diff --git a/src/core/tasks/scheduled/impl/internet_archives/probe/operator.py b/src/core/tasks/scheduled/impl/internet_archives/probe/operator.py
index f1ae27cd..f4773417 100644
--- a/src/core/tasks/scheduled/impl/internet_archives/probe/operator.py
+++ b/src/core/tasks/scheduled/impl/internet_archives/probe/operator.py
@@ -5,6 +5,8 @@
 from src.core.tasks.scheduled.impl.internet_archives.probe.convert import convert_ia_url_mapping_to_ia_metadata
 from src.core.tasks.scheduled.impl.internet_archives.probe.filter import filter_into_subsets
 from src.core.tasks.scheduled.impl.internet_archives.probe.models.subset import IAURLMappingSubsets
+from src.core.tasks.scheduled.impl.internet_archives.probe.queries.delete import \
+    DeleteOldUnsuccessfulIACheckedFlagsQueryBuilder
 from src.core.tasks.scheduled.impl.internet_archives.probe.queries.get import GetURLsForInternetArchivesTaskQueryBuilder
 from src.core.tasks.scheduled.impl.internet_archives.probe.queries.prereq import \
     CheckURLInternetArchivesTaskPrerequisitesQueryBuilder
@@ -45,6 +47,10 @@ async def meets_task_prerequisites(self) -> bool:
         )
 
     async def inner_task_logic(self) -> None:
+        await self.adb_client.run_query_builder(
+            DeleteOldUnsuccessfulIACheckedFlagsQueryBuilder()
+        )
+
         url_mappings: list[URLMapping] = await self._get_url_mappings()
         if len(url_mappings) == 0:
             return
diff --git a/src/core/tasks/scheduled/impl/internet_archives/probe/queries/cte.py b/src/core/tasks/scheduled/impl/internet_archives/probe/queries/cte.py
new file mode 100644
index 00000000..7de8b290
--- /dev/null
+++ b/src/core/tasks/scheduled/impl/internet_archives/probe/queries/cte.py
@@ -0,0 +1,42 @@
+from sqlalchemy import select, or_, exists, func, text, CTE, ColumnElement
+
+from src.db.helpers.query import not_exists_url
+from src.db.models.impl.flag.checked_for_ia.sqlalchemy import FlagURLCheckedForInternetArchives
+from src.db.models.impl.url.core.sqlalchemy import URL
+
+
+class CheckURLInternetArchivesCTEContainer:
+
+    def __init__(self):
+
+        self._cte = (
+            select(
+                URL.id.label("url_id"),
+                URL.url
+            )
+            .where(
+                or_(
+                    not_exists_url(FlagURLCheckedForInternetArchives),
+                    exists(
+                        select(FlagURLCheckedForInternetArchives.url_id)
+                        .where(
+                            FlagURLCheckedForInternetArchives.url_id == URL.id,
+                            ~FlagURLCheckedForInternetArchives.success,
+                            FlagURLCheckedForInternetArchives.created_at < func.now() - text("INTERVAL '1 week'")
+                        )
+                    )
+                )
+            ).cte("check_url_internet_archives_prereq")
+        )
+
+    @property
+    def cte(self) -> CTE:
+        return self._cte
+
+    @property
+    def url_id(self) -> ColumnElement[int]:
+        return self._cte.c.url_id
+
+    @property
+    def url(self) -> ColumnElement[str]:
+        return self._cte.c.url
\ No newline at end of file
diff --git a/src/core/tasks/scheduled/impl/internet_archives/probe/queries/delete.py b/src/core/tasks/scheduled/impl/internet_archives/probe/queries/delete.py
new file mode 100644
index 00000000..2d9a08e1
--- /dev/null
+++ b/src/core/tasks/scheduled/impl/internet_archives/probe/queries/delete.py
@@ -0,0 +1,24 @@
+from sqlalchemy import delete, exists, select
+from sqlalchemy.ext.asyncio import AsyncSession
+
+from src.core.tasks.scheduled.impl.internet_archives.probe.queries.cte import CheckURLInternetArchivesCTEContainer
+from src.db.models.impl.flag.checked_for_ia.sqlalchemy import FlagURLCheckedForInternetArchives
+from src.db.queries.base.builder import QueryBuilderBase
+
+class DeleteOldUnsuccessfulIACheckedFlagsQueryBuilder(QueryBuilderBase):
+
+    async def run(self, session: AsyncSession) -> None:
+        cte = CheckURLInternetArchivesCTEContainer()
+        query = (
+            delete(FlagURLCheckedForInternetArchives)
+            .where(
+                exists(
+                    select(cte.url_id)
+                    .where(
+                        FlagURLCheckedForInternetArchives.url_id == cte.url_id,
+                    )
+                )
+            )
+        )
+
+        await session.execute(query)
\ No newline at end of file
diff --git a/src/core/tasks/scheduled/impl/internet_archives/probe/queries/get.py b/src/core/tasks/scheduled/impl/internet_archives/probe/queries/get.py
index 94f2ad5e..3306943a 100644
--- a/src/core/tasks/scheduled/impl/internet_archives/probe/queries/get.py
+++ b/src/core/tasks/scheduled/impl/internet_archives/probe/queries/get.py
@@ -1,7 +1,9 @@
-from sqlalchemy import select
+from sqlalchemy import select, or_, exists, text, func
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from src.core.tasks.scheduled.impl.internet_archives.probe.queries.cte import CheckURLInternetArchivesCTEContainer
 from src.db.dtos.url.mapping import URLMapping
+from src.db.helpers.query import not_exists_url
 from src.db.models.impl.flag.checked_for_ia.sqlalchemy import FlagURLCheckedForInternetArchives
 from src.db.models.impl.url.core.sqlalchemy import URL
 from src.db.queries.base.builder import QueryBuilderBase
@@ -11,23 +13,19 @@
 class GetURLsForInternetArchivesTaskQueryBuilder(QueryBuilderBase):
 
