Check if filenames of the .csr .cnf pair match existing cert

hsm_orchestrator/__init__.py

@@ -68,6 +68,7 @@ def __init__(self, orchestrator_config_filename: Path, **kwargs: Any) -> None:
         self.usb_path = None
         # The path on the workstation to the certificate authorities directory
         self.local_ca_path = None
+        self.ca_cert_files_in_repo = []
 
     def get_openssl_cnf_config(self) -> None:
         """Parse the OpenSSL configuration (.cnf) file.
@@ -116,6 +117,43 @@ def get_openssl_cnf_config(self) -> None:
                         "", inline_comment
                     )
 
+    def get_ca_cert_filename_on_usb(self) -> str:
+        """Identify which file on USB stick is the CA cert
+
+        Compare files on the USB stick with CA certificate files in the repo
+        to identify which one is the CA certificate
+
+        :returns: The filename of the CA certificate on the USB stick
+        """
+        for private_key_directory in [
+            x
+            for x in Path(self.repo_dir / "certificate-authorities").iterdir()
+            if x.is_dir()
+        ]:
+            for certificate_authority_directory in private_key_directory.iterdir():
+                for certificate_file in certificate_authority_directory.iterdir():
+                    self.ca_cert_files_in_repo.append(certificate_file)
+        crt_filenames_on_usb = set(x.name for x in self.usb_path.glob("*.crt"))
+        ca_cert_filenames_on_usb = (
+            set(x.name for x in self.ca_cert_files_in_repo) & crt_filenames_on_usb
+        )
+        if len(ca_cert_filenames_on_usb) == 0:
+            print(
+                "No .crt files were found on the USB stick with names that match CA"
+                " certificate files.We would expect there to be one CA certificate file"
+                " on the USB stick."
+            )
+            exit(1)
+        if len(ca_cert_filenames_on_usb) > 1:
+            print(
+                "There are multiple .crt files on the USB stick with names that match"
+                " CA certificate files.We would only expect there to be one CA"
+                " certificate file on the USB stick."
+            )
+            exit(1)
+        ca_cert_filename_on_usb = next(iter(ca_cert_filenames_on_usb))
+        return ca_cert_filename_on_usb
+
     def check_update_private_key(self) -> None:
         """Validate and update the OpenSSL 'private_key' value.
 
@@ -329,6 +367,27 @@ def check_ca_files(self) -> None:
                 )
                 exit(1)
 
+    def check_for_matching_issued_cert(self):
+        """Check to see if there is an existing cert which matches the .cnf/.csr
+
+        To prevent issuing a duplicate cert with the same name as an existing
+        issued cert, compare the .cnf/.csr filenames with the existing certs
+        in the certs_issued directory.
+        """
+        issued_cert_map = {
+            x.name: x for x in Path(self.repo_dir / "certs_issued").glob("**/*.crt")
+        }
+        if self.csr_file.with_suffix(".crt").name in issued_cert_map.keys():
+            print(
+                f"The .csr file {self.csr_file}, were it to be used to create a .crt"
+                f" file, would create {self.csr_file.with_suffix('.crt').name} which"
+                " has the same name as the existing issued cert"
+                f" {issued_cert_map[self.csr_file.with_suffix('.crt').name]}. This"
+                f" could cause a collision. Please change the name of {self.csr_file}"
+                f" and {self.cnf_file} to something distinct."
+            )
+            exit(1)
+
     def check_update_cnf_file(self) -> None:
         """Perform validation and update of the OpenSSL .cnf file.
 
@@ -355,7 +414,6 @@ def check_update_cnf_file(self) -> None:
         self.check_update_ca_crt()
         self.check_update_unique_subject()
         self.check_ca_files()
-        print("Check completed.")
 
