diff --git a/pageserver/src/tenant.rs b/pageserver/src/tenant.rs
index c6fc3bfe6c8c..909f99ea9d07 100644
--- a/pageserver/src/tenant.rs
+++ b/pageserver/src/tenant.rs
@@ -39,6 +39,7 @@ use remote_timeline_client::UploadQueueNotReadyError;
 use std::collections::BTreeMap;
 use std::fmt;
 use std::future::Future;
+use std::sync::atomic::AtomicBool;
 use std::sync::Weak;
 use std::time::SystemTime;
 use storage_broker::BrokerClientChannel;
@@ -524,6 +525,9 @@ pub struct OffloadedTimeline {
     /// Prevent two tasks from deleting the timeline at the same time. If held, the
     /// timeline is being deleted. If 'true', the timeline has already been deleted.
     pub delete_progress: TimelineDeleteProgress,
+
+    /// Part of the `OffloadedTimeline` object's lifecycle: this needs to be set before we drop it
+    pub deleted_from_ancestor: AtomicBool,
 }
 
 impl OffloadedTimeline {
@@ -533,9 +537,16 @@ impl OffloadedTimeline {
     /// the timeline is not in a stopped state.
     /// Panics if the timeline is not archived.
     fn from_timeline(timeline: &Timeline) -> Result<Self, UploadQueueNotReadyError> {
-        let ancestor_retain_lsn = timeline
-            .get_ancestor_timeline_id()
-            .map(|_timeline_id| timeline.get_ancestor_lsn());
+        let (ancestor_retain_lsn, ancestor_timeline_id) =
+            if let Some(ancestor_timeline) = timeline.ancestor_timeline() {
+                let ancestor_lsn = timeline.get_ancestor_lsn();
+                let ancestor_timeline_id = ancestor_timeline.timeline_id;
+                let mut gc_info = ancestor_timeline.gc_info.write().unwrap();
+                gc_info.insert_child(timeline.timeline_id, ancestor_lsn, MaybeOffloaded::Yes);
+                (Some(ancestor_lsn), Some(ancestor_timeline_id))
+            } else {
+                (None, None)
+            };
         let archived_at = timeline
             .remote_client
             .archived_at_stopped_queue()?
@@ -543,14 +554,17 @@ impl OffloadedTimeline {
         Ok(Self {
             tenant_shard_id: timeline.tenant_shard_id,
             timeline_id: timeline.timeline_id,
-            ancestor_timeline_id: timeline.get_ancestor_timeline_id(),
+            ancestor_timeline_id,
             ancestor_retain_lsn,
             archived_at,
 
             delete_progress: timeline.delete_progress.clone(),
+            deleted_from_ancestor: AtomicBool::new(false),
         })
     }
     fn from_manifest(tenant_shard_id: TenantShardId, manifest: &OffloadedTimelineManifest) -> Self {
+        // We expect to reach this case in tenant loading, where the `retain_lsn` is populated in the parent's `gc_info`
+        // by the `initialize_gc_info` function.
         let OffloadedTimelineManifest {
             timeline_id,
             ancestor_timeline_id,
@@ -564,6 +578,7 @@ impl OffloadedTimeline {
             ancestor_retain_lsn,
             archived_at,
             delete_progress: TimelineDeleteProgress::default(),
+            deleted_from_ancestor: AtomicBool::new(false),
         }
     }
     fn manifest(&self) -> OffloadedTimelineManifest {
@@ -581,6 +596,33 @@ impl OffloadedTimeline {
             archived_at: *archived_at,
         }
     }
+    /// Delete this timeline's retain_lsn from its ancestor, if present in the given tenant
+    fn delete_from_ancestor_with_timelines(
+        &self,
+        timelines: &std::sync::MutexGuard<'_, HashMap<TimelineId, Arc<Timeline>>>,
+    ) {
+        if let (Some(_retain_lsn), Some(ancestor_timeline_id)) =
+            (self.ancestor_retain_lsn, self.ancestor_timeline_id)
+        {
+            if let Some((_, ancestor_timeline)) = timelines
+                .iter()
+                .find(|(tid, _tl)| **tid == ancestor_timeline_id)
+            {
+                ancestor_timeline
+                    .gc_info
+                    .write()
+                    .unwrap()
+                    .remove_child_offloaded(self.timeline_id);
+            }
+        }
+        self.deleted_from_ancestor.store(true, Ordering::Release);
+    }
+    /// Call [`Self::delete_from_ancestor_with_timelines`] instead if possible.
+    ///
+    /// As the entire tenant is being dropped, don't bother deregistering the `retain_lsn` from the ancestor.
+    fn defuse_for_tenant_drop(&self) {
+        self.deleted_from_ancestor.store(true, Ordering::Release);
+    }
 }
 
