diff --git a/core/src/main/java/haveno/core/trade/protocol/BuyerProtocol.java b/core/src/main/java/haveno/core/trade/protocol/BuyerProtocol.java
index 7299b08e76..6481212281 100644
--- a/core/src/main/java/haveno/core/trade/protocol/BuyerProtocol.java
+++ b/core/src/main/java/haveno/core/trade/protocol/BuyerProtocol.java
@@ -53,9 +53,9 @@ public class BuyerProtocol extends DisputeProtocol {
     protected void onInitialized() {
         super.onInitialized();
 
-        // re-send payment sent message if not arrived
+        // re-send payment sent message if not acked
         synchronized (trade) {
-            if (trade.getState().ordinal() >= Trade.State.BUYER_SENT_PAYMENT_SENT_MSG.ordinal() && trade.getState().ordinal() <= Trade.State.BUYER_SEND_FAILED_PAYMENT_SENT_MSG.ordinal()) {
+            if (trade.getState().ordinal() >= Trade.State.BUYER_SENT_PAYMENT_SENT_MSG.ordinal() && trade.getState().ordinal() < Trade.State.SELLER_RECEIVED_PAYMENT_SENT_MSG.ordinal()) {
                 latchTrade();
                 given(anyPhase(Trade.Phase.PAYMENT_SENT)
                     .with(BuyerEvent.STARTUP))
diff --git a/core/src/main/java/haveno/core/trade/protocol/SellerProtocol.java b/core/src/main/java/haveno/core/trade/protocol/SellerProtocol.java
index d45576fb2b..c6802aa3e6 100644
--- a/core/src/main/java/haveno/core/trade/protocol/SellerProtocol.java
+++ b/core/src/main/java/haveno/core/trade/protocol/SellerProtocol.java
@@ -49,9 +49,9 @@ public class SellerProtocol extends DisputeProtocol {
     protected void onInitialized() {
         super.onInitialized();
 
-        // re-send payment received message if not arrived
+        // re-send payment received message if payout not published
         synchronized (trade) {
-            if (trade.getState().ordinal() >= Trade.State.SELLER_SENT_PAYMENT_RECEIVED_MSG.ordinal() && trade.getState().ordinal() <= Trade.State.SELLER_SEND_FAILED_PAYMENT_RECEIVED_MSG.ordinal()) {
+            if (trade.getState().ordinal() >= Trade.State.SELLER_SENT_PAYMENT_RECEIVED_MSG.ordinal() && !trade.isPayoutPublished()) {
                 latchTrade();
                 given(anyPhase(Trade.Phase.PAYMENT_RECEIVED)
                     .with(SellerEvent.STARTUP))
diff --git a/core/src/main/java/haveno/core/trade/protocol/tasks/BuyerSendPaymentSentMessage.java b/core/src/main/java/haveno/core/trade/protocol/tasks/BuyerSendPaymentSentMessage.java
index 93ce52b486..5d52805a11 100644
--- a/core/src/main/java/haveno/core/trade/protocol/tasks/BuyerSendPaymentSentMessage.java
+++ b/core/src/main/java/haveno/core/trade/protocol/tasks/BuyerSendPaymentSentMessage.java
@@ -17,7 +17,10 @@
 
 package haveno.core.trade.protocol.tasks;
 
+import java.util.concurrent.TimeUnit;
+
 import haveno.common.Timer;
+import haveno.common.UserThread;
 import haveno.common.crypto.PubKeyRing;
 import haveno.common.taskrunner.TaskRunner;
 import haveno.core.network.MessageState;
@@ -45,6 +48,9 @@ import lombok.extern.slf4j.Slf4j;
 public abstract class BuyerSendPaymentSentMessage extends SendMailboxMessageTask {
     private ChangeListener<MessageState> listener;
     private Timer timer;
+    private static final int MAX_RESEND_ATTEMPTS = 10;
+    private int delayInMin = 10;
+    private int resendCounter = 0;
 
     public BuyerSendPaymentSentMessage(TaskRunner<Trade> taskHandler, Trade trade) {
         super(taskHandler, trade);
@@ -61,8 +67,6 @@ public abstract class BuyerSendPaymentSentMessage extends SendMailboxMessageTask
             super.run();
         } catch (Throwable t) {
             failed(t);
-        } finally {
-            cleanup();
         }
     }
 
