diff --git a/pageserver/src/tenant/remote_timeline_client.rs b/pageserver/src/tenant/remote_timeline_client.rs
index a1c7f6006185..3ff108aca2ad 100644
--- a/pageserver/src/tenant/remote_timeline_client.rs
+++ b/pageserver/src/tenant/remote_timeline_client.rs
@@ -1798,10 +1798,11 @@ impl RemoteTimelineClient {
         Ok(())
     }
 
-    /// Returns true if a can bypass b, i.e. if the operations don't conflict.
+    /// Returns true if a can bypass b, i.e. if the operations don't conflict. prev_index is the
+    /// active index below b.
     ///
     /// TODO: consider moving this and other associated logic into UploadOp and UploadQueue.
-    fn can_bypass(a: &UploadOp, b: &UploadOp) -> bool {
+    fn can_bypass(a: &UploadOp, b: &UploadOp, prev_index: &IndexPart) -> bool {
         match (a, b) {
             // Nothing can bypass a barrier or shutdown, and it can't bypass anything.
             (UploadOp::Barrier(_), _) | (_, UploadOp::Barrier(_)) => false,
@@ -1819,27 +1820,39 @@ impl RemoteTimelineClient {
                 .map(|(name, _)| name)
                 .contains(&u.layer_desc().layer_name()),
 
-            // Deletes are idempotent and can always bypass each other
+            // Deletes are idempotent and can always bypass each other.
             // TODO: verify this.
             (UploadOp::Delete(_), UploadOp::Delete(_)) => true,
 
-            // Uploads and indexes can bypass each other unless they overlap.
-            // TODO: what if the current index references the file? Can we clobber it?
-            (UploadOp::UploadLayer(u, _, _), UploadOp::UploadMetadata { uploaded: i })
-            | (UploadOp::UploadMetadata { uploaded: i }, UploadOp::UploadLayer(u, _, _)) => {
-                !i.layer_metadata.contains_key(&u.layer_desc().layer_name())
+            // Uploads and deletes can bypass an index upload as long as the index and the index
+            // below it doesn't reference the file. A layer can't be modified or deleted while
+            // referenced by an index.
+            (UploadOp::UploadLayer(u, _, _), UploadOp::UploadMetadata { uploaded: i }) => {
+                let layer_name = u.layer_desc().layer_name();
+                !i.layer_metadata.contains_key(&layer_name)
+                    && !prev_index.layer_metadata.contains_key(&layer_name)
+            }
+            (UploadOp::Delete(d), UploadOp::UploadMetadata { uploaded: i }) => {
+                d.layers.iter().all(|(layer_name, _)| {
+                    !i.layer_metadata.contains_key(layer_name)
+                        && !prev_index.layer_metadata.contains_key(layer_name)
+                })
             }
 
-            // A delete can't bypass an index. The queued index likely doesn't reference the file,
-            // but the current index may still reference it.
-            (UploadOp::Delete(_), UploadOp::UploadMetadata { .. }) => false,
-
-            // An index can bypass a delete if the index doesn't contain the deleted files. The
-            // existing index can't reference these files, otherwise they couldn't be deleted.
-            (UploadOp::UploadMetadata { uploaded: i }, UploadOp::Delete(d)) => !d
-                .layers
-                .iter()
-                .any(|(name, _)| i.layer_metadata.contains_key(name)),
+            // An index can bypass an upload or delete if the index doesn't contain the modified
+            // files. They can't be referenced by the previous index either, since it's not legal to
+            // modify a referenced file.
+            (UploadOp::UploadMetadata { uploaded: i }, UploadOp::UploadLayer(u, _, _)) => {
+                let layer_name = u.layer_desc().layer_name();
+                !i.layer_metadata.contains_key(&layer_name)
+                    && !prev_index.layer_metadata.contains_key(&layer_name)
+            }
+            (UploadOp::UploadMetadata { uploaded: i }, UploadOp::Delete(d)) => {
+                d.layers.iter().all(|(layer_name, _)| {
+                    !i.layer_metadata.contains_key(layer_name)
+                        && !prev_index.layer_metadata.contains_key(layer_name)
+                })
+            }
 
             // Indexes can never bypass each other.
             // TODO: they can coalesce though, consider this.
@@ -1855,18 +1868,32 @@ impl RemoteTimelineClient {
         // For each queued operation, check if it can bypass the in-progress and queued operations
         // ahead of it (if any).
         //
+        // TODO: this loop is a bit ugly, rewrite the internals as an iterator chain.
         // TODO: this is quadratic. Is that a problem? Consider optimizing.
-        for (i, op) in queue.queued_operations.iter().enumerate() {
+        'OUTER: for (i, op) in queue.queued_operations.iter().enumerate() {
+            // Visit the preceding operations in reverse order (front to back), to keep track of
+            // prev_index. The order really doesn't matter, since we must be able to bypass all.
+            //
+            // TODO: add assertions that an upload or delete is never referenced by the most recent
+            // index.
             let in_progress = queue.inprogress_tasks.values().map(|task| &task.op);
-            let ahead = queue.queued_operations.iter().take(i);
-            if ahead.chain(in_progress).all(|q| Self::can_bypass(op, q)) {
-                return queue.queued_operations.remove(i);
+            let ahead = queue.queued_operations.iter().take(i).rev();
+            let mut prev_index = &queue.clean.0;
+            for other in in_progress.chain(ahead) {
+                if !Self::can_bypass(op, other, prev_index) {
+                    // Nothing can cross a barrier, so give up if we find one.
+                    if matches!(op, UploadOp::Barrier(_) | UploadOp::Shutdown) {
+                        return None;
+                    }
+                    continue 'OUTER;
+                }
+                if let UploadOp::UploadMetadata { ref uploaded } = other {
+                    prev_index = uploaded;
+                }
             }
 
-            // Nothing can cross a barrier, so give up if we didn't already return it above.
-            if matches!(op, UploadOp::Barrier(_) | UploadOp::Shutdown) {
-                return None;
-            }
+            // We can bypass all preceding operations; go for it.
+            return queue.queued_operations.remove(i);
         }
         None
     }