diff --git a/cli/command/engine/activate.go b/cli/command/engine/activate.go
index a40438a13f..e37048f194 100644
--- a/cli/command/engine/activate.go
+++ b/cli/command/engine/activate.go
@@ -12,7 +12,6 @@ import (
 	"github.com/docker/licensing/model"
 	"github.com/pkg/errors"
 	"github.com/spf13/cobra"
-	"golang.org/x/sys/unix"
 )
 
 type activateOptions struct {
@@ -68,7 +67,7 @@ https://hub.docker.com/ then specify the file with the '--license' flag.
 }
 
 func runActivate(cli command.Cli, options activateOptions) error {
-	if unix.Geteuid() != 0 {
+	if !isRoot() {
 		return errors.New("must be privileged to activate engine")
 	}
 	ctx := context.Background()
@@ -108,12 +107,17 @@ func runActivate(cli command.Cli, options activateOptions) error {
 		EngineVersion:  options.version,
 	}
 
-	return client.ActivateEngine(ctx, opts, cli.Out(), authConfig,
+	err = client.ActivateEngine(ctx, opts, cli.Out(), authConfig,
 		func(ctx context.Context) error {
 			client := cli.Client()
 			_, err := client.Ping(ctx)
 			return err
 		})
+	if err != nil {
+		return err
+	}
+	fmt.Fprintln(cli.Out(), "To complete the activation, please restart docker with 'systemctl restart docker'")
+	return nil
 }
 
 func getLicenses(ctx context.Context, authConfig *types.AuthConfig, cli command.Cli, options activateOptions) (*model.IssuedLicense, error) {
diff --git a/cli/command/engine/activate_test.go b/cli/command/engine/activate_test.go
index 6936161eef..6fe552c7da 100644
--- a/cli/command/engine/activate_test.go
+++ b/cli/command/engine/activate_test.go
@@ -14,6 +14,7 @@ func TestActivateNoContainerd(t *testing.T) {
 			return nil, fmt.Errorf("some error")
 		},
 	)
+	isRoot = func() bool { return true }
 	cmd := newActivateCommand(testCli)
 	cmd.Flags().Set("license", "invalidpath")
 	cmd.SilenceUsage = true
@@ -28,6 +29,7 @@ func TestActivateBadLicense(t *testing.T) {
 			return &fakeContainerizedEngineClient{}, nil
 		},
 	)
+	isRoot = func() bool { return true }
 	cmd := newActivateCommand(testCli)
 	cmd.SilenceUsage = true
 	cmd.SilenceErrors = true
diff --git a/cli/command/engine/activate_unix.go b/cli/command/engine/activate_unix.go
new file mode 100644
index 0000000000..ed4777ae2e
--- /dev/null
+++ b/cli/command/engine/activate_unix.go
@@ -0,0 +1,13 @@
+// +build !windows
+
+package engine
+
+import (
+	"golang.org/x/sys/unix"
+)
+
+var (
+	isRoot = func() bool {
+		return unix.Geteuid() == 0
+	}
+)
diff --git a/cli/command/engine/activate_windows.go b/cli/command/engine/activate_windows.go
new file mode 100644
index 0000000000..35a4e88a36
--- /dev/null
+++ b/cli/command/engine/activate_windows.go
@@ -0,0 +1,9 @@
+// +build windows
+
+package engine
+
+var (
+	isRoot = func() bool {
+		return true
+	}
+)
diff --git a/cli/command/engine/check.go b/cli/command/engine/check.go
index 86d4243dca..b4d92cfa5e 100644
--- a/cli/command/engine/check.go
+++ b/cli/command/engine/check.go
@@ -1,14 +1,16 @@
 package engine
 
 import (
+	"context"
 	"fmt"
 
 	"github.com/docker/cli/cli"
 	"github.com/docker/cli/cli/command"
+	"github.com/docker/cli/cli/command/formatter"
+	"github.com/docker/cli/internal/versions"
 	clitypes "github.com/docker/cli/types"
 	"github.com/pkg/errors"
 	"github.com/spf13/cobra"
-	"golang.org/x/sys/unix"
 )
 
 const (
@@ -37,7 +39,7 @@ func newCheckForUpdatesCommand(dockerCli command.Cli) *cobra.Command {
 		},
 	}
 	flags := cmd.Flags()
-	flags.StringVar(&options.registryPrefix, "registry-prefix", "", "Override the existing location where engine images are pulled")
+	flags.StringVar(&options.registryPrefix, "registry-prefix", "docker.io/store/docker", "Override the existing location where engine images are pulled")
 	flags.BoolVar(&options.downgrades, "downgrades", false, "Report downgrades (default omits older versions)")
 	flags.BoolVar(&options.preReleases, "pre-releases", false, "Include pre-release versions")
 	flags.BoolVar(&options.upgrades, "upgrades", true, "Report available upgrades")
@@ -49,70 +51,67 @@ func newCheckForUpdatesCommand(dockerCli command.Cli) *cobra.Command {
 }
 
 func runCheck(dockerCli command.Cli, options checkOptions) error {
-	if unix.Geteuid() != 0 {
+	if !isRoot() {
 		return errors.New("must be privileged to activate engine")
 	}
+	ctx := context.Background()
+	client := dockerCli.Client()
+	serverVersion, err := client.ServerVersion(ctx)
+	if err != nil {
+		return err
+	}
 
-	/*
-		ctx := context.Background()
-		client, err := dockerCli.NewContainerizedEngineClient(options.sockPath)
-		if err != nil {
-			return errors.Wrap(err, "unable to access local containerd")
-		}
-		defer client.Close()
-			versions, err := client.GetEngineVersions(ctx, dockerCli.RegistryClient(false), currentVersion, imageName)
-			if err != nil {
-				return err
-			}
+	availVersions, err := versions.GetEngineVersions(ctx, dockerCli.RegistryClient(false), options.registryPrefix, serverVersion)
+	if err != nil {
+		return err
+	}
 
-			availUpdates := []clitypes.Update{
-				{Type: "current", Version: currentVersion},
-			}
-			if len(versions.Patches) > 0 {
-				availUpdates = append(availUpdates,
-					processVersions(
-						currentVersion,
-						"patch",
-						options.preReleases,
-						versions.Patches)...)
-			}
-			if options.upgrades {
-				availUpdates = append(availUpdates,
-					processVersions(
-						currentVersion,
-						"upgrade",
-						options.preReleases,
-						versions.Upgrades)...)
-			}
-			if options.downgrades {
-				availUpdates = append(availUpdates,
-					processVersions(
-						currentVersion,
-						"downgrade",
-						options.preReleases,
-						versions.Downgrades)...)
-			}
+	availUpdates := []clitypes.Update{
+		{Type: "current", Version: serverVersion.Version},
+	}
+	if len(availVersions.Patches) > 0 {
+		availUpdates = append(availUpdates,
+			processVersions(
+				serverVersion.Version,
+				"patch",
+				options.preReleases,
+				availVersions.Patches)...)
+	}
+	if options.upgrades {
+		availUpdates = append(availUpdates,
+			processVersions(
+				serverVersion.Version,
+				"upgrade",
+				options.preReleases,
+				availVersions.Upgrades)...)
+	}
+	if options.downgrades {
+		availUpdates = append(availUpdates,
+			processVersions(
+				serverVersion.Version,
+				"downgrade",
+				options.preReleases,
+				availVersions.Downgrades)...)
+	}
 
