diff --git a/src/installationmanager.cpp b/src/installationmanager.cpp
index 901c636cb..3f247b388 100644
--- a/src/installationmanager.cpp
+++ b/src/installationmanager.cpp
@@ -667,20 +667,21 @@ InstallationResult InstallationManager::install(const QString& fileName,
     if (category != 0 && categoryIndex == 0U &&
         Settings::instance().nexus().categoryMappings()) {
       QMessageBox nexusQuery;
+      nexusQuery.setWindowTitle(tr("No category found"));
       nexusQuery.setText(tr(
           "This Nexus category has not yet been mapped. Do you wish to proceed without "
           "setting a category, proceed and disable automatic Nexus mappings, or stop "
           "and configure your category mappings?"));
-      nexusQuery.addButton(tr("&Proceed"), QMessageBox::YesRole);
-      nexusQuery.addButton(tr("&Disable"), QMessageBox::AcceptRole);
-      nexusQuery.addButton(tr("&Stop && Configure"), QMessageBox::DestructiveRole);
-      auto ret = nexusQuery.exec();
-      switch (ret) {
-      case 1:
+      QPushButton* proceedButton =
+          nexusQuery.addButton(tr("&Proceed"), QMessageBox::YesRole);
+      QPushButton* disableButton =
+          nexusQuery.addButton(tr("&Disable"), QMessageBox::AcceptRole);
+      QPushButton* stopButton =
+          nexusQuery.addButton(tr("&Stop && Configure"), QMessageBox::DestructiveRole);
+      nexusQuery.exec();
+      if (nexusQuery.clickedButton() == disableButton) {
         Settings::instance().nexus().setCategoryMappings(false);
-      case 0:
-        break;
-      case 2:
+      } else if (nexusQuery.clickedButton() == stopButton) {
         return MOBase::IPluginInstaller::RESULT_CATEGORYREQUESTED;
       }
     } else {
diff --git a/src/modlistviewactions.cpp b/src/modlistviewactions.cpp
index a86c90676..fd2f5c68d 100644
--- a/src/modlistviewactions.cpp
+++ b/src/modlistviewactions.cpp
@@ -262,6 +262,21 @@ void ModListViewActions::checkModsForUpdates() const
 
 void ModListViewActions::assignCategories() const
 {
+  if (!GlobalSettings::hideAssignCategoriesQuestion()) {
+    QMessageBox warning;
+    warning.setWindowTitle(tr("Are you sure?"));
+    warning.setText(
+        tr("This action will remove any existing categories on any mod with a valid "
+           "Nexus category mapping. Are you certain you want to proceed?"));
+    warning.setStandardButtons(QMessageBox::Yes | QMessageBox::Cancel);
+    QCheckBox dontShow(tr("&Don't show this again"));
+    warning.setCheckBox(&dontShow);
+    auto result = warning.exec();
+    if (dontShow.isChecked())
+      GlobalSettings::setHideAssignCategoriesQuestion(true);
+    if (result == QMessageBox::Cancel)
+      return;
+  }
   for (auto mod : m_core.modList()->allMods()) {
     ModInfo::Ptr modInfo = ModInfo::getByName(mod);
     QString file         = modInfo->installationFile();
@@ -269,7 +284,7 @@ void ModListViewActions::assignCategories() const
     if (!nexusCategory) {
       auto download = m_core.downloadManager()->getDownloadIndex(file);
       if (download >= 0) {
-        int nexusCategory = m_core.downloadManager()->getCategoryID(download);
+        nexusCategory = m_core.downloadManager()->getCategoryID(download);
       }
     }
     int newCategory = CategoryFactory::instance()->resolveNexusID(nexusCategory);
diff --git a/src/settings.cpp b/src/settings.cpp
index 17de38eaa..04a094676 100644
--- a/src/settings.cpp
+++ b/src/settings.cpp
@@ -2450,6 +2450,16 @@ void GlobalSettings::setHideCategoryReminder(bool b)
   settings().setValue("HideCategoryReminder", b);
 }
 
+bool GlobalSettings::hideAssignCategoriesQuestion()
+{
+  return settings().value("HideAssignCategoriesQuestion", false).toBool();
+}
+
+void GlobalSettings::setHideAssignCategoriesQuestion(bool b)
+{
+  settings().setValue("HideAssignCategoriesQuestion", b);
+}
+
 bool GlobalSettings::nexusApiKey(QString& apiKey)
 {
   QString tempKey = getWindowsCredential("APIKEY");
diff --git a/src/settings.h b/src/settings.h
index e7ca47a97..30254c066 100644
--- a/src/settings.h
+++ b/src/settings.h
@@ -931,6 +931,9 @@ class GlobalSettings
   static bool hideCategoryReminder();
   static void setHideCategoryReminder(bool b);
 
+  static bool hideAssignCategoriesQuestion();
+  static void setHideAssignCategoriesQuestion(bool b);
+
   // if the key exists from the credentials store, puts it in `apiKey` and
   // returns true; otherwise, returns false and leaves `apiKey` untouched
   //