diff --git a/src/openjarvis/cli/ask.py b/src/openjarvis/cli/ask.py
index 9811f99a..d1c21075 100644
--- a/src/openjarvis/cli/ask.py
+++ b/src/openjarvis/cli/ask.py
@@ -8,6 +8,7 @@ import sys
 import click
 from rich.console import Console
 
+from openjarvis.cli.hints import hint_no_engine
 from openjarvis.core.config import load_config
 from openjarvis.core.events import EventBus
 from openjarvis.core.types import Message, Role
@@ -268,6 +269,7 @@ def ask(
             )
         except EngineConnectionError as exc:
             console.print(f"[red]Engine error:[/red] {exc}")
+            console.print(hint_no_engine())
             sys.exit(1)
 
         if output_json:
diff --git a/src/openjarvis/cli/hints.py b/src/openjarvis/cli/hints.py
new file mode 100644
index 00000000..41924b91
--- /dev/null
+++ b/src/openjarvis/cli/hints.py
@@ -0,0 +1,41 @@
+"""Rich-formatted error hints for common CLI failure modes."""
+
+from __future__ import annotations
+
+from typing import Optional
+
+
+def hint_no_config() -> str:
+    """Return a suggestion when no config file is found."""
+    return (
+        "[yellow]Hint:[/yellow] No config file found.\n"
+        "  Run [bold]jarvis init[/bold] to detect hardware and generate "
+        "[cyan]~/.openjarvis/config.toml[/cyan].\n"
+        "  Or run [bold]jarvis quickstart[/bold] for a guided setup."
+    )
+
+
+def hint_no_engine(engine_name: Optional[str] = None) -> str:
+    """Return a suggestion when the inference engine is unreachable."""
+    name = engine_name or "ollama"
+    return (
+        f"[yellow]Hint:[/yellow] Engine '{name}' is not reachable.\n"
+        f"  Make sure the {name} server is running.\n"
+        "  Run [bold]jarvis doctor[/bold] to check all engines.\n"
+        "  Run [bold]jarvis quickstart[/bold] for guided setup."
+    )
+
+
+def hint_no_model(model_name: Optional[str] = None) -> str:
+    """Return a suggestion when no model is available."""
+    if model_name:
+        return (
+            f"[yellow]Hint:[/yellow] Model '{model_name}' not found.\n"
+            f"  Try: [bold]ollama pull {model_name}[/bold]\n"
+            "  Run [bold]jarvis model list[/bold] to see available models."
+        )
+    return (
+        "[yellow]Hint:[/yellow] No models available.\n"
+        "  Pull a model first: [bold]ollama pull qwen3:8b[/bold]\n"
+        "  Run [bold]jarvis model list[/bold] to see available models."
+    )
diff --git a/tests/cli/test_hints.py b/tests/cli/test_hints.py
new file mode 100644
index 00000000..0ba4797a
--- /dev/null
+++ b/tests/cli/test_hints.py
@@ -0,0 +1,37 @@
+"""Tests for CLI error hint functions."""
+
+from __future__ import annotations
+
+from openjarvis.cli.hints import (
+    hint_no_config,
+    hint_no_engine,
+    hint_no_model,
+)
+
+
+class TestHintFunctions:
+    def test_hint_no_config_returns_string(self):
+        msg = hint_no_config()
+        assert isinstance(msg, str)
+        assert len(msg) > 0
+        assert "init" in msg.lower() or "config" in msg.lower()
+
+    def test_hint_no_engine_returns_string(self):
+        msg = hint_no_engine()
+        assert isinstance(msg, str)
+        assert len(msg) > 0
+        assert "engine" in msg.lower() or "ollama" in msg.lower()
+
+    def test_hint_no_engine_with_name(self):
+        msg = hint_no_engine("vllm")
+        assert "vllm" in msg.lower()
+
+    def test_hint_no_model_returns_string(self):
+        msg = hint_no_model()
+        assert isinstance(msg, str)
+        assert len(msg) > 0
+        assert "model" in msg.lower() or "pull" in msg.lower()
+
+    def test_hint_no_model_with_name(self):
+        msg = hint_no_model("qwen3:8b")
+        assert "qwen3:8b" in msg