2026 Meshtastic LLC
  *
  * This program is free software: you can redistribute it and/or modify
  * it under the terms of the GNU General Public License as published by
@@ -14,7 +14,6 @@
  * You should have received a copy of the GNU General Public License
  * along with this program.  If not, see <https://www.gnu.org/licenses/>.
  */
-
 package org.meshtastic.core.database.model
 
 import org.jetbrains.compose.resources.StringResource
@@ -88,6 +87,7 @@ data class Message(
     val viaMqtt: Boolean = false,
     val relayNode: Int? = null,
     val relays: Int = 0,
+    val retryCount: Int = 0,
 ) {
     fun getStatusStringRes(): Pair<StringResource, StringResource> {
         val title = if (routingError > 0) Res.string.error else Res.string.message_delivery_status
diff --git a/core/model/src/main/kotlin/org/meshtastic/core/model/DataPacket.kt b/core/model/src/main/kotlin/org/meshtastic/core/model/DataPacket.kt
index 80e7e97f9..f795eef01 100644
--- a/core/model/src/main/kotlin/org/meshtastic/core/model/DataPacket.kt
+++ b/core/model/src/main/kotlin/org/meshtastic/core/model/DataPacket.kt
@@ -63,6 +63,7 @@ data class DataPacket(
     var relayNode: Int? = null,
     var relays: Int = 0,
     var viaMqtt: Boolean = false, // True if this packet passed via MQTT somewhere along its path
+    var retryCount: Int = 0, // Number of automatic retry attempts
     var emoji: Int = 0,
 ) : Parcelable {
 
@@ -139,6 +140,7 @@ data class DataPacket(
         parcel.readInt().let { if (it == -1) null else it },
         parcel.readInt(), // relays
         parcel.readInt() == 1, // viaMqtt
+        parcel.readInt(), // retryCount
         parcel.readInt(), // emoji
     )
 
@@ -164,6 +166,7 @@ data class DataPacket(
         if (rssi != other.rssi) return false
         if (replyId != other.replyId) return false
         if (relayNode != other.relayNode) return false
+        if (retryCount != other.retryCount) return false
         if (emoji != other.emoji) return false
 
         return true
@@ -185,6 +188,7 @@ data class DataPacket(
         result = 31 * result + rssi
         result = 31 * result + replyId.hashCode()
         result = 31 * result + relayNode.hashCode()
+        result = 31 * result + retryCount
         result = 31 * result + emoji
         return result
     }
@@ -207,6 +211,7 @@ data class DataPacket(
         parcel.writeInt(relayNode ?: -1)
         parcel.writeInt(relays)
         parcel.writeInt(if (viaMqtt) 1 else 0)
+        parcel.writeInt(retryCount)
         parcel.writeInt(emoji)
     }
 
@@ -231,6 +236,7 @@ data class DataPacket(
         relayNode = parcel.readInt().let { if (it == -1) null else it }
         relays = parcel.readInt()
         viaMqtt = parcel.readInt() == 1
+        retryCount = parcel.readInt()
         emoji = parcel.readInt()
     }
 
diff --git a/core/strings/src/commonMain/composeResources/values/strings.xml b/core/strings/src/commonMain/composeResources/values/strings.xml
index d89f5b4e0..2d3f112d8 100644
--- a/core/strings/src/commonMain/composeResources/values/strings.xml
+++ b/core/strings/src/commonMain/composeResources/values/strings.xml
@@ -51,6 +51,7 @@
     <string name="unrecognized">Unrecognized</string>
     <string name="message_status_enroute">Waiting to be acknowledged</string>
     <string name="message_status_queued">Queued for sending</string>
+    <string name="message_retry_count">Retries: %1$d / %2$d</string>
     <string name="routing_error_none">Acknowledged</string>
     <string name="routing_error_no_route">No route</string>
     <string name="routing_error_got_nak">Received a negative acknowledgment</string>
diff --git a/feature/messaging/src/main/kotlin/org/meshtastic/feature/messaging/DeliveryInfoDialog.kt b/feature/messaging/src/main/kotlin/org/meshtastic/feature/messaging/DeliveryInfoDialog.kt
index 83d1da2a0..f27a798be 100644
--- a/feature/messaging/src/main/kotlin/org/meshtastic/feature/messaging/DeliveryInfoDialog.kt
+++ b/feature/messaging/src/main/kotlin/org/meshtastic/feature/messaging/DeliveryInfoDialog.kt
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2025 Meshtastic LLC
+ * Copyright (c) 2025-2026 Meshtastic LLC
  *
  * This program is free software: you can redistribute it and/or modify
  * it under the terms of the GNU General Public License as published by
@@ -14,7 +14,6 @@
  * You should have received a copy of the GNU General Public License
  * along with this program.  If not, see <https://www.gnu.org/licenses/>.
  */
-
 package org.meshtastic.feature.messaging
 