     async def run(self, session: AsyncSession) -> list[URLMapping]:
+        cte = CheckURLInternetArchivesCTEContainer()
         query = (
             select(
-                URL.id,
-                URL.url
+                cte.url_id,
+                cte.url
             )
-            .outerjoin(
-                FlagURLCheckedForInternetArchives,
-                URL.id == FlagURLCheckedForInternetArchives.url_id
-            )
-            .where(FlagURLCheckedForInternetArchives.url_id.is_(None))
             .limit(100)
         )
 
         db_mappings = await sh.mappings(session, query=query)
         return [
             URLMapping(
-                url_id=mapping["id"],
+                url_id=mapping["url_id"],
                 url=mapping["url"]
             ) for mapping in db_mappings
         ]
diff --git a/src/core/tasks/scheduled/impl/internet_archives/probe/queries/prereq.py b/src/core/tasks/scheduled/impl/internet_archives/probe/queries/prereq.py
index 7a7d8687..d8994641 100644
--- a/src/core/tasks/scheduled/impl/internet_archives/probe/queries/prereq.py
+++ b/src/core/tasks/scheduled/impl/internet_archives/probe/queries/prereq.py
@@ -1,6 +1,7 @@
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
+from src.core.tasks.scheduled.impl.internet_archives.probe.queries.cte import CheckURLInternetArchivesCTEContainer
 from src.db.helpers.query import not_exists_url
 from src.db.models.impl.flag.checked_for_ia.sqlalchemy import FlagURLCheckedForInternetArchives
 from src.db.models.impl.url.core.sqlalchemy import URL
@@ -11,12 +12,8 @@
 class CheckURLInternetArchivesTaskPrerequisitesQueryBuilder(QueryBuilderBase):
 
     async def run(self, session: AsyncSession) -> bool:
+        cte = CheckURLInternetArchivesCTEContainer()
         query = (
-            select(URL)
-            .where(
-                not_exists_url(FlagURLCheckedForInternetArchives)
-            )
-            .limit(1)
+            select(cte.url_id)
         )
-        result = await sh.one_or_none(session, query=query)
-        return result is not None
+        return await sh.results_exist(session, query=query)
diff --git a/src/db/models/impl/flag/checked_for_ia/sqlalchemy.py b/src/db/models/impl/flag/checked_for_ia/sqlalchemy.py
index 87914eb2..efdf9257 100644
--- a/src/db/models/impl/flag/checked_for_ia/sqlalchemy.py
+++ b/src/db/models/impl/flag/checked_for_ia/sqlalchemy.py
@@ -1,13 +1,14 @@
 from sqlalchemy import PrimaryKeyConstraint
 from sqlalchemy.orm import Mapped
 
-from src.db.models.mixins import URLDependentMixin
+from src.db.models.mixins import URLDependentMixin, CreatedAtMixin
 from src.db.models.templates_.base import Base
 from src.db.models.templates_.with_id import WithIDBase
 
 
 class FlagURLCheckedForInternetArchives(
     URLDependentMixin,
+    CreatedAtMixin,
     Base
 ):