diff --git a/cli-plugins/examples/helloworld/main.go b/cli-plugins/examples/helloworld/main.go
index 0461e01c8c1d..c68b57cdbbe7 100644
--- a/cli-plugins/examples/helloworld/main.go
+++ b/cli-plugins/examples/helloworld/main.go
@@ -12,7 +12,8 @@ import (
 )
 
 func main() {
-	plugin.Run(func(dockerCli command.Cli) *cobra.Command {
+	ctx := context.Background()
+	plugin.Run(ctx, func(ctx context.Context, dockerCli command.Cli) *cobra.Command {
 		goodbye := &cobra.Command{
 			Use:   "goodbye",
 			Short: "Say Goodbye instead of Hello",
diff --git a/cli-plugins/plugin/plugin.go b/cli-plugins/plugin/plugin.go
index 54471b41b09b..d41c7e5f7cee 100644
--- a/cli-plugins/plugin/plugin.go
+++ b/cli-plugins/plugin/plugin.go
@@ -65,14 +65,14 @@ func RunPlugin(dockerCli *command.DockerCli, plugin *cobra.Command, meta manager
 }
 
 // Run is the top-level entry point to the CLI plugin framework. It should be called from your plugin's `main()` function.
-func Run(makeCmd func(command.Cli) *cobra.Command, meta manager.Metadata) {
+func Run(ctx context.Context, makeCmd func(context.Context, command.Cli) *cobra.Command, meta manager.Metadata) {
 	dockerCli, err := command.NewDockerCli()
 	if err != nil {
 		fmt.Fprintln(os.Stderr, err)
 		os.Exit(1)
 	}
 
-	plugin := makeCmd(dockerCli)
+	plugin := makeCmd(ctx, dockerCli)
 
 	if err := RunPlugin(dockerCli, plugin, meta); err != nil {
 		if sterr, ok := err.(cli.StatusError); ok {
@@ -92,7 +92,7 @@ func Run(makeCmd func(command.Cli) *cobra.Command, meta manager.Metadata) {
 }
 
 func withPluginClientConn(name string) command.CLIOption {
-	return command.WithInitializeClient(func(dockerCli *command.DockerCli) (client.APIClient, error) {
+	return command.WithInitializeClient(func(ctx context.Context, dockerCli *command.DockerCli) (client.APIClient, error) {
 		cmd := "docker"
 		if x := os.Getenv(manager.ReexecEnvvar); x != "" {
 			cmd = x
@@ -119,7 +119,7 @@ func withPluginClientConn(name string) command.CLIOption {
 			return nil, err
 		}
 
-		return client.NewClientWithOpts(client.WithDialContext(helper.Dialer))
+		return client.NewClientWithOpts(ctx, client.WithDialContext(helper.Dialer))
 	})
 }
 
diff --git a/cli/command/cli.go b/cli/command/cli.go
index aa3b28d58124..20cc46315806 100644
--- a/cli/command/cli.go
+++ b/cli/command/cli.go
@@ -100,11 +100,12 @@ func (cli *DockerCli) DefaultVersion() string {
 // CurrentVersion returns the API version currently negotiated, or the default
 // version otherwise.
 func (cli *DockerCli) CurrentVersion() string {
+	ctx := context.TODO()
 	_ = cli.initialize()
 	if cli.client == nil {
 		return api.DefaultVersion
 	}
-	return cli.client.ClientVersion()
+	return cli.client.ClientVersion(ctx)
 }
 
 // Client returns the APIClient
@@ -203,10 +204,10 @@ func (cli *DockerCli) RegistryClient(allowInsecure bool) registryclient.Registry
 }
 
 // WithInitializeClient is passed to DockerCli.Initialize by callers who wish to set a particular API Client for use by the CLI.
-func WithInitializeClient(makeClient func(dockerCli *DockerCli) (client.APIClient, error)) CLIOption {
+func WithInitializeClient(makeClient func(ctx context.Context, dockerCli *DockerCli) (client.APIClient, error)) CLIOption {
 	return func(dockerCli *DockerCli) error {
 		var err error
-		dockerCli.client, err = makeClient(dockerCli)
+		dockerCli.client, err = makeClient(dockerCli.baseCtx, dockerCli)
 		return err
 	}
 }
@@ -245,7 +246,7 @@ func (cli *DockerCli) Initialize(opts *cliflags.ClientOptions, ops ...CLIOption)
 }
 
 // NewAPIClientFromFlags creates a new APIClient from command line flags
-func NewAPIClientFromFlags(opts *cliflags.ClientOptions, configFile *configfile.ConfigFile) (client.APIClient, error) {
+func NewAPIClientFromFlags(ctx context.Context, opts *cliflags.ClientOptions, configFile *configfile.ConfigFile) (client.APIClient, error) {
 	if opts.Context != "" && len(opts.Hosts) > 0 {
 		return nil, errors.New("conflicting options: either specify --host or --context, not both")
 	}
@@ -261,10 +262,10 @@ func NewAPIClientFromFlags(opts *cliflags.ClientOptions, configFile *configfile.
 	if err != nil {
 		return nil, errors.Wrap(err, "unable to resolve docker endpoint")
 	}
-	return newAPIClientFromEndpoint(endpoint, configFile)
+	return newAPIClientFromEndpoint(ctx, endpoint, configFile)
 }
 
-func newAPIClientFromEndpoint(ep docker.Endpoint, configFile *configfile.ConfigFile) (client.APIClient, error) {
+func newAPIClientFromEndpoint(ctx context.Context, ep docker.Endpoint, configFile *configfile.ConfigFile) (client.APIClient, error) {
 	opts, err := ep.ClientOpts()
 	if err != nil {
 		return nil, err
@@ -273,7 +274,7 @@ func newAPIClientFromEndpoint(ep docker.Endpoint, configFile *configfile.ConfigF
 		opts = append(opts, client.WithHTTPHeaders(configFile.HTTPHeaders))
 	}
 	opts = append(opts, client.WithUserAgent(UserAgent()))
-	return client.NewClientWithOpts(opts...)
+	return client.NewClientWithOpts(ctx, opts...)
 }
 
 func resolveDockerEndpoint(s store.Reader, contextName string) (docker.Endpoint, error) {
@@ -337,7 +338,7 @@ func (cli *DockerCli) initializeFromClient() {
 		cli.serverInfo = ServerInfo{HasExperimental: true}
 
 		if ping.APIVersion != "" {
-			cli.client.NegotiateAPIVersionPing(ping)
+			cli.client.NegotiateAPIVersionPing(cli.baseCtx, ping)
 		}
 		return
 	}
@@ -348,7 +349,7 @@ func (cli *DockerCli) initializeFromClient() {
 		BuildkitVersion: ping.BuilderVersion,
 		SwarmStatus:     ping.SwarmStatus,
 	}
-	cli.client.NegotiateAPIVersionPing(ping)
+	cli.client.NegotiateAPIVersionPing(cli.baseCtx, ping)
 }
 