     def check_environment(self, skip_git_fetch: bool) -> None:
         """Validate the git environment and prepare for CSR processing.
@@ -642,7 +700,8 @@ def process_usb_files(self, actions):
                 elif issubclass(type(actions[filename]), PurePath):
                     destination = Path(actions[filename] / filename.name)
                     shutil.copy2(filename, destination)
-                    # We only need to ensure that the execute bit isn't set because that's all that git records
+                    # We only need to ensure that the execute bit isn't set because
+                    # that's all that git records
                     # https://github.com/git/git/commit/e447947
                     destination.chmod(
                         destination.stat().st_mode
@@ -814,36 +873,16 @@ def pull_from_stick(
     """
     orchestrator = HsmOrchestrator(orchestrator_config_filename, repo_dir=repo_dir)
     orchestrator.choose_usb_disk()
+
     actions = {}  # Key is the file and value is the action to perform on that file
-    ca_cert_files_in_repo = {}
-    for private_key_directory in [
-        x
-        for x in Path(orchestrator.repo_dir / "certificate-authorities").iterdir()
-        if x.is_dir()
-    ]:
-        for certificate_authority_directory in private_key_directory.iterdir():
-            for certificate_file in certificate_authority_directory.iterdir():
-                ca_cert_files_in_repo[certificate_file.name] = certificate_file
-    crt_filenames_on_usb = set(x.name for x in orchestrator.usb_path.glob("*.crt"))
-    ca_cert_filenames_on_usb = ca_cert_files_in_repo.keys() & crt_filenames_on_usb
-    if len(ca_cert_filenames_on_usb) == 0:
-        print(
-            "No .crt files were found on the USB stick with names that match CA"
-            " certificate files.We would expect there to be one CA certificate file on"
-            " the USB stick."
-        )
-        exit(1)
-    if len(ca_cert_filenames_on_usb) > 1:
-        print(
-            "There are multiple .crt files on the USB stick with names that match CA"
-            " certificate files.We would only expect there to be one CA certificate"
-            " file on the USB stick."
-        )
-        exit(1)
-    ca_cert_filename_on_usb = next(iter(ca_cert_filenames_on_usb))
-    certificate_authority_directory = ca_cert_files_in_repo[
-        ca_cert_filename_on_usb
-    ].parent
+    ca_cert_filename_on_usb = orchestrator.get_ca_cert_filename_on_usb()
+    certificate_authority_directory = next(
+        iter([
+            x
+            for x in orchestrator.ca_cert_files_in_repo
+            if x.name == ca_cert_filename_on_usb
+        ])
+    ).parent
     # Delete the CA crt file on the USB stick
     actions[Path(orchestrator.usb_path / ca_cert_filename_on_usb)] = "delete"
 
@@ -925,6 +964,8 @@ def check(
     orchestrator.check_environment(skip_git_fetch)
     orchestrator.get_openssl_cnf_config()
     orchestrator.check_update_cnf_file()
+    orchestrator.check_for_matching_issued_cert()
+    print("Check completed.")
 
 
 if __name__ == "__main__":

tests/test_check.py

@@ -318,6 +318,29 @@ def test_missing_openssl_cnf(tmp_path, datafiles):
         re_search(r"The CSR .* has no associated \.cnf file\.", result.output)
 
 
+@pytest.mark.datafiles(FIXTURE_DIR / "example.csr", FIXTURE_DIR / "example.cnf")
+def test_cnf_csr_match_existing_certs_issued(tmp_path, datafiles, monkeypatch):
+    runner = CliRunner()
+    with runner.isolated_filesystem(tmp_path):
+        env = set_up_environment(tmp_path, datafiles, monkeypatch)
+        Path(datafiles / "example.cnf").rename(env["cnf_file"])
+        Path(env["repo_dir"] / "certs_issued" / "test" / "example.cnf").touch()
+        Path(env["repo_dir"] / "certs_issued" / "test" / "example.csr").touch()
+        Path(env["repo_dir"] / "certs_issued" / "test" / "example.crt").touch()
+        result = runner.invoke(
+            main,
+            ["check", "--skip-git-fetch", "--config", env["orchestrator_config_file"]],
+            input="",
+        )
+        re_search(
+            r"The \.csr file .*, were it to be used to create a \.crt file, would"
+            r" create example\.crt which has the same name as the existing issued cert"
+            r" .*\. This could cause a collision\. Please change the name of"
+            r" .*example\.csr and .*example\.cnf to something distinct\.",
+            result.output,
+        )
+
+
 @pytest.mark.datafiles(FIXTURE_DIR / "example.csr", FIXTURE_DIR / "example.cnf")
 def test_missing_default_ca_setting(tmp_path, datafiles, monkeypatch):
     runner = CliRunner()
@@ -783,7 +806,7 @@ def test_check(tmp_path, datafiles, monkeypatch):
     runner = CliRunner()
     with runner.isolated_filesystem(tmp_path):
         env = set_up_environment(tmp_path, datafiles, monkeypatch)
-        shutil.copy2(Path(datafiles / "example.cnf"), env["cnf_file"])
+        Path(datafiles / "example.cnf").rename(env["cnf_file"])
         result = runner.invoke(
             main,
             ["check", "--skip-git-fetch", "--config", env["orchestrator_config_file"]],

tests/test_pull.py

@@ -204,7 +204,8 @@ def test_file_actions(tmp_path, datafiles, monkeypatch):
         set_up_usb(env["usb_mount_point"])
         # Remove the certs_issued directory to make sure it gets created
         Path(env["repo_dir"] / "certs_issued" / "test").rmdir()
-        # Set the execute bits on the file so that we can test that they are cleared during the pull
+        # Set the execute bits on the file so that we can test that they are
+        # cleared during the pull
         Path(env["usb_mount_point"] / "AUT-123-testing.crt").chmod(0o755)
         keyboard_input = f"{env['usb_mount_point']}\nn\ny\n"
         result = runner.invoke(