diff --git a/compute_tools/src/compute.rs b/compute_tools/src/compute.rs
index 88dc4aca2b..40060f4117 100644
--- a/compute_tools/src/compute.rs
+++ b/compute_tools/src/compute.rs
@@ -818,9 +818,15 @@ impl ComputeNode {
                         Client::connect(zenith_admin_connstr.as_str(), NoTls)
                             .context("broken cloud_admin credential: tried connecting with cloud_admin but could not authenticate, and zenith_admin does not work either")?;
                     // Disable forwarding so that users don't get a cloud_admin role
-                    client.simple_query("SET neon.forward_ddl = false")?;
-                    client.simple_query("CREATE USER cloud_admin WITH SUPERUSER")?;
-                    client.simple_query("GRANT zenith_admin TO cloud_admin")?;
+
+                    let mut func = || {
+                        client.simple_query("SET neon.forward_ddl = false")?;
+                        client.simple_query("CREATE USER cloud_admin WITH SUPERUSER")?;
+                        client.simple_query("GRANT zenith_admin TO cloud_admin")?;
+                        Ok::<_, anyhow::Error>(())
+                    };
+                    func().context("apply_config setup cloud_admin")?;
+
                     drop(client);
 
                     // reconnect with connstring with expected name
@@ -832,24 +838,29 @@ impl ComputeNode {
         };
 
         // Disable DDL forwarding because control plane already knows about these roles/databases.
-        client.simple_query("SET neon.forward_ddl = false")?;
+        client
+            .simple_query("SET neon.forward_ddl = false")
+            .context("apply_config SET neon.forward_ddl = false")?;
 
         // Proceed with post-startup configuration. Note, that order of operations is important.
         let spec = &compute_state.pspec.as_ref().expect("spec must be set").spec;
-        create_neon_superuser(spec, &mut client)?;
-        cleanup_instance(&mut client)?;
-        handle_roles(spec, &mut client)?;
-        handle_databases(spec, &mut client)?;
-        handle_role_deletions(spec, connstr.as_str(), &mut client)?;
+        create_neon_superuser(spec, &mut client).context("apply_config create_neon_superuser")?;
+        cleanup_instance(&mut client).context("apply_config cleanup_instance")?;
+        handle_roles(spec, &mut client).context("apply_config handle_roles")?;
+        handle_databases(spec, &mut client).context("apply_config handle_databases")?;
+        handle_role_deletions(spec, connstr.as_str(), &mut client)
+            .context("apply_config handle_role_deletions")?;
         handle_grants(
             spec,
             &mut client,
             connstr.as_str(),
             self.has_feature(ComputeFeature::AnonExtension),
-        )?;
-        handle_extensions(spec, &mut client)?;
-        handle_extension_neon(&mut client)?;
-        create_availability_check_data(&mut client)?;
+        )
+        .context("apply_config handle_grants")?;
+        handle_extensions(spec, &mut client).context("apply_config handle_extensions")?;
+        handle_extension_neon(&mut client).context("apply_config handle_extension_neon")?;
+        create_availability_check_data(&mut client)
+            .context("apply_config create_availability_check_data")?;
 
         // 'Close' connection
         drop(client);
@@ -857,7 +868,7 @@ impl ComputeNode {
         // Run migrations separately to not hold up cold starts
         thread::spawn(move || {
             let mut client = Client::connect(connstr.as_str(), NoTls)?;
-            handle_migrations(&mut client)
+            handle_migrations(&mut client).context("apply_config handle_migrations")
         });
         Ok(())
     }
diff --git a/compute_tools/src/spec.rs b/compute_tools/src/spec.rs
index 5643634633..269177ee16 100644
--- a/compute_tools/src/spec.rs
+++ b/compute_tools/src/spec.rs
@@ -2,7 +2,7 @@ use std::fs::File;
 use std::path::Path;
 use std::str::FromStr;
 