 // NotaryClient provides a Notary Repository to interact with signed metadata for an image
@@ -444,7 +445,7 @@ func (cli *DockerCli) initialize() error {
 			return
 		}
 		if cli.client == nil {
-			if cli.client, cli.initErr = newAPIClientFromEndpoint(cli.dockerEndpoint, cli.configFile); cli.initErr != nil {
+			if cli.client, cli.initErr = newAPIClientFromEndpoint(cli.baseCtx, cli.dockerEndpoint, cli.configFile); cli.initErr != nil {
 				return
 			}
 		}
diff --git a/cli/command/cli_test.go b/cli/command/cli_test.go
index 7a0b4e727e2e..a46816627dfc 100644
--- a/cli/command/cli_test.go
+++ b/cli/command/cli_test.go
@@ -31,11 +31,14 @@ func TestNewAPIClientFromFlags(t *testing.T) {
 	if runtime.GOOS == "windows" {
 		host = "npipe://./"
 	}
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
 	opts := &flags.ClientOptions{Hosts: []string{host}}
-	apiClient, err := NewAPIClientFromFlags(opts, &configfile.ConfigFile{})
+	apiClient, err := NewAPIClientFromFlags(ctx, opts, &configfile.ConfigFile{})
 	assert.NilError(t, err)
-	assert.Equal(t, apiClient.DaemonHost(), host)
-	assert.Equal(t, apiClient.ClientVersion(), api.DefaultVersion)
+	assert.Equal(t, apiClient.DaemonHost(ctx), host)
+	assert.Equal(t, apiClient.ClientVersion(ctx), api.DefaultVersion)
 }
 
 func TestNewAPIClientFromFlagsForDefaultSchema(t *testing.T) {
@@ -44,11 +47,14 @@ func TestNewAPIClientFromFlagsForDefaultSchema(t *testing.T) {
 	if runtime.GOOS == "windows" {
 		slug = "tcp://127.0.0.1"
 	}
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
 	opts := &flags.ClientOptions{Hosts: []string{host}}
-	apiClient, err := NewAPIClientFromFlags(opts, &configfile.ConfigFile{})
+	apiClient, err := NewAPIClientFromFlags(ctx, opts, &configfile.ConfigFile{})
 	assert.NilError(t, err)
-	assert.Equal(t, apiClient.DaemonHost(), slug+host)
-	assert.Equal(t, apiClient.ClientVersion(), api.DefaultVersion)
+	assert.Equal(t, apiClient.DaemonHost(ctx), slug+host)
+	assert.Equal(t, apiClient.ClientVersion(ctx), api.DefaultVersion)
 }
 
 func TestNewAPIClientFromFlagsWithCustomHeaders(t *testing.T) {
@@ -69,10 +75,13 @@ func TestNewAPIClientFromFlagsWithCustomHeaders(t *testing.T) {
 		},
 	}
 
-	apiClient, err := NewAPIClientFromFlags(opts, configFile)
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	apiClient, err := NewAPIClientFromFlags(ctx, opts, configFile)
 	assert.NilError(t, err)
-	assert.Equal(t, apiClient.DaemonHost(), host)
-	assert.Equal(t, apiClient.ClientVersion(), api.DefaultVersion)
+	assert.Equal(t, apiClient.DaemonHost(ctx), host)
+	assert.Equal(t, apiClient.ClientVersion(ctx), api.DefaultVersion)
 
 	// verify User-Agent is not appended to the configfile. see https://github.com/docker/cli/pull/2756
 	assert.DeepEqual(t, configFile.HTTPHeaders, map[string]string{"My-Header": "Custom-Value"})
@@ -90,12 +99,14 @@ func TestNewAPIClientFromFlagsWithAPIVersionFromEnv(t *testing.T) {
 	customVersion := "v3.3.3"
 	t.Setenv("DOCKER_API_VERSION", customVersion)
 	t.Setenv("DOCKER_HOST", ":2375")
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
 
 	opts := &flags.ClientOptions{}
 	configFile := &configfile.ConfigFile{}
-	apiclient, err := NewAPIClientFromFlags(opts, configFile)
+	apiclient, err := NewAPIClientFromFlags(ctx, opts, configFile)
 	assert.NilError(t, err)
-	assert.Equal(t, apiclient.ClientVersion(), customVersion)
+	assert.Equal(t, apiclient.ClientVersion(ctx), customVersion)
 }
 
 type fakeClient struct {
@@ -109,11 +120,11 @@ func (c *fakeClient) Ping(_ context.Context) (types.Ping, error) {
 	return c.pingFunc()
 }
 
-func (c *fakeClient) ClientVersion() string {
+func (c *fakeClient) ClientVersion(_ context.Context) string {
 	return c.version
 }
 
-func (c *fakeClient) NegotiateAPIVersionPing(types.Ping) {
+func (c *fakeClient) NegotiateAPIVersionPing(_ context.Context, _ types.Ping) {
 	c.negotiated = true
 }
 
@@ -176,10 +187,13 @@ func TestInitializeFromClientHangs(t *testing.T) {
 	l, err := net.Listen("unix", socket)
 	assert.NilError(t, err)
 
-	receiveReqCh := make(chan bool)
-	timeoutCtx, cancel := context.WithTimeout(context.Background(), time.Second)
+	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
 
+	receiveReqCh := make(chan bool)
+	timeoutCtx, timeoutCancel := context.WithTimeout(ctx, time.Second)
+	defer timeoutCancel()
+
 	// Simulate a server that hangs on connections.
 	ts := httptest.NewUnstartedServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		select {
@@ -194,7 +208,7 @@ func TestInitializeFromClientHangs(t *testing.T) {
 
 	opts := &flags.ClientOptions{Hosts: []string{fmt.Sprintf("unix://%s", socket)}}
 	configFile := &configfile.ConfigFile{}
-	apiClient, err := NewAPIClientFromFlags(opts, configFile)
+	apiClient, err := NewAPIClientFromFlags(ctx, opts, configFile)
 	assert.NilError(t, err)
 
 	initializedCh := make(chan bool)
@@ -302,8 +316,8 @@ func TestNewDockerCliAndOperators(t *testing.T) {
 func TestInitializeShouldAlwaysCreateTheContextStore(t *testing.T) {
 	cli, err := NewDockerCli()
 	assert.NilError(t, err)
-	assert.NilError(t, cli.Initialize(flags.NewClientOptions(), WithInitializeClient(func(cli *DockerCli) (client.APIClient, error) {
-		return client.NewClientWithOpts()
+	assert.NilError(t, cli.Initialize(flags.NewClientOptions(), WithInitializeClient(func(ctx context.Context, cli *DockerCli) (client.APIClient, error) {
+		return client.NewClientWithOpts(ctx)
 	})))
 	assert.Check(t, cli.ContextStore() != nil)
 }
diff --git a/cli/command/container/client_test.go b/cli/command/container/client_test.go
index c45f34040f43..0b1f779e673d 100644
--- a/cli/command/container/client_test.go
+++ b/cli/command/container/client_test.go
@@ -128,7 +128,7 @@ func (f *fakeClient) ContainerLogs(_ context.Context, containerID string, option
 	return nil, nil
 }
 