 import androidx.compose.foundation.layout.Column
@@ -34,6 +33,7 @@ import org.jetbrains.compose.resources.pluralStringResource
 import org.jetbrains.compose.resources.stringResource
 import org.meshtastic.core.strings.Res
 import org.meshtastic.core.strings.close
+import org.meshtastic.core.strings.message_retry_count
 import org.meshtastic.core.strings.relays
 import org.meshtastic.core.strings.resend
 
@@ -45,6 +45,8 @@ fun DeliveryInfo(
     text: StringResource? = null,
     relayNodeName: String? = null,
     relays: Int = 0,
+    retryCount: Int = 0,
+    maxRetries: Int = 0,
     onConfirm: (() -> Unit) = {},
     onDismiss: () -> Unit = {},
 ) = AlertDialog(
@@ -78,6 +80,14 @@ fun DeliveryInfo(
                     style = MaterialTheme.typography.bodyMedium,
                 )
             }
+            if (maxRetries > 0) {
+                Text(
+                    text = stringResource(Res.string.message_retry_count, retryCount, maxRetries),
+                    modifier = Modifier.padding(top = 8.dp),
+                    textAlign = TextAlign.Center,
+                    style = MaterialTheme.typography.bodyMedium,
+                )
+            }
             if (relays != 0) {
                 Text(
                     text = pluralStringResource(Res.plurals.relays, relays, relays),
diff --git a/feature/messaging/src/main/kotlin/org/meshtastic/feature/messaging/MessageListPaged.kt b/feature/messaging/src/main/kotlin/org/meshtastic/feature/messaging/MessageListPaged.kt
index 7a342be9f..ed17ec107 100644
--- a/feature/messaging/src/main/kotlin/org/meshtastic/feature/messaging/MessageListPaged.kt
+++ b/feature/messaging/src/main/kotlin/org/meshtastic/feature/messaging/MessageListPaged.kt
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2025 Meshtastic LLC
+ * Copyright (c) 2025-2026 Meshtastic LLC
  *
  * This program is free software: you can redistribute it and/or modify
  * it under the terms of the GNU General Public License as published by
@@ -14,7 +14,6 @@
  * You should have received a copy of the GNU General Public License
  * along with this program.  If not, see <https://www.gnu.org/licenses/>.
  */
-
 package org.meshtastic.feature.messaging
 
 import androidx.compose.foundation.layout.Arrangement
@@ -118,6 +117,8 @@ internal fun MessageListPaged(
             nodes = state.nodes,
             ourNode = state.ourNode,
             resendOption = message.status?.equals(MessageStatus.ERROR) ?: false,
+            retryCount = message.retryCount,
+            maxRetries = 5,
             onResend = {
                 handlers.onDeleteMessages(listOf(message.uuid))
                 handlers.onSendMessage(message.text, state.contactKey)
@@ -436,6 +437,8 @@ internal fun MessageStatusDialog(
     nodes: List<Node>,
     ourNode: Node?,
     resendOption: Boolean,
+    retryCount: Int,
+    maxRetries: Int,
     onResend: () -> Unit,
     onDismiss: () -> Unit,
 ) {
@@ -454,6 +457,8 @@ internal fun MessageStatusDialog(
         text = text,
         relayNodeName = relayNodeName,
         relays = message.relays,
+        retryCount = retryCount,
+        maxRetries = maxRetries,
         onConfirm = onResend,
         onDismiss = onDismiss,
     )