-			format := options.format
-			if len(format) == 0 {
-				format = formatter.TableFormatKey
-			}
+	format := options.format
+	if len(format) == 0 {
+		format = formatter.TableFormatKey
+	}
 
-			updatesCtx := formatter.Context{
-				Output: dockerCli.Out(),
-				Format: formatter.NewUpdatesFormat(format, options.quiet),
-				Trunc:  false,
-			}
-			return formatter.UpdatesWrite(updatesCtx, availUpdates)
-	*/
-	return nil
+	updatesCtx := formatter.Context{
+		Output: dockerCli.Out(),
+		Format: formatter.NewUpdatesFormat(format, options.quiet),
+		Trunc:  false,
+	}
+	return formatter.UpdatesWrite(updatesCtx, availUpdates)
 }
 
 func processVersions(currentVersion, verType string,
 	includePrerelease bool,
-	versions []clitypes.DockerVersion) []clitypes.Update {
+	availVersions []clitypes.DockerVersion) []clitypes.Update {
 	availUpdates := []clitypes.Update{}
-	for _, ver := range versions {
+	for _, ver := range availVersions {
 		if !includePrerelease && ver.Prerelease() != "" {
 			continue
 		}
diff --git a/cli/command/engine/check_test.go b/cli/command/engine/check_test.go
index 14c6eddb27..89450e67f9 100644
--- a/cli/command/engine/check_test.go
+++ b/cli/command/engine/check_test.go
@@ -5,11 +5,13 @@ import (
 	"fmt"
 	"testing"
 
-	registryclient "github.com/docker/cli/cli/registry/client"
+	manifesttypes "github.com/docker/cli/cli/manifest/types"
 	"github.com/docker/cli/internal/test"
-	clitypes "github.com/docker/cli/types"
+	"github.com/docker/distribution"
+	"github.com/docker/distribution/reference"
+	"github.com/docker/docker/api/types"
 	"github.com/docker/docker/client"
-	ver "github.com/hashicorp/go-version"
+	"github.com/opencontainers/go-digest"
 	"gotest.tools/assert"
 	"gotest.tools/golden"
 )
@@ -18,126 +20,87 @@ var (
 	testCli = test.NewFakeCli(&client.Client{})
 )
 
-func TestCheckForUpdatesNoContainerd(t *testing.T) {
-	testCli.SetContainerizedEngineClient(
-		func(string) (clitypes.ContainerizedClient, error) {
-			return nil, fmt.Errorf("some error")
-		},
-	)
-	cmd := newCheckForUpdatesCommand(testCli)
-	cmd.SilenceUsage = true
-	cmd.SilenceErrors = true
-	err := cmd.Execute()
-	assert.ErrorContains(t, err, "unable to access local containerd")
+type verClient struct {
+	client.Client
+	ver    types.Version
+	verErr error
+}
+
+func (c *verClient) ServerVersion(ctx context.Context) (types.Version, error) {
+	return c.ver, c.verErr
+}
+
+type testRegistryClient struct {
+	tags []string
+}
+
+func (c testRegistryClient) GetManifest(ctx context.Context, ref reference.Named) (manifesttypes.ImageManifest, error) {
+	return manifesttypes.ImageManifest{}, nil
+}
+func (c testRegistryClient) GetManifestList(ctx context.Context, ref reference.Named) ([]manifesttypes.ImageManifest, error) {
+	return nil, nil
+}
+func (c testRegistryClient) MountBlob(ctx context.Context, source reference.Canonical, target reference.Named) error {
+	return nil
+}
+
+func (c testRegistryClient) PutManifest(ctx context.Context, ref reference.Named, manifest distribution.Manifest) (digest.Digest, error) {
+	return "", nil
+}
+func (c testRegistryClient) GetTags(ctx context.Context, ref reference.Named) ([]string, error) {
+	return c.tags, nil
 }
 
 func TestCheckForUpdatesNoCurrentVersion(t *testing.T) {
-	retErr := fmt.Errorf("some failure")
-	getCurrentEngineVersionFunc := func(ctx context.Context) (clitypes.EngineInitOptions, error) {
-		return clitypes.EngineInitOptions{}, retErr
-	}
-	testCli.SetContainerizedEngineClient(
-		func(string) (clitypes.ContainerizedClient, error) {
-			return &fakeContainerizedEngineClient{
-				getCurrentEngineVersionFunc: getCurrentEngineVersionFunc,
-			}, nil
-		},
-	)
-	cmd := newCheckForUpdatesCommand(testCli)
+	isRoot = func() bool { return true }
+	c := test.NewFakeCli(&verClient{client.Client{}, types.Version{}, nil})
+	c.SetRegistryClient(testRegistryClient{})
+	cmd := newCheckForUpdatesCommand(c)
 	cmd.SilenceUsage = true
 	cmd.SilenceErrors = true
 	err := cmd.Execute()
-	assert.Assert(t, err == retErr)
-}
-
-func TestCheckForUpdatesGetEngineVersionsFail(t *testing.T) {
-	retErr := fmt.Errorf("some failure")
-	getEngineVersionsFunc := func(ctx context.Context,
-		registryClient registryclient.RegistryClient,
-		currentVersion, imageName string) (clitypes.AvailableVersions, error) {
-		return clitypes.AvailableVersions{}, retErr
-	}
-	testCli.SetContainerizedEngineClient(
-		func(string) (clitypes.ContainerizedClient, error) {
-			return &fakeContainerizedEngineClient{
-				getEngineVersionsFunc: getEngineVersionsFunc,
-			}, nil
-		},
-	)
-	cmd := newCheckForUpdatesCommand(testCli)
-	cmd.SilenceUsage = true
-	cmd.SilenceErrors = true
-	err := cmd.Execute()
-	assert.Assert(t, err == retErr)
+	assert.ErrorContains(t, err, "alformed version")
 }
 
