diff --git a/core/src/main/java/ch/dissem/bitmessage/BitmessageContext.java b/core/src/main/java/ch/dissem/bitmessage/BitmessageContext.java
index d46c36c..23e8eff 100644
--- a/core/src/main/java/ch/dissem/bitmessage/BitmessageContext.java
+++ b/core/src/main/java/ch/dissem/bitmessage/BitmessageContext.java
@@ -153,7 +153,6 @@ public class BitmessageContext {
                 .to(to)
                 .message(subject, message)
                 .build();
-        labeler().markAsSending(msg);
         send(msg);
     }
 
@@ -161,7 +160,7 @@ public class BitmessageContext {
         if (msg.getFrom() == null || msg.getFrom().getPrivateKey() == null) {
             throw new IllegalArgumentException("'From' must be an identity, i.e. have a private key.");
         }
-        msg.setStatus(Plaintext.Status.DRAFT);
+        labeler().markAsSending(msg);
         BitmessageAddress to = msg.getTo();
         if (to != null) {
             if (to.getPubkey() == null) {
diff --git a/core/src/main/java/ch/dissem/bitmessage/DefaultMessageListener.java b/core/src/main/java/ch/dissem/bitmessage/DefaultMessageListener.java
index 14c405c..eb27dd9 100644
--- a/core/src/main/java/ch/dissem/bitmessage/DefaultMessageListener.java
+++ b/core/src/main/java/ch/dissem/bitmessage/DefaultMessageListener.java
@@ -24,6 +24,7 @@ import ch.dissem.bitmessage.entity.valueobject.InventoryVector;
 import ch.dissem.bitmessage.exception.DecryptionFailedException;
 import ch.dissem.bitmessage.ports.Labeler;
 import ch.dissem.bitmessage.ports.NetworkHandler;
+import ch.dissem.bitmessage.utils.TTL;
 import org.slf4j.Logger;
 import org.slf4j.LoggerFactory;
 
@@ -111,7 +112,7 @@ class DefaultMessageListener implements NetworkHandler.MessageListener {
         for (Plaintext msg : messages) {
             ctx.getLabeler().markAsSending(msg);
             ctx.getMessageRepository().save(msg);
-            ctx.send(msg, +2 * DAY);
+            ctx.send(msg, TTL.msg());
         }
     }
 
diff --git a/core/src/main/java/ch/dissem/bitmessage/ProofOfWorkService.java b/core/src/main/java/ch/dissem/bitmessage/ProofOfWorkService.java
index 6df0cc0..e886c22 100644
--- a/core/src/main/java/ch/dissem/bitmessage/ProofOfWorkService.java
+++ b/core/src/main/java/ch/dissem/bitmessage/ProofOfWorkService.java
@@ -1,9 +1,7 @@
 package ch.dissem.bitmessage;
 
 import ch.dissem.bitmessage.entity.*;
-import ch.dissem.bitmessage.entity.payload.Broadcast;
 import ch.dissem.bitmessage.entity.payload.Msg;
-import ch.dissem.bitmessage.entity.payload.ObjectPayload;
 import ch.dissem.bitmessage.entity.payload.Pubkey;
 import ch.dissem.bitmessage.ports.Cryptography;
 import ch.dissem.bitmessage.ports.MessageRepository;
diff --git a/core/src/main/java/ch/dissem/bitmessage/ports/DefaultLabeler.java b/core/src/main/java/ch/dissem/bitmessage/ports/DefaultLabeler.java
index 4f21b3e..e4c2105 100644
--- a/core/src/main/java/ch/dissem/bitmessage/ports/DefaultLabeler.java
+++ b/core/src/main/java/ch/dissem/bitmessage/ports/DefaultLabeler.java
@@ -43,7 +43,7 @@ public class DefaultLabeler implements Labeler, InternalContext.ContextHolder {
 
     @Override
     public void markAsSending(Plaintext msg) {
-        if (msg.getTo() != null || msg.getTo().getPubkey() == null) {
+        if (msg.getTo() != null && msg.getTo().getPubkey() == null) {
             msg.setStatus(PUBKEY_REQUESTED);
         } else {
             msg.setStatus(DOING_PROOF_OF_WORK);
diff --git a/core/src/main/java/ch/dissem/bitmessage/ports/ProofOfWorkRepository.java b/core/src/main/java/ch/dissem/bitmessage/ports/ProofOfWorkRepository.java
index 61dc2ab..b27a05d 100644
--- a/core/src/main/java/ch/dissem/bitmessage/ports/ProofOfWorkRepository.java
+++ b/core/src/main/java/ch/dissem/bitmessage/ports/ProofOfWorkRepository.java
@@ -1,6 +1,5 @@
 package ch.dissem.bitmessage.ports;
 
