diff --git a/interface/src/FileLogger.cpp b/interface/src/FileLogger.cpp
index 247eb66c99..f5f7ce6ebe 100644
--- a/interface/src/FileLogger.cpp
+++ b/interface/src/FileLogger.cpp
@@ -12,7 +12,6 @@
 #include "FileLogger.h"
 
 #include <QtCore/QDateTime>
-#include <QtCore/QFile>
 #include <QtCore/QDir>
 #include <QtGui/QDesktopServices>
 
@@ -25,11 +24,14 @@
 static const QString FILENAME_FORMAT = "hifi-log_%1_%2.txt";
 static const QString DATETIME_FORMAT = "yyyy-MM-dd_hh.mm.ss";
 static const QString LOGS_DIRECTORY = "Logs";
-// Max log size is 1 MB
-static const qint64 MAX_LOG_SIZE = 1024 * 1024;
+// Max log size is 512 KB. We send log files to our crash reporter, so we want to keep this relatively
+// small so it doesn't go over the 2MB zipped limit for all of the files we send.
+static const qint64 MAX_LOG_SIZE = 512 * 1024;
 // Max log age is 1 hour
 static const uint64_t MAX_LOG_AGE_USECS = USECS_PER_SECOND * 3600;
 
+static FilePersistThread* _persistThreadInstance;
+
 QString getLogRollerFilename() {
     QString result = FileUtils::standardPath(LOGS_DIRECTORY);
     QHostAddress clientAddress = getGuessedLocalAddress();
@@ -43,51 +45,53 @@ const QString& getLogFilename() {
     return fileName;
 }
 
+FilePersistThread::FilePersistThread(const FileLogger& logger) : _logger(logger) {
+    setObjectName("LogFileWriter");
 
-class FilePersistThread : public GenericQueueThread < QString > {    
-public:
-    FilePersistThread(const FileLogger& logger) : _logger(logger) {
-        setObjectName("LogFileWriter");
+    // A file may exist from a previous run - if it does, roll the file and suppress notifying listeners.
+    QFile file(_logger._fileName);
+    if (file.exists()) {
+        rollFileIfNecessary(file, false);
     }
+    _lastRollTime = usecTimestampNow();
+}
 
-protected:
-    void rollFileIfNecessary(QFile& file) {
-        uint64_t now = usecTimestampNow();
-        if ((file.size() > MAX_LOG_SIZE) || (now - _lastRollTime) > MAX_LOG_AGE_USECS) {
-            QString newFileName = getLogRollerFilename();
-            if (file.copy(newFileName)) {
-                _lastRollTime = now;
-                file.open(QIODevice::WriteOnly | QIODevice::Truncate);
-                file.close();
-                qDebug() << "Rolled log file:" << newFileName;
+void FilePersistThread::rollFileIfNecessary(QFile& file, bool notifyListenersIfRolled) {
+    uint64_t now = usecTimestampNow();
+    if ((file.size() > MAX_LOG_SIZE) || (now - _lastRollTime) > MAX_LOG_AGE_USECS) {
+        QString newFileName = getLogRollerFilename();
+        if (file.copy(newFileName)) {
+            file.open(QIODevice::WriteOnly | QIODevice::Truncate);
+            file.close();
+            qDebug() << "Rolled log file:" << newFileName;
+
+            if (notifyListenersIfRolled) {
+                emit rollingLogFile(newFileName);
             }
+
+            _lastRollTime = now;
         }
     }
+}
 
-    virtual bool processQueueItems(const Queue& messages) {
-        QFile file(_logger._fileName);
-        rollFileIfNecessary(file);
-        if (file.open(QIODevice::WriteOnly | QIODevice::Append | QIODevice::Text)) {
-            QTextStream out(&file);
-            foreach(const QString& message, messages) {
-                out << message;
-            }
+bool FilePersistThread::processQueueItems(const Queue& messages) {
+    QFile file(_logger._fileName);
+    rollFileIfNecessary(file);
+    if (file.open(QIODevice::WriteOnly | QIODevice::Append | QIODevice::Text)) {
+        QTextStream out(&file);
+        foreach(const QString& message, messages) {
+            out << message;
         }
-        return true;
     }
-private:
-    const FileLogger& _logger;
-    uint64_t _lastRollTime = 0; 
-};
-
-static FilePersistThread* _persistThreadInstance;
+    return true;
+}
 
 FileLogger::FileLogger(QObject* parent) :
     AbstractLoggerInterface(parent), _fileName(getLogFilename())
 {
     _persistThreadInstance = new FilePersistThread(*this);
     _persistThreadInstance->initialize(true, QThread::LowestPriority);
-
+    connect(_persistThreadInstance, &FilePersistThread::rollingLogFile, this, &FileLogger::rollingLogFile);
 }
 
 FileLogger::~FileLogger() {
diff --git a/interface/src/FileLogger.h b/interface/src/FileLogger.h
index 1053e6afa3..e9bae63a73 100644
--- a/interface/src/FileLogger.h
+++ b/interface/src/FileLogger.h
@@ -15,6 +15,8 @@
 #include "AbstractLoggerInterface.h"
 #include <GenericQueueThread.h>
 
+#include <QtCore/QFile>
+
 class FileLogger : public AbstractLoggerInterface {
     Q_OBJECT
 
@@ -27,11 +29,32 @@ public:
     virtual QString getLogData() override;
     virtual void locateLog() override;
 
+signals:
+    void rollingLogFile(QString newFilename);
+
 private:
     const QString _fileName;
     friend class FilePersistThread;
 };
 
+class FilePersistThread : public GenericQueueThread < QString > {
+    Q_OBJECT
+public:
+    FilePersistThread(const FileLogger& logger);
+
+signals:
+    void rollingLogFile(QString newFilename);
+
+protected:
+    void rollFileIfNecessary(QFile& file, bool notifyListenersIfRolled = true);
+    virtual bool processQueueItems(const Queue& messages);
+
+private:
+    const FileLogger& _logger;
+    uint64_t _lastRollTime;
+};
+
+
 
 
 #endif // hifi_FileLogger_h
diff --git a/interface/src/main.cpp b/interface/src/main.cpp
index f41046f7c2..be56ad12b1 100644
--- a/interface/src/main.cpp
+++ b/interface/src/main.cpp
@@ -178,8 +178,18 @@ int main(int argc, const char* argv[]) {
         });
 
         // BugSplat WILL NOT work with file paths that do not use OS native separators.
-        auto logPath = QDir::toNativeSeparators(app.getLogger()->getFilename());
+        auto logger = app.getLogger();
+        auto logPath = QDir::toNativeSeparators(logger->getFilename());
         mpSender.sendAdditionalFile(qPrintable(logPath));
+
+        QMetaObject::Connection connection;
+        connection = QObject::connect(logger, &FileLogger::rollingLogFile, &app, [&mpSender, &connection](QString newFilename) {
+            // We only want to add the first rolled log file (the "beginning" of the log) to BugSplat to ensure we don't exceed the 2MB
+            // zipped limit, so we disconnect here.
+            QObject::disconnect(connection);
+            auto rolledLogPath = QDir::toNativeSeparators(newFilename);
+            mpSender.sendAdditionalFile(qPrintable(rolledLogPath));
+        });
 #endif
 
         printSystemInformation();