diff --git a/src/cascadia/LocalTests_SettingsModel/SerializationTests.cpp b/src/cascadia/LocalTests_SettingsModel/SerializationTests.cpp
index 97251b8b2..164ac0bb8 100644
--- a/src/cascadia/LocalTests_SettingsModel/SerializationTests.cpp
+++ b/src/cascadia/LocalTests_SettingsModel/SerializationTests.cpp
@@ -229,10 +229,12 @@ namespace SettingsModelLocalTests
 
     void SerializationTests::Actions()
     {
+        // simple command
         const std::string actionsString1{ R"([
                                                 { "command": "paste" }
                                             ])" };
 
+        // complex command
         const std::string actionsString2A{ R"([
                                                 { "command": { "action": "setTabColor" } }
                                             ])" };
@@ -244,29 +246,35 @@ namespace SettingsModelLocalTests
                                                 { "command": { "action": "copy", "singleLine": true, "copyFormatting": "html" } }
                                             ])" };
 
+        // simple command with key chords
         const std::string actionsString3{ R"([
                                                 { "command": "toggleAlwaysOnTop", "keys": "ctrl+a" },
                                                 { "command": "toggleAlwaysOnTop", "keys": "ctrl+b" }
                                             ])" };
 
+        // complex command with key chords
         const std::string actionsString4{ R"([
                                                 { "command": { "action": "adjustFontSize", "delta": 1 }, "keys": "ctrl+c" },
                                                 { "command": { "action": "adjustFontSize", "delta": 1 }, "keys": "ctrl+d" }
                                             ])" };
 
+        // command with name and icon and multiple key chords
         const std::string actionsString5{ R"([
                                                 { "icon": "image.png", "name": "Scroll To Top Name", "command": "scrollToTop", "keys": "ctrl+e" },
                                                 { "command": "scrollToTop", "keys": "ctrl+f" }
                                             ])" };
 
+        // complex command with new terminal args
         const std::string actionsString6{ R"([
                                                 { "command": { "action": "newTab", "index": 0 }, "keys": "ctrl+g" },
                                             ])" };
 
+        // complex command with meaningful null arg
         const std::string actionsString7{ R"([
                                                 { "command": { "action": "renameWindow", "name": null }, "keys": "ctrl+h" }
                                             ])" };
 
+        // nested command
         const std::string actionsString8{ R"([
                                                 {
                                                     "name": "Change font size...",
@@ -278,6 +286,7 @@ namespace SettingsModelLocalTests
                                                 }
                                             ])" };
 
+        // iterable command
         const std::string actionsString9A{ R"([
                                                 {
                                                     "name": "New tab",
@@ -330,7 +339,20 @@ namespace SettingsModelLocalTests
                                                     "name": "Send Input (Evil) ..."
                                                 }
                                             ])"" };
+        const std::string actionsString9D{ R""([
+                                                {
+                                                    "command": 
+                                                    {
+                                                        "action": "newTab",
+                                                        "profile": "${profile.name}"
+                                                    },
+                                                    "icon": "${profile.icon}",
+                                                    "iterateOn": "profiles",
+                                                    "name": "${profile.name}: New tab"
+                                                }
+                                            ])"" };
 
+        // unbound command
         const std::string actionsString10{ R"([
                                                 { "command": "unbound", "keys": "ctrl+c" }
                                             ])" };
@@ -365,6 +387,7 @@ namespace SettingsModelLocalTests
         RoundtripTest<implementation::ActionMap>(actionsString9A);
         RoundtripTest<implementation::ActionMap>(actionsString9B);
         RoundtripTest<implementation::ActionMap>(actionsString9C);
+        RoundtripTest<implementation::ActionMap>(actionsString9D);
 
         Log::Comment(L"unbound command");
         RoundtripTest<implementation::ActionMap>(actionsString10);
diff --git a/src/cascadia/TerminalSettingsModel/ActionMap.cpp b/src/cascadia/TerminalSettingsModel/ActionMap.cpp
index 433535dc5..a9ab094e7 100644
--- a/src/cascadia/TerminalSettingsModel/ActionMap.cpp
+++ b/src/cascadia/TerminalSettingsModel/ActionMap.cpp
@@ -29,7 +29,8 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
     }
 
