diff --git a/src/cascadia/TerminalApp/AdminWarningPlaceholder.xaml b/src/cascadia/TerminalApp/AdminWarningPlaceholder.xaml
index e8bf5063a..e417d124b 100644
--- a/src/cascadia/TerminalApp/AdminWarningPlaceholder.xaml
+++ b/src/cascadia/TerminalApp/AdminWarningPlaceholder.xaml
@@ -28,7 +28,7 @@
                            TextWrapping="WrapWholeWords" />
 
                 <TextBlock x:Uid="ApproveCommandlineWarningPrefixTextBlock"
-                           HorizontalAlignment="Center"
+                           HorizontalAlignment="Left"
                            TextWrapping="WrapWholeWords" />
 
                 <TextBlock Margin="0,8,0,8"
diff --git a/src/cascadia/TerminalApp/TabManagement.cpp b/src/cascadia/TerminalApp/TabManagement.cpp
index 3340842d5..18f4d796f 100644
--- a/src/cascadia/TerminalApp/TabManagement.cpp
+++ b/src/cascadia/TerminalApp/TabManagement.cpp
@@ -305,56 +305,6 @@ namespace winrt::TerminalApp::implementation
         }
     }
 
-    void TerminalPage::_adminWarningPrimaryClicked(const TerminalApp::AdminWarningPlaceholder& sender,
-                                                   const winrt::Windows::UI::Xaml::RoutedEventArgs& /*args*/)
-    {
-        auto warningControl{ winrt::get_self<AdminWarningPlaceholder>(sender) };
-
-        for (const auto& tab : _tabs)
-        {
-            if (const auto& tabImpl{ _GetTerminalTabImpl(tab) })
-            {
-                tabImpl->GetRootPane()->WalkTree([warningControl](std::shared_ptr<Pane> pane) -> bool {
-                    if (pane->GetUserControl() == *warningControl)
-                    {
-                        pane->ReplaceControl(warningControl->Control());
-                        return true;
-                    }
-                    return false;
-                });
-            }
-        }
-
-        auto allowedCommandlines{ ElevatedState::SharedInstance().AllowedCommandlines() };
-        if (!allowedCommandlines)
-        {
-            allowedCommandlines = winrt::single_threaded_vector<winrt::hstring>();
-        }
-        allowedCommandlines.Append(warningControl->Commandline());
-        ElevatedState::SharedInstance().AllowedCommandlines(allowedCommandlines);
-    }
-
-    void TerminalPage::_adminWarningCancelClicked(const TerminalApp::AdminWarningPlaceholder& sender,
-                                                  const winrt::Windows::UI::Xaml::RoutedEventArgs& /*args*/)
-    {
-        auto warningControl{ winrt::get_self<AdminWarningPlaceholder>(sender) };
-
-        for (const auto& tab : _tabs)
-        {
-            if (const auto& tabImpl{ _GetTerminalTabImpl(tab) })
-            {
-                tabImpl->GetRootPane()->WalkTree([warningControl](std::shared_ptr<Pane> pane) -> bool {
-                    if (pane->GetUserControl() == *warningControl)
-                    {
-                        pane->Close();
-                        return true;
-                    }
-                    return false;
-                });
-            }
-        }
-    }
-
     // Method Description:
     // - Get the icon of the currently focused terminal control, and set its
     //   tab's icon to that icon.
diff --git a/src/cascadia/TerminalApp/TerminalPage.cpp b/src/cascadia/TerminalApp/TerminalPage.cpp
index c905fb308..021d9a319 100644
--- a/src/cascadia/TerminalApp/TerminalPage.cpp
+++ b/src/cascadia/TerminalApp/TerminalPage.cpp
@@ -1330,6 +1330,93 @@ namespace winrt::TerminalApp::implementation
         return true; // TODO! Change this to false. This is defaulted to true for testing.
     }
 