 func TestCheckForUpdatesGetEngineVersionsHappy(t *testing.T) {
-	getCurrentEngineVersionFunc := func(ctx context.Context) (clitypes.EngineInitOptions, error) {
-		return clitypes.EngineInitOptions{
-			EngineImage:   "current engine",
-			EngineVersion: "1.1.0",
-		}, nil
-	}
-	getEngineVersionsFunc := func(ctx context.Context,
-		registryClient registryclient.RegistryClient,
-		currentVersion, imageName string) (clitypes.AvailableVersions, error) {
-		return clitypes.AvailableVersions{
-			Downgrades: parseVersions(t, "1.0.1", "1.0.2", "1.0.3-beta1"),
-			Patches:    parseVersions(t, "1.1.1", "1.1.2", "1.1.3-beta1"),
-			Upgrades:   parseVersions(t, "1.2.0", "2.0.0", "2.1.0-beta1"),
-		}, nil
-	}
-	testCli.SetContainerizedEngineClient(
-		func(string) (clitypes.ContainerizedClient, error) {
-			return &fakeContainerizedEngineClient{
-				getEngineVersionsFunc:       getEngineVersionsFunc,
-				getCurrentEngineVersionFunc: getCurrentEngineVersionFunc,
-			}, nil
-		},
-	)
-	cmd := newCheckForUpdatesCommand(testCli)
+	c := test.NewFakeCli(&verClient{client.Client{}, types.Version{Version: "1.1.0"}, nil})
+	c.SetRegistryClient(testRegistryClient{[]string{
+		"1.0.1", "1.0.2", "1.0.3-beta1",
+		"1.1.1", "1.1.2", "1.1.3-beta1",
+		"1.2.0", "2.0.0", "2.1.0-beta1",
+	}})
+	isRoot = func() bool { return true }
+	cmd := newCheckForUpdatesCommand(c)
 	cmd.Flags().Set("pre-releases", "true")
 	cmd.Flags().Set("downgrades", "true")
+	cmd.SilenceUsage = true
+	cmd.SilenceErrors = true
 	err := cmd.Execute()
 	assert.NilError(t, err)
-	golden.Assert(t, testCli.OutBuffer().String(), "check-all.golden")
+	golden.Assert(t, c.OutBuffer().String(), "check-all.golden")
 
-	testCli.OutBuffer().Reset()
+	c.OutBuffer().Reset()
 	cmd.Flags().Set("pre-releases", "false")
 	cmd.Flags().Set("downgrades", "true")
 	err = cmd.Execute()
 	assert.NilError(t, err)
-	fmt.Println(testCli.OutBuffer().String())
-	golden.Assert(t, testCli.OutBuffer().String(), "check-no-prerelease.golden")
+	fmt.Println(c.OutBuffer().String())
+	golden.Assert(t, c.OutBuffer().String(), "check-no-prerelease.golden")
 
-	testCli.OutBuffer().Reset()
+	c.OutBuffer().Reset()
 	cmd.Flags().Set("pre-releases", "false")
 	cmd.Flags().Set("downgrades", "false")
 	err = cmd.Execute()
 	assert.NilError(t, err)
-	fmt.Println(testCli.OutBuffer().String())
-	golden.Assert(t, testCli.OutBuffer().String(), "check-no-downgrades.golden")
+	fmt.Println(c.OutBuffer().String())
+	golden.Assert(t, c.OutBuffer().String(), "check-no-downgrades.golden")
 
-	testCli.OutBuffer().Reset()
+	c.OutBuffer().Reset()
 	cmd.Flags().Set("pre-releases", "false")
 	cmd.Flags().Set("downgrades", "false")
 	cmd.Flags().Set("upgrades", "false")
 	err = cmd.Execute()
 	assert.NilError(t, err)
-	fmt.Println(testCli.OutBuffer().String())
-	golden.Assert(t, testCli.OutBuffer().String(), "check-patches-only.golden")
-}
-
-func makeVersion(t *testing.T, tag string) clitypes.DockerVersion {
-	v, err := ver.NewVersion(tag)
-	assert.NilError(t, err)
-	return clitypes.DockerVersion{Version: *v, Tag: tag}
-}
-
-func parseVersions(t *testing.T, tags ...string) []clitypes.DockerVersion {
-	ret := make([]clitypes.DockerVersion, len(tags))
-	for i, tag := range tags {
-		ret[i] = makeVersion(t, tag)
-	}
-	return ret
+	fmt.Println(c.OutBuffer().String())
+	golden.Assert(t, c.OutBuffer().String(), "check-patches-only.golden")
 }
diff --git a/cli/command/engine/cmd_test.go b/cli/command/engine/cmd_test.go
index 9378f0aa63..30639cbf3c 100644
--- a/cli/command/engine/cmd_test.go
+++ b/cli/command/engine/cmd_test.go
@@ -10,5 +10,5 @@ func TestNewEngineCommand(t *testing.T) {
 	cmd := NewEngineCommand(testCli)
 
 	subcommands := cmd.Commands()
-	assert.Assert(t, len(subcommands) == 5)
+	assert.Assert(t, len(subcommands) == 3)
 }
diff --git a/cli/command/engine/init.go b/cli/command/engine/init.go
index 9d1ff3e34e..f29001d086 100644
--- a/cli/command/engine/init.go
+++ b/cli/command/engine/init.go
@@ -1,62 +1,10 @@
 package engine
 
 import (
-	"context"
-
-	"github.com/docker/cli/cli"
-	"github.com/docker/cli/cli/command"
 	clitypes "github.com/docker/cli/types"
-	"github.com/pkg/errors"
-	"github.com/spf13/cobra"
 )
 
