From 6c99e83b44bcb1b58f10f3f95eca93c27d55f81c Mon Sep 17 00:00:00 2001
From: divesh <dgude@nvidia.com>
Date: Fri, 6 Nov 2026 10:55:52 -0800
Subject: [PATCH] fix(cli): report scheduling failures in provisioning timeouts

Fixes #5230

Signed-off-by: divesh <dgude@nvidia.com>
---
 crates/openshell-cli/src/commands/common.rs | 14 ++++-
 crates/openshell-cli/src/run.rs             | 67 +++++++++++++++++++++
 2 files changed, 78 insertions(+), 3 deletions(-)

diff --git a/crates/openshell-cli/src/commands/common.rs b/crates/openshell-cli/src/commands/common.rs
index 4afeeb569c..23670c0b19 100644
--- a/crates/openshell-cli/src/commands/common.rs
+++ b/crates/openshell-cli/src/commands/common.rs
@@ -576,9 +576,17 @@ pub fn print_sandbox_header(
 pub fn ready_false_condition_message(
     status: Option<&openshell_core::proto::SandboxStatus>,
 ) -> Option<String> {
-    let condition = status?.conditions.iter().find(|condition| {
-        condition.r#type == "Ready" && condition.status.eq_ignore_ascii_case("false")
-    })?;
+    let conditions = &status?.conditions;
+    let condition = conditions
+        .iter()
+        .find(|condition| {
+            condition.r#type == "PodScheduled" && condition.status.eq_ignore_ascii_case("false")
+        })
+        .or_else(|| {
+            conditions.iter().find(|condition| {
+                condition.r#type == "Ready" && condition.status.eq_ignore_ascii_case("false")
+            })
+        })?;
 
     if condition.message.is_empty() {
         if condition.reason.is_empty() {
diff --git a/crates/openshell-cli/src/run.rs b/crates/openshell-cli/src/run.rs
index eb224685ed..4c997f18e0 100644
--- a/crates/openshell-cli/src/run.rs
+++ b/crates/openshell-cli/src/run.rs
@@ -8241,6 +8241,73 @@ mod tests {
         );
     }
 
+    #[test]
+    fn provisioning_timeout_prefers_failed_scheduling_over_ready_placeholder() {
+        let ready = SandboxCondition {
+            r#type: "Ready".into(),
+            status: "False".into(),
+            reason: "ConfigurationPending".into(),
+            message: "Waiting for effective configuration validation before workload activation"
+                .into(),
+            transition_time: None,
+        };
+        let scheduled = SandboxCondition {
+            r#type: "PodScheduled".into(),
+            status: "false".into(),
+            reason: "Unschedulable".into(),
+            message: "0/5 nodes are available: 1 Too many pods".into(),
+            transition_time: None,
+        };
+        for conditions in [
+            vec![ready.clone(), scheduled.clone()],
+            vec![scheduled.clone(), ready],
+            vec![scheduled],
+        ] {
+            let status = SandboxStatus {
+                conditions,
+                ..Default::default()
+            };
+            let detail = ready_false_condition_message(Some(&status));
+            assert_eq!(
+                detail.as_deref(),
+                Some("Unschedulable: 0/5 nodes are available: 1 Too many pods")
+            );
+            assert_eq!(
+                provisioning_timeout_message(300, None, detail.as_deref()),
+                "sandbox provisioning timed out after 300s. Last reported status: Unschedulable: 0/5 nodes are available: 1 Too many pods"
+            );
+        }
+    }
+
+    #[test]
+    fn ready_false_condition_message_falls_back_when_scheduling_has_not_failed() {
+        for scheduled_status in ["True", "Unknown", ""] {
+            let status = SandboxStatus {
+                conditions: vec![
+                    SandboxCondition {
+                        r#type: "PodScheduled".into(),
+                        status: scheduled_status.into(),
+                        reason: "SchedulingStatus".into(),
+                        message: "Scheduling observation".into(),
+                        transition_time: None,
+                    },
+                    SandboxCondition {
+                        r#type: "Ready".into(),
+                        status: "False".into(),
+                        reason: "ConfigurationPending".into(),
+                        message: "Waiting for configuration".into(),
+                        transition_time: None,
+                    },
+                ],
+                ..Default::default()
+            };
+            assert_eq!(
+                ready_false_condition_message(Some(&status)).as_deref(),
+                Some("ConfigurationPending: Waiting for configuration")
+            );
+        }
+    }
+
     #[test]
     fn ready_false_condition_message_ignores_non_ready_conditions() {
         let status = SandboxStatus {