-func (f *fakeClient) ClientVersion() string {
+func (f *fakeClient) ClientVersion(_ context.Context) string {
 	return f.Version
 }
 
diff --git a/cli/command/container/create.go b/cli/command/container/create.go
index 70bf509c4e61..a3aa0a51da1a 100644
--- a/cli/command/container/create.go
+++ b/cli/command/container/create.go
@@ -85,7 +85,7 @@ func runCreate(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 		reportError(dockerCli.Err(), "create", err.Error(), true)
 		return cli.StatusError{StatusCode: 125}
 	}
-	proxyConfig := dockerCli.ConfigFile().ParseProxyConfig(dockerCli.Client().DaemonHost(), opts.ConvertKVStringsToMapWithNil(copts.env.GetAll()))
+	proxyConfig := dockerCli.ConfigFile().ParseProxyConfig(dockerCli.Client().DaemonHost(ctx), opts.ConvertKVStringsToMapWithNil(copts.env.GetAll()))
 	newEnv := []string{}
 	for k, v := range proxyConfig {
 		if v == nil {
@@ -100,7 +100,7 @@ func runCreate(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 		reportError(dockerCli.Err(), "create", err.Error(), true)
 		return cli.StatusError{StatusCode: 125}
 	}
-	if err = validateAPIVersion(containerCfg, dockerCli.Client().ClientVersion()); err != nil {
+	if err = validateAPIVersion(containerCfg, dockerCli.Client().ClientVersion(ctx)); err != nil {
 		reportError(dockerCli.Err(), "create", err.Error(), true)
 		return cli.StatusError{StatusCode: 125}
 	}
@@ -236,7 +236,7 @@ func createContainer(ctx context.Context, dockerCli command.Cli, containerCfg *c
 	// create. It will produce an error if you try to set a platform on older API
 	// versions, so check the API version here to maintain backwards
 	// compatibility for CLI users.
-	if options.platform != "" && versions.GreaterThanOrEqualTo(dockerCli.Client().ClientVersion(), "1.41") {
+	if options.platform != "" && versions.GreaterThanOrEqualTo(dockerCli.Client().ClientVersion(ctx), "1.41") {
 		p, err := platforms.Parse(options.platform)
 		if err != nil {
 			return "", errors.Wrap(err, "error parsing specified platform")
diff --git a/cli/command/container/run.go b/cli/command/container/run.go
index 2c4e8d41ea8f..fae684edaec9 100644
--- a/cli/command/container/run.go
+++ b/cli/command/container/run.go
@@ -94,7 +94,7 @@ func runRun(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet, ro
 		reportError(dockerCli.Err(), "run", err.Error(), true)
 		return cli.StatusError{StatusCode: 125}
 	}
-	proxyConfig := dockerCli.ConfigFile().ParseProxyConfig(dockerCli.Client().DaemonHost(), opts.ConvertKVStringsToMapWithNil(copts.env.GetAll()))
+	proxyConfig := dockerCli.ConfigFile().ParseProxyConfig(dockerCli.Client().DaemonHost(ctx), opts.ConvertKVStringsToMapWithNil(copts.env.GetAll()))
 	newEnv := []string{}
 	for k, v := range proxyConfig {
 		if v == nil {
diff --git a/cli/command/container/utils.go b/cli/command/container/utils.go
index 31b9df4aad63..8e0002d27b0f 100644
--- a/cli/command/container/utils.go
+++ b/cli/command/container/utils.go
@@ -22,7 +22,7 @@ func waitExitOrRemoved(ctx context.Context, apiClient client.APIClient, containe
 	// Older versions used the Events API, and even older versions did not
 	// support server-side removal. This legacyWaitExitOrRemoved method
 	// preserves that old behavior and any issues it may have.
-	if versions.LessThan(apiClient.ClientVersion(), "1.30") {
+	if versions.LessThan(apiClient.ClientVersion(ctx), "1.30") {
 		return legacyWaitExitOrRemoved(ctx, apiClient, containerID, waitRemove)
 	}
 
@@ -81,7 +81,7 @@ func legacyWaitExitOrRemoved(ctx context.Context, apiClient client.APIClient, co
 			}
 			if !waitRemove {
 				stopProcessing = true
-			} else if versions.LessThan(apiClient.ClientVersion(), "1.25") {
+			} else if versions.LessThan(apiClient.ClientVersion(ctx), "1.25") {
 				// If we are talking to an older daemon, `AutoRemove` is not supported.
 				// We need to fall back to the old behavior, which is client-side removal
 				go func() {
diff --git a/cli/command/context/create.go b/cli/command/context/create.go
index 1c93a1881aa3..9cde4a367462 100644
--- a/cli/command/context/create.go
+++ b/cli/command/context/create.go
@@ -5,6 +5,7 @@ package context
 
 import (
 	"bytes"
+	"context"
 	"fmt"
 
 	"github.com/docker/cli/cli"
@@ -47,7 +48,8 @@ func newCreateCommand(dockerCLI command.Cli) *cobra.Command {
 		Args:  cli.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			opts.Name = args[0]
-			return RunCreate(dockerCLI, opts)
+			ctx := cmd.Context()
+			return RunCreate(ctx, dockerCLI, opts)
 		},
 		Long:              longCreateDescription(),
 		ValidArgsFunction: completion.NoComplete,
@@ -60,7 +62,7 @@ func newCreateCommand(dockerCLI command.Cli) *cobra.Command {
 }
 
 // RunCreate creates a Docker context
-func RunCreate(dockerCLI command.Cli, o *CreateOptions) error {
+func RunCreate(ctx context.Context, dockerCLI command.Cli, o *CreateOptions) error {
 	s := dockerCLI.ContextStore()
 	err := checkContextNameForCreation(s, o.Name)
 	if err != nil {
@@ -72,7 +74,7 @@ func RunCreate(dockerCLI command.Cli, o *CreateOptions) error {
 	case o.From != "":
 		err = createFromExistingContext(s, o.From, o)
 	default:
-		err = createNewContext(s, o)
+		err = createNewContext(ctx, s, o)
 	}
 	if err == nil {
 		fmt.Fprintln(dockerCLI.Out(), o.Name)
@@ -81,11 +83,11 @@ func RunCreate(dockerCLI command.Cli, o *CreateOptions) error {
 	return err
 }
 
-func createNewContext(contextStore store.ReaderWriter, o *CreateOptions) error {
+func createNewContext(ctx context.Context, contextStore store.ReaderWriter, o *CreateOptions) error {
 	if o.Docker == nil {
 		return errors.New("docker endpoint configuration is required")
 	}
-	dockerEP, dockerTLS, err := getDockerEndpointMetadataAndTLS(contextStore, o.Docker)
+	dockerEP, dockerTLS, err := getDockerEndpointMetadataAndTLS(ctx, contextStore, o.Docker)
 	if err != nil {
 		return errors.Wrap(err, "unable to create docker endpoint config")
 	}
diff --git a/cli/command/context/create_test.go b/cli/command/context/create_test.go
index 3a7cb238258d..e28ec5e556f6 100644
--- a/cli/command/context/create_test.go
+++ b/cli/command/context/create_test.go
@@ -4,6 +4,7 @@
 package context
 
 import (
+	"context"
 	"fmt"
 	"testing"
 
