From cb39df63bcb976c7ed5633f16eba7cbad14030a4 Mon Sep 17 00:00:00 2001
From: Daniel Arroyo <darroylat@gmail.com>
Date: Thu, 9 Jul 2026 20:45:32 -0400
Subject: [PATCH] fix: deploy keys StdinPipe order and add structured logging

- sshmanager/deploy.go: StdinPipe() must be called BEFORE Start(),
  not after. Reordered the calls to fix "ssh: StdinPipe after
  process started" error.
- Return DeployResult instead of nil error on SSH dial failure
  so the frontend always gets a parseable response.
- Add slog.Debug for key upload, slog.Warn for ssh-keyscan and
  authorized_keys failures, slog.Info for final result summary.
---
 internal/sshmanager/deploy.go | 26 +++++++++++++++++++-------
 1 file changed, 19 insertions(+), 7 deletions(-)

diff --git a/internal/sshmanager/deploy.go b/internal/sshmanager/deploy.go
index 396e628..252d69e 100644
--- a/internal/sshmanager/deploy.go
+++ b/internal/sshmanager/deploy.go
@@ -4,6 +4,7 @@ import (
 	"bytes"
 	"context"
 	"fmt"
+	"log/slog"
 	"net"
 	"os"
 	"path/filepath"
@@ -55,7 +56,8 @@ func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string
 
 	conn, err := ssh.Dial("tcp", addr, cfg)
 	if err != nil {
-		return nil, fmt.Errorf("connecting to %s: %w", addr, err)
+		slog.Warn("deploy keys: SSH dial failed", "host", addr, "error", err)
+		return &DeployResult{Success: false, Messages: []string{}, Errors: []string{fmt.Sprintf("connecting to %s: %v", addr, err)}}, nil
 	}
 	defer conn.Close()
 
@@ -101,17 +103,22 @@ func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string
 		sess2.Stdout = &stdout
 		sess2.Stderr = &stderr
 
+		slog.Debug("deploy: uploading key", "local", k.LocalPath, "remote", k.RemotePath, "host", host)
+
 		cmd := fmt.Sprintf("cat > %s && chmod 0%o %s", k.RemotePath, mode, k.RemotePath)
-		if err := sess2.Start(cmd); err != nil {
-			result.Errors = append(result.Errors, fmt.Sprintf("starting command for %s: %v", k.RemotePath, err))
-			result.Success = false
-			continue
-		}
 
 		stdin, err := sess2.StdinPipe()
 		if err != nil {
 			result.Errors = append(result.Errors, fmt.Sprintf("stdin pipe for %s: %v", k.RemotePath, err))
 			result.Success = false
+			sess2.Close()
+			continue
+		}
+
+		if err := sess2.Start(cmd); err != nil {
+			result.Errors = append(result.Errors, fmt.Sprintf("starting command for %s: %v", k.RemotePath, err))
+			result.Success = false
+			sess2.Close()
 			continue
 		}
 
@@ -119,6 +126,8 @@ func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string
 		if err != nil {
 			result.Errors = append(result.Errors, fmt.Sprintf("writing key %s: %v", k.RemotePath, err))
 			result.Success = false
+			stdin.Close()
+			sess2.Close()
 			continue
 		}
 		stdin.Close()
@@ -143,6 +152,7 @@ func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string
 			err := session2.Run(fmt.Sprintf("ssh-keyscan -H -p %d %s 2>/dev/null >> %s/known_hosts", port, knownHostsHost, remoteSSHDir))
 			session2.Close()
 			if err != nil {
+				slog.Warn("deploy: ssh-keyscan failed", "host", knownHostsHost, "port", port, "error", err)
 				result.Errors = append(result.Errors, fmt.Sprintf("ssh-keyscan %s: %v (stderr: %s)", knownHostsHost, err, stderr.String()))
 				result.Success = false
 			} else {
@@ -151,7 +161,7 @@ func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string
 		}
 	}
 
-	if addServerPubKey && serverPubKey != "" {
+		if addServerPubKey && serverPubKey != "" {
 		session3, err := conn.NewSession()
 		if err != nil {
 			result.Errors = append(result.Errors, fmt.Sprintf("session for authorized_keys: %v", err))
@@ -163,6 +173,7 @@ func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string
 			err := session3.Run(fmt.Sprintf("mkdir -p ~/.ssh && chmod 700 ~/.ssh && echo '%s' >> ~/.ssh/authorized_keys && chmod 600 ~/.ssh/authorized_keys", pubKeyClean))
 			session3.Close()
 			if err != nil {
+				slog.Warn("deploy: adding to authorized_keys failed", "host", host, "error", err)
 				result.Errors = append(result.Errors, fmt.Sprintf("adding to authorized_keys: %v (stderr: %s)", err, stderr.String()))
 				result.Success = false
 			} else {
@@ -171,5 +182,6 @@ func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string
 		}
 	}
 
+	slog.Info("deploy keys result", "host", host, "success", result.Success, "messages", len(result.Messages), "errors", len(result.Errors))
 	return result, nil
 }