Add support for Debian package signing

CHANGES/1300.feature

@@ -0,0 +1 @@
+Added (tech preview) support for signing Debian packages when uploading to a Repository.

pulp_deb/app/migrations/0032_package_signing.py

@@ -0,0 +1,52 @@
+# Generated by Django 4.2.25 on 2025-10-23 21:43
+
+from django.db import migrations, models
+import django.db.models.deletion
+import django_lifecycle.mixins
+import pulpcore.app.models.base
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('core', '0145_domainize_import_export'),
+        ('deb', '0001_initial_squashed_0031_add_domains'),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name='AptPackageSigningService',
+            fields=[
+                ('signingservice_ptr', models.OneToOneField(auto_created=True, on_delete=django.db.models.deletion.CASCADE, parent_link=True, primary_key=True, serialize=False, to='core.signingservice')),
+            ],
+            options={
+                'abstract': False,
+            },
+            bases=('core.signingservice',),
+        ),
+        migrations.AddField(
+            model_name='aptrepository',
+            name='package_signing_fingerprint',
+            field=models.TextField(max_length=40, null=True),
+        ),
+        migrations.AddField(
+            model_name='aptrepository',
+            name='package_signing_service',
+            field=models.ForeignKey(null=True, on_delete=django.db.models.deletion.SET_NULL, to='deb.aptpackagesigningservice'),
+        ),
+        migrations.CreateModel(
+            name='AptRepositoryReleasePackageSigningFingerprintOverride',
+            fields=[
+                ('pulp_id', models.UUIDField(default=pulpcore.app.models.base.pulp_uuid, editable=False, primary_key=True, serialize=False)),
+                ('pulp_created', models.DateTimeField(auto_now_add=True)),
+                ('pulp_last_updated', models.DateTimeField(auto_now=True, null=True)),
+                ('package_signing_fingerprint', models.TextField(max_length=40)),
+                ('release_distribution', models.TextField()),
+                ('repository', models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, related_name='package_signing_fingerprint_release_overrides', to='deb.aptrepository')),
+            ],
+            options={
+                'unique_together': {('repository', 'release_distribution')},
+            },
+            bases=(django_lifecycle.mixins.LifecycleModelMixin, models.Model),
+        ),
+    ]

pulp_deb/app/models/__init__.py

@@ -9,7 +9,7 @@
     SourcePackage,
 )
 
-from .signing_service import AptReleaseSigningService
+from .signing_service import AptReleaseSigningService, AptPackageSigningService
 
 from .content.metadata import (
     Release,
@@ -28,4 +28,8 @@
 
 from .remote import AptRemote
 
-from .repository import AptRepository, AptRepositoryReleaseServiceOverride
+from .repository import (
+    AptRepository,
+    AptRepositoryReleaseServiceOverride,
+    AptRepositoryReleasePackageSigningFingerprintOverride,
+)

pulp_deb/app/models/repository.py

@@ -28,6 +28,7 @@
     SourceIndex,
     SourcePackage,
     SourcePackageReleaseComponent,
+    AptPackageSigningService,
 )
 
 import logging
@@ -66,13 +67,24 @@ class AptRepository(Repository, AutoAddObjPermsMixin):
     signing_service = models.ForeignKey(
         AptReleaseSigningService, on_delete=models.PROTECT, null=True
     )
+
+    package_signing_service = models.ForeignKey(
+        AptPackageSigningService, on_delete=models.SET_NULL, null=True
+    )
+
+    package_signing_fingerprint = models.TextField(null=True, max_length=40)
+
     # Implicit signing_service_release_overrides
+    # Implicit package_signing_fingerprint_release_overrides
 
     class Meta:
         default_related_name = "%(app_label)s_%(model_name)s"
         permissions = [
             ("manage_roles_aptrepository", "Can manage roles on APT repositories"),
-            ("modify_content_aptrepository", "Add content to, or remove content from a repository"),
+            (
+                "modify_content_aptrepository",
+                "Add content to, or remove content from a repository",
+            ),
             ("repair_aptrepository", "Copy an APT repository"),
             ("sync_aptrepository", "Sync an APT repository"),
             ("delete_aptrepository_version", "Delete a repository version"),
@@ -91,6 +103,21 @@ def release_signing_service(self, release):
         except AptRepositoryReleaseServiceOverride.DoesNotExist:
             return self.signing_service
 