@@ -93,10 +94,14 @@ func TestCreate(t *testing.T) {
 			expecterErr: `unable to parse docker host`,
 		},
 	}
+
+	ctx, cancel := context.WithCancel(context.TODO())
+	defer cancel()
+
 	for _, tc := range tests {
 		tc := tc
 		t.Run(tc.options.Name, func(t *testing.T) {
-			err := RunCreate(cli, &tc.options)
+			err := RunCreate(ctx, cli, &tc.options)
 			if tc.expecterErr == "" {
 				assert.NilError(t, err)
 			} else {
@@ -114,8 +119,10 @@ func assertContextCreateLogging(t *testing.T, cli *test.FakeCli, n string) {
 
 func TestCreateOrchestratorEmpty(t *testing.T) {
 	cli := makeFakeCli(t)
+	ctx, cancel := context.WithCancel(context.TODO())
+	defer cancel()
 
-	err := RunCreate(cli, &CreateOptions{
+	err := RunCreate(ctx, cli, &CreateOptions{
 		Name:   "test",
 		Docker: map[string]string{},
 	})
@@ -141,9 +148,12 @@ func TestCreateFromContext(t *testing.T) {
 		},
 	}
 
+	ctx, cancel := context.WithCancel(context.TODO())
+	defer cancel()
+
 	cli := makeFakeCli(t)
 	cli.ResetOutputBuffers()
-	assert.NilError(t, RunCreate(cli, &CreateOptions{
+	assert.NilError(t, RunCreate(ctx, cli, &CreateOptions{
 		Name:        "original",
 		Description: "original description",
 		Docker: map[string]string{
@@ -153,7 +163,7 @@ func TestCreateFromContext(t *testing.T) {
 	assertContextCreateLogging(t, cli, "original")
 
 	cli.ResetOutputBuffers()
-	assert.NilError(t, RunCreate(cli, &CreateOptions{
+	assert.NilError(t, RunCreate(ctx, cli, &CreateOptions{
 		Name:        "dummy",
 		Description: "dummy description",
 		Docker: map[string]string{
@@ -168,7 +178,7 @@ func TestCreateFromContext(t *testing.T) {
 		c := c
 		t.Run(c.name, func(t *testing.T) {
 			cli.ResetOutputBuffers()
-			err := RunCreate(cli, &CreateOptions{
+			err := RunCreate(ctx, cli, &CreateOptions{
 				From:        "original",
 				Name:        c.name,
 				Description: c.description,
@@ -189,6 +199,9 @@ func TestCreateFromContext(t *testing.T) {
 }
 
 func TestCreateFromCurrent(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.TODO())
+	defer cancel()
+
 	cases := []struct {
 		name                string
 		description         string
@@ -208,7 +221,7 @@ func TestCreateFromCurrent(t *testing.T) {
 
 	cli := makeFakeCli(t)
 	cli.ResetOutputBuffers()
-	assert.NilError(t, RunCreate(cli, &CreateOptions{
+	assert.NilError(t, RunCreate(ctx, cli, &CreateOptions{
 		Name:        "original",
 		Description: "original description",
 		Docker: map[string]string{
@@ -223,7 +236,7 @@ func TestCreateFromCurrent(t *testing.T) {
 		c := c
 		t.Run(c.name, func(t *testing.T) {
 			cli.ResetOutputBuffers()
-			err := RunCreate(cli, &CreateOptions{
+			err := RunCreate(ctx, cli, &CreateOptions{
 				Name:        c.name,
 				Description: c.description,
 			})
diff --git a/cli/command/context/list_test.go b/cli/command/context/list_test.go
index 98ac2e480c55..1e35eac5b238 100644
--- a/cli/command/context/list_test.go
+++ b/cli/command/context/list_test.go
@@ -1,6 +1,7 @@
 package context
 
 import (
+	"context"
 	"testing"
 
 	"github.com/docker/cli/cli/command"
@@ -10,8 +11,10 @@ import (
 
 func createTestContext(t *testing.T, cli command.Cli, name string) {
 	t.Helper()
+	ctx, cancel := context.WithCancel(context.TODO())
+	defer cancel()
 
-	err := RunCreate(cli, &CreateOptions{
+	err := RunCreate(ctx, cli, &CreateOptions{
 		Name:        name,
 		Description: "description of " + name,
 		Docker:      map[string]string{keyHost: "https://someswarmserver.example.com"},
diff --git a/cli/command/context/options.go b/cli/command/context/options.go
index ce79d57a4fe5..79896a96a07e 100644
--- a/cli/command/context/options.go
+++ b/cli/command/context/options.go
@@ -1,11 +1,12 @@
 package context
 
 import (
+	"context"
 	"fmt"
 	"strconv"
 	"strings"
 
-	"github.com/docker/cli/cli/context"
+	dockerContext "github.com/docker/cli/cli/context"
 	"github.com/docker/cli/cli/context/docker"
 	"github.com/docker/cli/cli/context/store"
 	"github.com/docker/docker/client"
@@ -85,7 +86,7 @@ func validateConfig(config map[string]string, allowedKeys map[string]struct{}) e
 	return errors.New(strings.Join(errs, "\n"))
 }
 
-func getDockerEndpoint(contextStore store.Reader, config map[string]string) (docker.Endpoint, error) {
+func getDockerEndpoint(ctx context.Context, contextStore store.Reader, config map[string]string) (docker.Endpoint, error) {
 	if err := validateConfig(config, allowedDockerConfigKeys); err != nil {
 		return docker.Endpoint{}, err
 	}
@@ -99,7 +100,7 @@ func getDockerEndpoint(contextStore store.Reader, config map[string]string) (doc
 		}
 		return docker.Endpoint{}, errors.Errorf("unable to get endpoint from context %q", contextName)
 	}
-	tlsData, err := context.TLSDataFromFiles(config[keyCA], config[keyCert], config[keyKey])
+	tlsData, err := dockerContext.TLSDataFromFiles(config[keyCA], config[keyCert], config[keyKey])
 	if err != nil {
 		return docker.Endpoint{}, err
 	}
@@ -119,14 +120,14 @@ func getDockerEndpoint(contextStore store.Reader, config map[string]string) (doc
 	if err != nil {
 		return docker.Endpoint{}, errors.Wrap(err, "invalid docker endpoint options")
 	}
-	if _, err := client.NewClientWithOpts(opts...); err != nil {
+	if _, err := client.NewClientWithOpts(ctx, opts...); err != nil {
 		return docker.Endpoint{}, errors.Wrap(err, "unable to apply docker endpoint options")
 	}
 	return ep, nil
 }
 
-func getDockerEndpointMetadataAndTLS(contextStore store.Reader, config map[string]string) (docker.EndpointMeta, *store.EndpointTLSData, error) {
-	ep, err := getDockerEndpoint(contextStore, config)
+func getDockerEndpointMetadataAndTLS(ctx context.Context, contextStore store.Reader, config map[string]string) (docker.EndpointMeta, *store.EndpointTLSData, error) {
+	ep, err := getDockerEndpoint(ctx, contextStore, config)
 	if err != nil {
 		return docker.EndpointMeta{}, nil, err
 	}
diff --git a/cli/command/context/update.go b/cli/command/context/update.go
index 98eba7d1ecaa..a6aa145b5cd8 100644
--- a/cli/command/context/update.go
+++ b/cli/command/context/update.go
@@ -2,6 +2,7 @@ package context
 
 import (
 	"bytes"
+	"context"
 	"fmt"
 
