diff --git a/chatterino.pro b/chatterino.pro
index 314090ddf..d24cde4ca 100644
--- a/chatterino.pro
+++ b/chatterino.pro
@@ -188,7 +188,6 @@ HEADERS  += \
     src/const.hpp \
     src/widgets/tooltipwidget.hpp \
     src/precompiled_headers.hpp \
-    src/messages/wordflags.hpp \
     src/singletons/thememanager.hpp \
     src/twitch/twitchaccountmanager.hpp \
     src/singletons/helper/completionmodel.hpp \
diff --git a/src/channel.cpp b/src/channel.cpp
index ee1ae9cfd..d1e94fe5b 100644
--- a/src/channel.cpp
+++ b/src/channel.cpp
@@ -56,15 +56,24 @@ void Channel::addMessage(std::shared_ptr<Message> message)
     this->messageAppended(message);
 }
 
-void Channel::addMessagesAtStart(std::vector<messages::SharedMessage> &messages)
+void Channel::addMessagesAtStart(std::vector<messages::SharedMessage> &_messages)
 {
-    std::vector<messages::SharedMessage> addedMessages = this->messages.pushFront(messages);
+    std::vector<messages::SharedMessage> addedMessages = this->messages.pushFront(_messages);
 
     if (addedMessages.size() != 0) {
         this->messagesAddedAtStart(addedMessages);
     }
 }
 
+void Channel::replaceMessage(messages::SharedMessage message, messages::SharedMessage replacement)
+{
+    int index = this->messages.replaceItem(message, replacement);
+
+    if (index >= 0) {
+        this->messageReplaced((size_t)index, replacement);
+    }
+}
+
 void Channel::addRecentChatter(const std::shared_ptr<messages::Message> &message)
 {
     assert(!message->loginName.isEmpty());
diff --git a/src/channel.hpp b/src/channel.hpp
index 0e3af4bd9..920987c08 100644
--- a/src/channel.hpp
+++ b/src/channel.hpp
@@ -27,12 +27,14 @@ public:
     boost::signals2::signal<void(messages::SharedMessage &)> messageRemovedFromStart;
     boost::signals2::signal<void(messages::SharedMessage &)> messageAppended;
     boost::signals2::signal<void(std::vector<messages::SharedMessage> &)> messagesAddedAtStart;
+    boost::signals2::signal<void(size_t index, messages::SharedMessage &)> messageReplaced;
 
     virtual bool isEmpty() const;
     messages::LimitedQueueSnapshot<messages::SharedMessage> getMessageSnapshot();
 
     void addMessage(messages::SharedMessage message);
     void addMessagesAtStart(std::vector<messages::SharedMessage> &messages);
+    void replaceMessage(messages::SharedMessage message, messages::SharedMessage replacement);
     void addRecentChatter(const std::shared_ptr<messages::Message> &message);
 
     struct NameOptions {
diff --git a/src/messages/limitedqueue.hpp b/src/messages/limitedqueue.hpp
index 8d19f7166..44e5b8c6c 100644
--- a/src/messages/limitedqueue.hpp
+++ b/src/messages/limitedqueue.hpp
@@ -132,6 +132,40 @@ public:
         return acceptedItems;
     }
 
+    // replaces a single item, return true if successful
+    int replaceItem(const T &item, const T &replacement)
+    {
+        std::lock_guard<std::mutex> lock(this->mutex);
+
+        int x = 0;
+
+        for (size_t i = 0; i < this->chunks->size(); i++) {
+            Chunk &chunk = this->chunks->at(i);
+
+            size_t start = i == 0 ? this->firstChunkOffset : 0;
+            size_t end = i == chunk->size() - 1 ? this->lastChunkEnd : chunk->size();
+
+            for (size_t j = start; j < end; j++) {
+                if (chunk->at(j) == item) {
+                    Chunk newChunk = std::make_shared<std::vector<T>>();
+                    newChunk->resize(chunk->size());
+
+                    for (size_t k = 0; k < chunk->size(); k++) {
+                        newChunk->at(k) = chunk->at(k);
+                    }
+
+                    newChunk->at(j) = replacement;
+                    this->chunks->at(i) = newChunk;
+
+                    return x;
+                }
+                x++;
+            }
+        }
+
+        return -1;
+    }
+
     //    void insertAfter(const std::vector<T> &items, const T &index)
 
     messages::LimitedQueueSnapshot<T> getSnapshot()
diff --git a/src/messages/message.cpp b/src/messages/message.cpp
index 281499843..26b01750e 100644
--- a/src/messages/message.cpp
+++ b/src/messages/message.cpp
@@ -55,6 +55,26 @@ std::vector<Word> &Message::getWords()
     return this->words;
 }
 