-import ch.dissem.bitmessage.entity.BitmessageAddress;
 import ch.dissem.bitmessage.entity.ObjectMessage;
 import ch.dissem.bitmessage.entity.Plaintext;
 
diff --git a/demo/src/test/java/ch/dissem/bitmessage/SystemTest.java b/demo/src/test/java/ch/dissem/bitmessage/SystemTest.java
index 06b6628..6751819 100644
--- a/demo/src/test/java/ch/dissem/bitmessage/SystemTest.java
+++ b/demo/src/test/java/ch/dissem/bitmessage/SystemTest.java
@@ -4,13 +4,19 @@ import ch.dissem.bitmessage.cryptography.bc.BouncyCryptography;
 import ch.dissem.bitmessage.entity.BitmessageAddress;
 import ch.dissem.bitmessage.entity.Plaintext;
 import ch.dissem.bitmessage.networking.DefaultNetworkHandler;
+import ch.dissem.bitmessage.ports.DefaultLabeler;
 import ch.dissem.bitmessage.repository.*;
 import ch.dissem.bitmessage.utils.TTL;
-import org.junit.*;
+import org.junit.After;
+import org.junit.Before;
+import org.junit.Test;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
 
 import java.util.UUID;
 import java.util.concurrent.TimeUnit;
 
+import static ch.dissem.bitmessage.entity.payload.Pubkey.Feature.DOES_ACK;
 import static ch.dissem.bitmessage.utils.UnixTime.MINUTE;
 import static org.hamcrest.CoreMatchers.equalTo;
 import static org.junit.Assert.assertThat;
@@ -47,9 +53,10 @@ public class SystemTest {
                 .networkHandler(new DefaultNetworkHandler())
                 .cryptography(new BouncyCryptography())
                 .listener(aliceListener)
+                .labeler(new DebugLabeler("Alice"))
                 .build();
         alice.startup();
-        aliceIdentity = alice.createIdentity(false);
+        aliceIdentity = alice.createIdentity(false, DOES_ACK);
 
         JdbcConfig bobDB = new JdbcConfig("jdbc:h2:mem:bob;DB_CLOSE_DELAY=-1", "sa", "");
         bob = new BitmessageContext.Builder()
@@ -62,9 +69,13 @@ public class SystemTest {
                 .networkHandler(new DefaultNetworkHandler())
                 .cryptography(new BouncyCryptography())
                 .listener(bobListener)
+                .labeler(new DebugLabeler("Bob"))
                 .build();
         bob.startup();
-        bobIdentity = bob.createIdentity(false);
+        bobIdentity = bob.createIdentity(false, DOES_ACK);
+
+        ((DebugLabeler) alice.labeler()).init(aliceIdentity, bobIdentity);
+        ((DebugLabeler) bob.labeler()).init(aliceIdentity, bobIdentity);
     }
 
     @After
@@ -95,4 +106,83 @@ public class SystemTest {
         assertThat(plaintext.getType(), equalTo(Plaintext.Type.BROADCAST));
         assertThat(plaintext.getText(), equalTo(originalMessage));
     }
+
+    private static class DebugLabeler extends DefaultLabeler {
+        private final Logger LOG = LoggerFactory.getLogger("Labeler");
+        final String name;
+        String alice;
+        String bob;
+
+        private DebugLabeler(String name) {
+            this.name = name;
+        }
+
+        private void init(BitmessageAddress alice, BitmessageAddress bob) {
+            this.alice = alice.getAddress();
+            this.bob = bob.getAddress();
+        }
+
+        @Override
+        public void setLabels(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Received");
+            super.setLabels(msg);
+        }
+
+        @Override
+        public void markAsDraft(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Draft");
+            super.markAsDraft(msg);
+        }
+
+        @Override
+        public void markAsSending(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Sending");
+            super.markAsSending(msg);
+        }
+
+        @Override
+        public void markAsSent(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Sent");
+            super.markAsSent(msg);
+        }
+
+        @Override
+        public void markAsAcknowledged(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Acknowledged");
+            super.markAsAcknowledged(msg);
+        }
+
+        @Override
+        public void markAsRead(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Read");
+            super.markAsRead(msg);
+        }
+
+        @Override
+        public void markAsUnread(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Unread");
+            super.markAsUnread(msg);
+        }
+
+        @Override
+        public void delete(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Cleared");
+            super.delete(msg);
+        }
+
+        @Override
+        public void archive(Plaintext msg) {
+            LOG.info(name + ": From " + name(msg.getFrom()) + ": Archived");
+            super.archive(msg);
+        }
+
+        private String name(BitmessageAddress address) {
+            if (alice.equals(address.getAddress()))
+                return "Alice";
+            else if (bob.equals(address.getAddress()))
+                return "Bob";
+            else
+                return "Unknown (" + address.getAddress() + ")";
+        }
+    }
 }