 type extendedEngineInitOptions struct {
 	clitypes.EngineInitOptions
 	sockPath string
 }
-
-func newInitCommand(dockerCli command.Cli) *cobra.Command {
-	var options extendedEngineInitOptions
-
-	cmd := &cobra.Command{
-		Use:   "init [OPTIONS]",
-		Short: "Initialize a local engine",
-		Long: `This command will initialize a local engine running on containerd.
-
-Configuration of the engine is managed through the daemon.json configuration
-file on the host and may be pre-created before running the 'init' command.
-`,
-		Args: cli.NoArgs,
-		RunE: func(cmd *cobra.Command, args []string) error {
-			return runInit(dockerCli, options)
-		},
-		Annotations: map[string]string{"experimentalCLI": ""},
-	}
-	flags := cmd.Flags()
-	flags.StringVar(&options.EngineVersion, "version", cli.Version, "Specify engine version")
-	flags.StringVar(&options.EngineImage, "engine-image", clitypes.CommunityEngineImage, "Specify engine image")
-	flags.StringVar(&options.RegistryPrefix, "registry-prefix", "docker.io/docker", "Override the default location where engine images are pulled")
-	flags.StringVar(&options.ConfigFile, "config-file", "/etc/docker/daemon.json", "Specify the location of the daemon configuration file on the host")
-	flags.StringVar(&options.sockPath, "containerd", "", "override default location of containerd endpoint")
-
-	return cmd
-}
-
-func runInit(dockerCli command.Cli, options extendedEngineInitOptions) error {
-	ctx := context.Background()
-	client, err := dockerCli.NewContainerizedEngineClient(options.sockPath)
-	if err != nil {
-		return errors.Wrap(err, "unable to access local containerd")
-	}
-	defer client.Close()
-	authConfig, err := getRegistryAuth(dockerCli, options.RegistryPrefix)
-	if err != nil {
-		return err
-	}
-	return client.InitEngine(ctx, options.EngineInitOptions, dockerCli.Out(), authConfig,
-		func(ctx context.Context) error {
-			client := dockerCli.Client()
-			_, err := client.Ping(ctx)
-			return err
-		})
-}
diff --git a/cli/command/engine/init_test.go b/cli/command/engine/init_test.go
deleted file mode 100644
index 5d6c91b1f4..0000000000
--- a/cli/command/engine/init_test.go
+++ /dev/null
@@ -1,33 +0,0 @@
-package engine
-
-import (
-	"fmt"
-	"testing"
-
-	clitypes "github.com/docker/cli/types"
-	"gotest.tools/assert"
-)
-
-func TestInitNoContainerd(t *testing.T) {
-	testCli.SetContainerizedEngineClient(
-		func(string) (clitypes.ContainerizedClient, error) {
-			return nil, fmt.Errorf("some error")
-		},
-	)
-	cmd := newInitCommand(testCli)
-	cmd.SilenceUsage = true
-	cmd.SilenceErrors = true
-	err := cmd.Execute()
-	assert.ErrorContains(t, err, "unable to access local containerd")
-}
-
-func TestInitHappy(t *testing.T) {
-	testCli.SetContainerizedEngineClient(
-		func(string) (clitypes.ContainerizedClient, error) {
-			return &fakeContainerizedEngineClient{}, nil
-		},
-	)
-	cmd := newInitCommand(testCli)
-	err := cmd.Execute()
-	assert.NilError(t, err)
-}
diff --git a/cli/command/engine/update.go b/cli/command/engine/update.go
index 73f3638629..0709f314e6 100644
--- a/cli/command/engine/update.go
+++ b/cli/command/engine/update.go
@@ -8,7 +8,6 @@ import (
 	"github.com/docker/cli/cli/command"
 	"github.com/pkg/errors"
 	"github.com/spf13/cobra"
-	"golang.org/x/sys/unix"
 )
 
 func newUpdateCommand(dockerCli command.Cli) *cobra.Command {
@@ -33,7 +32,7 @@ func newUpdateCommand(dockerCli command.Cli) *cobra.Command {
 }
 
 func runUpdate(dockerCli command.Cli, options extendedEngineInitOptions) error {
-	if unix.Geteuid() != 0 {
+	if !isRoot() {
 		return errors.New("must be privileged to activate engine")
 	}
 	ctx := context.Background()
@@ -43,11 +42,8 @@ func runUpdate(dockerCli command.Cli, options extendedEngineInitOptions) error {
 	}
 	defer client.Close()
 	if options.EngineImage == "" || options.RegistryPrefix == "" {
-		if options.EngineImage == "" {
-			options.EngineImage = "docker/engine-community"
-		}
 		if options.RegistryPrefix == "" {
-			options.RegistryPrefix = "docker.io"
+			options.RegistryPrefix = "docker.io/store/docker"
 		}
 	}
 	authConfig, err := getRegistryAuth(dockerCli, options.RegistryPrefix)
@@ -63,6 +59,6 @@ func runUpdate(dockerCli command.Cli, options extendedEngineInitOptions) error {
 		}); err != nil {
 		return err
 	}
-	fmt.Fprintln(dockerCli.Out(), "Success!  The docker engine is now running.")
+	fmt.Fprintln(dockerCli.Out(), "To complete the update, please restart docker with 'systemctl restart docker'")
 	return nil
 }
diff --git a/docker.Makefile b/docker.Makefile
index 4955be6088..69135e97a6 100644
--- a/docker.Makefile
+++ b/docker.Makefile
@@ -105,7 +105,7 @@ shellcheck: build_shell_validate_image ## run shellcheck validation
 	docker run -ti --rm $(ENVVARS) $(MOUNTS) $(VALIDATE_IMAGE_NAME) make shellcheck
 
 .PHONY: test-e2e ## run e2e tests
-test-e2e: test-e2e-non-experimental test-e2e-experimental test-e2e-containerized
+test-e2e: test-e2e-non-experimental test-e2e-experimental
 
 .PHONY: test-e2e-experimental
 test-e2e-experimental: build_e2e_image
@@ -115,14 +115,6 @@ test-e2e-experimental: build_e2e_image
 test-e2e-non-experimental: build_e2e_image
 	docker run --rm -v /var/run/docker.sock:/var/run/docker.sock $(E2E_IMAGE_NAME)
 
-.PHONY: test-e2e-containerized
-test-e2e-containerized: build_e2e_image
-	docker run --rm --privileged \
-	    -v /var/lib/docker \
-	    -v /var/lib/containerd \
-	    -v /lib/modules:/lib/modules \
-	    $(E2E_IMAGE_NAME) /go/src/github.com/docker/cli/scripts/test/engine/entry
-
 .PHONY: help
 help: ## print this help
 	@awk 'BEGIN {FS = ":.*?## "} /^[a-zA-Z_-]+:.*?## / {sub("\\\\n",sprintf("\n%22c"," "), $$2);printf "\033[36m%-20s\033[0m %s\n", $$1, $$2}' $(MAKEFILE_LIST)
diff --git a/e2eengine/utils.go b/e2eengine/utils.go
index 3f109f73db..9139adeda9 100644
--- a/e2eengine/utils.go
+++ b/e2eengine/utils.go
@@ -38,9 +38,13 @@ func CleanupEngine(t *testing.T) error {
 		return err
 	}
 	// TODO Consider nuking the docker dir too so there's no cached content between test cases
-	err = client.RemoveEngine(ctx)
-	if err != nil {
-		t.Logf("Failed to remove engine: %s", err)
-	}
+
+	// TODO - this needs refactoring still to actually work properly
+	/*
+		err = client.RemoveEngine(ctx)
+		if err != nil {
+			t.Logf("Failed to remove engine: %s", err)
+		}
+	*/
 	return err
 }
diff --git a/internal/containerizedengine/client_test.go b/internal/containerizedengine/client_test.go
index cc5c5770b2..62216c99dc 100644
--- a/internal/containerizedengine/client_test.go
+++ b/internal/containerizedengine/client_test.go
@@ -24,6 +24,8 @@ type (
 		getImageFunc         func(ctx context.Context, ref string) (containerd.Image, error)
 		contentStoreFunc     func() content.Store
 		containerServiceFunc func() containers.Store
+		installFunc          func(context.Context, containerd.Image, ...containerd.InstallOpts) error
+		versionFunc          func(ctx context.Context) (containerd.Version, error)
 	}
 	fakeContainer struct {
 		idFunc         func() string
@@ -109,6 +111,18 @@ func (w *fakeContainerdClient) ContainerService() containers.Store {
 func (w *fakeContainerdClient) Close() error {
 	return nil
 }
+func (w *fakeContainerdClient) Install(ctx context.Context, image containerd.Image, args ...containerd.InstallOpts) error {
+	if w.installFunc != nil {
+		return w.installFunc(ctx, image, args...)
+	}
+	return nil
+}
+func (w *fakeContainerdClient) Version(ctx context.Context) (containerd.Version, error) {
+	if w.versionFunc != nil {
+		return w.versionFunc(ctx)
+	}
+	return containerd.Version{}, nil
+}
 
