diff --git a/Userland/Applications/PixelPaint/MainWidget.cpp b/Userland/Applications/PixelPaint/MainWidget.cpp
index f341375bb2..084d673bf8 100644
--- a/Userland/Applications/PixelPaint/MainWidget.cpp
+++ b/Userland/Applications/PixelPaint/MainWidget.cpp
@@ -61,9 +61,11 @@ MainWidget::MainWidget()
 
     m_toolbox->on_tool_selection = [&](auto* tool) {
         auto* editor = current_image_editor();
-        VERIFY(editor);
-        editor->set_active_tool(tool);
-        m_tool_properties_widget->set_active_tool(tool);
+        // Ignore tool selection changes if we don't have an editor yet, e.g. if PixelPaint is started with a path argument.
+        if (editor) {
+            editor->set_active_tool(tool);
+            m_tool_properties_widget->set_active_tool(tool);
+        }
     };
 
     m_tab_widget->on_middle_click = [&](auto& widget) {
@@ -1298,6 +1300,7 @@ void MainWidget::open_image(FileSystemAccessClient::File file)
     editor.set_path(file.filename().to_byte_string());
     editor.set_unmodified();
     m_layer_list_widget->set_image(&image);
+    m_toolbox->ensure_tool_selection();
     GUI::Application::the()->set_most_recently_open_file(file.filename());
 }
 
diff --git a/Userland/Applications/PixelPaint/ToolboxWidget.cpp b/Userland/Applications/PixelPaint/ToolboxWidget.cpp
index 03dd21469e..0569db953d 100644
--- a/Userland/Applications/PixelPaint/ToolboxWidget.cpp
+++ b/Userland/Applications/PixelPaint/ToolboxWidget.cpp
@@ -55,8 +55,8 @@ void ToolboxWidget::setup_tools()
         auto action = GUI::Action::create_checkable(tool->tool_name(), shortcut, Gfx::Bitmap::load_from_file(ByteString::formatted("/res/icons/pixelpaint/{}.png", icon_name)).release_value_but_fixme_should_propagate_errors(),
             [this, tool = tool.ptr()](auto& action) {
                 if (action.is_checked()) {
-                    on_tool_selection(tool);
                     m_active_tool = tool;
+                    ensure_tool_selection();
                 } else {
                     on_tool_selection(nullptr);
                 }
@@ -70,11 +70,11 @@ void ToolboxWidget::setup_tools()
         tool->set_action(action);
         m_tools.append(move(tool));
         if (is_default_tool) {
+            VERIFY(m_active_tool == nullptr);
             action->set_checked(true);
-            auto default_tool_index = m_tools.size() - 1;
-            deferred_invoke([&, default_tool_index]() {
-                VERIFY(m_active_tool == nullptr);
-                on_tool_selection(m_tools[default_tool_index]);
+            m_active_tool = m_tools[m_tools.size() - 1];
+            deferred_invoke([&]() {
+                ensure_tool_selection();
             });
         }
     };
@@ -100,4 +100,9 @@ void ToolboxWidget::setup_tools()
     add_tool("gradients"sv, { Mod_Ctrl, Key_G }, make<GradientTool>());
 }
 
+void ToolboxWidget::ensure_tool_selection()
+{
+    if (on_tool_selection)
+        on_tool_selection(m_active_tool);
+}
 }
diff --git a/Userland/Applications/PixelPaint/ToolboxWidget.h b/Userland/Applications/PixelPaint/ToolboxWidget.h
index 2d71b99689..a0238105a7 100644
--- a/Userland/Applications/PixelPaint/ToolboxWidget.h
+++ b/Userland/Applications/PixelPaint/ToolboxWidget.h
@@ -30,6 +30,7 @@ public:
     }
 
     Tool* active_tool() const { return m_active_tool; }
+    void ensure_tool_selection();
 
 private:
     friend class ToolButton;