diff --git a/pageserver/src/tenant.rs b/pageserver/src/tenant.rs
index efe89cb982..d359270be4 100644
--- a/pageserver/src/tenant.rs
+++ b/pageserver/src/tenant.rs
@@ -37,6 +37,8 @@ use remote_timeline_client::manifest::{
     OffloadedTimelineManifest, TenantManifest, LATEST_TENANT_MANIFEST_VERSION,
 };
 use remote_timeline_client::UploadQueueNotReadyError;
+use remote_timeline_client::FAILED_REMOTE_OP_RETRIES;
+use remote_timeline_client::FAILED_UPLOAD_WARN_THRESHOLD;
 use std::collections::BTreeMap;
 use std::fmt;
 use std::future::Future;
@@ -5308,27 +5310,37 @@ impl Tenant {
             return Ok(());
         }
 
-        upload_tenant_manifest(
-            &self.remote_storage,
-            &self.tenant_shard_id,
-            self.generation,
-            &manifest,
+        // Remote storage does no retries internally, so wrap it
+        match backoff::retry(
+            || async {
+                upload_tenant_manifest(
+                    &self.remote_storage,
+                    &self.tenant_shard_id,
+                    self.generation,
+                    &manifest,
+                    &self.cancel,
+                )
+                .await
+            },
+            |_e| self.cancel.is_cancelled(),
+            FAILED_UPLOAD_WARN_THRESHOLD,
+            FAILED_REMOTE_OP_RETRIES,
+            "uploading tenant manifest",
             &self.cancel,
         )
         .await
-        .map_err(|e| {
-            if self.cancel.is_cancelled() {
-                TenantManifestError::Cancelled
-            } else {
-                TenantManifestError::RemoteStorage(e)
+        {
+            None => Err(TenantManifestError::Cancelled),
+            Some(Err(_)) if self.cancel.is_cancelled() => Err(TenantManifestError::Cancelled),
+            Some(Err(e)) => Err(TenantManifestError::RemoteStorage(e)),
+            Some(Ok(_)) => {
+                // Store the successfully uploaded manifest, so that future callers can avoid
+                // re-uploading the same thing.
+                *guard = Some(manifest);
+
+                Ok(())
             }
-        })?;
-
-        // Store the successfully uploaded manifest, so that future callers can avoid
-        // re-uploading the same thing.
-        *guard = Some(manifest);
-
-        Ok(())
+        }
     }
 }