diff --git a/commands/inspect.go b/commands/inspect.go
index 474981c1..090b676c 100644
--- a/commands/inspect.go
+++ b/commands/inspect.go
@@ -30,7 +30,8 @@ func newInspectCmd() *cobra.Command {
 			}
 			model, err = client.List(false, openai, model)
 			if err != nil {
-				return fmt.Errorf("Failed to list models: %v\n", err)
+				err = handleClientError(err, "Failed to list models")
+				return handleNotRunningError(err)
 			}
 			cmd.Println(model)
 			return nil
diff --git a/commands/list.go b/commands/list.go
index 12aed24f..00ca9c72 100644
--- a/commands/list.go
+++ b/commands/list.go
@@ -20,7 +20,8 @@ func newListCmd() *cobra.Command {
 			}
 			models, err := client.List(jsonFormat, openai, "")
 			if err != nil {
-				return fmt.Errorf("Failed to list models: %v\n", err)
+				err = handleClientError(err, "Failed to list models")
+				return handleNotRunningError(err)
 			}
 			cmd.Println(models)
 			return nil
diff --git a/commands/pull.go b/commands/pull.go
index 43b48fe7..1e1725a9 100644
--- a/commands/pull.go
+++ b/commands/pull.go
@@ -29,7 +29,8 @@ func newPullCmd() *cobra.Command {
 			}
 			response, err := client.Pull(model)
 			if err != nil {
-				return fmt.Errorf("Failed to pull model: %v\n", err)
+				err = handleClientError(err, "Failed to pull model")
+				return handleNotRunningError(err)
 			}
 			cmd.Println(response)
 			return nil
diff --git a/commands/rm.go b/commands/rm.go
index bb71ca46..3393e87b 100644
--- a/commands/rm.go
+++ b/commands/rm.go
@@ -29,7 +29,8 @@ func newRemoveCmd() *cobra.Command {
 			}
 			response, err := client.Remove(model)
 			if err != nil {
-				return fmt.Errorf("Failed to remove model: %v\n", err)
+				err = handleClientError(err, "Failed to remove model")
+				return handleNotRunningError(err)
 			}
 			cmd.Println(response)
 			return nil
diff --git a/commands/run.go b/commands/run.go
index 001733f3..8b31859d 100644
--- a/commands/run.go
+++ b/commands/run.go
@@ -39,19 +39,19 @@ func newRunCmd() *cobra.Command {
 
 			if _, err := client.List(false, false, model); err != nil {
 				if !errors.Is(err, desktop.ErrNotFound) {
-					return fmt.Errorf("Failed to list model: %v\n", err)
+					return handleNotRunningError(handleClientError(err, "Failed to list models"))
 				}
 				cmd.Println("Unable to find model '" + model + "' locally. Pulling from the server.")
 				response, err := client.Pull(model)
 				if err != nil {
-					return fmt.Errorf("Failed to pull model: %v\n", err)
+					return handleNotRunningError(handleClientError(err, "Failed to pull model"))
 				}
 				cmd.Println(response)
 			}
 
 			if prompt != "" {
 				if err := client.Chat(model, prompt); err != nil {
-					return fmt.Errorf("Failed to generate a response: %v\n", err)
+					return handleClientError(err, "Failed to generate a response")
 				}
 				cmd.Println()
 				return nil
@@ -75,7 +75,7 @@ func newRunCmd() *cobra.Command {
 				}
 
 				if err := client.Chat(model, userInput); err != nil {
-					cmd.PrintErrf("Failed to generate a response: %v\n", err)
+					cmd.PrintErr(handleClientError(err, "Failed to generate a response"))
 					cmd.Print("> ")
 					continue
 				}
diff --git a/commands/status.go b/commands/status.go
index cb6fc39a..3a4a6258 100644
--- a/commands/status.go
+++ b/commands/status.go
@@ -2,9 +2,11 @@ package commands
 
 import (
 	"fmt"
+	"os"
+
+	"github.com/docker/cli/cli-plugins/hooks"
 	"github.com/docker/model-cli/desktop"
 	"github.com/spf13/cobra"
-	"os"
 )
 
 func newStatusCmd() *cobra.Command {
@@ -24,6 +26,7 @@ func newStatusCmd() *cobra.Command {
 				cmd.Println("Docker Model Runner is running")
 			} else {
 				cmd.Println("Docker Model Runner is not running")
+				hooks.PrintNextSteps(os.Stdout, []string{enableViaCLI, enableViaGUI})
 				os.Exit(1)
 			}
 
diff --git a/commands/utils.go b/commands/utils.go
new file mode 100644
index 00000000..6ddb33ba
--- /dev/null
+++ b/commands/utils.go
@@ -0,0 +1,34 @@
+package commands
+
+import (
+	"bytes"
+	"fmt"
+	"strings"
+
+	"github.com/docker/cli/cli-plugins/hooks"
+	"github.com/docker/model-cli/desktop"
+	"github.com/pkg/errors"
+)
+
+const (
+	enableViaCLI = "Enable Docker Model Runner via the CLI → docker desktop enable model-runner"
+	enableViaGUI = "Enable Docker Model Runner via the GUI → Go to Settings->Features in development->Enable Docker Model Runner"
+)
+
+var notRunningErr = fmt.Errorf("Docker Model Runner is not running. Please start it and try again.\n")
+
+func handleClientError(err error, message string) error {
+	if errors.Is(err, desktop.ErrServiceUnavailable) {
+		return notRunningErr
+	}
+	return errors.Wrap(err, message)
+}
+
+func handleNotRunningError(err error) error {
+	if errors.Is(err, notRunningErr) {
+		var buf bytes.Buffer
+		hooks.PrintNextSteps(&buf, []string{enableViaCLI, enableViaGUI})
+		return fmt.Errorf("%w\n%s", err, strings.TrimRight(buf.String(), "\n"))
+	}
+	return err
+}
diff --git a/desktop/desktop.go b/desktop/desktop.go
index d0344fdd..683653fc 100644
--- a/desktop/desktop.go
+++ b/desktop/desktop.go
@@ -22,7 +22,10 @@ import (
 	"go.opentelemetry.io/otel"
 )
 