@@ -105,22 +109,21 @@ public abstract class BuyerSendPaymentSentMessage extends SendMailboxMessageTask
 
     @Override
     protected void setStateSent() {
-        if (trade.getState().ordinal() < Trade.State.BUYER_SENT_PAYMENT_SENT_MSG.ordinal()) {
-            trade.setStateIfValidTransitionTo(Trade.State.BUYER_SENT_PAYMENT_SENT_MSG);
-        }
+        if (trade.getState().ordinal() < Trade.State.BUYER_SENT_PAYMENT_SENT_MSG.ordinal()) trade.setStateIfValidTransitionTo(Trade.State.BUYER_SENT_PAYMENT_SENT_MSG);
+        tryToSendAgainLater();
         processModel.getTradeManager().requestPersistence();
     }
 
     @Override
     protected void setStateArrived() {
         trade.setStateIfValidTransitionTo(Trade.State.BUYER_SAW_ARRIVED_PAYMENT_SENT_MSG);
+        processModel.getTradeManager().requestPersistence();
     }
 
     @Override
     protected void setStateStoredInMailbox() {
         trade.setStateIfValidTransitionTo(Trade.State.BUYER_STORED_IN_MAILBOX_PAYMENT_SENT_MSG);
         processModel.getTradeManager().requestPersistence();
-        // TODO: schedule repeat sending like haveno?
     }
 
     @Override
@@ -137,4 +140,40 @@ public abstract class BuyerSendPaymentSentMessage extends SendMailboxMessageTask
             processModel.getPaymentSentMessageStateProperty().removeListener(listener);
         }
     }
+
+    private void tryToSendAgainLater() {
+
+        // skip if already acked
+        if (trade.getState().ordinal() >= Trade.State.SELLER_RECEIVED_PAYMENT_SENT_MSG.ordinal()) return;
+
+        if (resendCounter >= MAX_RESEND_ATTEMPTS) {
+            cleanup();
+            log.warn("We never received an ACK message when sending the PaymentSentMessage to the peer. We stop trying to send the message.");
+            return;
+        }
+
+        log.info("We will send the message again to the peer after a delay of {} min.", delayInMin);
+        if (timer != null) {
+            timer.stop();
+        }
+
+        timer = UserThread.runAfter(this::run, delayInMin, TimeUnit.MINUTES);
+
+        if (resendCounter == 0) {
+            listener = (observable, oldValue, newValue) -> onMessageStateChange(newValue);
+            processModel.getPaymentSentMessageStateProperty().addListener(listener);
+            onMessageStateChange(processModel.getPaymentSentMessageStateProperty().get());
+        }
+
+        delayInMin = delayInMin * 2;
+        resendCounter++;
+    }
+
+    private void onMessageStateChange(MessageState newValue) {
+        if (newValue == MessageState.ACKNOWLEDGED) {
+            trade.setStateIfValidTransitionTo(Trade.State.SELLER_RECEIVED_PAYMENT_SENT_MSG);
+            processModel.getTradeManager().requestPersistence();
+            cleanup();
+        }
+    }
 }
diff --git a/desktop/src/main/java/haveno/desktop/main/portfolio/pendingtrades/steps/buyer/BuyerStep2View.java b/desktop/src/main/java/haveno/desktop/main/portfolio/pendingtrades/steps/buyer/BuyerStep2View.java
index e29ec8240e..1bdacc8078 100644
--- a/desktop/src/main/java/haveno/desktop/main/portfolio/pendingtrades/steps/buyer/BuyerStep2View.java
+++ b/desktop/src/main/java/haveno/desktop/main/portfolio/pendingtrades/steps/buyer/BuyerStep2View.java
@@ -149,43 +149,43 @@ public class BuyerStep2View extends TradeStepView {
 