 func (c *fakeContainer) ID() string {
 	if c.idFunc != nil {
diff --git a/internal/containerizedengine/types.go b/internal/containerizedengine/types.go
index 8268e1e4fa..a0695ee93d 100644
--- a/internal/containerizedengine/types.go
+++ b/internal/containerizedengine/types.go
@@ -64,6 +64,12 @@ var (
 			NoNewPrivileges: false,
 		},
 	}
+
+	// RuntimeMetadataName is the name of the runtime metadata file
+	RuntimeMetadataName = "distribution_based_engine"
+
+	// ReleaseNotePrefix is where to point users to for release notes
+	ReleaseNotePrefix = "https://docs.docker.com/releasenotes"
 )
 
 type baseClient struct {
@@ -80,4 +86,12 @@ type containerdClient interface {
 	ContentStore() content.Store
 	ContainerService() containers.Store
 	Install(context.Context, containerd.Image, ...containerd.InstallOpts) error
+	Version(ctx context.Context) (containerd.Version, error)
+}
+
+// RuntimeMetadata holds platform information about the daemon
+type RuntimeMetadata struct {
+	Platform             string `json:"platform"`
+	ContainerdMinVersion string `json:"containerd_min_version"`
+	Runtime              string `json:"runtime"`
 }
diff --git a/internal/containerizedengine/update.go b/internal/containerizedengine/update.go
index d4626b96b6..bb551555eb 100644
--- a/internal/containerizedengine/update.go
+++ b/internal/containerizedengine/update.go
@@ -2,13 +2,22 @@ package containerizedengine
 
 import (
 	"context"
+	"encoding/json"
 	"fmt"
+	"io/ioutil"
+	"path/filepath"
+	"strings"
 
 	"github.com/containerd/containerd"
+	"github.com/containerd/containerd/content"
 	"github.com/containerd/containerd/errdefs"
+	"github.com/containerd/containerd/images"
 	"github.com/containerd/containerd/namespaces"
 	clitypes "github.com/docker/cli/types"
+	"github.com/docker/distribution/reference"
 	"github.com/docker/docker/api/types"
+	ver "github.com/hashicorp/go-version"
+	"github.com/opencontainers/image-spec/specs-go/v1"
 	"github.com/pkg/errors"
 )
 
@@ -34,6 +43,20 @@ func (c *baseClient) DoUpdate(ctx context.Context, opts clitypes.EngineInitOptio
 		return fmt.Errorf("please pick the version you want to update to")
 	}
 
+	localMetadata, err := c.GetCurrentRuntimeMetadata(ctx, "")
+	if err == nil {
+		if opts.EngineImage == "" {
+			if strings.Contains(strings.ToLower(localMetadata.Platform), "enterprise") {
+				opts.EngineImage = "engine-enterprise"
+			} else {
+				opts.EngineImage = "engine-community"
+			}
+		}
+	}
+	if opts.EngineImage == "" {
+		return fmt.Errorf("please pick the engine image to update with (engine-community or engine-enterprise)")
+	}
+
 	imageName := fmt.Sprintf("%s/%s:%s", opts.RegistryPrefix, opts.EngineImage, opts.EngineVersion)
 
