diff --git a/tests/CMakeLists.txt b/tests/CMakeLists.txt
index 9fab07eb..d633d732 100644
--- a/tests/CMakeLists.txt
+++ b/tests/CMakeLists.txt
@@ -175,6 +175,18 @@ target_sources(
           ${ADVSS_SOURCE_DIR}/lib/variables/variable-spinbox.cpp
           ${ADVSS_SOURCE_DIR}/lib/variables/variable-string.cpp)
 
+# --- macro-condition-file --- #
+
+target_include_directories(${PROJECT_NAME}
+                           PRIVATE ${ADVSS_SOURCE_DIR}/plugins/base)
+
+target_sources(
+  ${PROJECT_NAME}
+  PRIVATE test-macro-condition-file.cpp
+          ${ADVSS_SOURCE_DIR}/plugins/base/macro-condition-file.cpp
+          ${ADVSS_SOURCE_DIR}/lib/utils/file-selection.cpp
+          ${ADVSS_SOURCE_DIR}/lib/variables/variable-text-edit.cpp)
+
 # --- Testing --- #
 
 enable_testing()
diff --git a/tests/test-macro-condition-file.cpp b/tests/test-macro-condition-file.cpp
new file mode 100644
index 00000000..495af16e
--- /dev/null
+++ b/tests/test-macro-condition-file.cpp
@@ -0,0 +1,325 @@
+#include "catch.hpp"
+#include "macro-condition-file.hpp"
+
+#include <QDateTime>
+#include <QFile>
+#include <QFileDevice>
+#include <QTemporaryDir>
+#include <QTextStream>
+
+using advss::MacroConditionFile;
+
+// Write (or overwrite) a file with the given content.
+static void writeFile(const QString &path, const QString &content)
+{
+	QFile f(path);
+	f.open(QIODevice::WriteOnly | QIODevice::Text | QIODevice::Truncate);
+	QTextStream(&f) << content;
+}
+
+// ---------------------------------------------------------------------------
+// CONTENT_CHANGE
+// ---------------------------------------------------------------------------
+
+TEST_CASE("CONTENT_CHANGE: first check does not trigger for non-empty file",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "hello world");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::CONTENT_CHANGE);
+	cond._file = path.toStdString();
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+TEST_CASE("CONTENT_CHANGE: first check does not trigger for empty file",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::CONTENT_CHANGE);
+	cond._file = path.toStdString();
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+TEST_CASE("CONTENT_CHANGE: no trigger when content stays the same",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "same content");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::CONTENT_CHANGE);
+	cond._file = path.toStdString();
+
+	cond.CheckCondition(); // baseline
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+TEST_CASE("CONTENT_CHANGE: triggers when content changes",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "initial");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::CONTENT_CHANGE);
+	cond._file = path.toStdString();
+
+	cond.CheckCondition(); // baseline
+	writeFile(path, "changed");
+	REQUIRE(cond.CheckCondition());
+}
+
+TEST_CASE("CONTENT_CHANGE: no trigger after content stabilizes",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "initial");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::CONTENT_CHANGE);
+	cond._file = path.toStdString();
+
+	cond.CheckCondition(); // baseline
+	writeFile(path, "changed");
+	cond.CheckCondition();                // change detected
+	REQUIRE_FALSE(cond.CheckCondition()); // same content again
+}
+
+TEST_CASE("CONTENT_CHANGE: returns false when file cannot be opened",
+	  "[macro-condition-file]")
+{
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::CONTENT_CHANGE);
+	cond._file = "/nonexistent/path/to/file.txt";
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+// ---------------------------------------------------------------------------
+// DATE_CHANGE
+// ---------------------------------------------------------------------------
+
+TEST_CASE("DATE_CHANGE: first check does not trigger", "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "content");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::DATE_CHANGE);
+	cond._file = path.toStdString();
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+TEST_CASE("DATE_CHANGE: no trigger when modification date stays the same",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "content");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::DATE_CHANGE);
+	cond._file = path.toStdString();
+
+	cond.CheckCondition(); // baseline
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+TEST_CASE("DATE_CHANGE: triggers when modification date changes",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "content");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::DATE_CHANGE);
+	cond._file = path.toStdString();
+
+	cond.CheckCondition(); // baseline
+
+	// Explicitly set the modification time to a known future value so the
+	// test is not sensitive to filesystem mtime resolution.
+	QFile f(path);
+	f.open(QIODevice::ReadWrite);
+	f.setFileTime(QDateTime::currentDateTime().addSecs(10),
+		      QFileDevice::FileModificationTime);
+	f.close();
+
+	REQUIRE(cond.CheckCondition());
+}
+
+// ---------------------------------------------------------------------------
+// MATCH
+// ---------------------------------------------------------------------------
+
+TEST_CASE("MATCH: returns true when file content matches text",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "hello");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::MATCH);
+	cond._file = path.toStdString();
+	cond._text = "hello";
+
+	REQUIRE(cond.CheckCondition());
+}
+
+TEST_CASE("MATCH: returns false when file content does not match text",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "hello");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::MATCH);
+	cond._file = path.toStdString();
+	cond._text = "world";
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+TEST_CASE("MATCH: returns false when file cannot be opened",
+	  "[macro-condition-file]")
+{
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::MATCH);
+	cond._file = "/nonexistent/path/to/file.txt";
+	cond._text = "anything";
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+TEST_CASE("MATCH: regex enabled matches file content against pattern",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "hello world");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::MATCH);
+	cond._file = path.toStdString();
+	cond._text = "h.*d"; // matches "hello world" as a regex
+	cond._regex.SetEnabled(true);
+
+	REQUIRE(cond.CheckCondition());
+}
+
+TEST_CASE("MATCH: regex disabled treats pattern as literal text",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "hello world");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::MATCH);
+	cond._file = path.toStdString();
+	cond._text = "h.*d"; // does not literally appear in "hello world"
+	cond._regex.SetEnabled(false);
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+// ---------------------------------------------------------------------------
+// EXISTS
+// ---------------------------------------------------------------------------
+
+TEST_CASE("EXISTS: returns true for an existing file", "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::EXISTS);
+	cond._file = path.toStdString();
+
+	REQUIRE(cond.CheckCondition());
+}
+
+TEST_CASE("EXISTS: returns false for a non-existing path",
+	  "[macro-condition-file]")
+{
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::EXISTS);
+	cond._file = "/nonexistent/path/to/file.txt";
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+// ---------------------------------------------------------------------------
+// IS_FILE
+// ---------------------------------------------------------------------------
+
+TEST_CASE("IS_FILE: returns true for a regular file", "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::IS_FILE);
+	cond._file = path.toStdString();
+
+	REQUIRE(cond.CheckCondition());
+}
+
+TEST_CASE("IS_FILE: returns false for a directory", "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::IS_FILE);
+	cond._file = dir.path().toStdString();
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}
+
+// ---------------------------------------------------------------------------
+// IS_FOLDER
+// ---------------------------------------------------------------------------
+
+TEST_CASE("IS_FOLDER: returns true for a directory", "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::IS_FOLDER);
+	cond._file = dir.path().toStdString();
+
+	REQUIRE(cond.CheckCondition());
+}
+
+TEST_CASE("IS_FOLDER: returns false for a regular file",
+	  "[macro-condition-file]")
+{
+	QTemporaryDir dir;
+	QString path = dir.filePath("test.txt");
+	writeFile(path, "");
+
+	MacroConditionFile cond(nullptr);
+	cond.SetCondition(MacroConditionFile::Condition::IS_FOLDER);
+	cond._file = path.toStdString();
+
+	REQUIRE_FALSE(cond.CheckCondition());
+}