                 if (trade.isDepositsUnlocked() && !trade.isPaymentSent()) {
                     showPopup();
-                } else if (state.ordinal() <= Trade.State.BUYER_SEND_FAILED_PAYMENT_SENT_MSG.ordinal()) {
+                } else if (state.ordinal() <= Trade.State.SELLER_RECEIVED_PAYMENT_SENT_MSG.ordinal()) {
                     switch (state) {
-                    case BUYER_CONFIRMED_IN_UI_PAYMENT_SENT:
-                        busyAnimation.play();
-                        statusLabel.setText(Res.get("shared.preparingConfirmation"));
-                        break;
-                    case BUYER_SENT_PAYMENT_SENT_MSG:
-                        busyAnimation.play();
-                        statusLabel.setText(Res.get("shared.sendingConfirmation"));
-                        model.setMessageStateProperty(MessageState.SENT);
-                        timeoutTimer = UserThread.runAfter(() -> {
+                        case BUYER_CONFIRMED_IN_UI_PAYMENT_SENT:
+                            busyAnimation.play();
+                            statusLabel.setText(Res.get("shared.preparingConfirmation"));
+                            break;
+                        case BUYER_SENT_PAYMENT_SENT_MSG:
+                            busyAnimation.play();
+                            statusLabel.setText(Res.get("shared.sendingConfirmation"));
+                            model.setMessageStateProperty(MessageState.SENT);
+                            timeoutTimer = UserThread.runAfter(() -> {
+                                busyAnimation.stop();
+                                statusLabel.setText(Res.get("shared.sendingConfirmationAgain"));
+                            }, 10);
+                            break;
+                        case BUYER_STORED_IN_MAILBOX_PAYMENT_SENT_MSG:
+                            busyAnimation.stop();
+                            statusLabel.setText(Res.get("shared.messageStoredInMailbox"));
+                            model.setMessageStateProperty(MessageState.STORED_IN_MAILBOX);
+                            break;
+                        case SELLER_RECEIVED_PAYMENT_SENT_MSG:
+                            busyAnimation.stop();
+                            statusLabel.setText(Res.get("shared.messageArrived"));
+                            model.setMessageStateProperty(MessageState.ARRIVED);
+                            break;
+                        case BUYER_SEND_FAILED_PAYMENT_SENT_MSG:
+                            // We get a popup and the trade closed, so we dont need to show anything here
+                            busyAnimation.stop();
+                            statusLabel.setText("");
+                            model.setMessageStateProperty(MessageState.FAILED);
+                            break;
+                        default:
+                            log.warn("Unexpected case: State={}, tradeId={} ", state.name(), trade.getId());
                             busyAnimation.stop();
                             statusLabel.setText(Res.get("shared.sendingConfirmationAgain"));
-                        }, 10);
-                        break;
-                    case BUYER_SAW_ARRIVED_PAYMENT_SENT_MSG:
-                        busyAnimation.stop();
-                        statusLabel.setText(Res.get("shared.messageArrived"));
-                        model.setMessageStateProperty(MessageState.ARRIVED);
-                        break;
-                    case BUYER_STORED_IN_MAILBOX_PAYMENT_SENT_MSG:
-                        busyAnimation.stop();
-                        statusLabel.setText(Res.get("shared.messageStoredInMailbox"));
-                        model.setMessageStateProperty(MessageState.STORED_IN_MAILBOX);
-                        break;
-                    case BUYER_SEND_FAILED_PAYMENT_SENT_MSG:
-                        // We get a popup and the trade closed, so we dont need to show anything here
-                        busyAnimation.stop();
-                        statusLabel.setText("");
-                        model.setMessageStateProperty(MessageState.FAILED);
-                        break;
-                    default:
-                        log.warn("Unexpected case: State={}, tradeId={} ", state.name(), trade.getId());
-                        busyAnimation.stop();
-                        statusLabel.setText(Res.get("shared.sendingConfirmationAgain"));
-                        break;
-                    }
+                            break;
+                        }
                 }
             });
         }