+    def release_package_signing_fingerprint(self, release):
+        """
+        Return the Package Signing Fingerprint specified in the overrides if there is one for this
+        release, else return self.package_signing_fingerprint.
+        """
+        if isinstance(release, Release):
+            release = release.distribution
+        try:
+            override = self.package_signing_fingerprint_release_overrides.get(
+                release_distribution=release
+            )
+            return override.package_signing_fingerprint
+        except AptRepositoryReleasePackageSigningFingerprintOverride.DoesNotExist:
+            return self.package_signing_fingerprint
+
     def initialize_new_version(self, new_version):
         """
         Remove old metadata from the repo before performing anything else for the new version. This
@@ -125,7 +152,9 @@ class AptRepositoryReleaseServiceOverride(BaseModel):
     """
 
     repository = models.ForeignKey(
-        AptRepository, on_delete=models.CASCADE, related_name="signing_service_release_overrides"
+        AptRepository,
+        on_delete=models.CASCADE,
+        related_name="signing_service_release_overrides",
     )
     signing_service = models.ForeignKey(AptReleaseSigningService, on_delete=models.PROTECT)
     release_distribution = models.TextField()
@@ -134,6 +163,24 @@ class Meta:
         unique_together = (("repository", "release_distribution"),)
 
 
+class AptRepositoryReleasePackageSigningFingerprintOverride(BaseModel):
+    """
+    Override the signing fingerprint that a single Release will use in this AptRepository for
+    signing packages.
+    """
+
+    repository = models.ForeignKey(
+        AptRepository,
+        on_delete=models.CASCADE,
+        related_name="package_signing_fingerprint_release_overrides",
+    )
+    package_signing_fingerprint = models.TextField(max_length=40)
+    release_distribution = models.TextField()
+
+    class Meta:
+        unique_together = (("repository", "release_distribution"),)
+
+
 def find_dist_components(package_ids, content_set):
     """
     Given a list of package_ids and a content_set, this function will find all distribution-

pulp_deb/app/models/signing_service.py

@@ -1,8 +1,30 @@
 import os
+from pathlib import Path
+import shutil
+import subprocess
+from typing import Optional
 import gnupg
 import tempfile
 
 from pulpcore.plugin.models import SigningService
+from importlib_resources import files
+
+
+def prepare_gpg(temp_directory_name, public_key, pubkey_fingerprint):
+    # Prepare GPG:
+    # gpg = gnupg.GPG(gnupghome=temp_directory_name)
+    gpg = gnupg.GPG(keyring=str(Path(temp_directory_name) / ".keyring"))
+    gpg.import_keys(public_key)
+    imported_keys = gpg.list_keys()
+
+    if len(imported_keys) != 1:
+        message = "We have imported more than one key! Aborting validation!"
+        raise RuntimeError(message)
+
+    if imported_keys[0]["fingerprint"] != pubkey_fingerprint:
+        message = "The signing service fingerprint does not appear to match its public key!"
+        raise RuntimeError(message)
+    return gpg
 
 
 class AptReleaseSigningService(SigningService):
@@ -70,19 +92,7 @@ def validate(self):
                         raise RuntimeError(message.format(signature_file, signature_type))
 
                 # Prepare GPG:
-                gpg = gnupg.GPG(gnupghome=temp_directory_name)
-                gpg.import_keys(self.public_key)
-                imported_keys = gpg.list_keys()
-
-                if len(imported_keys) != 1:
-                    message = "We have imported more than one key! Aborting validation!"
-                    raise RuntimeError(message)
-
-                if imported_keys[0]["fingerprint"] != self.pubkey_fingerprint:
-                    message = (
-                        "The signing service fingerprint does not appear to match its public key!"
-                    )
-                    raise RuntimeError(message)
+                gpg = prepare_gpg(temp_directory_name, self.public_key, self.pubkey_fingerprint)
 
