diff --git a/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/MailboxManager.java b/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/MailboxManager.java
index d2c88aebb..89730f715 100644
--- a/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/MailboxManager.java
+++ b/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/MailboxManager.java
@@ -3,6 +3,7 @@ package org.briarproject.bramble.api.mailbox;
 import org.briarproject.bramble.api.db.DbException;
 import org.briarproject.bramble.api.db.Transaction;
 import org.briarproject.bramble.api.lifecycle.IoExecutor;
+import org.briarproject.bramble.api.mailbox.event.OwnMailboxConnectionStatusEvent;
 
 import javax.annotation.Nullable;
 
diff --git a/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/MailboxProblemEvent.java b/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/MailboxProblemEvent.java
new file mode 100644
index 000000000..4c00cac98
--- /dev/null
+++ b/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/MailboxProblemEvent.java
@@ -0,0 +1,19 @@
+package org.briarproject.bramble.api.mailbox.event;
+
+import org.briarproject.bramble.api.event.Event;
+import org.briarproject.bramble.api.mailbox.MailboxSettingsManager;
+import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
+
+import javax.annotation.concurrent.Immutable;
+
+/**
+ * An event that is broadcast by {@link MailboxSettingsManager} when
+ * recording a connection failure for own Mailbox
+ * that has persistent for long enough for the mailbox owner to become active
+ * and fix the problem with the mailbox.
+ */
+@Immutable
+@NotNullByDefault
+public class MailboxProblemEvent extends Event {
+
+}
diff --git a/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/OwnMailboxConnectionStatusEvent.java b/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/OwnMailboxConnectionStatusEvent.java
similarity index 76%
rename from bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/OwnMailboxConnectionStatusEvent.java
rename to bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/OwnMailboxConnectionStatusEvent.java
index b137052ea..4a4b6b93e 100644
--- a/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/OwnMailboxConnectionStatusEvent.java
+++ b/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/OwnMailboxConnectionStatusEvent.java
@@ -1,6 +1,8 @@
-package org.briarproject.bramble.api.mailbox;
+package org.briarproject.bramble.api.mailbox.event;
 
 import org.briarproject.bramble.api.event.Event;
+import org.briarproject.bramble.api.mailbox.MailboxSettingsManager;
+import org.briarproject.bramble.api.mailbox.MailboxStatus;
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 
 import javax.annotation.concurrent.Immutable;
diff --git a/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/RemoteMailboxUpdateEvent.java b/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/RemoteMailboxUpdateEvent.java
similarity index 87%
rename from bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/RemoteMailboxUpdateEvent.java
rename to bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/RemoteMailboxUpdateEvent.java
index f213eb27b..aeee7da39 100644
--- a/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/RemoteMailboxUpdateEvent.java
+++ b/bramble-api/src/main/java/org/briarproject/bramble/api/mailbox/event/RemoteMailboxUpdateEvent.java
@@ -1,7 +1,8 @@
-package org.briarproject.bramble.api.mailbox;
+package org.briarproject.bramble.api.mailbox.event;
 
 import org.briarproject.bramble.api.contact.ContactId;
 import org.briarproject.bramble.api.event.Event;
+import org.briarproject.bramble.api.mailbox.MailboxUpdate;
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 
 import javax.annotation.concurrent.Immutable;
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/mailbox/MailboxSettingsManagerImpl.java b/bramble-core/src/main/java/org/briarproject/bramble/mailbox/MailboxSettingsManagerImpl.java
index eee2a49c2..fa4232a57 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/mailbox/MailboxSettingsManagerImpl.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/mailbox/MailboxSettingsManagerImpl.java
@@ -9,7 +9,8 @@ import org.briarproject.bramble.api.mailbox.MailboxProperties;
 import org.briarproject.bramble.api.mailbox.MailboxSettingsManager;
 import org.briarproject.bramble.api.mailbox.MailboxStatus;
 import org.briarproject.bramble.api.mailbox.MailboxVersion;
-import org.briarproject.bramble.api.mailbox.OwnMailboxConnectionStatusEvent;
+import org.briarproject.bramble.api.mailbox.event.MailboxProblemEvent;
+import org.briarproject.bramble.api.mailbox.event.OwnMailboxConnectionStatusEvent;
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 import org.briarproject.bramble.api.settings.Settings;
 import org.briarproject.bramble.api.settings.SettingsManager;
@@ -22,6 +23,7 @@ import javax.annotation.Nullable;
 import javax.annotation.concurrent.Immutable;
 import javax.inject.Inject;
 
+import static java.util.concurrent.TimeUnit.DAYS;
 import static org.briarproject.bramble.util.StringUtils.isNullOrEmpty;
 
