diff --git a/cmd/docker-mcp/catalog/ls.go b/cmd/docker-mcp/catalog/ls.go
index 685e6fe7..73f793a6 100644
--- a/cmd/docker-mcp/catalog/ls.go
+++ b/cmd/docker-mcp/catalog/ls.go
@@ -6,10 +6,13 @@ import (
 	"fmt"
 	"time"
 
+	"github.com/docker/cli/cli/command"
+
+	"github.com/docker/mcp-gateway/cmd/docker-mcp/hints"
 	"github.com/docker/mcp-gateway/pkg/telemetry"
 )
 
-func Ls(ctx context.Context, format Format) error {
+func Ls(ctx context.Context, dockerCli command.Cli, format Format) error {
 	// Initialize telemetry
 	telemetry.Init()
 
@@ -32,13 +35,13 @@ func Ls(ctx context.Context, format Format) error {
 		}
 		fmt.Println(string(data))
 	} else {
-		humanPrintCatalog(*cfg)
+		humanPrintCatalog(dockerCli, *cfg)
 	}
 
 	return nil
 }
 
-func humanPrintCatalog(cfg Config) {
+func humanPrintCatalog(dockerCli command.Cli, cfg Config) {
 	if len(cfg.Catalogs) == 0 {
 		fmt.Println("No catalogs configured.")
 		return
@@ -47,4 +50,9 @@ func humanPrintCatalog(cfg Config) {
 	for name, catalog := range cfg.Catalogs {
 		fmt.Printf("%s: %s\n", name, catalog.DisplayName)
 	}
+	if hints.Enabled(dockerCli) {
+		hints.TipCyan.Print("Tip: To browse a catalog's servers, use ")
+		hints.TipCyanBoldItalic.Print("docker mcp catalog show <catalog-name>")
+		fmt.Println()
+	}
 }
diff --git a/cmd/docker-mcp/catalog/show.go b/cmd/docker-mcp/catalog/show.go
index 822ee975..0f5c273a 100644
--- a/cmd/docker-mcp/catalog/show.go
+++ b/cmd/docker-mcp/catalog/show.go
@@ -9,10 +9,12 @@ import (
 	"strings"
 	"time"
 
+	"github.com/docker/cli/cli/command"
 	"github.com/mikefarah/yq/v4/pkg/yqlib"
 	"github.com/moby/term"
 	"gopkg.in/yaml.v3"
 
+	"github.com/docker/mcp-gateway/cmd/docker-mcp/hints"
 	"github.com/docker/mcp-gateway/pkg/yq"
 )
 
@@ -53,7 +55,7 @@ func SupportedFormats() string {
 	return strings.Join(quoted, ", ")
 }
 
-func Show(ctx context.Context, name string, format Format, mcpOAuthDcrEnabled bool) error {
+func Show(ctx context.Context, dockerCli command.Cli, name string, format Format, mcpOAuthDcrEnabled bool) error {
 	cfg, err := ReadConfigWithDefaultCatalog(ctx)
 	if err != nil {
 		return err
@@ -153,6 +155,12 @@ func Show(ctx context.Context, name string, format Format, mcpOAuthDcrEnabled bo
 	fmt.Printf("  %s\n", strings.Repeat("─", headerLineWidth))
 	fmt.Printf("  %d servers total\n", serverCount)
 	fmt.Println()
+	if hints.Enabled(dockerCli) {
+		hints.TipCyan.Print("Tip: To view server details, use ")
+		hints.TipCyanBoldItalic.Print("docker mcp server inspect <server-name>")
+		hints.TipCyan.Print(". To add servers, use ")
+		hints.TipCyanBoldItalic.Println("docker mcp server enable <server-name>")
+	}
 
 	return nil
 }
diff --git a/cmd/docker-mcp/client/connect.go b/cmd/docker-mcp/client/connect.go
index 36f1390c..9eb918bc 100644
--- a/cmd/docker-mcp/client/connect.go
+++ b/cmd/docker-mcp/client/connect.go
@@ -3,9 +3,13 @@ package client
 import (
 	"context"
 	"fmt"
+
+	"github.com/docker/cli/cli/command"
+
+	"github.com/docker/mcp-gateway/cmd/docker-mcp/hints"
 )
 
