diff --git a/src/olympia/users/migrations/0027_restriction_history_matches.py b/src/olympia/users/migrations/0027_restriction_history_matches.py
new file mode 100644
index 000000000000..3503461a82e0
--- /dev/null
+++ b/src/olympia/users/migrations/0027_restriction_history_matches.py
@@ -0,0 +1,50 @@
+# Generated by Django 5.2.17 on 2026-08-24 16:23
+
+import django.db.models.deletion
+import django.utils.timezone
+import olympia.amo.models
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('contenttypes', '0002_remove_content_type_name'),
+        ('files', '0038_remove_enable_mv3_submissions_switch'),
+        ('users', '0026_alter_userrestrictionhistory_restriction_and_more'),
+        ('versions', '0053_auto_20260720_1345'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='userrestrictionhistory',
+            name='restriction_type',
+            field=models.PositiveSmallIntegerField(choices=[(1, 'Add-on Submission'), (2, 'Add-on Approval'), (3, 'Rating'), (4, 'Rating Flag for Moderation')], null=True),
+        ),
+        migrations.AddField(
+            model_name='userrestrictionhistory',
+            name='upload',
+            field=models.ForeignKey(null=True, on_delete=django.db.models.deletion.SET_NULL, related_name='restriction_history', to='files.fileupload'),
+        ),
+        migrations.AddField(
+            model_name='userrestrictionhistory',
+            name='version',
+            field=models.ForeignKey(null=True, on_delete=django.db.models.deletion.SET_NULL, related_name='restriction_history', to='versions.version'),
+        ),
+        migrations.CreateModel(
+            name='UserRestrictionHistoryMatch',
+            fields=[
+                ('id', models.AutoField(auto_created=True, primary_key=True, serialize=False, verbose_name='ID')),
+                ('created', models.DateTimeField(blank=True, default=django.utils.timezone.now, editable=False)),
+                ('modified', models.DateTimeField(auto_now=True)),
+                ('object_id', models.PositiveIntegerField()),
+                ('snapshot', models.CharField(max_length=255)),
+                ('content_type', models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, to='contenttypes.contenttype')),
+                ('history', models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, related_name='matches', to='users.userrestrictionhistory')),
+            ],
+            options={
+                'verbose_name_plural': 'User Restriction History Matches',
+            },
+            bases=(olympia.amo.models.SaveUpdateMixin, models.Model),
+        ),
+    ]
diff --git a/src/olympia/users/models.py b/src/olympia/users/models.py
index e6a5ba017840..9fc3c06a9299 100644
--- a/src/olympia/users/models.py
+++ b/src/olympia/users/models.py
@@ -13,6 +13,8 @@
 from django.conf import settings
 from django.contrib.auth.models import AbstractBaseUser, BaseUserManager
 from django.contrib.auth.signals import user_logged_in
+from django.contrib.contenttypes.fields import GenericForeignKey
+from django.contrib.contenttypes.models import ContentType
 from django.core import validators
 from django.core.exceptions import ValidationError
 from django.core.files.uploadedfile import SimpleUploadedFile
@@ -1430,6 +1432,27 @@ class UserRestrictionHistory(ModelBase):
     )
     ip_address = models.CharField(default='', max_length=45)
     last_login_ip = models.CharField(default='', max_length=45)
+    # The action that was being checked when the restriction fired. Null on
+    # records created before we started recording it.
+    restriction_type = models.PositiveSmallIntegerField(
+        null=True, choices=RESTRICTION_TYPES.choices
+    )
+    # Set by RestrictionChecker when it was given an upload (auto-approval),
+    # null on the request-based paths where there is no upload.
+    upload = models.ForeignKey(
+        'files.FileUpload',
+        related_name='restriction_history',
+        on_delete=models.SET_NULL,
+        null=True,
+    )
+    # Backfilled by Version.from_upload(): the checker runs before the version
+    # exists, so it can't set this itself.
+    version = models.ForeignKey(
+        'versions.Version',
+        related_name='restriction_history',
+        on_delete=models.SET_NULL,
+        null=True,
+    )
 
     class Meta:
         verbose_name_plural = 'User Restriction History'
@@ -1445,6 +1468,34 @@ class Meta:
         ]
 
 
+class UserRestrictionHistoryMatch(ModelBase):
+    """A specific restriction instance that matched during a failed check.
+
+    A single failed check can match more than one restriction (unlike the
+    boolean path, which stops at the first match), so these hang off
+    UserRestrictionHistory rather than being fields on it. A failure with no
+    matches at all is legitimate: several restriction classes aren't backed by
+    the database, and the database-backed ones can deny structurally, without
+    any row being involved.
+    """
+
+    history = models.ForeignKey(
+        UserRestrictionHistory, related_name='matches', on_delete=models.CASCADE
+    )
+    # The matched restriction can belong to any of the database-backed
+    # restriction models, hence a generic foreign key rather than a plain one.
+    content_type = models.ForeignKey(ContentType, on_delete=models.CASCADE)
+    object_id = models.PositiveIntegerField()
+    restriction = GenericForeignKey('content_type', 'object_id')
+    # str() of the restriction as it was when it matched. Restrictions get
+    # edited and bulk-deleted, so the foreign key above will eventually dangle
+    # or point at something that has since changed; this keeps history honest.
+    snapshot = models.CharField(max_length=255)
+
+    class Meta:
+        verbose_name_plural = 'User Restriction History Matches'
+
+
 class UserHistory(ModelBase):
     id = PositiveAutoField(primary_key=True)
     email = models.EmailField(max_length=75)