From 42fbc4b4c42bf458bb51b438a453d100068965e9 Mon Sep 17 00:00:00 2001
From: Vuong Hoang <vh@phasefinal.com>
Date: Fri, 24 Apr 2026 15:04:36 -0700
Subject: [PATCH] =?UTF-8?q?elway:=20lazy=20sudo=20probe=20=E2=80=94=20don'?=
 =?UTF-8?q?t=20prompt=20when=20every=20sudo=20step=20will=20skip?=
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Previously the startup logic ran `probe_sudo()` if any step in the
playbook declared `sudo: true`, regardless of whether that step's
creates:/when: gates would actually let it fire. The result on the
task-board deploy rerun was a spurious password prompt followed by
six SKIPPED lines — the prompt served no purpose.

New flow:
  - Remove the upfront probe in main().
  - SSHContext.sudo_password defaults to None; new sudo_probed flag
    tracks whether we've already prompted this session.
  - run_shell_step + run_upload_step call ensure_sudo(ctx) only at
    the point a sudo step is actually executing — i.e. after its
    skip conditions have been evaluated and passed. Idempotent:
    probes at most once per playbook run.

Tradeoff accepted: if the user fat-fingers the password, they see it
mid-run on the first sudo step rather than upfront. `stop_on_fail`
(default true) halts cleanly; they rerun. Lower friction for the
common idempotent-rerun case, same recoverability.

Verified against playbooks/deploy-task-board.yaml — prior run
prompted + completed in 1.7s; new run completes in 1.7s with no
prompt because every sudo step skip-gated.
---
 scripts/elway | 45 +++++++++++++++++++++++++++++----------------
 1 file changed, 29 insertions(+), 16 deletions(-)

diff --git a/scripts/elway b/scripts/elway
index 3d661c7..855939a 100755
--- a/scripts/elway
+++ b/scripts/elway
@@ -296,7 +296,8 @@ class SSHContext:
     host: str
     control_path: str
     verbose: bool
-    sudo_password: Optional[str]
+    sudo_password: Optional[str] = None
+    sudo_probed: bool = False   # so we probe at most once per run, lazily
 
     def _base_ssh_opts(self) -> list[str]:
         return [
@@ -329,8 +330,18 @@ class SSHContext:
             pass
 
 
-def probe_sudo(ctx: SSHContext) -> Optional[str]:
-    """Return a sudo password if one is needed, else None. Prompts locally."""
+def ensure_sudo(ctx: SSHContext) -> None:
+    """Idempotent lazy sudo probe. Called before the first sudo step that will
+    actually run — not at startup — so playbooks whose sudo steps all skip
+    never prompt for a password.
+
+    Sets ctx.sudo_password to None if NOPASSWD sudo works, or to the validated
+    password the user entered. Marks ctx.sudo_probed=True so subsequent sudo
+    steps reuse the already-acquired credential.
+    """
+    if ctx.sudo_probed:
+        return
+    ctx.sudo_probed = True
     # Is sudo configured NOPASSWD for this user? `sudo -n -v` exits 0 if so.
     p = subprocess.run(
         ctx.ssh_cmd("sudo -n -v"),
@@ -338,7 +349,8 @@ def probe_sudo(ctx: SSHContext) -> Optional[str]:
         stderr=subprocess.DEVNULL,
     )
     if p.returncode == 0:
-        return None
+        ctx.sudo_password = None
+        return
     pw = getpass.getpass(f"[elway] sudo password for {ctx.host}: ")
     # Validate it works; don't silently carry a wrong password through the whole run.
     validation = subprocess.run(
@@ -349,8 +361,8 @@ def probe_sudo(ctx: SSHContext) -> Optional[str]:
         stderr=subprocess.PIPE,
     )
     if validation.returncode != 0:
-        raise SystemExit("elway: sudo password validation failed; aborting before anything runs.")
-    return pw
+        raise SystemExit("elway: sudo password validation failed; aborting.")
+    ctx.sudo_password = pw
 
 
 # ─── Step execution ────────────────────────────────────────────────────────
@@ -383,10 +395,11 @@ def run_shell_step(ctx: SSHContext, step: Step, prefix: str) -> int:
     """Run a shell step on the remote host. Returns exit code."""
     cmd_inner = step.shell or ""
     if step.sudo:
-        # bash -s eats stdin for script; sudo -S reads password from stdin.
-        # We prepend the password line ourselves and pipe cmd_inner via bash -c after.
-        # Using `sudo -S -p '' bash -c <script>` lets sudo consume its password line,
-        # then runs the script. The password arrives as one line on stdin.
+        # Lazy: probe (and prompt if needed) right before the first sudo step
+        # actually executes. Skipped sudo steps never trigger a prompt.
+        ensure_sudo(ctx)
+        # `sudo -S -p '' bash -c <script>` lets sudo consume its password
+        # line from stdin, then runs the script. Password comes as one line.
         remote = "sudo -S -p '' bash -c " + shlex.quote(cmd_inner)
         stdin_data = (ctx.sudo_password or "") + "\n"
     else:
@@ -431,7 +444,8 @@ def run_upload_step(ctx: SSHContext, step: Step, prefix: str) -> int:
             )
         return rc
 
-    # Sudo path: scp to /tmp as user, then sudo mv + chmod server-side.
+    # Sudo path: probe lazily, then scp to /tmp as user, then sudo mv + chmod server-side.
+    ensure_sudo(ctx)
     staging = f"/tmp/elway.{os.getpid()}.{int(time.time() * 1000)}.{src.name}"
     if ctx.verbose:
         print(DIM(f"{prefix}$ scp {up.src} {ctx.host}:{staging}"))
@@ -704,8 +718,6 @@ def main(argv: Optional[list[str]] = None) -> int:
     merged_vars = dict(pb.vars)
     merged_vars.update(parse_var_args(args.var))
 
-    needs_sudo = any(s.sudo for s in pb.steps + pb.verify)
-
     # ControlMaster socket in a temp dir scoped to this run.
     with tempfile.TemporaryDirectory(prefix="elway-") as tmp:
         control_path = os.path.join(tmp, "cm-%r@%h:%p")
@@ -713,10 +725,11 @@ def main(argv: Optional[list[str]] = None) -> int:
             host=args.host,
             control_path=control_path,
             verbose=args.verbose,
-            sudo_password=None,
         )
-        if needs_sudo and not args.dry_run:
-            ctx.sudo_password = probe_sudo(ctx)
+        # No upfront sudo probe — lazily triggered from run_shell_step /
+        # run_upload_step the first time a sudo step actually runs (i.e.
+        # after its when:/creates: skip conditions pass). Playbooks whose
+        # sudo steps all skip never prompt.
         try:
             print(BOLD(f"── {args.host} ─ playbook: {args.playbook or 'ad-hoc'}  "
                       f"({len(pb.steps)} steps"