-func Connect(ctx context.Context, cwd string, config Config, vendor string, global, quiet bool) error {
+func Connect(ctx context.Context, dockerCli command.Cli, cwd string, config Config, vendor string, global, quiet bool) error {
 	if vendor == vendorCodex {
 		if !global {
 			return fmt.Errorf("codex only supports global configuration. Re-run with --global or -g")
@@ -33,5 +37,11 @@ func Connect(ctx context.Context, cwd string, config Config, vendor string, glob
 		return err
 	}
 	fmt.Printf("You might have to restart '%s'.\n", vendor)
+	if hints.Enabled(dockerCli) {
+		hints.TipCyan.Print("Tip: Your client is now connected! Use ")
+		hints.TipCyanBoldItalic.Print("docker mcp tools ls")
+		hints.TipCyan.Println(" to see your available tools")
+		fmt.Println()
+	}
 	return nil
 }
diff --git a/cmd/docker-mcp/commands/catalog.go b/cmd/docker-mcp/commands/catalog.go
index b550cfd8..eb3c20aa 100644
--- a/cmd/docker-mcp/commands/catalog.go
+++ b/cmd/docker-mcp/commands/catalog.go
@@ -23,7 +23,7 @@ func catalogCommand(dockerCli command.Cli) *cobra.Command {
 	cmd.AddCommand(bootstrapCatalogCommand())
 	cmd.AddCommand(importCatalogCommand())
 	cmd.AddCommand(exportCatalogCommand())
-	cmd.AddCommand(lsCatalogCommand())
+	cmd.AddCommand(lsCatalogCommand(dockerCli))
 	cmd.AddCommand(rmCatalogCommand())
 	cmd.AddCommand(updateCatalogCommand(dockerCli))
 	cmd.AddCommand(showCatalogCommand(dockerCli))
@@ -86,7 +86,7 @@ cannot be exported as it is managed by Docker.`,
 	}
 }
 
-func lsCatalogCommand() *cobra.Command {
+func lsCatalogCommand(dockerCli command.Cli) *cobra.Command {
 	var opts struct {
 		Format catalog.Format
 	}
@@ -101,7 +101,7 @@ func lsCatalogCommand() *cobra.Command {
   # List catalogs in JSON format
   docker mcp catalog ls --format=json`,
 		RunE: func(cmd *cobra.Command, _ []string) error {
-			return catalog.Ls(cmd.Context(), opts.Format)
+			return catalog.Ls(cmd.Context(), dockerCli, opts.Format)
 		},
 	}
 	flags := cmd.Flags()
@@ -165,7 +165,7 @@ If no name is provided, shows the Docker official catalog.`,
 			}
 
 			mcpOAuthDcrEnabled := isMcpOAuthDcrFeatureEnabled(dockerCli)
-			return catalog.Show(cmd.Context(), name, opts.Format, mcpOAuthDcrEnabled)
+			return catalog.Show(cmd.Context(), dockerCli, name, opts.Format, mcpOAuthDcrEnabled)
 		},
 	}
 	flags := cmd.Flags()
diff --git a/cmd/docker-mcp/commands/client.go b/cmd/docker-mcp/commands/client.go
index 27d540f7..5cdf07b4 100644
--- a/cmd/docker-mcp/commands/client.go
+++ b/cmd/docker-mcp/commands/client.go
@@ -5,21 +5,21 @@ import (
 	"fmt"
 	"strings"
 
-	"github.com/spf13/pflag"
-
+	"github.com/docker/cli/cli/command"
 	"github.com/spf13/cobra"
+	"github.com/spf13/pflag"
 