+Message::MessageFlags Message::getFlags() const
+{
+    return this->flags;
+}
+
+void Message::setFlags(MessageFlags _flags)
+{
+    this->flags = flags;
+}
+
+void Message::addFlags(MessageFlags _flags)
+{
+    this->flags = (MessageFlags)((MessageFlagsType)this->flags | (MessageFlagsType)_flags);
+}
+
+void Message::removeFlags(MessageFlags _flags)
+{
+    this->flags = (MessageFlags)((MessageFlagsType)this->flags & ~((MessageFlagsType)_flags));
+}
+
 bool Message::isDisabled() const
 {
     return this->disabled;
@@ -147,12 +167,13 @@ Message *Message::createSystemMessage(const QString &text)
                                            MessageColor(MessageColor::Type::System),
                                            singletons::FontManager::Medium, word, QString()));
     }
+    message->addFlags(Message::System);
 
     return message;
 }
 
 Message *Message::createTimeoutMessage(const QString &username, const QString &durationInSeconds,
-                                       const QString &reason)
+                                       const QString &reason, bool multipleTimes)
 {
     QString text;
 
@@ -181,7 +202,14 @@ Message *Message::createTimeoutMessage(const QString &username, const QString &d
     }
     text.append(".");
 
-    return Message::createSystemMessage(text);
+    if (multipleTimes) {
+        text.append(" (multiple times)");
+    }
+
+    Message *message = Message::createSystemMessage(text);
+    message->addFlags(Message::Timeout);
+    message->timeoutUser = username;
+    return message;
 }
 
 }  // namespace messages
diff --git a/src/messages/message.hpp b/src/messages/message.hpp
index c6f405228..ead25b538 100644
--- a/src/messages/message.hpp
+++ b/src/messages/message.hpp
@@ -14,10 +14,17 @@ namespace messages {
 class Message;
 
 typedef std::shared_ptr<Message> SharedMessage;
+typedef uint32_t MessageFlagsType;
 
 class Message
 {
 public:
+    enum MessageFlags : uint32_t {
+        None = 0,
+        System = (1 << 1),
+        Timeout = (1 << 2),
+    };
+
     bool containsHighlightedPhrase() const;
     void setHighlight(bool value);
     const QString &getTimeoutUser() const;
@@ -25,6 +32,10 @@ public:
     const QString &getContent() const;
     const std::chrono::time_point<std::chrono::system_clock> &getParseTime() const;
     std::vector<Word> &getWords();
+    MessageFlags getFlags() const;
+    void setFlags(MessageFlags flags);
+    void addFlags(MessageFlags flags);
+    void removeFlags(MessageFlags flags);
     bool isDisabled() const;
     void setDisabled(bool value);
     const QString &getId() const;
@@ -45,7 +56,7 @@ public:
     static Message *createSystemMessage(const QString &text);
 
     static Message *createTimeoutMessage(const QString &username, const QString &durationInSeconds,
-                                         const QString &reason);
+                                         const QString &reason, bool multipleTimes);
 
 private:
     static LazyLoadedImage *badgeStaff;
@@ -58,6 +69,8 @@ private:
 
     static QRegularExpression *cheerRegex;
 
+    MessageFlags flags = MessageFlags::None;
+
     // what is highlightTab?
     bool highlightTab = false;
 
diff --git a/src/messages/wordflags.hpp b/src/messages/wordflags.hpp
deleted file mode 100644
index 50e96676b..000000000
--- a/src/messages/wordflags.hpp
+++ /dev/null
@@ -1 +0,0 @@
-#pragma once
diff --git a/src/singletons/helper/ircmessagehandler.cpp b/src/singletons/helper/ircmessagehandler.cpp
index 69a6d98c9..60b7ebdda 100644
--- a/src/singletons/helper/ircmessagehandler.cpp
+++ b/src/singletons/helper/ircmessagehandler.cpp
@@ -71,8 +71,7 @@ void IrcMessageHandler::handleClearChatMessage(Communi::IrcMessage *message)
 
