From 9e89f310a24fc759f83bacc80ceae4ba9284ee20 Mon Sep 17 00:00:00 2001
From: Alon Gubkin <alon.gubkin@gmail.com>
Date: Sun, 30 Aug 2026 12:12:13 -0700
Subject: [PATCH] fix(cli): prepare failed setup retries

---
 crates/alien-deploy-cli/src/commands/up.rs | 42 +++++++++++++++++-----
 1 file changed, 34 insertions(+), 8 deletions(-)

diff --git a/crates/alien-deploy-cli/src/commands/up.rs b/crates/alien-deploy-cli/src/commands/up.rs
index be0495440..072b501e8 100644
--- a/crates/alien-deploy-cli/src/commands/up.rs
+++ b/crates/alien-deploy-cli/src/commands/up.rs
@@ -442,6 +442,27 @@ mod tests {
         assert!(!hosted_setup_reconcile_required("running", None, None));
     }
 
+    #[test]
+    fn failed_setup_states_are_prepared_before_retrying() {
+        for status in [
+            DeploymentStatus::Running,
+            DeploymentStatus::UpdateFailed,
+            DeploymentStatus::RefreshFailed,
+            DeploymentStatus::InitialSetupFailed,
+            DeploymentStatus::ProvisioningFailed,
+        ] {
+            assert!(requires_direct_setup_preparation(&status), "{status:?}");
+        }
+
+        for status in [
+            DeploymentStatus::Pending,
+            DeploymentStatus::InitialSetup,
+            DeploymentStatus::Provisioning,
+        ] {
+            assert!(!requires_direct_setup_preparation(&status), "{status:?}");
+        }
+    }
+
     #[test]
     fn setup_refresh_prefers_desired_release_and_falls_back_to_current() {
         assert_eq!(
@@ -2926,8 +2947,7 @@ fn hosted_setup_reconcile_required(
             | "refresh-failed"
             | "initial-setup-failed"
             | "provisioning-failed"
-    )
-        && packaged_revision.is_some()
+    ) && packaged_revision.is_some()
         && packaged_revision != applied_revision
 }
 
@@ -4206,12 +4226,7 @@ pub async fn push_initial_setup(
             message: "Failed to deserialize runtime_metadata from manager".to_string(),
         })?;
 
-    if matches!(
-        state.status,
-        DeploymentStatus::Running
-            | DeploymentStatus::UpdateFailed
-            | DeploymentStatus::RefreshFailed
-    ) {
+    if requires_direct_setup_preparation(&state.status) {
         let stack_state = state.stack_state.as_ref().ok_or_else(|| {
             AlienError::new(ErrorData::ConfigurationError {
                 message: "A running deployment has no stack state for setup update".to_string(),
@@ -4317,6 +4332,17 @@ pub async fn push_initial_setup(
     }
 }
 
+fn requires_direct_setup_preparation(status: &DeploymentStatus) -> bool {
+    matches!(
+        status,
+        DeploymentStatus::Running
+            | DeploymentStatus::UpdateFailed
+            | DeploymentStatus::RefreshFailed
+            | DeploymentStatus::InitialSetupFailed
+            | DeploymentStatus::ProvisioningFailed
+    )
+}
+
 fn should_collect_push_setup_environment_info(platform: Platform) -> bool {
     !matches!(platform, Platform::Machines)
 }