 	"github.com/docker/mcp-gateway/cmd/docker-mcp/client"
 )
 
-func clientCommand(cwd string) *cobra.Command {
+func clientCommand(dockerCli command.Cli, cwd string) *cobra.Command {
 	cfg := client.ReadConfig()
 	cmd := &cobra.Command{
 		Use:   fmt.Sprintf("client (Supported: %s)", strings.Join(client.GetSupportedMCPClients(*cfg), ", ")),
 		Short: "Manage MCP clients",
 	}
 	cmd.AddCommand(listClientCommand(cwd, *cfg))
-	cmd.AddCommand(connectClientCommand(cwd, *cfg))
+	cmd.AddCommand(connectClientCommand(dockerCli, cwd, *cfg))
 	cmd.AddCommand(disconnectClientCommand(cwd, *cfg))
 	cmd.AddCommand(manualClientCommand())
 	return cmd
@@ -44,7 +44,7 @@ func listClientCommand(cwd string, cfg client.Config) *cobra.Command {
 	return cmd
 }
 
-func connectClientCommand(cwd string, cfg client.Config) *cobra.Command {
+func connectClientCommand(dockerCli command.Cli, cwd string, cfg client.Config) *cobra.Command {
 	var opts struct {
 		Global bool
 		Quiet  bool
@@ -54,7 +54,7 @@ func connectClientCommand(cwd string, cfg client.Config) *cobra.Command {
 		Short: fmt.Sprintf("Connect the Docker MCP Toolkit to a client. Supported clients: %s", strings.Join(client.GetSupportedMCPClients(cfg), " ")),
 		Args:  cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			return client.Connect(cmd.Context(), cwd, cfg, args[0], opts.Global, opts.Quiet)
+			return client.Connect(cmd.Context(), dockerCli, cwd, cfg, args[0], opts.Global, opts.Quiet)
 		},
 	}
 	flags := cmd.Flags()
diff --git a/cmd/docker-mcp/commands/root.go b/cmd/docker-mcp/commands/root.go
index 615a01e3..7ef4e53f 100644
--- a/cmd/docker-mcp/commands/root.go
+++ b/cmd/docker-mcp/commands/root.go
@@ -71,7 +71,7 @@ func Root(ctx context.Context, cwd string, dockerCli command.Cli) *cobra.Command
 	dockerClient := docker.NewClient(dockerCli)
 
 	cmd.AddCommand(catalogCommand(dockerCli))
-	cmd.AddCommand(clientCommand(cwd))
+	cmd.AddCommand(clientCommand(dockerCli, cwd))
 	cmd.AddCommand(configCommand(dockerClient))
 	cmd.AddCommand(featureCommand(dockerCli))
 	cmd.AddCommand(gatewayCommand(dockerClient, dockerCli))
@@ -80,7 +80,7 @@ func Root(ctx context.Context, cwd string, dockerCli command.Cli) *cobra.Command
 	cmd.AddCommand(registryCommand())
 	cmd.AddCommand(secretCommand(dockerClient))
 	cmd.AddCommand(serverCommand(dockerClient, dockerCli))
-	cmd.AddCommand(toolsCommand(dockerClient))
+	cmd.AddCommand(toolsCommand(dockerClient, dockerCli))
 	cmd.AddCommand(versionCommand())
 
 	if os.Getenv("DOCKER_MCP_SHOW_HIDDEN") == "1" {
diff --git a/cmd/docker-mcp/commands/server.go b/cmd/docker-mcp/commands/server.go
index 34a04012..40b2d9f6 100644
--- a/cmd/docker-mcp/commands/server.go
+++ b/cmd/docker-mcp/commands/server.go
@@ -8,6 +8,7 @@ import (
 	"github.com/docker/cli/cli/command"
 	"github.com/spf13/cobra"
 