 	"github.com/docker/cli/cli"
@@ -41,7 +42,8 @@ func newUpdateCommand(dockerCli command.Cli) *cobra.Command {
 		Args:  cli.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			opts.Name = args[0]
-			return RunUpdate(dockerCli, opts)
+			ctx := cmd.Context()
+			return RunUpdate(ctx, dockerCli, opts)
 		},
 		Long: longUpdateDescription(),
 	}
@@ -52,7 +54,7 @@ func newUpdateCommand(dockerCli command.Cli) *cobra.Command {
 }
 
 // RunUpdate updates a Docker context
-func RunUpdate(dockerCLI command.Cli, o *UpdateOptions) error {
+func RunUpdate(ctx context.Context, dockerCLI command.Cli, o *UpdateOptions) error {
 	if err := store.ValidateContextName(o.Name); err != nil {
 		return err
 	}
@@ -74,7 +76,7 @@ func RunUpdate(dockerCLI command.Cli, o *UpdateOptions) error {
 	tlsDataToReset := make(map[string]*store.EndpointTLSData)
 
 	if o.Docker != nil {
-		dockerEP, dockerTLS, err := getDockerEndpointMetadataAndTLS(s, o.Docker)
+		dockerEP, dockerTLS, err := getDockerEndpointMetadataAndTLS(ctx, s, o.Docker)
 		if err != nil {
 			return errors.Wrap(err, "unable to create docker endpoint config")
 		}
diff --git a/cli/command/context/update_test.go b/cli/command/context/update_test.go
index 5bad6dec2f79..371bfc0b8313 100644
--- a/cli/command/context/update_test.go
+++ b/cli/command/context/update_test.go
@@ -1,6 +1,7 @@
 package context
 
 import (
+	"context"
 	"testing"
 
 	"github.com/docker/cli/cli/command"
@@ -10,15 +11,19 @@ import (
 )
 
 func TestUpdateDescriptionOnly(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.TODO())
+	defer cancel()
+
 	cli := makeFakeCli(t)
-	err := RunCreate(cli, &CreateOptions{
+	err := RunCreate(ctx, cli, &CreateOptions{
 		Name:   "test",
 		Docker: map[string]string{},
 	})
 	assert.NilError(t, err)
 	cli.OutBuffer().Reset()
 	cli.ErrBuffer().Reset()
-	assert.NilError(t, RunUpdate(cli, &UpdateOptions{
+
+	assert.NilError(t, RunUpdate(ctx, cli, &UpdateOptions{
 		Name:        "test",
 		Description: "description",
 	}))
@@ -35,7 +40,11 @@ func TestUpdateDescriptionOnly(t *testing.T) {
 func TestUpdateDockerOnly(t *testing.T) {
 	cli := makeFakeCli(t)
 	createTestContext(t, cli, "test")
-	assert.NilError(t, RunUpdate(cli, &UpdateOptions{
+
+	ctx, cancel := context.WithCancel(context.TODO())
+	defer cancel()
+
+	assert.NilError(t, RunUpdate(ctx, cli, &UpdateOptions{
 		Name: "test",
 		Docker: map[string]string{
 			keyHost: "tcp://some-host",
@@ -52,12 +61,17 @@ func TestUpdateDockerOnly(t *testing.T) {
 
 func TestUpdateInvalidDockerHost(t *testing.T) {
 	cli := makeFakeCli(t)
-	err := RunCreate(cli, &CreateOptions{
+
+	ctx, cancel := context.WithCancel(context.TODO())
+	defer cancel()
+
+	err := RunCreate(ctx, cli, &CreateOptions{
 		Name:   "test",
 		Docker: map[string]string{},
 	})
 	assert.NilError(t, err)
-	err = RunUpdate(cli, &UpdateOptions{
+
+	err = RunUpdate(ctx, cli, &UpdateOptions{
 		Name: "test",
 		Docker: map[string]string{
 			keyHost: "some///invalid/host",
diff --git a/cli/command/context/use_test.go b/cli/command/context/use_test.go
index 0d95ee2cb33b..5db65580d07b 100644
--- a/cli/command/context/use_test.go
+++ b/cli/command/context/use_test.go
@@ -2,6 +2,7 @@ package context
 
 import (
 	"bytes"
+	"context"
 	"errors"
 	"io"
 	"os"
@@ -19,11 +20,14 @@ import (
 )
 
 func TestUse(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
 	configDir := t.TempDir()
 	configFilePath := filepath.Join(configDir, "config.json")
 	testCfg := configfile.New(configFilePath)
 	cli := makeFakeCli(t, withCliConfig(testCfg))
-	err := RunCreate(cli, &CreateOptions{
+	err := RunCreate(ctx, cli, &CreateOptions{
 		Name:   "test",
 		Docker: map[string]string{},
 	})
@@ -84,12 +88,14 @@ func TestUseDefaultWithoutConfigFile(t *testing.T) {
 
 func TestUseHostOverride(t *testing.T) {
 	t.Setenv("DOCKER_HOST", "tcp://ed:2375/")
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
 
 	configDir := t.TempDir()
 	configFilePath := filepath.Join(configDir, "config.json")
 	testCfg := configfile.New(configFilePath)
 	cli := makeFakeCli(t, withCliConfig(testCfg))
-	err := RunCreate(cli, &CreateOptions{
+	err := RunCreate(ctx, cli, &CreateOptions{
 		Name:   "test",
 		Docker: map[string]string{},
 	})
@@ -119,6 +125,9 @@ func TestUseHostOverride(t *testing.T) {
 func TestUseHostOverrideEmpty(t *testing.T) {
 	t.Setenv("DOCKER_HOST", "")
 
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
 	configDir := t.TempDir()
 	config.SetDir(configDir)
 
@@ -136,7 +145,7 @@ func TestUseHostOverrideEmpty(t *testing.T) {
 		assert.NilError(t, cli.Initialize(flags.NewClientOptions()))
 	}
 	loadCli()
-	err := RunCreate(cli, &CreateOptions{
+	err := RunCreate(ctx, cli, &CreateOptions{
 		Name:   "test",
 		Docker: map[string]string{"host": socketPath},
 	})
@@ -153,5 +162,5 @@ func TestUseHostOverrideEmpty(t *testing.T) {
 	assert.Assert(t, is.Contains(out.String(), "test"))
 
 	apiclient := cli.Client()
-	assert.Equal(t, apiclient.DaemonHost(), socketPath)
+	assert.Equal(t, apiclient.DaemonHost(ctx), socketPath)
 }
diff --git a/cli/command/image/build.go b/cli/command/image/build.go
index 61a5ed4dbb86..b93c086092b4 100644
--- a/cli/command/image/build.go
+++ b/cli/command/image/build.go
@@ -325,7 +325,7 @@ func runBuild(ctx context.Context, dockerCli command.Cli, options buildOptions)
 	for k, auth := range creds {
 		authConfigs[k] = registrytypes.AuthConfig(auth)
 	}
-	buildOptions := imageBuildOptions(dockerCli, options)
+	buildOptions := imageBuildOptions(ctx, dockerCli, options)
 	buildOptions.Version = types.BuilderV1
 	buildOptions.Dockerfile = relDockerfile
 	buildOptions.AuthConfigs = authConfigs
@@ -529,7 +529,7 @@ func replaceDockerfileForContentTrust(ctx context.Context, inputTarStream io.Rea
 	return pipeReader
 }
 
