diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3ed1ebea8..9dc821bc6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -15,6 +15,7 @@
 - Minor: Prevent user from entering incorrect characters in Live Notifications channels list. (#3715, #3730)
 - Minor: Fixed automod caught message notice appearing twice for mods. (#3717)
 - Minor: Added `/requests` command. Usage: `/requests [channel]`. Opens the channel points requests queue for the provided channel or the current channel if no input is provided. (#3746)
+- Minor: Added ability to execute commands on chat messages using the message context menu. (#3738)
 - Bugfix: Fixed live notifications for usernames containing uppercase characters. (#3646)
 - Bugfix: Fixed live notifications not getting updated for closed streams going offline. (#3678)
 - Bugfix: Fixed certain settings dialogs appearing behind the main window, when `Always on top` was used. (#3679)
diff --git a/src/controllers/commands/Command.cpp b/src/controllers/commands/Command.cpp
index 81abe9d0a..e7113db9c 100644
--- a/src/controllers/commands/Command.cpp
+++ b/src/controllers/commands/Command.cpp
@@ -15,11 +15,14 @@ Command::Command(const QString &_text)
 
     this->name = _text.mid(0, index).trimmed();
     this->func = _text.mid(index + 1).trimmed();
+    this->showInMsgContextMenu = false;
 }
 
-Command::Command(const QString &_name, const QString &_func)
+Command::Command(const QString &_name, const QString &_func,
+                 bool _showInMsgContextMenu)
     : name(_name.trimmed())
     , func(_func.trimmed())
+    , showInMsgContextMenu(_showInMsgContextMenu)
 {
 }
 
diff --git a/src/controllers/commands/Command.hpp b/src/controllers/commands/Command.hpp
index 9dd80a4bb..1b365a23f 100644
--- a/src/controllers/commands/Command.hpp
+++ b/src/controllers/commands/Command.hpp
@@ -10,10 +10,12 @@ namespace chatterino {
 struct Command {
     QString name;
     QString func;
+    bool showInMsgContextMenu;
 
     Command() = default;
     explicit Command(const QString &text);
-    Command(const QString &name, const QString &func);
+    Command(const QString &name, const QString &func,
+            bool showInMsgContextMenu = false);
 
     QString toString() const;
 };
@@ -31,6 +33,8 @@ struct Serialize<chatterino::Command> {
 
         chatterino::rj::set(ret, "name", value.name, a);
         chatterino::rj::set(ret, "func", value.func, a);
+        chatterino::rj::set(ret, "showInMsgContextMenu",
+                            value.showInMsgContextMenu, a);
 
         return ret;
     }
@@ -59,6 +63,15 @@ struct Deserialize<chatterino::Command> {
             PAJLADA_REPORT_ERROR(error);
             return command;
         }
+        if (!chatterino::rj::getSafe(value, "showInMsgContextMenu",
+                                     command.showInMsgContextMenu))
+        {
+            command.showInMsgContextMenu = false;
+
+            PAJLADA_REPORT_ERROR(error);
+
+            return command;
+        }
 
         return command;
     }
diff --git a/src/controllers/commands/CommandModel.cpp b/src/controllers/commands/CommandModel.cpp
index d12a81c69..a3117d3ab 100644
--- a/src/controllers/commands/CommandModel.cpp
+++ b/src/controllers/commands/CommandModel.cpp
@@ -6,7 +6,7 @@ namespace chatterino {
 
 // commandmodel
 CommandModel::CommandModel(QObject *parent)
-    : SignalVectorModel<Command>(2, parent)
+    : SignalVectorModel<Command>(Column::COUNT, parent)
 {
 }
 
@@ -14,16 +14,21 @@ CommandModel::CommandModel(QObject *parent)
 Command CommandModel::getItemFromRow(std::vector<QStandardItem *> &row,
                                      const Command &original)
 {
-    return Command(row[0]->data(Qt::EditRole).toString(),
-                   row[1]->data(Qt::EditRole).toString());
+    return Command(row[Column::Trigger]->data(Qt::EditRole).toString(),
+                   row[Column::CommandFunc]->data(Qt::EditRole).toString(),
+                   row[Column::ShowInMessageContextMenu]
+                       ->data(Qt::CheckStateRole)
+                       .toBool());
 }
 
 // turns a row in the model into a vector item
 void CommandModel::getRowFromItem(const Command &item,
                                   std::vector<QStandardItem *> &row)
 {
-    setStringItem(row[0], item.name);
-    setStringItem(row[1], item.func);
+    setStringItem(row[Column::Trigger], item.name);
+    setStringItem(row[Column::CommandFunc], item.func);
+    setBoolItem(row[Column::ShowInMessageContextMenu],
+                item.showInMsgContextMenu);
 }
 