+	"github.com/docker/mcp-gateway/cmd/docker-mcp/hints"
 	"github.com/docker/mcp-gateway/cmd/docker-mcp/server"
 	"github.com/docker/mcp-gateway/pkg/config"
 	"github.com/docker/mcp-gateway/pkg/docker"
@@ -42,6 +43,11 @@ func serverCommand(docker docker.Client, dockerCli command.Cli) *cobra.Command {
 				fmt.Fprintln(cmd.OutOrStdout(), "No server is enabled")
 			} else {
 				fmt.Fprintln(cmd.OutOrStdout(), strings.Join(list, ", "))
+				if hints.Enabled(dockerCli) {
+					hints.TipCyan.Fprint(cmd.OutOrStdout(), "Tip: To use these servers, connect to a client (IE: claude/cursor) with ")
+					hints.TipCyanBoldItalic.Fprintln(cmd.OutOrStdout(), "docker mcp client connect <client-name>")
+					fmt.Fprintln(cmd.OutOrStdout(), "")
+				}
 			}
 
 			return nil
@@ -57,7 +63,7 @@ func serverCommand(docker docker.Client, dockerCli command.Cli) *cobra.Command {
 		Args:    cobra.MinimumNArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			mcpOAuthDcrEnabled := isMcpOAuthDcrFeatureEnabled(dockerCli)
-			return server.Enable(cmd.Context(), docker, args, mcpOAuthDcrEnabled)
+			return server.Enable(cmd.Context(), docker, dockerCli, args, mcpOAuthDcrEnabled)
 		},
 	})
 
@@ -68,7 +74,7 @@ func serverCommand(docker docker.Client, dockerCli command.Cli) *cobra.Command {
 		Args:    cobra.MinimumNArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			mcpOAuthDcrEnabled := isMcpOAuthDcrFeatureEnabled(dockerCli)
-			return server.Disable(cmd.Context(), docker, args, mcpOAuthDcrEnabled)
+			return server.Disable(cmd.Context(), docker, dockerCli, args, mcpOAuthDcrEnabled)
 		},
 	})
 
diff --git a/cmd/docker-mcp/commands/tools.go b/cmd/docker-mcp/commands/tools.go
index e4793667..bf44de6b 100644
--- a/cmd/docker-mcp/commands/tools.go
+++ b/cmd/docker-mcp/commands/tools.go
@@ -1,13 +1,14 @@
 package commands
 
 import (
+	"github.com/docker/cli/cli/command"
 	"github.com/spf13/cobra"
 
 	"github.com/docker/mcp-gateway/cmd/docker-mcp/tools"
 	"github.com/docker/mcp-gateway/pkg/docker"
 )
 
-func toolsCommand(docker docker.Client) *cobra.Command {
+func toolsCommand(docker docker.Client, dockerCli command.Cli) *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "tools",
 		Short: "Manage tools",
@@ -30,7 +31,7 @@ func toolsCommand(docker docker.Client) *cobra.Command {
 		Short:   "List tools",
 		Args:    cobra.NoArgs,
 		RunE: func(cmd *cobra.Command, _ []string) error {
-			return tools.List(cmd.Context(), version, gatewayArgs, verbose, "list", "", format)
+			return tools.List(cmd.Context(), dockerCli, version, gatewayArgs, verbose, "list", "", format)
 		},
 	})
 
@@ -39,7 +40,7 @@ func toolsCommand(docker docker.Client) *cobra.Command {
 		Short: "Count tools",
 		Args:  cobra.NoArgs,
 		RunE: func(cmd *cobra.Command, _ []string) error {
-			return tools.List(cmd.Context(), version, gatewayArgs, verbose, "count", "", format)
+			return tools.List(cmd.Context(), dockerCli, version, gatewayArgs, verbose, "count", "", format)
 		},
 	})
 