     ActionMap::ActionMap() :
-        _NestedCommands{ single_threaded_map<hstring, Model::Command>() }
+        _NestedCommands{ single_threaded_map<hstring, Model::Command>() },
+        _IterableCommands{ single_threaded_vector<Model::Command>() }
     {
     }
 
@@ -87,7 +88,7 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
         {
             // populate _NameMapCache
             std::unordered_map<hstring, Model::Command> nameMap{};
-            _PopulateNameMapWithNestedCommands(nameMap);
+            _PopulateNameMapWithSpecialCommands(nameMap);
             _PopulateNameMapWithStandardCommands(nameMap);
 
             _NameMapCache = single_threaded_map<hstring, Model::Command>(std::move(nameMap));
@@ -96,18 +97,19 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
     }
 
     // Method Description:
-    // - Populates the provided nameMap with all of our nested commands and our parents nested commands
-    // - Performs a top-down approach by going to the root first, then recursively adding the nested commands layer-by-layer
+    // - Populates the provided nameMap with all of our special commands and our parent's special commands.
+    // - Special commands include nested and iterable commands.
+    // - Performs a top-down approach by going to the root first, then recursively adding the nested commands layer-by-layer.
     // Arguments:
     // - nameMap: the nameMap we're populating. This maps the name (hstring) of a command to the command itself.
-    void ActionMap::_PopulateNameMapWithNestedCommands(std::unordered_map<hstring, Model::Command>& nameMap) const
+    void ActionMap::_PopulateNameMapWithSpecialCommands(std::unordered_map<hstring, Model::Command>& nameMap) const
     {
         // Update NameMap with our parents.
         // Starting with this means we're doing a top-down approach.
         FAIL_FAST_IF(_parents.size() > 1);
         for (const auto& parent : _parents)
         {
-            parent->_PopulateNameMapWithNestedCommands(nameMap);
+            parent->_PopulateNameMapWithSpecialCommands(nameMap);
         }
 
         // Add NestedCommands to NameMap _after_ we handle our parents.
@@ -125,6 +127,12 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
                 nameMap.erase(name);
             }
         }
+
+        // Add IterableCommands to NameMap
+        for (const auto& cmd : _IterableCommands)
+        {
+            nameMap.insert_or_assign(cmd.Name(), cmd);
+        }
     }
 
     // Method Description:
@@ -296,6 +304,12 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
             actionMap->_NestedCommands.Insert(name, *(get_self<Command>(cmd)->Copy()));
         }
 
+        // copy _IterableCommands
+        for (const auto& cmd : _IterableCommands)
+        {
+            actionMap->_IterableCommands.Append(*(get_self<Command>(cmd)->Copy()));
+        }
+
         // repeat this for each of our parents
         FAIL_FAST_IF(_parents.size() > 1);
         for (const auto& parent : _parents)
@@ -336,6 +350,13 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
             return;
         }
 
+        // Handle iterable commands
+        if (cmdImpl->IterateOn() != ExpandCommandType::None)
+        {
+            _IterableCommands.Append(cmd);
+            return;
+        }
+
         // General Case:
         //  Add the new command to the KeyMap.
         //  This map directs you to an entry in the ActionMap.
diff --git a/src/cascadia/TerminalSettingsModel/ActionMap.h b/src/cascadia/TerminalSettingsModel/ActionMap.h
index e33638cff..3435d120c 100644
--- a/src/cascadia/TerminalSettingsModel/ActionMap.h
+++ b/src/cascadia/TerminalSettingsModel/ActionMap.h
@@ -81,7 +81,7 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
         std::optional<Model::Command> _GetActionByID(const InternalActionID actionID) const;
         std::optional<Model::Command> _GetActionByKeyChordInternal(Control::KeyChord const& keys) const;
 
