diff --git a/src/user.cpp b/src/user.cpp
index 361cc4877069c4731c23de478c968b5dc29143a8..86f908bd7ffb8ee462cdc29174a4965508b23f58 100644
--- a/src/user.cpp
+++ b/src/user.cpp
@@ -186,6 +186,9 @@ void User::setConnected(bool connected) {
 }
 
 void User::setCacheMessages(bool cacheMessages) {
+	if (m_component->inServerMode() && !m_cacheMessages && cacheMessages) {
+		m_conversationManager->sendCachedChatMessages();
+	}
 	m_cacheMessages = cacheMessages;
 }