diff --git a/pageserver/src/controller_upcall_client.rs b/pageserver/src/controller_upcall_client.rs
index 8462594607..6d5c727958 100644
--- a/pageserver/src/controller_upcall_client.rs
+++ b/pageserver/src/controller_upcall_client.rs
@@ -84,6 +84,7 @@ impl ControllerUpcallClient {
         })
     }
 
+    #[tracing::instrument(skip_all)]
     async fn retry_http_forever<R, T>(
         &self,
         url: &url::Url,
@@ -108,7 +109,7 @@ impl ControllerUpcallClient {
             |_| false,
             3,
             u32::MAX,
-            "calling control plane generation validation API",
+            "storage controller upcall",
             &self.cancel,
         )
         .await
@@ -125,11 +126,12 @@ impl ControllerUpcallClient {
 
 impl ControlPlaneGenerationsApi for ControllerUpcallClient {
     /// Block until we get a successful response, or error out if we are shut down
+    #[tracing::instrument(skip_all)] // so that warning logs from retry_http_forever have context
     async fn re_attach(
         &self,
         conf: &PageServerConf,
     ) -> Result<HashMap<TenantShardId, ReAttachResponseTenant>, RetryForeverError> {
-        let re_attach_path = self
+        let url = self
             .base_url
             .join("re-attach")
             .expect("Failed to build re-attach path");
@@ -205,7 +207,7 @@ impl ControlPlaneGenerationsApi for ControllerUpcallClient {
             register: register.clone(),
         };
 
-        let response: ReAttachResponse = self.retry_http_forever(&re_attach_path, request).await?;
+        let response: ReAttachResponse = self.retry_http_forever(&url, request).await?;
         tracing::info!(
             "Received re-attach response with {} tenants (node {}, register: {:?})",
             response.tenants.len(),
@@ -223,11 +225,12 @@ impl ControlPlaneGenerationsApi for ControllerUpcallClient {
     }
 
     /// Block until we get a successful response, or error out if we are shut down
+    #[tracing::instrument(skip_all)] // so that warning logs from retry_http_forever have context
     async fn validate(
         &self,
         tenants: Vec<(TenantShardId, Generation)>,
     ) -> Result<HashMap<TenantShardId, bool>, RetryForeverError> {
-        let re_attach_path = self
+        let url = self
             .base_url
             .join("validate")
             .expect("Failed to build validate path");
@@ -257,8 +260,7 @@ impl ControlPlaneGenerationsApi for ControllerUpcallClient {
                 return Err(RetryForeverError::ShuttingDown);
             }
 
-            let response: ValidateResponse =
-                self.retry_http_forever(&re_attach_path, request).await?;
+            let response: ValidateResponse = self.retry_http_forever(&url, request).await?;
             for rt in response.tenants {
                 result.insert(rt.id, rt.valid);
             }
diff --git a/test_runner/fixtures/pageserver/allowed_errors.py b/test_runner/fixtures/pageserver/allowed_errors.py
index 748ac0d569..4fce558840 100755
--- a/test_runner/fixtures/pageserver/allowed_errors.py
+++ b/test_runner/fixtures/pageserver/allowed_errors.py
@@ -94,7 +94,9 @@ DEFAULT_PAGESERVER_ALLOWED_ERRORS = (
     ".*Flushed oversized open layer with size.*",
     # During teardown, we stop the storage controller before the pageservers, so pageservers
     # can experience connection errors doing background deletion queue work.
-    ".*WARN deletion backend: calling control plane generation validation API failed.*error sending request.*",
+    ".*WARN deletion backend:.* storage controller upcall failed, will retry.*error sending request.*",
+    # Can happen when the pageserver starts faster than the storage controller
+    ".*WARN init_tenant_mgr:.* storage controller upcall failed, will retry.*error sending request.*",
     # Can happen when the test shuts down the storage controller while it is calling the utilization API
     ".*WARN.*path=/v1/utilization .*request was dropped before completing",
     # Can happen during shutdown