 @Immutable
@@ -141,6 +143,9 @@ class MailboxSettingsManagerImpl implements MailboxSettingsManager {
 		settingsManager.mergeSettings(txn, newSettings, SETTINGS_NAMESPACE);
 		MailboxStatus status = new MailboxStatus(now, lastSuccess, newAttempts);
 		txn.attach(new OwnMailboxConnectionStatusEvent(status));
+		if (now - lastSuccess > DAYS.toMillis(3) && newAttempts > 10) {
+			txn.attach(new MailboxProblemEvent());
+		}
 	}
 
 	@Override
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/mailbox/MailboxUpdateManagerImpl.java b/bramble-core/src/main/java/org/briarproject/bramble/mailbox/MailboxUpdateManagerImpl.java
index 5262e4ebd..174b979e3 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/mailbox/MailboxUpdateManagerImpl.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/mailbox/MailboxUpdateManagerImpl.java
@@ -25,7 +25,7 @@ import org.briarproject.bramble.api.mailbox.MailboxUpdate;
 import org.briarproject.bramble.api.mailbox.MailboxUpdateManager;
 import org.briarproject.bramble.api.mailbox.MailboxUpdateWithMailbox;
 import org.briarproject.bramble.api.mailbox.MailboxVersion;
-import org.briarproject.bramble.api.mailbox.RemoteMailboxUpdateEvent;
+import org.briarproject.bramble.api.mailbox.event.RemoteMailboxUpdateEvent;
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 import org.briarproject.bramble.api.sync.Group;
 import org.briarproject.bramble.api.sync.Group.Visibility;
diff --git a/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxPairingTaskImplTest.java b/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxPairingTaskImplTest.java
index 10c1a74fa..9d43995c2 100644
--- a/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxPairingTaskImplTest.java
+++ b/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxPairingTaskImplTest.java
@@ -13,7 +13,7 @@ import org.briarproject.bramble.api.mailbox.MailboxSettingsManager;
 import org.briarproject.bramble.api.mailbox.MailboxUpdate;
 import org.briarproject.bramble.api.mailbox.MailboxUpdateManager;
 import org.briarproject.bramble.api.mailbox.MailboxVersion;
-import org.briarproject.bramble.api.mailbox.OwnMailboxConnectionStatusEvent;
+import org.briarproject.bramble.api.mailbox.event.OwnMailboxConnectionStatusEvent;
 import org.briarproject.bramble.api.system.Clock;
 import org.briarproject.bramble.test.BrambleMockTestCase;
 import org.briarproject.bramble.test.DbExpectations;
diff --git a/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxSettingsManagerImplTest.java b/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxSettingsManagerImplTest.java
index 963093fb5..fe8d34cce 100644
--- a/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxSettingsManagerImplTest.java
+++ b/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxSettingsManagerImplTest.java
@@ -7,7 +7,7 @@ import org.briarproject.bramble.api.mailbox.MailboxProperties;
 import org.briarproject.bramble.api.mailbox.MailboxSettingsManager;
 import org.briarproject.bramble.api.mailbox.MailboxStatus;
 import org.briarproject.bramble.api.mailbox.MailboxVersion;
-import org.briarproject.bramble.api.mailbox.OwnMailboxConnectionStatusEvent;
+import org.briarproject.bramble.api.mailbox.event.OwnMailboxConnectionStatusEvent;
 import org.briarproject.bramble.api.settings.Settings;
 import org.briarproject.bramble.api.settings.SettingsManager;
 import org.briarproject.bramble.test.BrambleMockTestCase;
diff --git a/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxUpdateManagerImplTest.java b/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxUpdateManagerImplTest.java
index e1bdcf934..36b49b00a 100644
--- a/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxUpdateManagerImplTest.java
+++ b/bramble-core/src/test/java/org/briarproject/bramble/mailbox/MailboxUpdateManagerImplTest.java
@@ -18,7 +18,7 @@ import org.briarproject.bramble.api.mailbox.MailboxSettingsManager;
 import org.briarproject.bramble.api.mailbox.MailboxUpdate;
 import org.briarproject.bramble.api.mailbox.MailboxUpdateWithMailbox;
 import org.briarproject.bramble.api.mailbox.MailboxVersion;
-import org.briarproject.bramble.api.mailbox.RemoteMailboxUpdateEvent;
+import org.briarproject.bramble.api.mailbox.event.RemoteMailboxUpdateEvent;
 import org.briarproject.bramble.api.sync.Group;
 import org.briarproject.bramble.api.sync.GroupId;
 import org.briarproject.bramble.api.sync.Message;