diff --git a/include/mainwindow.h b/include/mainwindow.h
index 3fe187f3..2d065b37 100644
--- a/include/mainwindow.h
+++ b/include/mainwindow.h
@@ -367,7 +367,7 @@ private:
     void scrollMapListToCurrentMap(MapTree *list);
     void scrollMapListToCurrentLayout(MapTree *list);
     void resetMapListFilters();
-    void showFileWatcherWarning(QString filepath);
+    void showFileWatcherWarning();
     QString getExistingDirectory(QString);
     bool openProject(QString dir, bool initial = false);
     bool closeProject();
diff --git a/include/project.h b/include/project.h
index fcdde462..f3a1093b 100644
--- a/include/project.h
+++ b/include/project.h
@@ -71,7 +71,7 @@ public:
     QMap<QString, QString> facingDirections;
     ParseUtil parser;
     QFileSystemWatcher fileWatcher;
-    QMap<QString, qint64> modifiedFileTimestamps;
+    QSet<QString> modifiedFiles;
     bool usingAsmTilesets;
     QSet<QString> disabledSettingsNames;
     QSet<QString> topLevelMapFields;
@@ -252,6 +252,7 @@ public:
 
 private:
     QMap<QString, QString> mapSectionDisplayNames;
+    QMap<QString, qint64> modifiedFileTimestamps;
 
     void updateLayout(Layout *);
 
@@ -259,6 +260,7 @@ private:
     void setNewLayoutBorder(Layout *layout);
 
     void ignoreWatchedFileTemporarily(QString filepath);
+    void recordFileChange(const QString &filepath);
 
     static int num_tiles_primary;
     static int num_tiles_total;
@@ -270,7 +272,7 @@ private:
     static int max_object_events;
 
 signals:
-    void fileChanged(QString filepath);
+    void fileChanged(const QString &filepath);
     void mapLoaded(Map *map);
     void mapCreated(Map *newMap, const QString &groupName);
     void layoutCreated(Layout *newLayout);
diff --git a/src/mainwindow.cpp b/src/mainwindow.cpp
index 277aaf97..9e59758e 100644
--- a/src/mainwindow.cpp
+++ b/src/mainwindow.cpp
@@ -69,6 +69,8 @@ MainWindow::MainWindow(QWidget *parent) :
     QCoreApplication::setApplicationVersion(PORYMAP_VERSION);
     QApplication::setApplicationDisplayName(QApplication::applicationName());
     QApplication::setWindowIcon(QIcon(":/icons/porymap-icon-2.ico"));
+    connect(qApp, &QApplication::applicationStateChanged, this, &MainWindow::showFileWatcherWarning);
+
     ui->setupUi(this);
 
     cleanupLargeLog();
@@ -791,26 +793,46 @@ void MainWindow::openSubWindow(QWidget * window) {
     }
 }
 
-void MainWindow::showFileWatcherWarning(QString filepath) {
-    if (!porymapConfig.monitorFiles || !isProjectOpen())
+void MainWindow::showFileWatcherWarning() {
+     if (!porymapConfig.monitorFiles || !isProjectOpen())
+        return;
+
+    // Only show the file watcher warning if Porymap is the currently active application.
+    // This stops Porymap from bugging users when they switch to their projects to make edits;
+    // we'll warn them about the need to reload when they return to Porymap.
+    if (QGuiApplication::applicationState() != Qt::ApplicationActive)
         return;
 
     Project *project = this->editor->project;
-    if (project->modifiedFileTimestamps.contains(filepath)) {
-        if (QDateTime::currentMSecsSinceEpoch() < project->modifiedFileTimestamps[filepath]) {
-            return;
-        }
-        project->modifiedFileTimestamps.remove(filepath);
+    QStringList modifiedFiles(project->modifiedFiles.constBegin(),  project->modifiedFiles.constEnd());
+    if (modifiedFiles.isEmpty())
+        return;
+    project->modifiedFiles.clear();
+
+    // Only allow one of these warnings at a single time.
+    // Additional file changes are ignored while the warning is already active. 
+    static bool showing = false;
+    if (showing)
+        return;
+    showing = true;
+
+    // Strip project root from filepaths
+    const QString root = project->root + "/";
+    for (auto &path : modifiedFiles) {
+        path.remove(root);
     }
 
-    static bool showing = false;
-    if (showing) return;
+    QuestionMessage msgBox("", this);
+    if (modifiedFiles.count() == 1) {
+        msgBox.setText(QString("The file %1 has changed on disk. Would you like to reload the project?").arg(modifiedFiles.first()));
+    } else {
+        msgBox.setText(QStringLiteral("Some project files have changed on disk. Would you like to reload the project?"));
+        msgBox.setDetailedText(QStringLiteral("The following files have changed:\n") + modifiedFiles.join("\n"));
+    }
 
-    QuestionMessage msgBox(QString("The file %1 has changed on disk. Would you like to reload the project?").arg(filepath.remove(project->root + "/")), this);
     QCheckBox showAgainCheck("Do not ask again.");
     msgBox.setCheckBox(&showAgainCheck);
 
-    showing = true;
     auto reply = msgBox.exec();
     if (reply == QMessageBox::Yes) {
         on_action_Reload_Project_triggered();
diff --git a/src/project.cpp b/src/project.cpp
index fb2d3d2b..3f510e6b 100644
--- a/src/project.cpp
+++ b/src/project.cpp
@@ -35,7 +35,7 @@ int Project::max_object_events = 64;
 Project::Project(QObject *parent) :
     QObject(parent)
 {
-    QObject::connect(&this->fileWatcher, &QFileSystemWatcher::fileChanged, this, &Project::fileChanged);
+    QObject::connect(&this->fileWatcher, &QFileSystemWatcher::fileChanged, this, &Project::recordFileChange);
 }
 
 Project::~Project()
@@ -660,7 +660,25 @@ void Project::saveMapLayouts() {
 
 void Project::ignoreWatchedFileTemporarily(QString filepath) {
     // Ignore any file-change events for this filepath for the next 5 seconds.
-    modifiedFileTimestamps.insert(filepath, QDateTime::currentMSecsSinceEpoch() + 5000);
+    this->modifiedFileTimestamps.insert(filepath, QDateTime::currentMSecsSinceEpoch() + 5000);
+}
+
+void Project::recordFileChange(const QString &filepath) {
+    if (this->modifiedFiles.contains(filepath)) {
+        // We already recorded a change to this file
+        return;
+    }
+
+    if (this->modifiedFileTimestamps.contains(filepath)) {
+        if (QDateTime::currentMSecsSinceEpoch() < this->modifiedFileTimestamps[filepath]) {
+            // We're still ignoring changes to this file
+            return;
+        }
+        this->modifiedFileTimestamps.remove(filepath);
+    }
+
+    this->modifiedFiles.insert(filepath);
+    emit fileChanged(filepath);
 }
 
 void Project::saveMapGroups() {