diff --git a/src/cli/src/main.cpp b/src/cli/src/main.cpp
index 5c8becf03..cdec290a9 100644
--- a/src/cli/src/main.cpp
+++ b/src/cli/src/main.cpp
@@ -3,9 +3,10 @@
 #include <QSettings>
 #include <QString>
 #include <QStringList>
+#include "cli.h"
 #include "functions.h"
+#include "logger.h"
 #include "models/profile.h"
-#include "cli.h"
 
 
 int main(int argc, char *argv[])
@@ -17,6 +18,8 @@ int main(int argc, char *argv[])
 	app.setOrganizationDomain("bionus.fr.cr");
 	QSettings::setDefaultFormat(QSettings::IniFormat);
 
+	Logger::getInstance().initialize();
+
 	auto *profile = new Profile(savePath());
 	profile->purgeTemp(24 * 60 * 60);
 
diff --git a/src/e2e/src/main.cpp b/src/e2e/src/main.cpp
index 3916b62ce..15852a539 100644
--- a/src/e2e/src/main.cpp
+++ b/src/e2e/src/main.cpp
@@ -51,6 +51,9 @@ int main(int argc, char *argv[])
 {
 	const QCoreApplication app(argc, argv);
 
+	Logger::getInstance().initialize();
+	Logger::getInstance().setLogLevel(Logger::Warning);
+
 	QCommandLineParser parser;
 	parser.addHelpOption();
 
@@ -60,8 +63,6 @@ int main(int argc, char *argv[])
 	parser.addOption(outputOption);
 	parser.process(app);
 
-	Logger::getInstance().setLogLevel(Logger::Warning);
-
 	QFile f(parser.value(inputOption));
 	if (!f.open(QFile::ReadOnly | QFile::Text)) {
 		return 1;
diff --git a/src/gui-qml/src/main.cpp b/src/gui-qml/src/main.cpp
index ec511b14a..e56af44c4 100644
--- a/src/gui-qml/src/main.cpp
+++ b/src/gui-qml/src/main.cpp
@@ -10,6 +10,7 @@
 #include "loaders/gallery-search-loader.h"
 #include "loaders/image-loader.h"
 #include "loaders/tag-search-loader.h"
+#include "logger.h"
 #include "main-screen.h"
 #include "models/image.h"
 #include "models/profile.h"
@@ -50,6 +51,8 @@ int main(int argc, char *argv[])
 	app.setOrganizationName("Bionus");
 	app.setOrganizationDomain("bionus.fr.cr");
 
+	Logger::getInstance().initialize();
+
 	qmlRegisterType<StatusBar>("StatusBar", 0, 1, "StatusBar");
 	qmlRegisterType<SyntaxHighlighterHelper>("Grabber", 1, 0, "SyntaxHighlighterHelper");
 	qmlRegisterType<GallerySearchLoader>("Grabber", 1, 0, "GallerySearchLoader");
diff --git a/src/gui/src/main/main.cpp b/src/gui/src/main/main.cpp
index 8a70113d1..3035f3095 100644
--- a/src/gui/src/main/main.cpp
+++ b/src/gui/src/main/main.cpp
@@ -38,6 +38,7 @@
 #include "analytics.h"
 #include "cli.h"
 #include "functions.h"
+#include "logger.h"
 #include "main-window.h"
 #include "models/page-api.h"
 #include "models/profile.h"
@@ -74,6 +75,8 @@ int main(int argc, char *argv[])
 	app.setOrganizationDomain("bionus.fr.cr");
 	QSettings::setDefaultFormat(QSettings::IniFormat);
 
+	Logger::getInstance().initialize();
+
 	// Handler for custom URL protocols, redirecting to the main program through HTTP calls
 	if (argc == 3 && QString(argv[1]) == "--url-protocol") {
 		QNetworkAccessManager manager;
diff --git a/src/lib/src/logger.cpp b/src/lib/src/logger.cpp
index dd98f6561..1cb62fe40 100644
--- a/src/lib/src/logger.cpp
+++ b/src/lib/src/logger.cpp
@@ -1,5 +1,6 @@
 #include "logger.h"
 #include <QDateTime>
+#include <QDir>
 #include <QFile>
 #include <QStringList>
 #include <stdexcept>
@@ -9,6 +10,31 @@
 	#include <QDebug>
 #endif
 
+
+void Logger::initialize()
+{
+	// Create the "logs/" directory if it doesn't exist
+	const QDir logsDirectory = savePath(QStringLiteral("logs/"), false, true);
+	if (!logsDirectory.exists()) {
+		logsDirectory.mkpath(".");
+	}
+
+	// Clean-up old log files if we have too many
+	const QFileInfoList list = logsDirectory.entryInfoList(QDir::Files | QDir::Hidden | QDir::NoSymLinks, QDir::Time | QDir::Reversed);
+	if (list.count() > MAX_LOG_FILES) {
+		for (int i = 0; i < (list.count() - MAX_LOG_FILES); i++) {
+			QFile::remove(list[i].absoluteFilePath());
+		}
+	}
+
+	// Generate a new file for each run
+	const QString logFilename = QString("main_%1-%2.log")
+			.arg(QDate::currentDate().toString("yyyy.MM.dd"))
+			.arg(QTime::currentTime().toString("hh.mm.ss.zzz"));
+	setLogFile(logsDirectory.filePath(logFilename));
+}
+
+
 void Logger::logToConsole()
 {
 	if (m_logFile.isOpen()) {
@@ -94,6 +120,7 @@ void Logger::log(const QString &l, LogLevel level)
 		return;
 	}
 
+	// Fallback to "main.log" if no log file is open
 	if (!m_logFile.isOpen()) {
 		setLogFile(savePath(QStringLiteral("main.log"), false, true));
 	}
diff --git a/src/lib/src/logger.h b/src/lib/src/logger.h
index 8aaeef76c..f4bc14b03 100644
--- a/src/lib/src/logger.h
+++ b/src/lib/src/logger.h
@@ -7,6 +7,8 @@
 #include <QFile>
 #include <QObject>
 
+#define MAX_LOG_FILES 20
+
 
 class QString;
 
@@ -37,6 +39,7 @@ class Logger : public QObject
 		static void noMessageOutput(QtMsgType type, const QMessageLogContext &context, const QString &message);
 		static void setupMessageOutput(bool log);
 
+		void initialize();
 		void setExitOnError(bool val);
 		void setLogFile(const QString &path);
 		void setLogLevel(LogLevel level);