 	// Look for desired image
@@ -48,5 +71,137 @@ func (c *baseClient) DoUpdate(ctx context.Context, opts clitypes.EngineInitOptio
 			return errors.Wrapf(err, "unable to check for image %s", imageName)
 		}
 	}
-	return c.cclient.Install(ctx, image, containerd.WithInstallReplace, containerd.WithInstallPath("/usr"))
+
+	// Make sure we're safe to proceed
+	newMetadata, err := c.PreflightCheck(ctx, image)
+	if err != nil {
+		return err
+	}
+	// Grab current metadata for comparison purposes
+	if localMetadata != nil {
+		if localMetadata.Platform != newMetadata.Platform {
+			fmt.Fprintf(out, "\nNotice: you have switched to \"%s\".  Please refer to %s for update instructions.\n\n", newMetadata.Platform, c.GetReleaseNotesURL(imageName))
+		}
+	}
+
+	err = c.cclient.Install(ctx, image, containerd.WithInstallReplace, containerd.WithInstallPath("/usr"))
+	if err != nil {
+		return err
+	}
+
+	return c.WriteRuntimeMetadata(ctx, "", newMetadata)
+}
+
+var defaultDockerRoot = "/var/lib/docker"
+
+// GetCurrentRuntimeMetadata loads the current daemon runtime metadata information from the local host
+func (c *baseClient) GetCurrentRuntimeMetadata(_ context.Context, dockerRoot string) (*RuntimeMetadata, error) {
+	if dockerRoot == "" {
+		dockerRoot = defaultDockerRoot
+	}
+	filename := filepath.Join(dockerRoot, RuntimeMetadataName+".json")
+
+	data, err := ioutil.ReadFile(filename)
+	if err != nil {
+		return nil, err
+	}
+	var res RuntimeMetadata
+	err = json.Unmarshal(data, &res)
+	if err != nil {
+		return nil, errors.Wrapf(err, "malformed runtime metadata file %s", filename)
+	}
+	return &res, nil
+}
+
+func (c *baseClient) WriteRuntimeMetadata(_ context.Context, dockerRoot string, metadata *RuntimeMetadata) error {
+	if dockerRoot == "" {
+		dockerRoot = defaultDockerRoot
+	}
+	filename := filepath.Join(dockerRoot, RuntimeMetadataName+".json")
+
+	data, err := json.Marshal(metadata)
+	if err != nil {
+		return err
+	}
+
+	return ioutil.WriteFile(filename, data, 0644)
+}
+
+// PreflightCheck verifies the specified image is compatible with the local system before proceeding to update/activate
+// If things look good, the RuntimeMetadata for the new image is returned and can be written out to the host
+func (c *baseClient) PreflightCheck(ctx context.Context, image containerd.Image) (*RuntimeMetadata, error) {
+	var metadata RuntimeMetadata
+	ic, err := image.Config(ctx)
+	if err != nil {
+		return nil, err
+	}
+	var (
+		ociimage v1.Image
+		config   v1.ImageConfig
+	)
+	switch ic.MediaType {
+	case v1.MediaTypeImageConfig, images.MediaTypeDockerSchema2Config:
+		p, err := content.ReadBlob(ctx, image.ContentStore(), ic)
+		if err != nil {
+			return nil, err
+		}
+
+		if err := json.Unmarshal(p, &ociimage); err != nil {
+			return nil, err
+		}
+		config = ociimage.Config
+	default:
+		return nil, fmt.Errorf("unknown image %s config media type %s", image.Name(), ic.MediaType)
+	}
+
+	metadataString, ok := config.Labels[RuntimeMetadataName]
+	if !ok {
+		return nil, fmt.Errorf("image %s does not contain runtime metadata label %s", image.Name(), RuntimeMetadataName)
+	}
+	err = json.Unmarshal([]byte(metadataString), &metadata)
+	if err != nil {
+		return nil, errors.Wrapf(err, "malformed runtime metadata file in %s", image.Name())
+	}
+
+	// Current CLI only supports host install runtime
+	if metadata.Runtime != "host_install" {
+		return nil, fmt.Errorf("unsupported runtime: %s\nPlease consult the release notes at %s for upgrade instructions", metadata.Runtime, c.GetReleaseNotesURL(image.Name()))
+	}
+
+	// Verify local containerd is new enough
+	localVersion, err := c.cclient.Version(ctx)
+	if err != nil {
+		return nil, err
+	}
+	if metadata.ContainerdMinVersion != "" {
+		lv, err := ver.NewVersion(localVersion.Version)
+		if err != nil {
+			return nil, err
+		}
+		mv, err := ver.NewVersion(metadata.ContainerdMinVersion)
+		if err != nil {
+			return nil, err
+		}
+		if lv.LessThan(mv) {
+			return nil, fmt.Errorf("local containerd is too old: %s - this engine version requires %s or newer.\nPlease consult the release notes at %s for upgrade instructions",
+				localVersion.Version, metadata.ContainerdMinVersion, c.GetReleaseNotesURL(image.Name()))
+		}
+	} // If omitted on metadata, no hard dependency on containerd version beyond 18.09 baseline
+
+	// All checks look OK, proceed with update
+	return &metadata, nil
+}
+
+// GetReleaseNotesURL returns a release notes url
+// If the image name does not contain a version tag, the base release notes URL is returned
+func (c *baseClient) GetReleaseNotesURL(imageName string) string {
+	versionTag := ""
+	distributionRef, err := reference.ParseNormalizedNamed(imageName)
+	if err == nil {
+		taggedRef, ok := distributionRef.(reference.NamedTagged)
+		if ok {
+			versionTag = taggedRef.Tag()
+		}
+	}
+	return fmt.Sprintf("%s/%s", ReleaseNotePrefix, versionTag)
 }
diff --git a/internal/containerizedengine/update_test.go b/internal/containerizedengine/update_test.go
index cb1e06dd68..9f25b1311c 100644
--- a/internal/containerizedengine/update_test.go
+++ b/internal/containerizedengine/update_test.go
@@ -4,6 +4,9 @@ import (
 	"bytes"
 	"context"
 	"fmt"
+	"io/ioutil"
+	"os"
+	"path/filepath"
 	"testing"
 
 	"github.com/containerd/containerd"
@@ -12,162 +15,20 @@ import (
 	"github.com/docker/cli/cli/command"
 	clitypes "github.com/docker/cli/types"
 	"github.com/docker/docker/api/types"
+	ocispec "github.com/opencontainers/image-spec/specs-go/v1"
 	"gotest.tools/assert"
 )
 
-func TestGetCurrentEngineVersionHappy(t *testing.T) {
-	ctx := context.Background()
-	image := &fakeImage{
-		nameFunc: func() string {
-			return "acme.com/dockermirror/" + clitypes.CommunityEngineImage + ":engineversion"
-		},
-	}
-	container := &fakeContainer{
-		imageFunc: func(context.Context) (containerd.Image, error) {
-			return image, nil
-		},
-	}
-	client := baseClient{
-		cclient: &fakeContainerdClient{
-			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
-				return []containerd.Container{container}, nil
-			},
-		},
-	}
-
-	opts, err := client.GetCurrentEngineVersion(ctx)
-	assert.NilError(t, err)
-	assert.Equal(t, opts.EngineImage, clitypes.CommunityEngineImage)
-	assert.Equal(t, opts.RegistryPrefix, "acme.com/dockermirror")
-	assert.Equal(t, opts.EngineVersion, "engineversion")
-}
-
-func TestGetCurrentEngineVersionEnterpriseHappy(t *testing.T) {
-	ctx := context.Background()
-	image := &fakeImage{
-		nameFunc: func() string {
-			return "docker.io/docker/" + clitypes.EnterpriseEngineImage + ":engineversion"
-		},
-	}
-	container := &fakeContainer{
-		imageFunc: func(context.Context) (containerd.Image, error) {
-			return image, nil
-		},
-	}
-	client := baseClient{
-		cclient: &fakeContainerdClient{
-			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
-				return []containerd.Container{container}, nil
-			},
-		},
-	}
-
-	opts, err := client.GetCurrentEngineVersion(ctx)
-	assert.NilError(t, err)
-	assert.Equal(t, opts.EngineImage, clitypes.EnterpriseEngineImage)
-	assert.Equal(t, opts.EngineVersion, "engineversion")
-	assert.Equal(t, opts.RegistryPrefix, "docker.io/docker")
-}
-
-func TestGetCurrentEngineVersionNoEngine(t *testing.T) {
-	ctx := context.Background()
-	client := baseClient{
-		cclient: &fakeContainerdClient{
-			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
-				return []containerd.Container{}, nil
-			},
-		},
-	}
-
-	_, err := client.GetCurrentEngineVersion(ctx)
-	assert.ErrorContains(t, err, "failed to find existing engine")
-}
-
-func TestGetCurrentEngineVersionMiscEngineError(t *testing.T) {
-	ctx := context.Background()
-	expectedError := fmt.Errorf("some container lookup error")
-	client := baseClient{
-		cclient: &fakeContainerdClient{
-			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
-				return nil, expectedError
-			},
-		},
-	}
-
-	_, err := client.GetCurrentEngineVersion(ctx)
-	assert.Assert(t, err == expectedError)
-}
-
-func TestGetCurrentEngineVersionImageFailure(t *testing.T) {
-	ctx := context.Background()
-	container := &fakeContainer{
-		imageFunc: func(context.Context) (containerd.Image, error) {
-			return nil, fmt.Errorf("container image failure")
-		},
-	}
-	client := baseClient{
-		cclient: &fakeContainerdClient{
-			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
-				return []containerd.Container{container}, nil
-			},
-		},
-	}
-
-	_, err := client.GetCurrentEngineVersion(ctx)
-	assert.ErrorContains(t, err, "container image failure")
-}
-
-func TestGetCurrentEngineVersionMalformed(t *testing.T) {
-	ctx := context.Background()
-	image := &fakeImage{
-		nameFunc: func() string {
-			return "imagename"
-		},
-	}
-	container := &fakeContainer{
-		imageFunc: func(context.Context) (containerd.Image, error) {
-			return image, nil
-		},
-	}
-	client := baseClient{
-		cclient: &fakeContainerdClient{
-			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
-				return []containerd.Container{container}, nil
-			},
-		},
-	}
-
-	_, err := client.GetCurrentEngineVersion(ctx)
-	assert.Assert(t, err == ErrEngineImageMissingTag)
-}
-
-func TestActivateNoEngine(t *testing.T) {
-	ctx := context.Background()
-	client := baseClient{
-		cclient: &fakeContainerdClient{
-			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
-				return []containerd.Container{}, nil
-			},
-		},
-	}
-	opts := clitypes.EngineInitOptions{
-		EngineVersion:  "engineversiongoeshere",
-		RegistryPrefix: "registryprefixgoeshere",
-		ConfigFile:     "/tmp/configfilegoeshere",
-		EngineImage:    clitypes.EnterpriseEngineImage,
-	}
-
-	err := client.ActivateEngine(ctx, opts, command.NewOutStream(&bytes.Buffer{}), &types.AuthConfig{}, healthfnHappy)
-	assert.ErrorContains(t, err, "unable to find")
-}
-
-func TestActivateNoChange(t *testing.T) {
+func TestActivateConfigFailure(t *testing.T) {
 	ctx := context.Background()
 	registryPrefix := "registryprefixgoeshere"
 	image := &fakeImage{
 		nameFunc: func() string {
 			return registryPrefix + "/" + clitypes.EnterpriseEngineImage + ":engineversion"
 		},
+		configFunc: func(ctx context.Context) (ocispec.Descriptor, error) {
+			return ocispec.Descriptor{}, fmt.Errorf("config lookup failure")
+		},
 	}
 	container := &fakeContainer{
 		imageFunc: func(context.Context) (containerd.Image, error) {
@@ -185,6 +46,9 @@ func TestActivateNoChange(t *testing.T) {
 			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
 				return []containerd.Container{container}, nil
 			},
+			getImageFunc: func(ctx context.Context, ref string) (containerd.Image, error) {
+				return image, nil
+			},
 		},
 	}
 	opts := clitypes.EngineInitOptions{
@@ -195,7 +59,7 @@ func TestActivateNoChange(t *testing.T) {
 	}
 