@@ -48,7 +49,7 @@ func toolsCommand(docker docker.Client) *cobra.Command {
 		Short: "Inspect a tool",
 		Args:  cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			return tools.List(cmd.Context(), version, gatewayArgs, verbose, "inspect", args[0], format)
+			return tools.List(cmd.Context(), dockerCli, version, gatewayArgs, verbose, "inspect", args[0], format)
 		},
 	})
 	cmd.AddCommand(&cobra.Command{
diff --git a/cmd/docker-mcp/hints/hints.go b/cmd/docker-mcp/hints/hints.go
new file mode 100644
index 00000000..0e57766d
--- /dev/null
+++ b/cmd/docker-mcp/hints/hints.go
@@ -0,0 +1,31 @@
+package hints
+
+import (
+	"github.com/docker/cli/cli/command"
+	"github.com/fatih/color"
+)
+
+func Enabled(dockerCli command.Cli) bool {
+	configFile := dockerCli.ConfigFile()
+	if configFile == nil || configFile.Plugins == nil {
+		return true
+	}
+
+	pluginConfig, ok := configFile.Plugins["-x-cli-hints"]
+	if !ok {
+		return true
+	}
+
+	enabledValue, exists := pluginConfig["enabled"]
+	if !exists {
+		return true
+	}
+
+	return enabledValue == "true"
+}
+
+var (
+	TipCyan           = color.New(color.FgCyan)
+	TipCyanBoldItalic = color.New(color.FgCyan, color.Bold, color.Italic)
+	TipGreen          = color.New(color.FgGreen)
+)
diff --git a/cmd/docker-mcp/server/enable.go b/cmd/docker-mcp/server/enable.go
index ca7a84ea..df5b4795 100644
--- a/cmd/docker-mcp/server/enable.go
+++ b/cmd/docker-mcp/server/enable.go
@@ -5,23 +5,25 @@ import (
 	"context"
 	"fmt"
 
+	"github.com/docker/cli/cli/command"
 	"gopkg.in/yaml.v3"
 
+	"github.com/docker/mcp-gateway/cmd/docker-mcp/hints"
 	"github.com/docker/mcp-gateway/pkg/catalog"
 	"github.com/docker/mcp-gateway/pkg/config"
 	"github.com/docker/mcp-gateway/pkg/docker"
 	"github.com/docker/mcp-gateway/pkg/oauth"
 )
 
-func Disable(ctx context.Context, docker docker.Client, serverNames []string, mcpOAuthDcrEnabled bool) error {
-	return update(ctx, docker, nil, serverNames, mcpOAuthDcrEnabled)
+func Disable(ctx context.Context, docker docker.Client, dockerCli command.Cli, serverNames []string, mcpOAuthDcrEnabled bool) error {
+	return update(ctx, docker, dockerCli, nil, serverNames, mcpOAuthDcrEnabled)
 }
 
-func Enable(ctx context.Context, docker docker.Client, serverNames []string, mcpOAuthDcrEnabled bool) error {
-	return update(ctx, docker, serverNames, nil, mcpOAuthDcrEnabled)
+func Enable(ctx context.Context, docker docker.Client, dockerCli command.Cli, serverNames []string, mcpOAuthDcrEnabled bool) error {
+	return update(ctx, docker, dockerCli, serverNames, nil, mcpOAuthDcrEnabled)
 }
 
-func update(ctx context.Context, docker docker.Client, add []string, remove []string, mcpOAuthDcrEnabled bool) error {
+func update(ctx context.Context, docker docker.Client, dockerCli command.Cli, add []string, remove []string, mcpOAuthDcrEnabled bool) error {
 	// Read registry.yaml that contains which servers are enabled.
 	registryYAML, err := config.ReadRegistry(ctx, docker)
 	if err != nil {
@@ -94,5 +96,21 @@ func update(ctx context.Context, docker docker.Client, add []string, remove []st
 		return fmt.Errorf("writing registry config: %w", err)
 	}
 