-func imageBuildOptions(dockerCli command.Cli, options buildOptions) types.ImageBuildOptions {
+func imageBuildOptions(ctx context.Context, dockerCli command.Cli, options buildOptions) types.ImageBuildOptions {
 	configFile := dockerCli.ConfigFile()
 	return types.ImageBuildOptions{
 		Memory:         options.memory.Value(),
@@ -549,7 +549,7 @@ func imageBuildOptions(dockerCli command.Cli, options buildOptions) types.ImageB
 		CgroupParent:   options.cgroupParent,
 		ShmSize:        options.shmSize.Value(),
 		Ulimits:        options.ulimits.GetList(),
-		BuildArgs:      configFile.ParseProxyConfig(dockerCli.Client().DaemonHost(), opts.ConvertKVStringsToMapWithNil(options.buildArgs.GetAll())),
+		BuildArgs:      configFile.ParseProxyConfig(dockerCli.Client().DaemonHost(ctx), opts.ConvertKVStringsToMapWithNil(options.buildArgs.GetAll())),
 		Labels:         opts.ConvertKVStringsToMap(options.labels.GetAll()),
 		CacheFrom:      options.cacheFrom,
 		SecurityOpt:    options.securityOpt,
diff --git a/cli/command/plugin/install.go b/cli/command/plugin/install.go
index f1aa9d872593..6d9ea7da5fda 100644
--- a/cli/command/plugin/install.go
+++ b/cli/command/plugin/install.go
@@ -136,13 +136,12 @@ func runInstall(ctx context.Context, dockerCli command.Cli, opts pluginOptions)
 	return nil
 }
 
-func acceptPrivileges(dockerCli command.Cli, name string) func(privileges types.PluginPrivileges) (bool, error) {
-	return func(privileges types.PluginPrivileges) (bool, error) {
+func acceptPrivileges(dockerCli command.Cli, name string) func(ctx context.Context, privileges types.PluginPrivileges) (bool, error) {
+	return func(ctx context.Context, privileges types.PluginPrivileges) (bool, error) {
 		fmt.Fprintf(dockerCli.Out(), "Plugin %q is requesting the following privileges:\n", name)
 		for _, privilege := range privileges {
 			fmt.Fprintf(dockerCli.Out(), " - %s: %v\n", privilege.Name, privilege.Value)
 		}
-		ctx := context.TODO()
 		return command.PromptForConfirmation(ctx, dockerCli.In(), dockerCli.Out(), "Do you grant the above permissions?")
 	}
 }
diff --git a/cli/command/registry.go b/cli/command/registry.go
index a1a499eee46a..3afda4d970f9 100644
--- a/cli/command/registry.go
+++ b/cli/command/registry.go
@@ -2,6 +2,7 @@ package command
 
 import (
 	"bufio"
+	"context"
 	"fmt"
 	"io"
 	"os"
@@ -27,7 +28,7 @@ const patSuggest = "You can log in with your password or a Personal Access " +
 // RegistryAuthenticationPrivilegedFunc returns a RequestPrivilegeFunc from the specified registry index info
 // for the given command.
 func RegistryAuthenticationPrivilegedFunc(cli Cli, index *registrytypes.IndexInfo, cmdName string) types.RequestPrivilegeFunc {
-	return func() (string, error) {
+	return func(ctx context.Context) (string, error) {
 		fmt.Fprintf(cli.Out(), "\nPlease login prior to %s:\n", cmdName)
 		indexServer := registry.GetAuthConfigKey(index)
 		isDefaultRegistry := indexServer == registry.IndexServer
diff --git a/cli/command/service/create.go b/cli/command/service/create.go
index 6e49558609a1..08341f1db26f 100644
--- a/cli/command/service/create.go
+++ b/cli/command/service/create.go
@@ -85,7 +85,7 @@ func runCreate(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 		return err
 	}
 
-	if err = validateAPIVersion(service, dockerCli.Client().ClientVersion()); err != nil {
+	if err = validateAPIVersion(service, dockerCli.Client().ClientVersion(ctx)); err != nil {
 		return err
 	}
 
@@ -118,7 +118,7 @@ func runCreate(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 	}
 
 	// query registry if flag disabling it was not set
-	if !opts.noResolveImage && versions.GreaterThanOrEqualTo(apiClient.ClientVersion(), "1.30") {
+	if !opts.noResolveImage && versions.GreaterThanOrEqualTo(apiClient.ClientVersion(ctx), "1.30") {
 		createOpts.QueryRegistry = true
 	}
 
@@ -133,7 +133,7 @@ func runCreate(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 
 	fmt.Fprintf(dockerCli.Out(), "%s\n", response.ID)
 
-	if opts.detach || versions.LessThan(apiClient.ClientVersion(), "1.29") {
+	if opts.detach || versions.LessThan(apiClient.ClientVersion(ctx), "1.29") {
 		return nil
 	}
 
diff --git a/cli/command/service/rollback.go b/cli/command/service/rollback.go
index 06be65bb9084..7bfcb95f12f1 100644
--- a/cli/command/service/rollback.go
+++ b/cli/command/service/rollback.go
@@ -58,7 +58,7 @@ func runRollback(ctx context.Context, dockerCli command.Cli, options *serviceOpt
 
 	fmt.Fprintf(dockerCli.Out(), "%s\n", serviceID)
 
-	if options.detach || versions.LessThan(apiClient.ClientVersion(), "1.29") {
+	if options.detach || versions.LessThan(apiClient.ClientVersion(ctx), "1.29") {
 		return nil
 	}
 
diff --git a/cli/command/service/scale.go b/cli/command/service/scale.go
index fd863049893d..5ad80bc46da4 100644
--- a/cli/command/service/scale.go
+++ b/cli/command/service/scale.go
@@ -78,7 +78,7 @@ func runScale(ctx context.Context, dockerCli command.Cli, options *scaleOptions,
 	}
 
 	if len(serviceIDs) > 0 {
-		if !options.detach && versions.GreaterThanOrEqualTo(dockerCli.Client().ClientVersion(), "1.29") {
+		if !options.detach && versions.GreaterThanOrEqualTo(dockerCli.Client().ClientVersion(ctx), "1.29") {
 			for _, serviceID := range serviceIDs {
 				if err := WaitOnService(ctx, dockerCli, serviceID, false); err != nil {
 					errs = append(errs, fmt.Sprintf("%s: %v", serviceID, err))
diff --git a/cli/command/service/update.go b/cli/command/service/update.go
index d25229802e18..c2a0f9da0cd3 100644
--- a/cli/command/service/update.go
+++ b/cli/command/service/update.go
@@ -164,7 +164,7 @@ func runUpdate(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 			return errors.New("other flags may not be combined with --rollback")
 		}
 