                 # Verify InRelease file
                 inline_path = signatures.get("inline")
@@ -138,3 +148,105 @@ def validate(self):
                         if verified.pubkey_fingerprint != self.pubkey_fingerprint:
                             message = "'{}' appears to have been signed using the wrong key!"
                             raise RuntimeError(message.format(detached_path))
+
+
+class AptPackageSigningService(SigningService):
+    """
+    A model used for signing Apt packages.
+
+    The pubkey_fingerprint should be passed explicitly in the sign method.
+    """
+
+    def _env_variables(self, env_vars=None):
+        # Prevent the signing service pubkey to be used for signing a package.
+        # The pubkey should be provided explicitly.
+        _env_vars = {"PULP_SIGNING_KEY_FINGERPRINT": None}
+        if env_vars:
+            _env_vars.update(env_vars)
+        return super()._env_variables(_env_vars)
+
+    def sign(
+        self,
+        filename: str,
+        env_vars: Optional[dict] = None,
+        pubkey_fingerprint: Optional[str] = None,
+    ):
+        """
+        Sign a package @filename using @pubkey_fingerprint.
+
+        Args:
+            filename: The absolute path to the package to be signed.
+            env_vars: (optional) Dict of env_vars to be passed to the signing script.
+            pubkey_fingerprint: The V4 fingerprint that correlates with the private key to use.
+        """
+        if not pubkey_fingerprint:
+            raise ValueError("A pubkey_fingerprint must be provided.")
+        _env_vars = env_vars or {}
+        _env_vars["PULP_SIGNING_KEY_FINGERPRINT"] = pubkey_fingerprint
+        return super().sign(filename, _env_vars)
+
+    def validate(self):
+        """
+        Validate a signing service for an Apt package signature.
+
+        Specifically, it validates that self.signing_script can sign an apt package with
+        the sample key self.pubkey and that the self.sign() method returns:
+
+        ```json
+        {"apt_package": "<path/to/package.deb>"}
+        ```
+
+        Recreates the check that "debsig-verify" would be doing because debsig-verify is
+        complicated to set up correctly, and doing so would add a dependency that is not available
+        on rpm-based systems.
+        """
+        with tempfile.TemporaryDirectory() as temp_directory_name:
+            # copy test deb package
+            sample_deb = shutil.copy(
+                files("pulp_deb").joinpath("tests/functional/data/packages/frigg_1.0_ppc64.deb"),
+                temp_directory_name,
+            )
+            return_value = self.sign(sample_deb, pubkey_fingerprint=self.pubkey_fingerprint)
+            try:
+                signed_deb = return_value["deb_package"]
+            except KeyError:
+                raise Exception(f"Malformed output from signing script: {return_value}")
+
+            # Prepare GPG:
+            gpg = prepare_gpg(temp_directory_name, self.public_key, self.pubkey_fingerprint)
+
+            self._validate_deb_package(signed_deb, self.pubkey_fingerprint, temp_directory_name, gpg)
+
+
+    @staticmethod
+    def _validate_deb_package(deb_package_path: str, pubkey_fingerprint: str, temp_directory_name: str, gpg: gnupg.GPG):
+        """
+        Validate that the deb package at @deb_package_path is correctly signed.
+
+        This is a placeholder for future validation logic if needed.
+        """
+        # unpack the archive
+        cmd = ["ar", "x", deb_package_path]
+        res = subprocess.run(cmd, cwd=temp_directory_name, capture_output=True)
+        if res.returncode != 0:
+            raise Exception(f"Failed to read package {deb_package_path}. Please check the package.")
+
+        # cat the unpacked archive bits together
+        temp_dir = Path(temp_directory_name)
+        with (temp_dir / "combined").open("wb") as combined:
+            for filename in ("debian-binary", "control.*", "data.*"):
+                # There will only be one control.tar.gz (or whatever) file, but we have to glob
+                # and iterate because the compression type can vary.
+                for x in temp_dir.glob(filename):
+                    with x.open("rb") as f:
+                        shutil.copyfileobj(f, combined)
+
+        # verify combined data with _gpgorigin detached signature
+        with (temp_dir / "_gpgorigin").open("rb") as gpgorigin:
+            verified = gpg.verify_file(gpgorigin, str(temp_dir / "combined"))
+            if not verified.valid:
+                raise Exception(f"GPG Verification of the signed package {deb_package_path} failed!")
+            if verified.pubkey_fingerprint != pubkey_fingerprint:
+                raise Exception(
+                    f"'{deb_package_path}' appears to have been signed using the wrong key!"
+                )

pulp_deb/app/serializers/content_serializers.py

@@ -694,6 +694,37 @@ def deferred_validate(self, data):
 
         return data
 
+    def validate(self, data):
+        validated_data = super().validate(data)
+        sign_package = self.context.get("sign_package", None)
+        # choose branch, if not set externally
+        if sign_package is None:
+            sign_package = bool(
+                validated_data.get("repository")
+                and validated_data["repository"].package_signing_service
+            )
+            self.context["sign_package"] = sign_package
+
+        # normal branch
+        if sign_package is False:
+            return validated_data
+
+        # signing branch
+        if not validated_data["repository"].package_signing_fingerprint:
+            raise ValidationError(
+                _(
+                    "To sign a package on upload, the associated Repository must set both"
+                    "'package_signing_service' and 'package_signing_fingerprint'."
+                )
+            )
+
+        if not validated_data.get("file") and not validated_data.get("upload"):
+            raise ValidationError(
+                _("To sign a package on upload, a file or upload must be provided.")
+            )
+
+        return validated_data
+
     class Meta(SinglePackageUploadSerializer.Meta):
         fields = (
             SinglePackageUploadSerializer.Meta.fields