+	if len(add) > 0 && hints.Enabled(dockerCli) {
+		hints.TipCyan.Print("Tip: ")
+		hints.TipGreen.Print("✓")
+		hints.TipCyan.Print(" Server enabled. To view all enabled servers, use ")
+		hints.TipCyanBoldItalic.Println("docker mcp server ls")
+		fmt.Println()
+	}
+
+	if len(remove) > 0 && hints.Enabled(dockerCli) {
+		hints.TipCyan.Print("Tip: ")
+		hints.TipGreen.Print("✓")
+		hints.TipCyan.Print(" Server disabled. To see remaining enabled servers, use ")
+		hints.TipCyanBoldItalic.Println("docker mcp server ls")
+		fmt.Println()
+	}
+
 	return nil
 }
diff --git a/cmd/docker-mcp/server/server_test.go b/cmd/docker-mcp/server/server_test.go
index 6447fa36..7dd9aae3 100644
--- a/cmd/docker-mcp/server/server_test.go
+++ b/cmd/docker-mcp/server/server_test.go
@@ -10,6 +10,8 @@ import (
 	"strconv"
 	"testing"
 
+	"github.com/docker/cli/cli/command"
+	"github.com/docker/cli/cli/config/configfile"
 	"github.com/docker/docker/api/types/volume"
 	"github.com/docker/docker/errdefs"
 	"github.com/stretchr/testify/assert"
@@ -20,7 +22,7 @@ import (
 )
 
 func TestListVolumeNotFound(t *testing.T) {
-	ctx, home, docker := setup(t, withoutPromptsVolume())
+	ctx, home, docker := setupForList(t, withoutPromptsVolume())
 
 	enabled, err := List(ctx, docker)
 	require.NoError(t, err)
@@ -30,7 +32,7 @@ func TestListVolumeNotFound(t *testing.T) {
 }
 
 func TestListEmptyVolume(t *testing.T) {
-	ctx, home, docker := setup(t, withEmptyPromptsVolume())
+	ctx, home, docker := setupForList(t, withEmptyPromptsVolume())
 
 	enabled, err := List(ctx, docker)
 	require.NoError(t, err)
@@ -40,7 +42,7 @@ func TestListEmptyVolume(t *testing.T) {
 }
 
 func TestListImportVolume(t *testing.T) {
-	ctx, home, docker := setup(t, withRegistryYamlInPromptsVolume("registry:\n  github-official:\n    ref: \"\""))
+	ctx, home, docker := setupForList(t, withRegistryYamlInPromptsVolume("registry:\n  github-official:\n    ref: \"\""))
 
 	enabled, err := List(ctx, docker)
 	require.NoError(t, err)
@@ -50,7 +52,7 @@ func TestListImportVolume(t *testing.T) {
 }
 
 func TestListEmpty(t *testing.T) {
-	ctx, _, docker := setup(t, withEmptyRegistryYaml())
+	ctx, _, docker := setupForList(t, withEmptyRegistryYaml())
 
 	enabled, err := List(ctx, docker)
 	require.NoError(t, err)
@@ -58,7 +60,7 @@ func TestListEmpty(t *testing.T) {
 }
 
 func TestList(t *testing.T) {
-	ctx, _, docker := setup(t, withRegistryYaml("registry:\n  git:\n    ref: \"\""))
+	ctx, _, docker := setupForList(t, withRegistryYaml("registry:\n  git:\n    ref: \"\""))
 
 	enabled, err := List(ctx, docker)
 	require.NoError(t, err)
@@ -66,16 +68,16 @@ func TestList(t *testing.T) {
 }
 
 func TestEnableNotFound(t *testing.T) {
-	ctx, _, docker := setup(t, withEmptyRegistryYaml(), withEmptyCatalog())
+	ctx, _, docker, dockerCli := setup(t, withEmptyRegistryYaml(), withEmptyCatalog())
 
