diff --git a/internal/cmd/server/create.go b/internal/cmd/server/create.go
index 038b62688..7fafe1a03 100644
--- a/internal/cmd/server/create.go
+++ b/internal/cmd/server/create.go
@@ -263,7 +263,8 @@ func createOptsFromFlags(
 
 	// check if ssh-key flag was set, otherwise set to defaults
 	if !flags.Changed("ssh-key") {
-		if ctx := s.Config().ActiveContext(); ctx != nil {
+		if ctx := s.Config().ActiveContext(); ctx != nil && len(ctx.SSHKeys) > 0 {
+			cmd.Println("Using SSH key(s) from active context")
 			sshKeys = ctx.SSHKeys
 		}
 	}
diff --git a/internal/cmd/server/enable_rescue.go b/internal/cmd/server/enable_rescue.go
index 9ff91a026..4c74391f0 100644
--- a/internal/cmd/server/enable_rescue.go
+++ b/internal/cmd/server/enable_rescue.go
@@ -49,7 +49,8 @@ var EnableRescueCmd = base.Cmd{
 
 		// check if ssh-key flag was set, otherwise set to defaults
 		if !cmd.Flags().Changed("ssh-key") {
-			if ctx := s.Config().ActiveContext(); ctx != nil {
+			if ctx := s.Config().ActiveContext(); ctx != nil && len(ctx.SSHKeys) > 0 {
+				cmd.Println("Using SSH key(s) from active context")
 				sshKeys = ctx.SSHKeys
 			}
 		}