 impl fmt::Debug for OffloadedTimeline {
@@ -589,6 +631,17 @@ impl fmt::Debug for OffloadedTimeline {
     }
 }
 
+impl Drop for OffloadedTimeline {
+    fn drop(&mut self) {
+        if !self.deleted_from_ancestor.load(Ordering::Acquire) {
+            tracing::warn!(
+                "offloaded timeline {} was dropped without having cleaned it up at the ancestor",
+                self.timeline_id
+            );
+        }
+    }
+}
+
 #[derive(Copy, Clone, PartialEq, Eq, Hash, Debug)]
 pub enum MaybeOffloaded {
     Yes,
@@ -1531,7 +1584,7 @@ impl Tenant {
         }
         // Complete deletions for offloaded timeline id's.
         offloaded_timelines_list
-            .retain(|(offloaded_id, _offloaded)| {
+            .retain(|(offloaded_id, offloaded)| {
                 // At this point, offloaded_timeline_ids has the list of all offloaded timelines
                 // without a prefix in S3, so they are inexistent.
                 // In the end, existence of a timeline is finally determined by the existence of an index-part.json in remote storage.
@@ -1539,6 +1592,7 @@ impl Tenant {
                 let delete = offloaded_timeline_ids.contains(offloaded_id);
                 if delete {
                     tracing::info!("Removing offloaded timeline {offloaded_id} from manifest as no remote prefix was found");
+                    offloaded.defuse_for_tenant_drop();
                 }
                 !delete
         });
@@ -1927,9 +1981,15 @@ impl Tenant {
                 )));
             };
             let mut offloaded_timelines = self.timelines_offloaded.lock().unwrap();
-            if offloaded_timelines.remove(&timeline_id).is_none() {
-                warn!("timeline already removed from offloaded timelines");
+            match offloaded_timelines.remove(&timeline_id) {
+                Some(offloaded) => {
+                    offloaded.delete_from_ancestor_with_timelines(&timelines);
+                }
+                None => warn!("timeline already removed from offloaded timelines"),
             }
+
+            self.initialize_gc_info(&timelines, &offloaded_timelines, Some(timeline_id));
+
             Arc::clone(timeline)
         };
 
@@ -2667,7 +2727,7 @@ impl Tenant {
                 .filter(|timeline| !(timeline.is_broken() || timeline.is_stopping()));
 
             // Before activation, populate each Timeline's GcInfo with information about its children
-            self.initialize_gc_info(&timelines_accessor, &timelines_offloaded_accessor);
+            self.initialize_gc_info(&timelines_accessor, &timelines_offloaded_accessor, None);
 