 }  // namespace chatterino
diff --git a/src/controllers/commands/CommandModel.hpp b/src/controllers/commands/CommandModel.hpp
index f5c4e735a..701a65f3e 100644
--- a/src/controllers/commands/CommandModel.hpp
+++ b/src/controllers/commands/CommandModel.hpp
@@ -13,6 +13,13 @@ class CommandModel : public SignalVectorModel<Command>
 {
     explicit CommandModel(QObject *parent);
 
+    enum Column {
+        Trigger = 0,
+        CommandFunc = 1,
+        ShowInMessageContextMenu = 2,
+        COUNT,
+    };
+
 protected:
     // turn a vector item into a model row
     virtual Command getItemFromRow(std::vector<QStandardItem *> &row,
diff --git a/src/widgets/helper/ChannelView.cpp b/src/widgets/helper/ChannelView.cpp
index c938ceee2..c2fb1d2cc 100644
--- a/src/widgets/helper/ChannelView.cpp
+++ b/src/widgets/helper/ChannelView.cpp
@@ -1885,6 +1885,10 @@ void ChannelView::addContextMenuItems(
     // Add hidden options (e.g. copy message ID) if the user held down Shift
     this->addHiddenContextMenuItems(hoveredElement, layout, event, *menu);
 
+    // Add executable command options
+    this->addCommandExecutionContextMenuItems(hoveredElement, layout, event,
+                                              *menu);
+
     menu->popup(QCursor::pos());
     menu->raise();
 }
@@ -2081,6 +2085,62 @@ void ChannelView::addHiddenContextMenuItems(
                        });
     }
 }
+
+void ChannelView::addCommandExecutionContextMenuItems(
+    const MessageLayoutElement * /*hoveredElement*/, MessageLayoutPtr layout,
+    QMouseEvent * /*event*/, QMenu &menu)
+{
+    /* Get commands to be displayed in context menu; 
+     * only those that had the showInMsgContextMenu check box marked in the Commands page */
+    std::vector<Command> cmds;
+    for (auto &cmd : getApp()->commands->items)
+    {
+        if (cmd.showInMsgContextMenu)
+        {
+            cmds.push_back(cmd);
+        }
+    }
+
+    if (cmds.empty())
+    {
+        return;
+    }
+
+    menu.addSeparator();
+    auto executeAction = menu.addAction("Execute command");
+    auto cmdMenu = new QMenu;
+    executeAction->setMenu(cmdMenu);
+
+    for (auto &cmd : cmds)
+    {
+        QString inputText = this->selection_.isEmpty()
+                                ? layout->getMessage()->messageText
+                                : this->getSelectedText();
+
+        inputText.push_front(cmd.name + " ");
+
+        cmdMenu->addAction(cmd.name, [this, inputText] {
+            ChannelPtr channel;
+
+            /* Search popups and user message history's underlyingChannels aren't of type TwitchChannel, but
+             * we would still like to execute commands from them. Use their source channel instead if applicable. */
+            if (this->hasSourceChannel())
+            {
+                channel = this->sourceChannel();
+            }
+            else
+            {
+                channel = this->underlyingChannel_;
+            }
+
+            QString value =
+                getApp()->commands->execCommand(inputText, channel, false);
+
+            channel->sendMessage(value);
+        });
+    }
+}
+
 void ChannelView::mouseDoubleClickEvent(QMouseEvent *event)
 {
     if (event->button() != Qt::LeftButton)
diff --git a/src/widgets/helper/ChannelView.hpp b/src/widgets/helper/ChannelView.hpp
index 05f2becb0..994f1e762 100644
--- a/src/widgets/helper/ChannelView.hpp
+++ b/src/widgets/helper/ChannelView.hpp
@@ -184,6 +184,10 @@ private:
     void addHiddenContextMenuItems(const MessageLayoutElement *hoveredElement,
                                    MessageLayoutPtr layout, QMouseEvent *event,
                                    QMenu &menu);
+    void addCommandExecutionContextMenuItems(
+        const MessageLayoutElement *hoveredElement, MessageLayoutPtr layout,
+        QMouseEvent *event, QMenu &menu);
+
     int getLayoutWidth() const;
     void updatePauses();
     void unpaused();
diff --git a/src/widgets/settingspages/CommandPage.cpp b/src/widgets/settingspages/CommandPage.cpp
index ea43105e1..a202f46ae 100644
--- a/src/widgets/settingspages/CommandPage.cpp
+++ b/src/widgets/settingspages/CommandPage.cpp
@@ -44,8 +44,9 @@ CommandPage::CommandPage()
         layout.emplace<EditableModelView>(app->commands->createModel(nullptr))
             .getElement();
 
-    view->setTitles({"Trigger", "Command"});
-    view->getTableView()->horizontalHeader()->setStretchLastSection(true);
+    view->setTitles({"Trigger", "Command", "Show In\nMessage Menu"});
+    view->getTableView()->horizontalHeader()->setSectionResizeMode(
+        1, QHeaderView::Stretch);
     view->addButtonPressed.connect([] {
         getApp()->commands->items.append(
             Command{"/command", "I made a new command HeyGuys"});