-        void _PopulateNameMapWithNestedCommands(std::unordered_map<hstring, Model::Command>& nameMap) const;
+        void _PopulateNameMapWithSpecialCommands(std::unordered_map<hstring, Model::Command>& nameMap) const;
         void _PopulateNameMapWithStandardCommands(std::unordered_map<hstring, Model::Command>& nameMap) const;
         void _PopulateKeyBindingMapWithStandardCommands(std::unordered_map<Control::KeyChord, Model::Command, KeyChordHash, KeyChordEquality>& keyBindingsMap, std::unordered_set<Control::KeyChord, KeyChordHash, KeyChordEquality>& unboundKeys) const;
         std::vector<Model::Command> _GetCumulativeActions() const noexcept;
@@ -94,6 +94,7 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
         Windows::Foundation::Collections::IMap<Control::KeyChord, Model::Command> _GlobalHotkeysCache{ nullptr };
         Windows::Foundation::Collections::IMap<Control::KeyChord, Model::Command> _KeyBindingMapCache{ nullptr };
         Windows::Foundation::Collections::IMap<hstring, Model::Command> _NestedCommands{ nullptr };
+        Windows::Foundation::Collections::IVector<Model::Command> _IterableCommands{ nullptr };
         std::unordered_map<Control::KeyChord, InternalActionID, KeyChordHash, KeyChordEquality> _KeyMap;
         std::unordered_map<InternalActionID, Model::Command> _ActionMap;
 
diff --git a/src/cascadia/TerminalSettingsModel/ActionMapSerialization.cpp b/src/cascadia/TerminalSettingsModel/ActionMapSerialization.cpp
index 1358c7865..5956bf757 100644
--- a/src/cascadia/TerminalSettingsModel/ActionMapSerialization.cpp
+++ b/src/cascadia/TerminalSettingsModel/ActionMapSerialization.cpp
@@ -60,34 +60,40 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
     {
         Json::Value actionList{ Json::ValueType::arrayValue };
 
-        // Serialize all standard Command objects in the current layer
-        for (const auto& [_, cmd] : _ActionMap)
-        {
-            // Command serializes to an array of JSON objects.
-            // This is because a Command may have multiple key chords associated with it.
-            // The name and icon are only serialized in the first object.
-            // Example:
-            // { "name": "Custom Copy", "command": "copy", "keys": "ctrl+c" }
-            // {                        "command": "copy", "keys": "ctrl+shift+c" }
-            // {                        "command": "copy", "keys": "ctrl+ins" }
+        // Command serializes to an array of JSON objects.
+        // This is because a Command may have multiple key chords associated with it.
+        // The name and icon are only serialized in the first object.
+        // Example:
+        // { "name": "Custom Copy", "command": "copy", "keys": "ctrl+c" }
+        // {                        "command": "copy", "keys": "ctrl+shift+c" }
+        // {                        "command": "copy", "keys": "ctrl+ins" }
+        auto toJson = [&actionList](const Model::Command& cmd) {
             const auto cmdImpl{ winrt::get_self<implementation::Command>(cmd) };
             const auto& cmdJsonArray{ cmdImpl->ToJson() };
             for (const auto& cmdJson : cmdJsonArray)
             {
                 actionList.append(cmdJson);
             }
+        };
+
+        // Serialize all standard Command objects in the current layer
+        for (const auto& [_, cmd] : _ActionMap)
+        {
+            toJson(cmd);
         }
 
         // Serialize all nested Command objects added in the current layer
         for (const auto& [_, cmd] : _NestedCommands)
         {
-            const auto cmdImpl{ winrt::get_self<implementation::Command>(cmd) };
-            const auto& cmdJsonArray{ cmdImpl->ToJson() };
-            for (const auto& cmdJson : cmdJsonArray)
-            {
-                actionList.append(cmdJson);
-            }
+            toJson(cmd);
         }
+
+        // Serialize all iterable Command objects added in the current layer
+        for (const auto& cmd : _IterableCommands)
+        {
+            toJson(cmd);
+        }
+
         return actionList;
     }
 
diff --git a/src/cascadia/TerminalSettingsModel/Command.cpp b/src/cascadia/TerminalSettingsModel/Command.cpp
index ee560b78d..dbdfd6e5c 100644
--- a/src/cascadia/TerminalSettingsModel/Command.cpp
+++ b/src/cascadia/TerminalSettingsModel/Command.cpp
@@ -394,10 +394,10 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
     {
         Json::Value cmdList{ Json::ValueType::arrayValue };
 
-        if (_nestedCommand)
+        if (_nestedCommand || _IterateOn != ExpandCommandType::None)
         {
-            // handle nested command
-            // For nested commands, we can trust _originalJson to be correct.
+            // handle special commands
+            // For these, we can trust _originalJson to be correct.
             // In fact, we _need_ to use it here because we don't actually deserialize `iterateOn`
             //   until we expand the command.
             cmdList.append(_originalJson);