             // Spawn gc and compaction loops. The loops will shut themselves
             // down when they notice that the tenant is inactive.
@@ -2782,8 +2842,14 @@ impl Tenant {
                 let timeline_id = timeline.timeline_id;
                 let span = tracing::info_span!("timeline_shutdown", %timeline_id, ?shutdown_mode);
                 js.spawn(async move { timeline.shutdown(shutdown_mode).instrument(span).await });
-            })
-        };
+            });
+        }
+        {
+            let timelines_offloaded = self.timelines_offloaded.lock().unwrap();
+            timelines_offloaded.values().for_each(|timeline| {
+                timeline.defuse_for_tenant_drop();
+            });
+        }
         // test_long_timeline_create_then_tenant_delete is leaning on this message
         tracing::info!("Waiting for timelines...");
         while let Some(res) = js.join_next().await {
@@ -3767,10 +3833,13 @@ impl Tenant {
         &self,
         timelines: &std::sync::MutexGuard<HashMap<TimelineId, Arc<Timeline>>>,
         timelines_offloaded: &std::sync::MutexGuard<HashMap<TimelineId, Arc<OffloadedTimeline>>>,
+        restrict_to_timeline: Option<TimelineId>,
     ) {
-        // This function must be called before activation: after activation timeline create/delete operations
-        // might happen, and this function is not safe to run concurrently with those.
-        assert!(!self.is_active());
+        if restrict_to_timeline.is_none() {
+            // This function must be called before activation: after activation timeline create/delete operations
+            // might happen, and this function is not safe to run concurrently with those.
+            assert!(!self.is_active());
+        }
 
         // Scan all timelines. For each timeline, remember the timeline ID and
         // the branch point where it was created.
@@ -3803,7 +3872,12 @@ impl Tenant {
         let horizon = self.get_gc_horizon();
 
         // Populate each timeline's GcInfo with information about its child branches
-        for timeline in timelines.values() {
+        let timelines_to_write = if let Some(timeline_id) = restrict_to_timeline {
+            itertools::Either::Left(timelines.get(&timeline_id).into_iter())
+        } else {
+            itertools::Either::Right(timelines.values())
+        };
+        for timeline in timelines_to_write {
             let mut branchpoints: Vec<(Lsn, TimelineId, MaybeOffloaded)> = all_branchpoints
                 .remove(&timeline.timeline_id)
                 .unwrap_or_default();
@@ -9650,4 +9724,54 @@ mod tests {
 
         Ok(())
     }
+
+    #[cfg(feature = "testing")]
+    #[tokio::test]
+    async fn test_timeline_offload_retain_lsn() -> anyhow::Result<()> {
+        let harness = TenantHarness::create("test_timeline_offload_retain_lsn")
+            .await
+            .unwrap();
+        let (tenant, ctx) = harness.load().await;
+        let tline_parent = tenant
+            .create_test_timeline(TIMELINE_ID, Lsn(0x10), DEFAULT_PG_VERSION, &ctx)
+            .await
+            .unwrap();
+        let tline_child = tenant
+            .branch_timeline_test(&tline_parent, NEW_TIMELINE_ID, Some(Lsn(0x20)), &ctx)
+            .await
+            .unwrap();
+        {
+            let gc_info_parent = tline_parent.gc_info.read().unwrap();
+            assert_eq!(
+                gc_info_parent.retain_lsns,
+                vec![(Lsn(0x20), tline_child.timeline_id, MaybeOffloaded::No)]
+            );
+        }
+        // We have to directly call the remote_client instead of using the archive function to avoid constructing broker client...
+        tline_child
+            .remote_client
+            .schedule_index_upload_for_timeline_archival_state(TimelineArchivalState::Archived)
+            .unwrap();
+        tline_child.remote_client.wait_completion().await.unwrap();
+        offload_timeline(&tenant, &tline_child)
+            .instrument(tracing::info_span!(parent: None, "offload_test", tenant_id=%"test", shard_id=%"test", timeline_id=%"test"))
+            .await.unwrap();
+        let child_timeline_id = tline_child.timeline_id;
+        Arc::try_unwrap(tline_child).unwrap();
+
+        {
+            let gc_info_parent = tline_parent.gc_info.read().unwrap();
+            assert_eq!(
+                gc_info_parent.retain_lsns,
+                vec![(Lsn(0x20), child_timeline_id, MaybeOffloaded::Yes)]
+            );
+        }
+
+        tenant
+            .get_offloaded_timeline(child_timeline_id)
+            .unwrap()
+            .defuse_for_tenant_drop();
+
+        Ok(())
+    }
 }
diff --git a/pageserver/src/tenant/timeline.rs b/pageserver/src/tenant/timeline.rs
index 09ddb1976535..2bc14ec3172c 100644
--- a/pageserver/src/tenant/timeline.rs
+++ b/pageserver/src/tenant/timeline.rs
@@ -477,8 +477,21 @@ impl GcInfo {
         self.retain_lsns.sort_by_key(|i| i.0);
     }
 