-		if versions.LessThan(apiClient.ClientVersion(), "1.28") {
+		if versions.LessThan(apiClient.ClientVersion(ctx), "1.28") {
 			clientSideRollback = true
 			spec = service.PreviousSpec
 			if spec == nil {
@@ -189,7 +189,7 @@ func runUpdate(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 		if err := resolveServiceImageDigestContentTrust(dockerCli, spec); err != nil {
 			return err
 		}
-		if !options.noResolveImage && versions.GreaterThanOrEqualTo(apiClient.ClientVersion(), "1.30") {
+		if !options.noResolveImage && versions.GreaterThanOrEqualTo(apiClient.ClientVersion(ctx), "1.30") {
 			updateOpts.QueryRegistry = true
 		}
 	}
@@ -245,7 +245,7 @@ func runUpdate(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 
 	fmt.Fprintf(dockerCli.Out(), "%s\n", serviceID)
 
-	if options.detach || versions.LessThan(apiClient.ClientVersion(), "1.29") {
+	if options.detach || versions.LessThan(apiClient.ClientVersion(ctx), "1.29") {
 		return nil
 	}
 
diff --git a/cli/command/stack/client_test.go b/cli/command/stack/client_test.go
index 4cb8a3b5db2e..050f4516266d 100644
--- a/cli/command/stack/client_test.go
+++ b/cli/command/stack/client_test.go
@@ -50,7 +50,7 @@ func (cli *fakeClient) ServerVersion(context.Context) (types.Version, error) {
 	}, nil
 }
 
-func (cli *fakeClient) ClientVersion() string {
+func (cli *fakeClient) ClientVersion(_ context.Context) string {
 	return cli.version
 }
 
diff --git a/cli/command/stack/swarm/client_test.go b/cli/command/stack/swarm/client_test.go
index afb93458f061..e19e9ba5635f 100644
--- a/cli/command/stack/swarm/client_test.go
+++ b/cli/command/stack/swarm/client_test.go
@@ -50,7 +50,7 @@ func (cli *fakeClient) ServerVersion(context.Context) (types.Version, error) {
 	}, nil
 }
 
-func (cli *fakeClient) ClientVersion() string {
+func (cli *fakeClient) ClientVersion(ctx context.Context) string {
 	return cli.version
 }
 
diff --git a/cli/command/stack/swarm/deploy.go b/cli/command/stack/swarm/deploy.go
index 7fe52f67fd72..c184c837b29e 100644
--- a/cli/command/stack/swarm/deploy.go
+++ b/cli/command/stack/swarm/deploy.go
@@ -29,7 +29,7 @@ func RunDeploy(ctx context.Context, dockerCli command.Cli, flags *pflag.FlagSet,
 	}
 	// client side image resolution should not be done when the supported
 	// server version is older than 1.30
-	if versions.LessThan(dockerCli.Client().ClientVersion(), "1.30") {
+	if versions.LessThan(dockerCli.Client().ClientVersion(ctx), "1.30") {
 		opts.ResolveImage = ResolveImageNever
 	}
 
diff --git a/cli/command/stack/swarm/remove.go b/cli/command/stack/swarm/remove.go
index 5a901fbf8c55..124308f96b4f 100644
--- a/cli/command/stack/swarm/remove.go
+++ b/cli/command/stack/swarm/remove.go
@@ -32,7 +32,7 @@ func RunRemove(ctx context.Context, dockerCli command.Cli, opts options.Remove)
 		}
 
 		var secrets []swarm.Secret
-		if versions.GreaterThanOrEqualTo(client.ClientVersion(), "1.25") {
+		if versions.GreaterThanOrEqualTo(client.ClientVersion(ctx), "1.25") {
 			secrets, err = getStackSecrets(ctx, client, namespace)
 			if err != nil {
 				return err
@@ -40,7 +40,7 @@ func RunRemove(ctx context.Context, dockerCli command.Cli, opts options.Remove)
 		}
 
 		var configs []swarm.Config
-		if versions.GreaterThanOrEqualTo(client.ClientVersion(), "1.30") {
+		if versions.GreaterThanOrEqualTo(client.ClientVersion(ctx), "1.30") {
 			configs, err = getStackConfigs(ctx, client, namespace)
 			if err != nil {
 				return err
diff --git a/cli/command/system/client_test.go b/cli/command/system/client_test.go
index 01dc4b3d25fc..a9853758a922 100644
--- a/cli/command/system/client_test.go
+++ b/cli/command/system/client_test.go
@@ -23,7 +23,7 @@ func (cli *fakeClient) ServerVersion(ctx context.Context) (types.Version, error)
 	return cli.serverVersion(ctx)
 }
 
-func (cli *fakeClient) ClientVersion() string {
+func (cli *fakeClient) ClientVersion(context.Context) string {
 	return cli.version
 }
 
diff --git a/cli/command/system/dial_stdio.go b/cli/command/system/dial_stdio.go
index d4193ce8af78..20c7abd9d1f6 100644
--- a/cli/command/system/dial_stdio.go
+++ b/cli/command/system/dial_stdio.go
@@ -32,7 +32,7 @@ func runDialStdio(ctx context.Context, dockerCli command.Cli) error {
 	ctx, cancel := context.WithCancel(ctx)
 	defer cancel()
 
-	dialer := dockerCli.Client().Dialer()
+	dialer := dockerCli.Client().Dialer(ctx)
 	conn, err := dialer(ctx)
 	if err != nil {
 		return errors.Wrap(err, "failed to open the raw stream connection")
diff --git a/cli/command/system/prune.go b/cli/command/system/prune.go
index b3200ecfad86..7768157c4af7 100644
--- a/cli/command/system/prune.go
+++ b/cli/command/system/prune.go
@@ -39,7 +39,8 @@ func newPruneCommand(dockerCli command.Cli) *cobra.Command {
 		Short: "Remove unused data",
 		Args:  cli.NoArgs,
 		RunE: func(cmd *cobra.Command, args []string) error {
-			options.pruneBuildCache = versions.GreaterThanOrEqualTo(dockerCli.Client().ClientVersion(), "1.31")
+			ctx := cmd.Context()
+			options.pruneBuildCache = versions.GreaterThanOrEqualTo(dockerCli.Client().ClientVersion(ctx), "1.31")
 			return runPrune(cmd.Context(), dockerCli, options)
 		},
 		Annotations:       map[string]string{"version": "1.25"},
diff --git a/cli/compose/convert/service.go b/cli/compose/convert/service.go
index 708c5a7d202f..d79628dcb37a 100644
--- a/cli/compose/convert/service.go
+++ b/cli/compose/convert/service.go
@@ -42,7 +42,7 @@ func Services(
 			return nil, errors.Wrapf(err, "service %s", service.Name)
 		}
 