 	err := client.ActivateEngine(ctx, opts, command.NewOutStream(&bytes.Buffer{}), &types.AuthConfig{}, healthfnHappy)
-	assert.NilError(t, err)
+	assert.ErrorContains(t, err, "config lookup failure")
 }
 
 func TestActivateDoUpdateFail(t *testing.T) {
@@ -292,30 +156,112 @@ func TestDoUpdatePullFail(t *testing.T) {
 	assert.ErrorContains(t, err, "pull failure")
 }
 
-func TestDoUpdateEngineMissing(t *testing.T) {
+func TestActivateDoUpdateVerifyImageName(t *testing.T) {
 	ctx := context.Background()
+	registryPrefix := "registryprefixgoeshere"
+	image := &fakeImage{
+		nameFunc: func() string {
+			return registryPrefix + "/ce-engine:engineversion"
+		},
+	}
+	container := &fakeContainer{
+		imageFunc: func(context.Context) (containerd.Image, error) {
+			return image, nil
+		},
+	}
+	requestedImage := "unset"
+	client := baseClient{
+		cclient: &fakeContainerdClient{
+			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
+				return []containerd.Container{container}, nil
+			},
+			getImageFunc: func(ctx context.Context, ref string) (containerd.Image, error) {
+				requestedImage = ref
+				return nil, fmt.Errorf("something went wrong")
+
+			},
+		},
+	}
 	opts := clitypes.EngineInitOptions{
 		EngineVersion:  "engineversiongoeshere",
 		RegistryPrefix: "registryprefixgoeshere",
 		ConfigFile:     "/tmp/configfilegoeshere",
-		EngineImage:    "testnamegoeshere",
+		//EngineImage:    clitypes.EnterpriseEngineImage,
 	}
-	image := &fakeImage{
-		nameFunc: func() string {
-			return "imagenamehere"
-		},
-	}
-	client := baseClient{
-		cclient: &fakeContainerdClient{
-			getImageFunc: func(ctx context.Context, ref string) (containerd.Image, error) {
-				return image, nil
 