-    pub(super) fn remove_child(&mut self, child_id: TimelineId) {
-        self.retain_lsns.retain(|i| i.1 != child_id);
+    pub(super) fn remove_child_maybe_offloaded(
+        &mut self,
+        child_id: TimelineId,
+        maybe_offloaded: MaybeOffloaded,
+    ) {
+        self.retain_lsns
+            .retain(|i| !(i.1 == child_id && i.2 == maybe_offloaded));
+    }
+
+    pub(super) fn remove_child_not_offloaded(&mut self, child_id: TimelineId) {
+        self.remove_child_maybe_offloaded(child_id, MaybeOffloaded::No);
+    }
+
+    pub(super) fn remove_child_offloaded(&mut self, child_id: TimelineId) {
+        self.remove_child_maybe_offloaded(child_id, MaybeOffloaded::Yes);
     }
 }
 
@@ -4501,7 +4514,7 @@ impl Drop for Timeline {
             // This lock should never be poisoned, but in case it is we do a .map() instead of
             // an unwrap(), to avoid panicking in a destructor and thereby aborting the process.
             if let Ok(mut gc_info) = ancestor.gc_info.write() {
-                gc_info.remove_child(self.timeline_id)
+                gc_info.remove_child_not_offloaded(self.timeline_id)
             }
         }
     }
@@ -5030,7 +5043,7 @@ impl Timeline {
 
             // 1. Is it newer than GC horizon cutoff point?
             if l.get_lsn_range().end > space_cutoff {
-                debug!(
+                info!(
                     "keeping {} because it's newer than space_cutoff {}",
                     l.layer_name(),
                     space_cutoff,
@@ -5041,7 +5054,7 @@ impl Timeline {
 
             // 2. It is newer than PiTR cutoff point?
             if l.get_lsn_range().end > time_cutoff {
-                debug!(
+                info!(
                     "keeping {} because it's newer than time_cutoff {}",
                     l.layer_name(),
                     time_cutoff,
@@ -5060,7 +5073,7 @@ impl Timeline {
             for retain_lsn in &retain_lsns {
                 // start_lsn is inclusive
                 if &l.get_lsn_range().start <= retain_lsn {
-                    debug!(
+                    info!(
                         "keeping {} because it's still might be referenced by child branch forked at {} is_dropped: xx is_incremental: {}",
                         l.layer_name(),
                         retain_lsn,
@@ -5075,7 +5088,7 @@ impl Timeline {
             if let Some(lsn) = &max_lsn_with_valid_lease {
                 // keep if layer start <= any of the lease
                 if &l.get_lsn_range().start <= lsn {
-                    debug!(
+                    info!(
                         "keeping {} because there is a valid lease preventing GC at {}",
                         l.layer_name(),
                         lsn,
@@ -5107,13 +5120,13 @@ impl Timeline {
             if !layers
                 .image_layer_exists(&l.get_key_range(), &(l.get_lsn_range().end..new_gc_cutoff))
             {
-                debug!("keeping {} because it is the latest layer", l.layer_name());
+                info!("keeping {} because it is the latest layer", l.layer_name());
                 result.layers_not_updated += 1;
                 continue 'outer;
             }
 