-use anyhow::{anyhow, bail, Result};
+use anyhow::{anyhow, bail, Context, Result};
 use postgres::config::Config;
 use postgres::{Client, NoTls};
 use reqwest::StatusCode;
@@ -698,7 +698,8 @@ pub fn handle_grants(
 
         // it is important to run this after all grants
         if enable_anon_extension {
-            handle_extension_anon(spec, &db.owner, &mut db_client, false)?;
+            handle_extension_anon(spec, &db.owner, &mut db_client, false)
+                .context("handle_grants handle_extension_anon")?;
         }
     }
 
@@ -813,28 +814,36 @@ $$;"#,
         // Add new migrations below.
     ];
 
-    let mut query = "CREATE SCHEMA IF NOT EXISTS neon_migration";
-    client.simple_query(query)?;
+    let mut func = || {
+        let query = "CREATE SCHEMA IF NOT EXISTS neon_migration";
+        client.simple_query(query)?;
 
-    query = "CREATE TABLE IF NOT EXISTS neon_migration.migration_id (key INT NOT NULL PRIMARY KEY, id bigint NOT NULL DEFAULT 0)";
-    client.simple_query(query)?;
+        let query = "CREATE TABLE IF NOT EXISTS neon_migration.migration_id (key INT NOT NULL PRIMARY KEY, id bigint NOT NULL DEFAULT 0)";
+        client.simple_query(query)?;
 
-    query = "INSERT INTO neon_migration.migration_id VALUES (0, 0) ON CONFLICT DO NOTHING";
-    client.simple_query(query)?;
+        let query = "INSERT INTO neon_migration.migration_id VALUES (0, 0) ON CONFLICT DO NOTHING";
+        client.simple_query(query)?;
 
-    query = "ALTER SCHEMA neon_migration OWNER TO cloud_admin";
-    client.simple_query(query)?;
+        let query = "ALTER SCHEMA neon_migration OWNER TO cloud_admin";
+        client.simple_query(query)?;
 
-    query = "REVOKE ALL ON SCHEMA neon_migration FROM PUBLIC";
-    client.simple_query(query)?;
+        let query = "REVOKE ALL ON SCHEMA neon_migration FROM PUBLIC";
+        client.simple_query(query)?;
+        Ok::<_, anyhow::Error>(())
+    };
+    func().context("handle_migrations prepare")?;
 
-    query = "SELECT id FROM neon_migration.migration_id";
-    let row = client.query_one(query, &[])?;
+    let query = "SELECT id FROM neon_migration.migration_id";
+    let row = client
+        .query_one(query, &[])
+        .context("handle_migrations get migration_id")?;
     let mut current_migration: usize = row.get::<&str, i64>("id") as usize;
     let starting_migration_id = current_migration;
 
-    query = "BEGIN";
-    client.simple_query(query)?;
+    let query = "BEGIN";
+    client
+        .simple_query(query)
+        .context("handle_migrations begin")?;
 
     while current_migration < migrations.len() {
         let migration = &migrations[current_migration];
@@ -842,7 +851,9 @@ $$;"#,
             info!("Skip migration id={}", current_migration);
         } else {
             info!("Running migration:\n{}\n", migration);
-            client.simple_query(migration)?;
+            client.simple_query(migration).with_context(|| {
+                format!("handle_migrations current_migration={}", current_migration)
+            })?;
         }
         current_migration += 1;
     }
@@ -850,10 +861,14 @@ $$;"#,
         "UPDATE neon_migration.migration_id SET id={}",
         migrations.len()
     );
-    client.simple_query(&setval)?;
+    client
+        .simple_query(&setval)
+        .context("handle_migrations update id")?;
 
-    query = "COMMIT";
-    client.simple_query(query)?;
+    let query = "COMMIT";
+    client
+        .simple_query(query)
+        .context("handle_migrations commit")?;
 
     info!(
         "Ran {} migrations",