diff --git a/internal/api/handlers_machines.go b/internal/api/handlers_machines.go
index 6baf583..0bed76e 100644
--- a/internal/api/handlers_machines.go
+++ b/internal/api/handlers_machines.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"database/sql"
 	"encoding/json"
+	"fmt"
 	"log/slog"
 	"net/http"
 	"os"
@@ -367,45 +368,33 @@ func (h *MachineHandler) DeployKeys(w http.ResponseWriter, r *http.Request) {
 		}
 	}
 
-	pairRepo := models.NewSyncPairRepository(h.db)
-	allPairs, err := pairRepo.GetAll()
+	allMachines, err := repo.GetAll()
 	if err != nil {
-		slog.Warn("failed to fetch sync pairs for auto-detect", "error", err)
+		slog.Warn("failed to fetch machines for auto-detect", "error", err)
 	}
 
 	var keys []sshmanager.DeployKey
+	seenKeys := make(map[string]bool)
+	knownHostsHosts := []string{}
 
-	for _, pair := range allPairs {
-		if pair.SourceMachineID != nil && *pair.SourceMachineID == m.ID {
-			if pair.DestMachineID != nil {
-				destMachine, err := repo.GetByID(*pair.DestMachineID)
-				if err == nil && destMachine.SSHKeyID != nil {
-					skRepo := models.NewSSHKeyRepository(h.db)
-					sk, err := skRepo.GetByID(*destMachine.SSHKeyID)
-					if err == nil && sk.PrivateKeyPath != "" {
-						keys = append(keys, sshmanager.DeployKey{
-							LocalPath:  sk.PrivateKeyPath,
-							RemotePath: "/var/lib/syncserver/ssh/keys/" + filepath.Base(sk.PrivateKeyPath),
-							Mode:       0600,
-						})
-					}
-				}
-			}
+	for _, other := range allMachines {
+		if other.ID == m.ID {
+			continue
 		}
-		if pair.DestMachineID != nil && *pair.DestMachineID == m.ID {
-			if pair.SourceMachineID != nil {
-				srcMachine, err := repo.GetByID(*pair.SourceMachineID)
-				if err == nil && srcMachine.SSHKeyID != nil {
-					skRepo := models.NewSSHKeyRepository(h.db)
-					sk, err := skRepo.GetByID(*srcMachine.SSHKeyID)
-					if err == nil && sk.PrivateKeyPath != "" {
-						keys = append(keys, sshmanager.DeployKey{
-							LocalPath:  sk.PrivateKeyPath,
-							RemotePath: "/var/lib/syncserver/ssh/keys/" + filepath.Base(sk.PrivateKeyPath),
-							Mode:       0600,
-						})
-					}
+		knownHostsHosts = append(knownHostsHosts, fmt.Sprintf("%s:%d", other.Host, other.Port))
+		if other.SSHKeyID != nil {
+			skRepo := models.NewSSHKeyRepository(h.db)
+			sk, err := skRepo.GetByID(*other.SSHKeyID)
+			if err == nil && sk.PrivateKeyPath != "" {
+				if seenKeys[sk.PrivateKeyPath] {
+					continue
 				}
+				seenKeys[sk.PrivateKeyPath] = true
+				keys = append(keys, sshmanager.DeployKey{
+					LocalPath:  sk.PrivateKeyPath,
+					RemotePath: "/var/lib/syncserver/ssh/keys/" + filepath.Base(sk.PrivateKeyPath),
+					Mode:       0600,
+				})
 			}
 		}
 	}
@@ -422,7 +411,7 @@ func (h *MachineHandler) DeployKeys(w http.ResponseWriter, r *http.Request) {
 		m.Port,
 		m.SSHUser,
 		keys,
-		req.KnownHostsHost,
+		knownHostsHosts,
 		req.IncludeServerKey,
 	)
 	if err != nil {
diff --git a/internal/sshmanager/deploy.go b/internal/sshmanager/deploy.go
index 252d69e..21f18bf 100644
--- a/internal/sshmanager/deploy.go
+++ b/internal/sshmanager/deploy.go
@@ -26,7 +26,7 @@ type DeployResult struct {
 	Errors   []string
 }
 
-func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string, host string, port int, user string, keys []DeployKey, knownHostsHost string, addServerPubKey bool) (*DeployResult, error) {
+func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string, host string, port int, user string, keys []DeployKey, knownHostsHosts []string, addServerPubKey bool) (*DeployResult, error) {
 	result := &DeployResult{Success: true, Messages: []string{}, Errors: []string{}}
 
 	addr := fmt.Sprintf("%s:%d", host, port)
@@ -141,22 +141,24 @@ func DeployKeysToMachine(ctx context.Context, serverKeyPath, serverPubKey string
 		result.Messages = append(result.Messages, fmt.Sprintf("Uploaded %s to %s:%s", filepath.Base(k.LocalPath), host, k.RemotePath))
 	}
 
-	if knownHostsHost != "" {
-		session2, err := conn.NewSession()
-		if err != nil {
-			result.Errors = append(result.Errors, fmt.Sprintf("session for ssh-keyscan: %v", err))
-			result.Success = false
-		} else {
+	if len(knownHostsHosts) > 0 {
+		for _, khHost := range knownHostsHosts {
+			session2, err := conn.NewSession()
+			if err != nil {
+				result.Errors = append(result.Errors, fmt.Sprintf("session for ssh-keyscan %s: %v", khHost, err))
+				result.Success = false
+				continue
+			}
 			session2.Stdout = &stdout
 			session2.Stderr = &stderr
-			err := session2.Run(fmt.Sprintf("ssh-keyscan -H -p %d %s 2>/dev/null >> %s/known_hosts", port, knownHostsHost, remoteSSHDir))
+			err = session2.Run(fmt.Sprintf("ssh-keyscan -H -p %s 2>/dev/null >> %s/known_hosts", khHost, 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()))
+				slog.Warn("deploy: ssh-keyscan failed", "host", khHost, "error", err)
+				result.Errors = append(result.Errors, fmt.Sprintf("ssh-keyscan %s: %v (stderr: %s)", khHost, err, stderr.String()))
 				result.Success = false
 			} else {
-				result.Messages = append(result.Messages, fmt.Sprintf("Populated known_hosts with %s:%d", knownHostsHost, port))
+				result.Messages = append(result.Messages, fmt.Sprintf("Populated known_hosts with %s", khHost))
 			}
 		}
 	}