             // We didn't find any reason to keep this file, so remove it.
-            debug!(
+            info!(
                 "garbage collecting {} is_dropped: xx is_incremental: {}",
                 l.layer_name(),
                 l.is_incremental(),
diff --git a/pageserver/src/tenant/timeline/delete.rs b/pageserver/src/tenant/timeline/delete.rs
index 69001a6c4022..13a8dfa51a2e 100644
--- a/pageserver/src/tenant/timeline/delete.rs
+++ b/pageserver/src/tenant/timeline/delete.rs
@@ -141,9 +141,10 @@ async fn remove_maybe_offloaded_timeline_from_tenant(
             );
         }
         TimelineOrOffloaded::Offloaded(timeline) => {
-            timelines_offloaded
+            let offloaded_timeline = timelines_offloaded
                 .remove(&timeline.timeline_id)
                 .expect("timeline that we were deleting was concurrently removed from 'timelines_offloaded' map");
+            offloaded_timeline.delete_from_ancestor_with_timelines(&timelines);
         }
     }
 
diff --git a/pageserver/src/tenant/timeline/offload.rs b/pageserver/src/tenant/timeline/offload.rs
index 139484346747..3595d743bc2e 100644
--- a/pageserver/src/tenant/timeline/offload.rs
+++ b/pageserver/src/tenant/timeline/offload.rs
@@ -66,7 +66,7 @@ pub(crate) async fn offload_timeline(
     let conf = &tenant.conf;
     delete_local_timeline_directory(conf, tenant.tenant_shard_id, &timeline).await;
 
-    remove_timeline_from_tenant(tenant, &timeline, &guard);
+    let remaining_refcount = remove_timeline_from_tenant(tenant, &timeline, &guard);
 
     {
         let mut offloaded_timelines = tenant.timelines_offloaded.lock().unwrap();
@@ -87,16 +87,20 @@ pub(crate) async fn offload_timeline(
     // not our actual state of offloaded timelines.
     tenant.store_tenant_manifest().await?;
 
+    tracing::info!("Timeline offload complete (remaining arc refcount: {remaining_refcount})");
+
     Ok(())
 }
 
 /// It is important that this gets called when DeletionGuard is being held.
 /// For more context see comments in [`DeleteTimelineFlow::prepare`]
+///
+/// Returns the strong count of the timeline `Arc`
 fn remove_timeline_from_tenant(
     tenant: &Tenant,
     timeline: &Timeline,
     _: &DeletionGuard, // using it as a witness
-) {
+) -> usize {
     // Remove the timeline from the map.
     let mut timelines = tenant.timelines.lock().unwrap();
     let children_exist = timelines
@@ -109,7 +113,9 @@ fn remove_timeline_from_tenant(
         panic!("Timeline grew children while we removed layer files");
     }
 
-    timelines
+    let timeline = timelines
         .remove(&timeline.timeline_id)
         .expect("timeline that we were deleting was concurrently removed from 'timelines' map");
+
+    Arc::strong_count(&timeline)
 }
diff --git a/test_runner/regress/test_timeline_archive.py b/test_runner/regress/test_timeline_archive.py
index 83631405abf4..ba4e79c3430d 100644
--- a/test_runner/regress/test_timeline_archive.py
+++ b/test_runner/regress/test_timeline_archive.py
@@ -15,13 +15,19 @@
     last_flush_lsn_upload,
 )
 from fixtures.pageserver.http import PageserverApiException
-from fixtures.pageserver.utils import assert_prefix_empty, assert_prefix_not_empty, list_prefix
+from fixtures.pageserver.utils import (
+    assert_prefix_empty,
+    assert_prefix_not_empty,
+    list_prefix,
+    wait_until_tenant_active,
+)
 from fixtures.pg_version import PgVersion
 from fixtures.remote_storage import S3Storage, s3_storage
 from fixtures.utils import run_only_on_default_postgres, wait_until
 from mypy_boto3_s3.type_defs import (
     ObjectTypeDef,
 )
+from psycopg2.errors import IoError, UndefinedTable
 
 
 @pytest.mark.parametrize("shard_count", [0, 4])
@@ -641,8 +647,21 @@ def worker():
     assert violations == []
 