+    void TerminalPage::_adminWarningPrimaryClicked(const TerminalApp::AdminWarningPlaceholder& sender,
+                                                   const winrt::Windows::UI::Xaml::RoutedEventArgs& /*args*/)
+    {
+        auto warningControl{ winrt::get_self<AdminWarningPlaceholder>(sender) };
+        const auto& cmdline{ warningControl->Commandline() };
+        // Look through the tabs and panes to look for us. Whichever pane had us
+        // as content - replace their content with the TermControl we were
+        // holding on to.
+        for (const auto& tab : _tabs)
+        {
+            if (const auto& tabImpl{ _GetTerminalTabImpl(tab) })
+            {
+                tabImpl->GetRootPane()->WalkTree([warningControl, cmdline](std::shared_ptr<Pane> pane) -> bool {
+                    if (pane->GetUserControl() == *warningControl)
+                    {
+                        // Hooray, we found us!
+                        pane->ReplaceControl(warningControl->Control());
+                        // Don't return true here. We want to make sure to chekc
+                        // all the panes for the same commandline we just
+                        // approved.
+                    }
+                    else if (const auto& otherWarning{ winrt::get_self<AdminWarningPlaceholder>(pane->GetUserControl().try_as<TerminalApp::AdminWarningPlaceholder>()) })
+                    {
+                        // This pane wasn't us, but it did have a warning in it.
+                        // Was it a warning for the same commandline that we
+                        // just approved?
+                        if (otherWarning->Commandline() == cmdline)
+                        {
+                            // Go ahead and allow them as well.
+                            pane->ReplaceControl(otherWarning->Control());
+                        }
+                    }
+                    return false;
+                });
+            }
+        }
+
+        // Update the list of approved commandlines.
+        auto allowedCommandlines{ ElevatedState::SharedInstance().AllowedCommandlines() };
+        if (!allowedCommandlines)
+        {
+            allowedCommandlines = winrt::single_threaded_vector<winrt::hstring>();
+        }
+
+        // But of course, we don't need to add this commandline if it's already
+        // in the list of approved commandlines.
+        bool foundCopy = false;
+        for (const auto& approved : allowedCommandlines)
+        {
+            if (approved == cmdline)
+            {
+                foundCopy = true;
+                break;
+            }
+        }
+        if (!foundCopy)
+        {
+            allowedCommandlines.Append(cmdline);
+        }
+        ElevatedState::SharedInstance().AllowedCommandlines(allowedCommandlines);
+    }
+
+    void TerminalPage::_adminWarningCancelClicked(const TerminalApp::AdminWarningPlaceholder& sender,
+                                                  const winrt::Windows::UI::Xaml::RoutedEventArgs& /*args*/)
+    {
+        auto warningControl{ winrt::get_self<AdminWarningPlaceholder>(sender) };
+
+        for (const auto& tab : _tabs)
+        {
+            if (const auto& tabImpl{ _GetTerminalTabImpl(tab) })
+            {
+                tabImpl->GetRootPane()->WalkTree([warningControl](std::shared_ptr<Pane> pane) -> bool {
+                    if (pane->GetUserControl() == *warningControl)
+                    {
+                        pane->Close();
+                        return true;
+                    }
+                    // We're not going to auto-close all the other panes with
+                    // the same commandline warning, akin to what we're doing in
+                    // the approve handler. If they want to reject one pane, but
+                    // accept the next one, that's okay.
+                    return false;
+                });
+            }
+        }
+    }
+
     // Method Description:
     // - Split the focused pane either horizontally or vertically, and place the
     //   given TermControl into the newly created pane.
diff --git a/src/cascadia/TerminalSettingsModel/ApplicationState.cpp b/src/cascadia/TerminalSettingsModel/ApplicationState.cpp
index 0eab17d2f..c5061f9a2 100644
--- a/src/cascadia/TerminalSettingsModel/ApplicationState.cpp
+++ b/src/cascadia/TerminalSettingsModel/ApplicationState.cpp
@@ -11,52 +11,6 @@
 
 constexpr std::wstring_view stateFileName{ L"state.json" };
 