     // check if the chat has been cleared by a moderator
     if (message->parameters().length() == 1) {
-        std::shared_ptr<Message> msg(
-            Message::createSystemMessage("Chat has been cleared by a moderator."));
+        SharedMessage msg(Message::createSystemMessage("Chat has been cleared by a moderator."));
 
         c->addMessage(msg);
 
@@ -95,20 +94,35 @@ void IrcMessageHandler::handleClearChatMessage(Communi::IrcMessage *message)
     }
 
     // add the notice that the user has been timed out
-    SharedMessage msg(Message::createTimeoutMessage(username, durationInSeconds, reason));
+    LimitedQueueSnapshot<SharedMessage> snapshot = c->getMessageSnapshot();
+    bool addMessage = true;
 
-    c->addMessage(msg);
+    for (int i = std::max(0, (int)snapshot.getLength() - 20); i < snapshot.getLength(); i++) {
+        if (snapshot[i]->getFlags() & Message::Timeout && snapshot[i]->timeoutUser == username) {
+            SharedMessage replacement(
+                Message::createTimeoutMessage(username, durationInSeconds, reason, true));
+            c->replaceMessage(snapshot[i], replacement);
+            addMessage = false;
+            break;
+        }
+    }
+
+    if (addMessage) {
+        SharedMessage msg(
+            Message::createTimeoutMessage(username, durationInSeconds, reason, false));
+        c->addMessage(msg);
+    }
 
     // disable the messages from the user
-    LimitedQueueSnapshot<SharedMessage> snapshot = c->getMessageSnapshot();
     for (int i = 0; i < snapshot.getLength(); i++) {
-        if (snapshot[i]->getTimeoutUser() == username) {
+        if (!(snapshot[i]->getFlags() & Message::Timeout) &&
+            snapshot[i]->getTimeoutUser() == username) {
             snapshot[i]->setDisabled(true);
         }
     }
 
     // refresh all
-    WindowManager::getInstance().layoutVisibleChatWidgets(c.get());
+    WindowManager::getInstance().repaintVisibleChatWidgets(c.get());
 }
 
 void IrcMessageHandler::handleUserStateMessage(Communi::IrcMessage *message)
diff --git a/src/widgets/helper/channelview.cpp b/src/widgets/helper/channelview.cpp
index 16351f3bf..11a33484f 100644
--- a/src/widgets/helper/channelview.cpp
+++ b/src/widgets/helper/channelview.cpp
@@ -104,6 +104,8 @@ ChannelView::~ChannelView()
     this->messageRemovedConnection.disconnect();
     this->repaintGifsConnection.disconnect();
     this->layoutConnection.disconnect();
+    this->messageAddedAtStartConnection.disconnect();
+    this->messageReplacedConnection.disconnect();
 }
 
 void ChannelView::queueUpdate()
@@ -429,6 +431,15 @@ void ChannelView::setChannel(std::shared_ptr<Channel> newChannel)
             this->layoutMessages();
         });
 
+    // on message replaced
+    this->messageReplacedConnection =
+        newChannel->messageReplaced.connect([this](size_t index, SharedMessage replacement) {
+            SharedMessageRef newItem(new MessageRef(replacement));
+
+            this->messages.replaceItem(this->messages.getSnapshot()[index], newItem);
+            this->layoutMessages();
+        });
+
     auto snapshot = newChannel->getMessageSnapshot();
 
     for (size_t i = 0; i < snapshot.getLength(); i++) {
diff --git a/src/widgets/helper/channelview.hpp b/src/widgets/helper/channelview.hpp
index 37a7b2319..3ea1f0eb3 100644
--- a/src/widgets/helper/channelview.hpp
+++ b/src/widgets/helper/channelview.hpp
@@ -117,6 +117,7 @@ private:
     boost::signals2::connection messageAppendedConnection;
     boost::signals2::connection messageAddedAtStartConnection;
     boost::signals2::connection messageRemovedConnection;
+    boost::signals2::connection messageReplacedConnection;
     boost::signals2::connection repaintGifsConnection;
     boost::signals2::connection layoutConnection;