 
-@pytest.mark.parametrize("offload_child", ["offload", "offload-corrupt", "archive", None])
-def test_timeline_retain_lsn(neon_env_builder: NeonEnvBuilder, offload_child: Optional[str]):
+@pytest.mark.parametrize("with_intermediary", [False, True])
+@pytest.mark.parametrize(
+    "offload_child",
+    [
+        "offload",
+        "offload-corrupt",
+        "offload-no-restart",
+        "offload-parent",
+        "archive",
+        None,
+    ],
+)
+def test_timeline_retain_lsn(
+    neon_env_builder: NeonEnvBuilder, with_intermediary: bool, offload_child: Optional[str]
+):
     """
     Ensure that retain_lsn functionality for timelines works, both for offloaded and non-offloaded ones
     """
@@ -650,6 +669,7 @@ def test_timeline_retain_lsn(neon_env_builder: NeonEnvBuilder, offload_child: Op
         # Our corruption code only works with S3 compatible storage
         neon_env_builder.enable_pageserver_remote_storage(s3_storage())
 
+    neon_env_builder.rust_log_override = "info,[gc_timeline]=debug"
     env = neon_env_builder.init_start()
     ps_http = env.pageserver.http_client()
 
@@ -657,22 +677,30 @@ def test_timeline_retain_lsn(neon_env_builder: NeonEnvBuilder, offload_child: Op
     tenant_id, root_timeline_id = env.create_tenant(
         conf={
             # small checkpointing and compaction targets to ensure we generate many upload operations
-            "checkpoint_distance": 128 * 1024,
+            "checkpoint_distance": 32 * 1024,
             "compaction_threshold": 1,
-            "compaction_target_size": 128 * 1024,
+            "compaction_target_size": 32 * 1024,
             # set small image creation thresholds so that gc deletes data
-            "image_creation_threshold": 2,
+            "image_creation_threshold": 1,
             # disable background compaction and GC. We invoke it manually when we want it to happen.
             "gc_period": "0s",
             "compaction_period": "0s",
             # Disable pitr, we only want the latest lsn
             "pitr_interval": "0s",
+            "gc_horizon": 0,
             # Don't rely on endpoint lsn leases
             "lsn_lease_length": "0s",
         }
     )
 
-    with env.endpoints.create_start("main", tenant_id=tenant_id) as endpoint:
+    if with_intermediary:
+        parent_branch_name = "test_archived_parent"
+        parent_timeline_id = env.create_branch("test_archived_parent", tenant_id)
+    else:
+        parent_branch_name = "main"
+        parent_timeline_id = root_timeline_id
+
+    with env.endpoints.create_start(parent_branch_name, tenant_id=tenant_id) as endpoint:
         endpoint.safe_psql_many(
             [
                 "CREATE TABLE foo(v int, key serial primary key, t text default 'data_content')",
@@ -682,14 +710,16 @@ def test_timeline_retain_lsn(neon_env_builder: NeonEnvBuilder, offload_child: Op
         )
         pre_branch_sum = endpoint.safe_psql("SELECT sum(key) from foo where v < 51200")
         log.info(f"Pre branch sum: {pre_branch_sum}")
-        last_flush_lsn_upload(env, endpoint, tenant_id, root_timeline_id)
+        last_flush_lsn_upload(env, endpoint, tenant_id, parent_timeline_id)
 
     # Create a branch and write some additional data to the parent
-    child_timeline_id = env.create_branch("test_archived_branch", tenant_id)
+    child_timeline_id = env.create_branch(
+        "test_archived_branch", tenant_id, ancestor_branch_name=parent_branch_name
+    )
 
