diff --git a/glass/src/lib/native/cpp/Window.cpp b/glass/src/lib/native/cpp/Window.cpp
index 64b043ffb1e..8a69ed8b6ed 100644
--- a/glass/src/lib/native/cpp/Window.cpp
+++ b/glass/src/lib/native/cpp/Window.cpp
@@ -57,12 +57,22 @@ void Window::Display() {
     ImGui::PushStyleVar(ImGuiStyleVar_WindowPadding, m_padding);
   }
 
-  std::string label;
+  std::string* name = &m_name;
   if (m_name.empty()) {
-    label = fmt::format("{}###{}", m_defaultName, m_id);
-  } else {
-    label = fmt::format("{}###{}", m_name, m_id);
+    name = &m_defaultName;
+  }
+  std::string label = fmt::format("{}###{}", *name, m_id);
+
+  // Accounts for size of title, collapse button, and close button
+  float minWidth =
+      ImGui::CalcTextSize(name->c_str()).x + ImGui::GetFontSize() * 2 +
+      ImGui::GetStyle().ItemInnerSpacing.x * 3 +
+      ImGui::GetStyle().FramePadding.x * 2 + ImGui::GetStyle().WindowBorderSize;
+  // Accounts for size of hamburger button
+  if (m_renamePopupEnabled || m_view->HasSettings()) {
+    minWidth += ImGui::GetFontSize() + ImGui::GetStyle().FramePadding.x;
   }
+  ImGui::SetNextWindowSizeConstraints({minWidth, 0}, ImVec2{FLT_MAX, FLT_MAX});
 
   if (Begin(label.c_str(), &m_visible, m_flags)) {
     if (m_renamePopupEnabled || m_view->HasSettings()) {
diff --git a/glass/src/lib/native/cpp/hardware/LEDDisplay.cpp b/glass/src/lib/native/cpp/hardware/LEDDisplay.cpp
index 6ad7fc54a74..8e02be30a4c 100644
--- a/glass/src/lib/native/cpp/hardware/LEDDisplay.cpp
+++ b/glass/src/lib/native/cpp/hardware/LEDDisplay.cpp
@@ -33,7 +33,7 @@ void glass::DisplayLEDDisplay(LEDDisplayModel* model, int index) {
   int& order = storage.GetInt("order", LEDConfig::RowMajor);
   int& start = storage.GetInt("start", LEDConfig::UpperLeft);
 
-  ImGui::PushItemWidth(ImGui::GetFontSize() * 6);
+  ImGui::PushItemWidth(ImGui::GetFontSize() * 7);
   ImGui::LabelText("Length", "%d", length);
   ImGui::LabelText("Running", "%s", running ? "Yes" : "No");
   ImGui::InputInt("Columns", &numColumns);
diff --git a/simulation/halsim_gui/src/main/native/cpp/DriverStationGui.cpp b/simulation/halsim_gui/src/main/native/cpp/DriverStationGui.cpp
index 3ed8fa71127..541437a95d3 100644
--- a/simulation/halsim_gui/src/main/native/cpp/DriverStationGui.cpp
+++ b/simulation/halsim_gui/src/main/native/cpp/DriverStationGui.cpp
@@ -1104,7 +1104,15 @@ static void DriverStationExecute() {
     }
 
     ImGui::SetNextWindowPos(ImVec2{5, 20}, ImGuiCond_FirstUseEver);
-    ImGui::Begin("Robot State", nullptr, ImGuiWindowFlags_AlwaysAutoResize);
+    const char* title = "Robot State";
+    // Accounts for size of title and collapse button
+    float minWidth = ImGui::CalcTextSize(title).x + ImGui::GetFontSize() +
+                     ImGui::GetStyle().ItemInnerSpacing.x * 2 +
+                     ImGui::GetStyle().FramePadding.x * 2 +
+                     ImGui::GetStyle().WindowBorderSize;
+    ImGui::SetNextWindowSizeConstraints(ImVec2{minWidth, 0},
+                                        ImVec2{FLT_MAX, FLT_MAX});
+    ImGui::Begin(title, nullptr, ImGuiWindowFlags_AlwaysAutoResize);
     if (ImGui::Selectable("Disconnected", !isAttached)) {
       HALSIM_SetDriverStationEnabled(false);
       HALSIM_SetDriverStationDsAttached(false);