-	err := Enable(ctx, docker, []string{"duckduckgo"}, false)
+	err := Enable(ctx, docker, dockerCli, []string{"duckduckgo"}, false)
 	require.ErrorContains(t, err, "server duckduckgo not found in catalog")
 }
 
 func TestEnable(t *testing.T) {
-	ctx, _, docker := setup(t, withEmptyRegistryYaml(), withCatalog("registry:\n  duckduckgo:\n"))
+	ctx, _, docker, dockerCli := setup(t, withEmptyRegistryYaml(), withCatalog("registry:\n  duckduckgo:\n"))
 
-	err := Enable(ctx, docker, []string{"duckduckgo"}, false)
+	err := Enable(ctx, docker, dockerCli, []string{"duckduckgo"}, false)
 	require.NoError(t, err)
 
 	enabled, err := List(ctx, docker)
@@ -84,9 +86,9 @@ func TestEnable(t *testing.T) {
 }
 
 func TestDisable(t *testing.T) {
-	ctx, _, docker := setup(t, withRegistryYaml("registry:\n  duckduckgo:\n    ref: \"\"\n  git:\n    ref: \"\""), withCatalog("registry:\n  git:\n  duckduckgo:\n"))
+	ctx, _, docker, dockerCli := setup(t, withRegistryYaml("registry:\n  duckduckgo:\n    ref: \"\"\n  git:\n    ref: \"\""), withCatalog("registry:\n  git:\n  duckduckgo:\n"))
 
-	err := Disable(ctx, docker, []string{"duckduckgo"}, false)
+	err := Disable(ctx, docker, dockerCli, []string{"duckduckgo"}, false)
 	require.NoError(t, err)
 
 	enabled, err := List(ctx, docker)
@@ -95,9 +97,9 @@ func TestDisable(t *testing.T) {
 }
 
 func TestDisableUnknown(t *testing.T) {
-	ctx, _, docker := setup(t, withRegistryYaml("registry:\n  duckduckgo:\n    ref: \"\""), withCatalog("registry:\n  duckduckgo:\n"))
+	ctx, _, docker, dockerCli := setup(t, withRegistryYaml("registry:\n  duckduckgo:\n    ref: \"\""), withCatalog("registry:\n  duckduckgo:\n"))
 
-	err := Disable(ctx, docker, []string{"unknown"}, false)
+	err := Disable(ctx, docker, dockerCli, []string{"unknown"}, false)
 	require.NoError(t, err)
 
 	enabled, err := List(ctx, docker)
@@ -106,9 +108,9 @@ func TestDisableUnknown(t *testing.T) {
 }
 
 func TestRemoveOutdatedServerOnEnable(t *testing.T) {
-	ctx, _, docker := setup(t, withRegistryYaml("registry:\n  outdated:\n    ref: \"\""), withCatalog("registry:\n  git:\n"))
+	ctx, _, docker, dockerCli := setup(t, withRegistryYaml("registry:\n  outdated:\n    ref: \"\""), withCatalog("registry:\n  git:\n"))
 
-	err := Enable(ctx, docker, []string{"git"}, false)
+	err := Enable(ctx, docker, dockerCli, []string{"git"}, false)
 	require.NoError(t, err)
 
 	enabled, err := List(ctx, docker)
@@ -117,9 +119,9 @@ func TestRemoveOutdatedServerOnEnable(t *testing.T) {
 }
 
 func TestRemoveOutdatedServerOnDisable(t *testing.T) {
-	ctx, _, docker := setup(t, withRegistryYaml("registry:\n  outdated:\n    ref: \"\""), withEmptyCatalog())
+	ctx, _, docker, dockerCli := setup(t, withRegistryYaml("registry:\n  outdated:\n    ref: \"\""), withEmptyCatalog())
 