-    with env.endpoints.create_start("main", tenant_id=tenant_id) as endpoint:
-        # Do some churn of the data. This is important so that we can overwrite image layers.
-        for i in range(10):
+    with env.endpoints.create_start(parent_branch_name, tenant_id=tenant_id) as endpoint:
+        # Do some overwriting churn with compactions in between. This is important so that we can overwrite image layers.
+        for i in range(5):
             endpoint.safe_psql_many(
                 [
                     f"SELECT setseed(0.23{i})",
@@ -698,9 +728,9 @@ def test_timeline_retain_lsn(neon_env_builder: NeonEnvBuilder, offload_child: Op
                     "UPDATE foo SET v=(random() * 409600)::int WHERE v % 3 = 0",
                 ]
             )
+            last_flush_lsn_upload(env, endpoint, tenant_id, parent_timeline_id)
         post_branch_sum = endpoint.safe_psql("SELECT sum(key) from foo where v < 51200")
         log.info(f"Post branch sum: {post_branch_sum}")
-        last_flush_lsn_upload(env, endpoint, tenant_id, root_timeline_id)
 
     if offload_child is not None:
         ps_http.timeline_archival_config(
@@ -715,9 +745,19 @@ def test_timeline_retain_lsn(neon_env_builder: NeonEnvBuilder, offload_child: Op
         assert leaf_detail["is_archived"] is True
         if "offload" in offload_child:
             ps_http.timeline_offload(tenant_id, child_timeline_id)
+        if "offload-parent" in offload_child:
+            # Also offload the parent to ensure the retain_lsn of the child
+            # is entered in the parent at unoffloading
+            ps_http.timeline_archival_config(
+                tenant_id,
+                parent_timeline_id,
+                state=TimelineArchivalState.ARCHIVED,
+            )
+            ps_http.timeline_offload(tenant_id, parent_timeline_id)
 
     # Do a restart to get rid of any in-memory objects (we only init gc info once, at attach)
-    env.pageserver.stop()
+    if offload_child is None or "no-restart" not in offload_child:
+        env.pageserver.stop()
     if offload_child == "offload-corrupt":
         assert isinstance(env.pageserver_remote_storage, S3Storage)
         listing = list_prefix(
@@ -752,13 +792,21 @@ def test_timeline_retain_lsn(neon_env_builder: NeonEnvBuilder, offload_child: Op
                 ".*page_service_conn_main.*could not find data for key.*",
             ]
         )
-    env.pageserver.start()
+    if offload_child is None or "no-restart" not in offload_child:
+        env.pageserver.start()
+        if offload_child == "offload-parent":
+            wait_until_tenant_active(ps_http, tenant_id=tenant_id)
+            ps_http.timeline_archival_config(
+                tenant_id,
+                parent_timeline_id,
+                state=TimelineArchivalState.UNARCHIVED,
+            )
 
     # Do an agressive gc and compaction of the parent branch
-    ps_http.timeline_gc(tenant_id=tenant_id, timeline_id=root_timeline_id, gc_horizon=0)
+    ps_http.timeline_gc(tenant_id=tenant_id, timeline_id=parent_timeline_id, gc_horizon=0)
     ps_http.timeline_checkpoint(
         tenant_id,
-        root_timeline_id,
+        parent_timeline_id,
         force_l0_compaction=True,
         force_repartition=True,
         wait_until_uploaded=True,
@@ -774,10 +822,15 @@ def test_timeline_retain_lsn(neon_env_builder: NeonEnvBuilder, offload_child: Op
 
     # Now, after unarchival, the child timeline should still have its data accessible (or corrupted)
     if offload_child == "offload-corrupt":
-        with pytest.raises(RuntimeError, match=".*failed to get basebackup.*"):
-            env.endpoints.create_start(
+        if with_intermediary:
+            error_regex = "(.*could not read .* from page server.*|.*relation .* does not exist)"
+        else:
+            error_regex = ".*failed to get basebackup.*"
+        with pytest.raises((RuntimeError, IoError, UndefinedTable), match=error_regex):
+            with env.endpoints.create_start(
                 "test_archived_branch", tenant_id=tenant_id, basebackup_request_tries=1
-            )
+            ) as endpoint:
+                endpoint.safe_psql("SELECT sum(key) from foo where v < 51200")
     else:
         with env.endpoints.create_start("test_archived_branch", tenant_id=tenant_id) as endpoint:
             sum = endpoint.safe_psql("SELECT sum(key) from foo where v < 51200")