-var ErrNotFound = errors.New("model not found")
+var (
+	ErrNotFound           = errors.New("model not found")
+	ErrServiceUnavailable = errors.New("service unavailable")
+)
 
 type otelErrorSilencer struct{}
 
@@ -79,13 +82,14 @@ func (c *Client) Pull(model string) (string, error) {
 		return "", fmt.Errorf("error marshaling request: %w", err)
 	}
 
-	resp, err := c.dockerClient.HTTPClient().Post(
-		url(inference.ModelsPrefix+"/create"),
-		"application/json",
+	createPath := inference.ModelsPrefix + "/create"
+	resp, err := c.doRequest(
+		http.MethodPost,
+		createPath,
 		bytes.NewReader(jsonData),
 	)
 	if err != nil {
-		return "", fmt.Errorf("error querying %s: %w", inference.ModelsPrefix+"/create", err)
+		return "", c.handleQueryError(err, createPath)
 	}
 	defer resp.Body.Close()
 
@@ -118,17 +122,20 @@ func (c *Client) List(jsonFormat, openai bool, model string) (string, error) {
 		}
 		modelsRoute += "/" + model
 	}
-	resp, err := c.dockerClient.HTTPClient().Get(url(modelsRoute))
+
+	resp, err := c.doRequest(http.MethodGet, modelsRoute, nil)
 	if err != nil {
-		return "", err
+		return "", c.handleQueryError(err, modelsRoute)
 	}
 	defer resp.Body.Close()
+
 	if resp.StatusCode != http.StatusOK {
 		if model != "" && resp.StatusCode == http.StatusNotFound {
 			return "", errors.Wrap(ErrNotFound, model)
 		}
 		return "", fmt.Errorf("failed to list models: %s", resp.Status)
 	}
+
 	body, err := io.ReadAll(resp.Body)
 	if err != nil {
 		return "", fmt.Errorf("failed to read response body: %w", err)
@@ -188,13 +195,14 @@ func (c *Client) Chat(model, prompt string) error {
 		return fmt.Errorf("error marshaling request: %w", err)
 	}
 
-	resp, err := c.dockerClient.HTTPClient().Post(
-		url(inference.InferencePrefix+"/v1/chat/completions"),
-		"application/json",
+	chatCompletionsPath := inference.InferencePrefix + "/v1/chat/completions"
+	resp, err := c.doRequest(
+		http.MethodPost,
+		chatCompletionsPath,
 		bytes.NewReader(jsonData),
 	)
 	if err != nil {
-		return fmt.Errorf("error querying %s: %w", inference.InferencePrefix+"/v1/chat/completions", err)
+		return c.handleQueryError(err, chatCompletionsPath)
 	}
 	defer resp.Body.Close()
 
@@ -239,18 +247,14 @@ func (c *Client) Chat(model, prompt string) error {
 }
 
 func (c *Client) Remove(model string) (string, error) {
-	req, err := http.NewRequest(http.MethodDelete, url(inference.ModelsPrefix+"/"+model), nil)
+	removePath := inference.ModelsPrefix + "/" + model
+	resp, err := c.doRequest(http.MethodDelete, removePath, nil)
 	if err != nil {
-		return "", fmt.Errorf("error creating request: %w", err)
-	}
-
-	resp, err := c.dockerClient.HTTPClient().Do(req)
-	if err != nil {
-		return "", fmt.Errorf("error querying %s: %w", inference.ModelsPrefix+"/"+model, err)
+		return "", c.handleQueryError(err, removePath)
 	}
 	defer resp.Body.Close()
 
-	if resp.StatusCode != http.StatusOK { // from common/pkg/inference/models/manager.go
+	if resp.StatusCode != http.StatusOK {
 		var bodyStr string
 		body, err := io.ReadAll(resp.Body)
 		if err != nil {
@@ -268,6 +272,36 @@ func url(path string) string {
 	return fmt.Sprintf("http://localhost" + inference.ExperimentalEndpointsPrefix + path)
 }
 
+// doRequest is a helper function that performs HTTP requests and handles 503 responses
+func (c *Client) doRequest(method, path string, body io.Reader) (*http.Response, error) {
+	req, err := http.NewRequest(method, url(path), body)
+	if err != nil {
+		return nil, fmt.Errorf("error creating request: %w", err)
+	}
+	if body != nil {
+		req.Header.Set("Content-Type", "application/json")
+	}
+
+	resp, err := c.dockerClient.HTTPClient().Do(req)
+	if err != nil {
+		return nil, err
+	}
+
+	if resp.StatusCode == http.StatusServiceUnavailable {
+		resp.Body.Close()
+		return nil, ErrServiceUnavailable
+	}
+
+	return resp, nil
+}
+
+func (c *Client) handleQueryError(err error, path string) error {
+	if errors.Is(err, ErrServiceUnavailable) {
+		return ErrServiceUnavailable
+	}
+	return fmt.Errorf("error querying %s: %w", path, err)
+}
+
 func prettyPrintModels(models []Model) string {
 	var buf bytes.Buffer
 	table := tablewriter.NewWriter(&buf)