diff --git a/cmd/root.go b/cmd/root.go
index e887152..637fd39 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -83,6 +83,8 @@ func init() {
 	flags.Bool("page-all", false, "Auto-paginate, emit NDJSON")
 
 	rootCmd.PersistentPreRunE = func(cmd *cobra.Command, args []string) error {
+		maybeHintSkillsInstall(cmd)
+
 		// Select the active profile before any credential access so that auth
 		// commands and credential lookups all resolve against the same profile.
 		if profile, _ := cmd.Flags().GetString("profile"); profile != "" {
diff --git a/cmd/skills_hint.go b/cmd/skills_hint.go
new file mode 100644
index 0000000..7285a3e
--- /dev/null
+++ b/cmd/skills_hint.go
@@ -0,0 +1,48 @@
+package cmd
+
+import (
+	"fmt"
+	"os"
+	"path/filepath"
+	"strings"
+
+	"github.com/spf13/cobra"
+)
+
+// maybeHintSkillsInstall prints a one-time hint to stderr when the bootstrap
+// skill hasn't been installed yet. It only fires on an interactive terminal and
+// skips commands where the hint would be noise (skills install itself, prime,
+// help, completion).
+func maybeHintSkillsInstall(cmd *cobra.Command) {
+	if !shouldHintSkillsInstall(cmd) {
+		return
+	}
+	fmt.Fprintln(cmd.ErrOrStderr(), "Tip: run \"cio skills install\" to set up AI agent skills for Claude Code and Codex.")
+}
+
+func shouldHintSkillsInstall(cmd *cobra.Command) bool {
+	path := cmd.CommandPath()
+	if strings.HasPrefix(path, "cio skills") ||
+		strings.HasPrefix(path, "cio prime") ||
+		strings.HasPrefix(path, "cio help") ||
+		strings.HasPrefix(path, "cio completion") {
+		return false
+	}
+
+	stderr, ok := cmd.ErrOrStderr().(*os.File)
+	if !ok || !isTerminalInput(stderr.Fd()) {
+		return false
+	}
+
+	home, err := os.UserHomeDir()
+	if err != nil {
+		return false
+	}
+
+	skillPath := filepath.Join(home, ".claude", "skills", "cli", "SKILL.md")
+	if _, err := os.Stat(skillPath); err == nil {
+		return false
+	}
+
+	return true
+}