diff --git a/pageserver/src/tenant/timeline.rs b/pageserver/src/tenant/timeline.rs
index 28d5efd421..6809cb1da4 100644
--- a/pageserver/src/tenant/timeline.rs
+++ b/pageserver/src/tenant/timeline.rs
@@ -5096,33 +5096,130 @@ impl Timeline {
             //
             // If we don't have a base image, then the oldest WAL record better initialize
             // the page
-            if data.img.is_none() && !data.records.first().unwrap().1.will_init() {
-                Err(PageReconstructError::from(anyhow!(
-                    "Base image for {} at {} not found, but got {} WAL records",
-                    key,
-                    request_lsn,
-                    data.records.len()
-                )))
-            } else {
-                if data.img.is_some() {
+
+            let have_img = data.img.is_some();
+            let will_init = data
+                .records
+                .first()
+                .map(|(_, rec)| rec.will_init())
+                .expect("already checked to have records");
+
+            match (have_img, will_init) {
+                (false, false) => {
+                    return Err(PageReconstructError::from(anyhow!(
+                        "Base image for {} at {} not found, but got {} WAL records",
+                        key,
+                        request_lsn,
+                        data.records.len()
+                    )))
+                }
+                (true, _) => {
                     trace!(
                         "found {} WAL records and a base image for {} at {}, performing WAL redo",
                         data.records.len(),
                         key,
                         request_lsn
                     );
-                } else {
+                }
+                (false, _) => {
+                    assert!(will_init, "already checked above");
                     trace!("found {} WAL records that will init the page for {} at {}, performing WAL redo", data.records.len(), key, request_lsn);
-                };
-                let res = self
-                    .walredo_mgr
-                    .as_ref()
-                    .context("timeline has no walredo manager")
-                    .map_err(PageReconstructError::WalRedo)?
-                    .request_redo(key, request_lsn, data.img, data.records, self.pg_version)
+                }
+            }
+
+            let oldest_lsn = data
+                .records
+                .first()
+                .map(|(lsn, _)| lsn)
+                .expect("again, checked");
+
+            // walk up the ancestry until we have found an ancestor covering the lsn range
+            let ancestry = std::iter::successors(Some(self), |tl| tl.ancestor_timeline.as_deref())
+                // 100 - initdb R pg14
+                // 150 - branch S pg14
+                // 200 - branch T pg15
+                // 250 - branch U pg15
+                // 300 - branch V pg16
+                //
+                // oldest_lsn = 155:
+                //   get [V pg16, U pg15(one_more=true), T pg15(one_more=true), S pg14(one_more=false)]
+                .take_while({
+                    let mut one_more = true;
+
+                    move |tl| {
+                        if *oldest_lsn < tl.ancestor_lsn {
+                            assert!(one_more);
+                            true
+                        } else {
+                            let prev = one_more;
+                            one_more = false;
+                            prev
+                        }
+                    }
+                })
+                // remove consecutive same pg_versions, which might be all in case we can use the
+                // same timeline for all reconstruction.
+                // [V pg16, U pg15, T pg15, S pg14] => [V pg16, T pg15, S pg14]
+                .fold(Vec::<&Timeline>::with_capacity(4), |mut acc, next| {
+                    if acc
+                        .last()
+                        .map(|tl| tl.pg_version == next.pg_version)
+                        .unwrap_or(false)
+                    {
+                        // overwrite with an earlier timeline; additionally we only allow upgrades,
+                        // so we cannot go backwards like pg14 (branch) pg15 (branch) pg14
+                        *acc.last_mut().unwrap() = next;
+                    } else {
+                        acc.push(next);
+                    }
+                    acc
+                });
+
+            // shifted for the purpose of timeline_pairs
+            let later_timelines = ancestry
+                .iter()
+                .rev()
+                .skip(1)
+                .map(Some)
+                .chain(std::iter::once(None));
+
+            // zip older and later timelines into pair, which we then use to select parts of
+            // wal records to be executed on which version walredo
+            let timeline_pairs = ancestry.iter().rev().zip(later_timelines);
+
+            let mgr = self
+                .walredo_mgr
+                .as_ref()
+                .context("timeline has no walredo manager")
+                .map_err(PageReconstructError::WalRedo)?;
+
+            let mut img = data.img.clone();
+            let mut records = &data.records[..];
+
+            for (older, later) in timeline_pairs {
+                let scratch = records
+                    .iter()
+                    .take_while(|(lsn, _)| {
+                        // if there is no later, take all remaining
+                        later.map(|later| lsn < &later.ancestor_lsn).unwrap_or(true)
+                    })
+                    .cloned()
+                    .collect::<Vec<_>>();
+                records = &records[scratch.len()..];
+                if later.is_none() {
+                    assert!(records.is_empty());
+                }
+
+                // this is only used for logging on the next round
+                let last_lsn = scratch.last().unwrap().0;
+
+                // is request_lsn ok? it's not used for anything important, just logging.
+                let res = mgr
+                    .request_redo(key, request_lsn, img, scratch, older.pg_version)
                     .await;
-                let img = match res {
-                    Ok(img) => img,
+
+                img = match res {
+                    Ok(img) => Some((last_lsn, img)),
                     Err(walredo::Error::Cancelled) => return Err(PageReconstructError::Cancelled),
                     Err(walredo::Error::Other(e)) => {
                         return Err(PageReconstructError::WalRedo(
@@ -5130,8 +5227,9 @@ impl Timeline {
                         ))
                     }
                 };
-                Ok(img)
             }
+
+            Ok(img.unwrap().1)
         }
     }