From 14fee4f11265728c427b5afb1942179ba6aba7f7 Mon Sep 17 00:00:00 2001
From: brooklyn! <brooklyn.bb.nicholson@gmail.com>
Date: Fri, 5 Jun 2026 08:37:16 -0500
Subject: [PATCH] fix(update/windows): retry handoff `hermes update` once on
 first-run crash (#39831)
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The in-app updater (Hermes-Setup --update) runs `hermes update`, which lazily
imports the freshly-pulled modules — but the dependency-install step runs the
already-in-memory PRE-pull code for one invocation. When a release changes an
updater-path contract across that boundary, the FIRST update on the parked
population crashes even though the fix is already on disk.

Concretely this is #39780's `_UvResult`: its `__iter__` yields (path, bool), so
Windows `subprocess.list2cmdline([uv_bin, "pip", ...])` injects the bool and
dies with `TypeError: sequence item 1: expected str instance, bool found`
(fixed in #39820). A parked Windows user clicking Update pulls #39820 to disk,
then still crashes on the in-memory pre-merge module; only the SECOND click runs
clean. Field repro: ryanc's bootstrap.log (2026-06-05 12:41:41).

Fix: when the first `hermes update` exits non-zero (and it isn't the
concurrent-instance guard, exit 2, which a retry can't fix), retry once
automatically. The retry loads the now-current module from the start and
succeeds — so the parked user gets a working one-click update instead of a
scary crash + manual second attempt.

Verified: cargo check clean.
---
 .../src-tauri/src/update.rs                   | 34 ++++++++++++++++++-
 1 file changed, 33 insertions(+), 1 deletion(-)

diff --git a/apps/bootstrap-installer/src-tauri/src/update.rs b/apps/bootstrap-installer/src-tauri/src/update.rs
index bd0595af2f8..658bff6c540 100644
--- a/apps/bootstrap-installer/src-tauri/src/update.rs
+++ b/apps/bootstrap-installer/src-tauri/src/update.rs
@@ -183,7 +183,7 @@ async fn run_update(app: AppHandle) -> Result<()> {
 
     emit_stage(&app, "update", StageState::Running, None, None);
     let started = Instant::now();
-    let update = run_streamed(
+    let mut update = run_streamed(
         &app,
         &hermes,
         &update_args,
@@ -192,6 +192,38 @@ async fn run_update(app: AppHandle) -> Result<()> {
         Some("update"),
     )
     .await?;
+
+    // Retry-once for the update-boundary crash. `hermes update` lazily imports
+    // the FRESHLY PULLED modules, but the dependency-install step still runs the
+    // already-in-memory pre-pull code for one invocation. A release that changed
+    // an updater-path contract across that boundary (e.g. #39780's `_UvResult`,
+    // whose `__iter__` injected a bool into the argv and crashed Windows
+    // `list2cmdline` with `TypeError: sequence item 1: expected str instance,
+    // bool found`, fixed in #39820) therefore kills the FIRST update on the
+    // parked population — even though the fix is already on disk by then. A
+    // second `hermes update` runs clean because the now-current module is loaded
+    // from the start. Rather than make the parked user click Update twice (and
+    // stare at a scary crash first), retry once automatically. Skip the retry
+    // for the concurrent-instance guard (exit 2) — that's a "close Hermes" state
+    // a retry can't fix.
+    if !matches!(update.exit_code, Some(0) | Some(UPDATE_EXIT_CONCURRENT)) {
+        emit_log(
+            &app,
+            Some("update"),
+            LogStream::Stdout,
+            "[update] first update attempt failed; retrying once (the fix it just \
+             pulled loads on the second run)…",
+        );
+        update = run_streamed(
+            &app,
+            &hermes,
+            &update_args,
+            &install_root,
+            &child_env,
+            Some("update"),
+        )
+        .await?;
+    }
     let update_ms = started.elapsed().as_millis() as u64;
 
     match update.exit_code {