-	err := Disable(ctx, docker, []string{"git"}, false)
+	err := Disable(ctx, docker, dockerCli, []string{"git"}, false)
 	require.NoError(t, err)
 
 	enabled, err := List(ctx, docker)
@@ -129,7 +131,7 @@ func TestRemoveOutdatedServerOnDisable(t *testing.T) {
 
 // Fixtures
 
-func setup(t *testing.T, options ...option) (context.Context, string, docker.Client) {
+func setup(t *testing.T, options ...option) (context.Context, string, docker.Client, command.Cli) {
 	t.Helper()
 
 	// Mock for Docker API
@@ -147,7 +149,13 @@ func setup(t *testing.T, options ...option) (context.Context, string, docker.Cli
 		o(t, home, docker)
 	}
 
-	return t.Context(), home, docker
+	return t.Context(), home, docker, &fakeCli{}
+}
+
+func setupForList(t *testing.T, options ...option) (context.Context, string, docker.Client) {
+	t.Helper()
+	ctx, home, docker, _ := setup(t, options...)
+	return ctx, home, docker
 }
 
 func writeFile(t *testing.T, path string, content []byte) {
@@ -168,6 +176,14 @@ func (f *fakeDocker) InspectVolume(context.Context, string) (volume.Volume, erro
 	return f.volume, f.inspectErr
 }
 
+type fakeCli struct {
+	command.Cli
+}
+
+func (fakeCli) ConfigFile() *configfile.ConfigFile {
+	return &configfile.ConfigFile{}
+}
+
 type exitCodeErr struct {
 	exitCode int
 }
diff --git a/cmd/docker-mcp/tools/list.go b/cmd/docker-mcp/tools/list.go
index d6fb4de4..0e393050 100644
--- a/cmd/docker-mcp/tools/list.go
+++ b/cmd/docker-mcp/tools/list.go
@@ -6,13 +6,16 @@ import (
 	"fmt"
 	"strings"
 
+	"github.com/docker/cli/cli/command"
 	"github.com/modelcontextprotocol/go-sdk/mcp"
 	"go.opentelemetry.io/otel"
 	"go.opentelemetry.io/otel/attribute"
 	"go.opentelemetry.io/otel/metric"
+
+	"github.com/docker/mcp-gateway/cmd/docker-mcp/hints"
 )
 
-func List(ctx context.Context, version string, gatewayArgs []string, debug bool, show, tool, format string) error {
+func List(ctx context.Context, dockerCli command.Cli, version string, gatewayArgs []string, debug bool, show, tool, format string) error {
 	// Initialize telemetry for CLI operations
 	meter := otel.GetMeterProvider().Meter("github.com/docker/mcp-gateway")
 	toolsDiscoveredGauge, _ := meter.Int64Gauge("mcp.cli.tools.discovered",
@@ -50,12 +53,24 @@ func List(ctx context.Context, version string, gatewayArgs []string, debug bool,
 			for _, tool := range response.Tools {
 				fmt.Println(" -", tool.Name, "-", toolDescription(tool))
 			}
+			if hints.Enabled(dockerCli) {
+				hints.TipCyan.Print("Tip: For tool details, use ")
+				hints.TipCyanBoldItalic.Print("docker mcp tools inspect <tool-name>")
+				hints.TipCyan.Print(". To test the tool, use ")
+				hints.TipCyanBoldItalic.Println("docker mcp tools call <tool-name>")
+				fmt.Println()
+			}
 		}
 	case "count":
 		if format == "json" {
 			fmt.Printf("{\"count\": %d}\n", len(response.Tools))
 		} else {
 			fmt.Println(len(response.Tools), "tools")
+			if hints.Enabled(dockerCli) {
+				hints.TipCyan.Print("Tip: To see all available tools, use ")
+				hints.TipCyanBoldItalic.Println("docker mcp tools ls")
+				fmt.Println()
+			}
 		}
 	case "inspect":
 		var found *mcp.Tool