-			},
-			containersFunc: func(ctx context.Context, filters ...string) ([]containerd.Container, error) {
-				return []containerd.Container{}, nil
-			},
-		},
-	}
-	err := client.DoUpdate(ctx, opts, command.NewOutStream(&bytes.Buffer{}), &types.AuthConfig{}, healthfnHappy)
-	assert.ErrorContains(t, err, "unable to find existing engine")
+	tmpdir, err := ioutil.TempDir("", "docker-root")
+	assert.NilError(t, err)
+	defer os.RemoveAll(tmpdir)
+	defaultDockerRoot = tmpdir
+	metadata := RuntimeMetadata{Platform: "platformgoeshere"}
+	err = client.WriteRuntimeMetadata(ctx, tmpdir, &metadata)
+	assert.NilError(t, err)
+
+	err = client.ActivateEngine(ctx, opts, command.NewOutStream(&bytes.Buffer{}), &types.AuthConfig{}, healthfnHappy)
+	assert.ErrorContains(t, err, "check for image")
+	assert.ErrorContains(t, err, "something went wrong")
+	expectedImage := fmt.Sprintf("%s/%s:%s", opts.RegistryPrefix, "engine-community", opts.EngineVersion)
+	assert.Assert(t, requestedImage == expectedImage, "%s != %s", requestedImage, expectedImage)
+
+	// Redo with enterprise set
+	metadata = RuntimeMetadata{Platform: "Docker Engine - Enterprise"}
+	err = client.WriteRuntimeMetadata(ctx, tmpdir, &metadata)
+	assert.NilError(t, err)
+
+	err = client.ActivateEngine(ctx, opts, command.NewOutStream(&bytes.Buffer{}), &types.AuthConfig{}, healthfnHappy)
+	assert.ErrorContains(t, err, "check for image")
+	assert.ErrorContains(t, err, "something went wrong")
+	expectedImage = fmt.Sprintf("%s/%s:%s", opts.RegistryPrefix, "engine-enterprise", opts.EngineVersion)
+	assert.Assert(t, requestedImage == expectedImage, "%s != %s", requestedImage, expectedImage)
+}
+
+func TestGetCurrentRuntimeMetadataNotPresent(t *testing.T) {
+	ctx := context.Background()
+	tmpdir, err := ioutil.TempDir("", "docker-root")
+	assert.NilError(t, err)
+	defer os.RemoveAll(tmpdir)
+	client := baseClient{}
+	_, err = client.GetCurrentRuntimeMetadata(ctx, tmpdir)
+	assert.ErrorType(t, err, os.IsNotExist)
+}
+
+func TestGetCurrentRuntimeMetadataBadJson(t *testing.T) {
+	ctx := context.Background()
+	tmpdir, err := ioutil.TempDir("", "docker-root")
+	assert.NilError(t, err)
+	defer os.RemoveAll(tmpdir)
+	filename := filepath.Join(tmpdir, RuntimeMetadataName+".json")
+	err = ioutil.WriteFile(filename, []byte("not json"), 0644)
+	assert.NilError(t, err)
+	client := baseClient{}
+	_, err = client.GetCurrentRuntimeMetadata(ctx, tmpdir)
+	assert.ErrorContains(t, err, "malformed runtime metadata file")
+}
+
+func TestGetCurrentRuntimeMetadataHappyPath(t *testing.T) {
+	ctx := context.Background()
+	tmpdir, err := ioutil.TempDir("", "docker-root")
+	assert.NilError(t, err)
+	defer os.RemoveAll(tmpdir)
+	client := baseClient{}
+	metadata := RuntimeMetadata{Platform: "platformgoeshere"}
+	err = client.WriteRuntimeMetadata(ctx, tmpdir, &metadata)
+	assert.NilError(t, err)
+
+	res, err := client.GetCurrentRuntimeMetadata(ctx, tmpdir)
+	assert.NilError(t, err)
+	assert.Equal(t, res.Platform, "platformgoeshere")
+}
+
+func TestGetReleaseNotesURL(t *testing.T) {
+	client := baseClient{}
+	imageName := "bogus image name #$%&@!"
+	url := client.GetReleaseNotesURL(imageName)
+	assert.Equal(t, url, ReleaseNotePrefix+"/")
+	imageName = "foo.bar/valid/repowithouttag"
+	url = client.GetReleaseNotesURL(imageName)
+	assert.Equal(t, url, ReleaseNotePrefix+"/")
+	imageName = "foo.bar/valid/repowithouttag:tag123"
+	url = client.GetReleaseNotesURL(imageName)
+	assert.Equal(t, url, ReleaseNotePrefix+"/tag123")
 }
diff --git a/internal/containerizedengine/versions.go b/internal/versions/versions.go
similarity index 69%
rename from internal/containerizedengine/versions.go
rename to internal/versions/versions.go
index 63ac4a2dc2..27c4557c67 100644
--- a/internal/containerizedengine/versions.go
+++ b/internal/versions/versions.go
@@ -1,19 +1,23 @@
-package containerizedengine
+package versions
 
 import (
 	"context"
+	"path"
 	"sort"
+	"strings"
 
 	registryclient "github.com/docker/cli/cli/registry/client"
 	clitypes "github.com/docker/cli/types"
 	"github.com/docker/distribution/reference"
+	"github.com/docker/docker/api/types"
 	ver "github.com/hashicorp/go-version"
 	"github.com/pkg/errors"
 	"github.com/sirupsen/logrus"
 )
 
 // GetEngineVersions reports the versions of the engine that are available
-func (c *baseClient) GetEngineVersions(ctx context.Context, registryClient registryclient.RegistryClient, currentVersion, imageName string) (clitypes.AvailableVersions, error) {
+func GetEngineVersions(ctx context.Context, registryClient registryclient.RegistryClient, registryPrefix string, serverVersion types.Version) (clitypes.AvailableVersions, error) {
+	imageName := getEngineImage(registryPrefix, serverVersion)
 	imageRef, err := reference.ParseNormalizedNamed(imageName)
 	if err != nil {
 		return clitypes.AvailableVersions{}, err
@@ -24,7 +28,23 @@ func (c *baseClient) GetEngineVersions(ctx context.Context, registryClient regis
 		return clitypes.AvailableVersions{}, err
 	}
 
-	return parseTags(tags, currentVersion)
+	return parseTags(tags, serverVersion.Version)
+}
+
+func getEngineImage(registryPrefix string, serverVersion types.Version) string {
+	communityImage := "engine-community"
+	enterpriseImage := "engine-enterprise"
+	platform := strings.ToLower(serverVersion.Platform.Name)
+	if platform != "" {
+		if strings.Contains(platform, "enterprise") {
+			return path.Join(registryPrefix, enterpriseImage)
+		}
+		return path.Join(registryPrefix, communityImage)
+	}
+	if strings.Contains(serverVersion.Version, "ee") {
+		return path.Join(registryPrefix, enterpriseImage)
+	}
+	return path.Join(registryPrefix, communityImage)
 }
 
 func parseTags(tags []string, currentVersion string) (clitypes.AvailableVersions, error) {
diff --git a/internal/containerizedengine/versions_test.go b/internal/versions/versions_test.go
similarity index 91%
rename from internal/containerizedengine/versions_test.go
rename to internal/versions/versions_test.go
index eec782471b..1828ad0249 100644
--- a/internal/containerizedengine/versions_test.go
+++ b/internal/versions/versions_test.go
@@ -1,19 +1,19 @@
-package containerizedengine
+package versions
 
 import (
 	"context"
 	"testing"
 
+	"github.com/docker/docker/api/types"
 	"gotest.tools/assert"
 )
 
 func TestGetEngineVersionsBadImage(t *testing.T) {
 	ctx := context.Background()
-	client := baseClient{}
 
-	currentVersion := "currentversiongoeshere"
-	imageName := "this is an illegal image $%^&"
-	_, err := client.GetEngineVersions(ctx, nil, currentVersion, imageName)
+	registryPrefix := "this is an illegal image $%^&"
+	currentVersion := types.Version{Version: "currentversiongoeshere"}
+	_, err := GetEngineVersions(ctx, nil, registryPrefix, currentVersion)
 	assert.ErrorContains(t, err, "invalid reference format")
 }
 
diff --git a/types/types.go b/types/types.go
index cec01377dd..72d9ab314d 100644
--- a/types/types.go
+++ b/types/types.go
@@ -4,7 +4,6 @@ import (
 	"context"
 	"io"
 
-	registryclient "github.com/docker/cli/cli/registry/client"
 	"github.com/docker/docker/api/types"
 	ver "github.com/hashicorp/go-version"
 )
@@ -36,7 +35,6 @@ type ContainerizedClient interface {
 		out OutStream,
 		authConfig *types.AuthConfig,
 		healthfn func(context.Context) error) error
-	GetEngineVersions(ctx context.Context, registryClient registryclient.RegistryClient, currentVersion, imageName string) (AvailableVersions, error)
 }
 
 // EngineInitOptions contains the configuration settings