fix(merge): Handle unique constraint conflicts in merge_users_for_model_in_org

src/sentry/backup/dependencies.py

@@ -7,7 +7,7 @@
 from typing import NamedTuple
 
 from django.db import models
-from django.db.models import Q, UniqueConstraint
+from django.db.models import Exists, OuterRef, Q, UniqueConstraint
 from django.db.models.fields.related import ForeignKey, OneToOneField
 
 from sentry.backup.helpers import EXCLUDED_APPS
@@ -704,6 +704,26 @@ def dedupe_and_reassign_groupsubscription_in_org(
     GroupSubscription.objects.filter(scoped, user_id=from_user_id).update(user_id=to_user_id)
 
 
+def _get_unique_constraints_for_field(
+    model: type[models.base.Model], field_name: str
+) -> list[tuple[frozenset[str], Q | None]]:
+    """
+    Return all unique constraints on ``model`` that include ``field_name``.
+    Each entry is ``(frozenset_of_field_names, optional_condition_Q)``.
+    """
+    results: list[tuple[frozenset[str], Q | None]] = []
+    for combo in model._meta.unique_together:
+        fields = frozenset(combo)
+        if field_name in fields:
+            results.append((fields, None))
+    for constraint in model._meta.constraints:
+        if isinstance(constraint, UniqueConstraint):
+            fields = frozenset(constraint.fields)
+            if field_name in fields:
+                results.append((fields, getattr(constraint, "condition", None)))
+    return results
+
+
 def merge_users_for_model_in_org(
     model: type[models.base.Model], *, organization_id: int, from_user_id: int, to_user_id: int
 ) -> None:
@@ -739,5 +759,26 @@ def merge_users_for_model_in_org(
     for_this_org = Q(**{field_name: organization_id for field_name in org_refs})
 
     for user_ref in user_refs:
+        # Delete from_user rows that would violate unique constraints when updated.
+        for unique_fields, condition in _get_unique_constraints_for_field(model, user_ref):
+            other_fields = unique_fields - {user_ref}
+            if not other_fields:
+                continue
+
+            # Build Exists subquery: find to_user rows matching on all non-user fields.
+            subquery_kwargs: dict[str, object] = {user_ref: to_user_id}
+            for field in other_fields:
+                subquery_kwargs[field] = OuterRef(field)
+
+            subquery = model.objects.filter(**subquery_kwargs)
+            if condition is not None:
+                subquery = subquery.filter(condition)
+
+            qs = model.objects.filter(for_this_org, **{user_ref: from_user_id})
+            if condition is not None:
+                qs = qs.filter(condition)
+            qs.filter(Exists(subquery)).delete()
+
+        # Now safe to update remaining rows.
         q = for_this_org & Q(**{user_ref: from_user_id})
         model.objects.filter(q).update(**{user_ref: to_user_id})

tests/sentry/users/models/test_user.py

@@ -307,6 +307,56 @@ def test_merge_handles_groupsubscription_conflicts(self) -> None:
             assert not GroupSubscription.objects.filter(group=group, user_id=from_user.id).exists()
             assert GroupSubscription.objects.filter(group=group, user_id=to_user.id).count() == 1
 
+    def test_merge_handles_recentsearch_conflicts(self) -> None:
+        from sentry.utils.hashlib import md5_text
+
+        from_user = self.create_user("from-user@example.com")
+        to_user = self.create_user("to-user@example.com")
+        org = self.create_organization(name="recentsearch-conflict-org")
+
+        with outbox_runner():
+            with assume_test_silo_mode(SiloMode.CELL):
+                self.create_member(user=from_user, organization=org)
+
+        with assume_test_silo_mode(SiloMode.CELL):
+            query = "is:unresolved"
+            query_hash = md5_text(query).hexdigest()
+            RecentSearch.objects.create(
+                organization=org, user_id=from_user.id, type=0, query=query, query_hash=query_hash
+            )
+            RecentSearch.objects.create(
+                organization=org, user_id=to_user.id, type=0, query=query, query_hash=query_hash
+            )
+
+        with outbox_runner():
+            from_user.merge_to(to_user)
+
+        with assume_test_silo_mode(SiloMode.CELL):
+            assert not RecentSearch.objects.filter(organization=org, user_id=from_user.id).exists()
+            assert RecentSearch.objects.filter(organization=org, user_id=to_user.id).count() == 1
+
+    def test_merge_handles_groupbookmark_conflicts(self) -> None:
+        from_user = self.create_user("from-user@example.com")
+        to_user = self.create_user("to-user@example.com")
+        org = self.create_organization(name="bookmark-conflict-org")
+
+        with outbox_runner():
+            with assume_test_silo_mode(SiloMode.CELL):
+                self.create_member(user=from_user, organization=org)
+
+        with assume_test_silo_mode(SiloMode.CELL):
+            project = self.create_project(organization=org)
+            group = self.create_group(project=project)
+            GroupBookmark.objects.create(project=project, group=group, user_id=from_user.id)
+            GroupBookmark.objects.create(project=project, group=group, user_id=to_user.id)
+
+        with outbox_runner():
+            from_user.merge_to(to_user)
+
+        with assume_test_silo_mode(SiloMode.CELL):
+            assert not GroupBookmark.objects.filter(group=group, user_id=from_user.id).exists()
+            assert GroupBookmark.objects.filter(group=group, user_id=to_user.id).count() == 1
+
     @expect_models(
         ORG_MEMBER_MERGE_TESTED,
         OrgAuthToken,