diff --git a/bramble-api/src/main/java/org/briarproject/bramble/api/db/DatabaseComponent.java b/bramble-api/src/main/java/org/briarproject/bramble/api/db/DatabaseComponent.java
index cf6bfb61a..b5cf1d617 100644
--- a/bramble-api/src/main/java/org/briarproject/bramble/api/db/DatabaseComponent.java
+++ b/bramble-api/src/main/java/org/briarproject/bramble/api/db/DatabaseComponent.java
@@ -342,7 +342,7 @@ public interface DatabaseComponent extends TransactionManager {
 	 * <p/>
 	 * Read-only.
 	 */
-	Map<MessageId, GroupId> getMessagesToDelete(Transaction txn)
+	Map<GroupId, Collection<MessageId>> getMessagesToDelete(Transaction txn)
 			throws DbException;
 
 	/**
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/cleanup/CleanupManagerImpl.java b/bramble-core/src/main/java/org/briarproject/bramble/cleanup/CleanupManagerImpl.java
index 5cc70dbad..b87c53f4c 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/cleanup/CleanupManagerImpl.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/cleanup/CleanupManagerImpl.java
@@ -20,9 +20,7 @@ import org.briarproject.bramble.api.system.Clock;
 import org.briarproject.bramble.api.system.TaskScheduler;
 import org.briarproject.bramble.api.versioning.ClientMajorVersion;
 
-import java.util.ArrayList;
 import java.util.Collection;
-import java.util.HashMap;
 import java.util.HashSet;
 import java.util.Map;
 import java.util.Map.Entry;
@@ -132,39 +130,25 @@ class CleanupManagerImpl implements CleanupManager, Service, EventListener {
 	}
 
 	private void deleteMessages(Transaction txn) throws DbException {
-		Map<GroupId, ClientMajorVersion> clientCache = new HashMap<>();
-		Map<GroupId, Collection<MessageId>> deleted = new HashMap<>();
-		Map<MessageId, GroupId> ids = db.getMessagesToDelete(txn);
-		if (LOG.isLoggable(INFO)) LOG.info(ids.size() + " messages to delete");
-		for (Entry<MessageId, GroupId> e : ids.entrySet()) {
-			MessageId m = e.getKey();
-			GroupId g = e.getValue();
-			ClientMajorVersion cv = clientCache.get(g);
-			if (cv == null) {
-				Group group = db.getGroup(txn, g);
-				cv = new ClientMajorVersion(group.getClientId(),
-						group.getMajorVersion());
-				clientCache.put(g, cv);
+		Map<GroupId, Collection<MessageId>> ids = db.getMessagesToDelete(txn);
+		for (Entry<GroupId, Collection<MessageId>> e : ids.entrySet()) {
+			GroupId groupId = e.getKey();
+			Collection<MessageId> messageIds = e.getValue();
+			if (LOG.isLoggable(INFO)) {
+				LOG.info(messageIds.size() + " messages to delete");
 			}
+			Group group = db.getGroup(txn, groupId);
+			ClientMajorVersion cv = new ClientMajorVersion(group.getClientId(),
+					group.getMajorVersion());
 			CleanupHook hook = hooks.get(cv);
 			if (hook == null) {
 				throw new IllegalStateException("No cleanup hook for " + cv);
 			}
-			if (hook.deleteMessage(txn, g, m)) {
-				Collection<MessageId> messageIds = deleted.get(g);
-				if (messageIds == null) {
-					messageIds = new ArrayList<>();
-					deleted.put(g, messageIds);
-				}
-				messageIds.add(m);
-			} else {
-				LOG.info("Message was not deleted");
-				// Stop the timer so we don't keep trying to delete this message
+			for (MessageId m : messageIds) {
+				hook.deleteMessage(txn, groupId, m);
 				db.stopCleanupTimer(txn, m);
 			}
-		}
-		for (Entry<GroupId, Collection<MessageId>> e : deleted.entrySet()) {
-			txn.attach(new MessagesCleanedUpEvent(e.getKey(), e.getValue()));
+			txn.attach(new MessagesCleanedUpEvent(groupId, messageIds));
 		}
 	}
 
