diff --git a/pageserver/src/tenant/timeline.rs b/pageserver/src/tenant/timeline.rs
index d7ff70a29ce1..7b6c6dbfadce 100644
--- a/pageserver/src/tenant/timeline.rs
+++ b/pageserver/src/tenant/timeline.rs
@@ -1724,11 +1724,18 @@ impl Timeline {
                 for (name, decision) in decided {
                     let decision = match decision {
                         Ok(UseRemote { local, remote }) => {
-                            path.push(name.file_name());
-                            init::cleanup_local_file_for_remote(&path, &local, &remote)?;
-                            path.pop();
-
-                            UseRemote { local, remote }
+                            // Remote is authoritative, but we may still choose to retain
+                            // the local file if the contents appear to match
+                            if local.file_size() == remote.file_size() {
+                                // Use the local file, but take the remote metadata so that we pick up
+                                // the correct generation.
+                                UseLocal(remote)
+                            } else {
+                                path.push(name.file_name());
+                                init::cleanup_local_file_for_remote(&path, &local, &remote)?;
+                                path.pop();
+                                UseRemote { local, remote }
+                            }
                         }
                         Ok(decision) => decision,
                         Err(FutureLayer { local }) => {
diff --git a/pageserver/src/tenant/timeline/init.rs b/pageserver/src/tenant/timeline/init.rs
index 33effb431878..22976a514df7 100644
--- a/pageserver/src/tenant/timeline/init.rs
+++ b/pageserver/src/tenant/timeline/init.rs
@@ -147,11 +147,7 @@ pub(super) fn reconcile(
                 Err(FutureLayer { local })
             } else {
                 Ok(match (local, remote) {
-                    (Some(local), Some(remote)) if local != remote => {
-                        assert_eq!(local.generation, remote.generation);
-
-                        UseRemote { local, remote }
-                    }
+                    (Some(local), Some(remote)) if local != remote => UseRemote { local, remote },
                     (Some(x), Some(_)) => UseLocal(x),
                     (None, Some(x)) => Evicted(x),
                     (Some(x), None) => NeedsUpload(x),