-namespace Microsoft::Terminal::Settings::Model::JsonUtils
-{
-    // This trait exists in order to serialize the std::unordered_set for GeneratedProfiles.
-    template<typename T>
-    struct ConversionTrait<std::unordered_set<T>>
-    {
-        std::unordered_set<T> FromJson(const Json::Value& json) const
-        {
-            ConversionTrait<T> trait;
-            std::unordered_set<T> val;
-            val.reserve(json.size());
-
-            for (const auto& element : json)
-            {
-                val.emplace(trait.FromJson(element));
-            }
-
-            return val;
-        }
-
-        bool CanConvert(const Json::Value& json) const
-        {
-            ConversionTrait<T> trait;
-            return json.isArray() && std::all_of(json.begin(), json.end(), [trait](const auto& json) -> bool { return trait.CanConvert(json); });
-        }
-
-        Json::Value ToJson(const std::unordered_set<T>& val)
-        {
-            ConversionTrait<T> trait;
-            Json::Value json{ Json::arrayValue };
-
-            for (const auto& key : val)
-            {
-                json.append(trait.ToJson(key));
-            }
-
-            return json;
-        }
-
-        std::string TypeDescription() const
-        {
-            return fmt::format("{}[]", ConversionTrait<GUID>{}.TypeDescription());
-        }
-    };
-}
-
 using namespace ::Microsoft::Terminal::Settings::Model;
 
 namespace winrt::Microsoft::Terminal::Settings::Model::implementation
diff --git a/src/cascadia/TerminalSettingsModel/ApplicationState.h b/src/cascadia/TerminalSettingsModel/ApplicationState.h
index 67b91121e..299f2acf0 100644
--- a/src/cascadia/TerminalSettingsModel/ApplicationState.h
+++ b/src/cascadia/TerminalSettingsModel/ApplicationState.h
@@ -34,12 +34,6 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
         virtual void FromJson(const Json::Value& root) const noexcept override;
         virtual Json::Value ToJson() const noexcept override;
 
-        // // Methods
-        // void Reload() const noexcept;
-
-        // // General getters/setters
-        // winrt::hstring FilePath() const noexcept;
-
         // State getters/setters
 #define MTSM_APPLICATION_STATE_GEN(type, name, key, ...) \
     type name() const noexcept;                          \
@@ -55,12 +49,6 @@ namespace winrt::Microsoft::Terminal::Settings::Model::implementation
 #undef MTSM_APPLICATION_STATE_GEN
         };
         til::shared_mutex<state_t> _state;
-
-        // void _write() const noexcept;
-        // void _read() const noexcept;
-
-        // std::filesystem::path _path;
-        // til::throttled_func_trailing<> _throttler;
     };
 }
 
diff --git a/src/cascadia/TerminalSettingsModel/JsonUtils.h b/src/cascadia/TerminalSettingsModel/JsonUtils.h
index c5370cdbf..6799ceee7 100644
--- a/src/cascadia/TerminalSettingsModel/JsonUtils.h
+++ b/src/cascadia/TerminalSettingsModel/JsonUtils.h
@@ -218,6 +218,48 @@ namespace Microsoft::Terminal::Settings::Model::JsonUtils
         }
     };
 
+    template<typename T>
+    struct ConversionTrait<std::unordered_set<T>>
+    {
+        std::unordered_set<T> FromJson(const Json::Value& json) const
+        {
+            ConversionTrait<T> trait;
+            std::unordered_set<T> val;
+            val.reserve(json.size());
+
+            for (const auto& element : json)
+            {
+                val.emplace(trait.FromJson(element));
+            }
+
+            return val;
+        }
+
+        bool CanConvert(const Json::Value& json) const
+        {
+            ConversionTrait<T> trait;
+            return json.isArray() && std::all_of(json.begin(), json.end(), [trait](const auto& json) -> bool { return trait.CanConvert(json); });
+        }
+
+        Json::Value ToJson(const std::unordered_set<T>& val)
+        {
+            ConversionTrait<T> trait;
+            Json::Value json{ Json::arrayValue };
+
+            for (const auto& key : val)
+            {
+                json.append(trait.ToJson(key));
+            }
+
+            return json;
+        }
+
+        std::string TypeDescription() const
+        {
+            return fmt::format("{}[]", ConversionTrait<GUID>{}.TypeDescription());
+        }
+    };
+
     template<typename T>
     struct ConversionTrait<std::unordered_map<std::string, T>>
     {