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/db/Database.java b/bramble-core/src/main/java/org/briarproject/bramble/db/Database.java
index 657cbf33f..6cc9ba8a5 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/db/Database.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/db/Database.java
@@ -503,7 +503,8 @@ interface Database<T> {
 	 * <p/>
 	 * Read-only.
 	 */
-	Map<MessageId, GroupId> getMessagesToDelete(T txn) throws DbException;
+	Map<GroupId, Collection<MessageId>> getMessagesToDelete(T txn)
+			throws DbException;
 
 	/**
 	 * Returns the next time (in milliseconds since the Unix epoch) when a
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/db/DatabaseComponentImpl.java b/bramble-core/src/main/java/org/briarproject/bramble/db/DatabaseComponentImpl.java
index f3eae963c..9b7ac74fa 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/db/DatabaseComponentImpl.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/db/DatabaseComponentImpl.java
@@ -608,8 +608,8 @@ class DatabaseComponentImpl<T> implements DatabaseComponent {
 	}
 
 	@Override
-	public Map<MessageId, GroupId> getMessagesToDelete(Transaction transaction)
-			throws DbException {
+	public Map<GroupId, Collection<MessageId>> getMessagesToDelete(
+			Transaction transaction) throws DbException {
 		T txn = unbox(transaction);
 		return db.getMessagesToDelete(txn);
 	}
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/db/JdbcDatabase.java b/bramble-core/src/main/java/org/briarproject/bramble/db/JdbcDatabase.java
index 187024f24..54d7a28ef 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/db/JdbcDatabase.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/db/JdbcDatabase.java
@@ -2241,8 +2241,8 @@ abstract class JdbcDatabase implements Database<Connection> {
 	}
 
 	@Override
-	public Map<MessageId, GroupId> getMessagesToDelete(Connection txn)
-			throws DbException {
+	public Map<GroupId, Collection<MessageId>> getMessagesToDelete(
+			Connection txn) throws DbException {
 		long now = clock.currentTimeMillis();
 		PreparedStatement ps = null;
 		ResultSet rs = null;
@@ -2252,10 +2252,16 @@ abstract class JdbcDatabase implements Database<Connection> {
 			ps = txn.prepareStatement(sql);
 			ps.setLong(1, now);
 			rs = ps.executeQuery();
-			Map<MessageId, GroupId> ids = new HashMap<>();
+			Map<GroupId, Collection<MessageId>> ids = new HashMap<>();
 			while (rs.next()) {
-				ids.put(new MessageId(rs.getBytes(1)),
-						new GroupId(rs.getBytes(2)));
+				MessageId m = new MessageId(rs.getBytes(1));
+				GroupId g = new GroupId(rs.getBytes(2));
+				Collection<MessageId> messageIds = ids.get(g);
+				if (messageIds == null) {
+					messageIds = new ArrayList<>();
+					ids.put(g, messageIds);
+				}
+				messageIds.add(m);
 			}
 			rs.close();
 			ps.close();
diff --git a/bramble-core/src/test/java/org/briarproject/bramble/db/JdbcDatabaseTest.java b/bramble-core/src/test/java/org/briarproject/bramble/db/JdbcDatabaseTest.java
index 3fdd13735..e9d35e315 100644
--- a/bramble-core/src/test/java/org/briarproject/bramble/db/JdbcDatabaseTest.java
+++ b/bramble-core/src/test/java/org/briarproject/bramble/db/JdbcDatabaseTest.java
@@ -2409,14 +2409,14 @@ public abstract class JdbcDatabaseTest extends BrambleTestCase {
 		// When the timer expires, the message should be due and scheduled for
 		// deletion
 		time.set(now + duration);
-		assertEquals(singletonMap(messageId, groupId),
+		assertEquals(singletonMap(groupId, singletonList(messageId)),
 				db.getMessagesToDelete(txn));
 		assertEquals(now + duration, db.getNextCleanupDeadline(txn));
 
 		// 1 ms after the timer expires, the message should be due and
 		// scheduled for deletion
 		time.set(now + duration + 1);
-		assertEquals(singletonMap(messageId, groupId),
+		assertEquals(singletonMap(groupId, singletonList(messageId)),
 				db.getMessagesToDelete(txn));
 		assertEquals(now + duration, db.getNextCleanupDeadline(txn));