diff --git a/tests/test_analysis.py b/tests/test_analysis.py
new file mode 100644
index 0000000..548f2d2
--- /dev/null
+++ b/tests/test_analysis.py
@@ -0,0 +1,82 @@
+# tests/test_analysis.py
+from pathlib import Path
+import pytest
+from click.testing import CliRunner
+from ctf.analysis import run_analysis, RouteResult
+
+TEST_ENV = Path("tests/env")
+
+def test_run_analysis_no_file():
+    """
+    Verifies that run_analysis returns non-executed metadata route when file_path is None.
+    """
+    result = run_analysis(None)
+    assert not result.success
+    assert len(result.routes) == 1
+    assert not result.routes[0].executed
+    assert "No file attached" in result.routes[0].message
+
+def test_run_analysis_file_not_found():
+    """
+    Verifies that run_analysis returns a failed metadata route when path does not exist.
+    """
+    result = run_analysis(Path("non_existent_file_xyz.jpg"))
+    assert not result.success
+    assert len(result.routes) == 1
+    assert result.routes[0].executed
+    assert not result.routes[0].success
+    assert "File not found" in result.routes[0].message
+
+def test_run_analysis_success_with_flag():
+    """
+    Verifies that run_analysis successfully extracts flag from file comment.
+    """
+    import struct
+    comment_text = b"flag{metadata_analyse_success}"
+    comment_len = len(comment_text) + 2
+    mock_jpeg = b"\xff\xd8\xff\xfe" + struct.pack(">H", comment_len) + comment_text + b"\xff\xd9"
+    
+    test_file = TEST_ENV / "mock_analyse_flag.jpg"
+    with open(test_file, "wb") as f:
+        f.write(mock_jpeg)
+        
+    result = run_analysis(test_file)
+    assert result.success
+    assert len(result.routes) == 1
+    assert result.routes[0].success
+    assert "flag{metadata_analyse_success}" in result.routes[0].extracted_flags
+
+def test_cli_analyse_success():
+    """
+    Verifies that 'ctf analyse' CLI successfully runs and outputs the extracted flags.
+    """
+    from ctf.main import cli
+    runner = CliRunner()
+    
+    import struct
+    comment_text = b"flag{cli_analyse_success}"
+    comment_len = len(comment_text) + 2
+    mock_jpeg = b"\xff\xd8\xff\xfe" + struct.pack(">H", comment_len) + comment_text + b"\xff\xd9"
+    
+    test_file = TEST_ENV / "mock_cli_analyse_flag.jpg"
+    with open(test_file, "wb") as f:
+        f.write(mock_jpeg)
+        
+    result = runner.invoke(cli, ["analyse", "-f", str(test_file)])
+    assert result.exit_code == 0
+    assert "Starting dynamic challenge analysis" in result.output
+    assert "Route: File Metadata Extraction" in result.output
+    assert "flag{cli_analyse_success}" in result.output
+    assert "Challenge solved successfully!" in result.output
+
+def test_cli_analyse_no_file():
+    """
+    Verifies that 'ctf analyse' CLI displays warnings when run without -f option.
+    """
+    from ctf.main import cli
+    runner = CliRunner()
+    
+    result = runner.invoke(cli, ["analyse"])
+    assert result.exit_code == 0
+    assert "No file attached to analyze" in result.output
+    assert "No clear flag found yet" in result.output