-		serviceSpec, err := Service(apiClient.ClientVersion(), namespace, service, config.Networks, config.Volumes, secrets, configs)
+		serviceSpec, err := Service(apiClient.ClientVersion(ctx), namespace, service, config.Networks, config.Volumes, secrets, configs)
 		if err != nil {
 			return nil, errors.Wrapf(err, "service %s", service.Name)
 		}
diff --git a/cmd/docker/docker.go b/cmd/docker/docker.go
index cfc53a6fa170..9f5ffe3a043e 100644
--- a/cmd/docker/docker.go
+++ b/cmd/docker/docker.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"context"
 	"fmt"
 	"net"
 	"os"
@@ -25,6 +26,16 @@ import (
 )
 
 func main() {
+	ctx := context.Background()
+	otelShutdown, err := setupOTelSDK(ctx)
+	if err != nil {
+		return
+	}
+	// Handle shutdown properly so nothing leaks.
+	defer func() {
+		otelShutdown(context.Background())
+	}()
+
 	dockerCli, err := command.NewDockerCli()
 	if err != nil {
 		fmt.Fprintln(os.Stderr, err)
diff --git a/cmd/docker/otel.go b/cmd/docker/otel.go
new file mode 100644
index 000000000000..30ddf4ae79b7
--- /dev/null
+++ b/cmd/docker/otel.go
@@ -0,0 +1,104 @@
+package main
+
+import (
+	"context"
+	"errors"
+	"time"
+
+	"go.opentelemetry.io/otel"
+	"go.opentelemetry.io/otel/exporters/otlp/otlptrace"
+	"go.opentelemetry.io/otel/exporters/otlp/otlptrace/otlptracehttp"
+	"go.opentelemetry.io/otel/exporters/stdout/stdoutmetric"
+	"go.opentelemetry.io/otel/propagation"
+	"go.opentelemetry.io/otel/sdk/metric"
+	"go.opentelemetry.io/otel/sdk/resource"
+	"go.opentelemetry.io/otel/sdk/trace"
+	semconv "go.opentelemetry.io/otel/semconv/v1.24.0"
+)
+
+// setupOTelSDK bootstraps the OpenTelemetry pipeline.
+// If it does not return an error, make sure to call shutdown for proper cleanup.
+func setupOTelSDK(ctx context.Context) (shutdown func(context.Context) error, err error) {
+	var shutdownFuncs []func(context.Context) error
+
+	// shutdown calls cleanup functions registered via shutdownFuncs.
+	// The errors from the calls are joined.
+	// Each registered cleanup will be invoked once.
+	shutdown = func(ctx context.Context) error {
+		var err error
+		for _, fn := range shutdownFuncs {
+			err = errors.Join(err, fn(ctx))
+		}
+		shutdownFuncs = nil
+		return err
+	}
+
+	// handleErr calls shutdown for cleanup and makes sure that all errors are returned.
+	handleErr := func(inErr error) {
+		err = errors.Join(inErr, shutdown(ctx))
+	}
+
+	// Set up propagator.
+	prop := newPropagator()
+	otel.SetTextMapPropagator(prop)
+
+	exporter, err := otlptrace.New(
+		context.Background(),
+		otlptracehttp.NewClient(otlptracehttp.WithInsecure()),
+	)
+
+	// rpcmetricsObserver := rpcmetrics.NewObserver(metricsFactory, rpcmetrics.DefaultNameNormalizer)
+
+	res, err := resource.New(
+		context.Background(),
+		resource.WithSchemaURL(semconv.SchemaURL),
+		resource.WithAttributes(semconv.ServiceNameKey.String("TEST")),
+		resource.WithTelemetrySDK(),
+		resource.WithHost(),
+		resource.WithOSType(),
+	)
+	if err != nil {
+		panic(err)
+	}
+
+	tp := trace.NewTracerProvider(
+		trace.WithBatcher(exporter, trace.WithBatchTimeout(1000*time.Millisecond)),
+		// trace.WithSpanProcessor(rpcmetricsObserver),
+		trace.WithResource(res),
+	)
+
+	shutdownFuncs = append(shutdownFuncs, tp.Shutdown)
+	otel.SetTracerProvider(tp)
+
+	// Set up meter provider.
+	meterProvider, err := newMeterProvider()
+	if err != nil {
+		handleErr(err)
+		return
+	}
+	shutdownFuncs = append(shutdownFuncs, meterProvider.Shutdown)
+	otel.SetMeterProvider(meterProvider)
+
+	return
+}
+
+func newPropagator() propagation.TextMapPropagator {
+	return propagation.NewCompositeTextMapPropagator(
+		propagation.TraceContext{},
+		propagation.Baggage{},
+	)
+}
+
+func newMeterProvider() (*metric.MeterProvider, error) {
+	metricExporter, err := stdoutmetric.New()
+	if err != nil {
+		return nil, err
+	}
+
+	meterProvider := metric.NewMeterProvider(
+		metric.WithReader(metric.NewPeriodicReader(metricExporter,
+			// Default is 1m. Set to 3s for demonstrative purposes.
+			metric.WithInterval(3*time.Second))),
+	)
+	return meterProvider, nil
+}
diff --git a/e2e/cli-plugins/plugins/nopersistentprerun/main.go b/e2e/cli-plugins/plugins/nopersistentprerun/main.go
index 5f07bf7e012e..4e63d1d86149 100644
--- a/e2e/cli-plugins/plugins/nopersistentprerun/main.go
+++ b/e2e/cli-plugins/plugins/nopersistentprerun/main.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"context"
 	"fmt"
 
 	"github.com/docker/cli/cli-plugins/manager"
@@ -10,7 +11,8 @@ import (
 )
 
 func main() {
-	plugin.Run(func(dockerCli command.Cli) *cobra.Command {
+	ctx := context.Background()
+	plugin.Run(ctx, func(ctx context.Context, dockerCli command.Cli) *cobra.Command {
 		cmd := &cobra.Command{
 			Use:   "nopersistentprerun",
 			Short: "Testing without PersistentPreRun hooks",
diff --git a/e2e/cli-plugins/plugins/presocket/main.go b/e2e/cli-plugins/plugins/presocket/main.go
index 6cdf87a42402..5986c4a9cb72 100644
--- a/e2e/cli-plugins/plugins/presocket/main.go
+++ b/e2e/cli-plugins/plugins/presocket/main.go
@@ -1,6 +1,7 @@
 package main
 
 import (
+	"context"
 	"fmt"
 	"os"
 	"os/signal"
@@ -14,14 +15,15 @@ import (
 )
 
 func main() {
-	plugin.Run(RootCmd, manager.Metadata{
+	ctx := context.TODO()
+	plugin.Run(ctx, RootCmd, manager.Metadata{
 		SchemaVersion: "0.1.0",
 		Vendor:        "Docker Inc.",
 		Version:       "test",
 	})
 }
 
-func RootCmd(dockerCli command.Cli) *cobra.Command {
+func RootCmd(ctx context.Context, dockerCli command.Cli) *cobra.Command {
 	cmd := cobra.Command{
 		Use:   "presocket",
 		Short: "testing plugin that does not connect to the socket",
diff --git a/internal/test/cli.go b/internal/test/cli.go
index 2315a7a1f22b..005f0fd720cb 100644
--- a/internal/test/cli.go
+++ b/internal/test/cli.go
@@ -40,6 +40,8 @@ type FakeCli struct {
 	dockerEndpoint   docker.Endpoint
 }
 
+var _ command.Cli = (*FakeCli)(nil)
+
 // NewFakeCli returns a fake for the command.Cli interface
 func NewFakeCli(apiClient client.APIClient, opts ...func(*FakeCli)) *FakeCli {
 	outBuffer := new(bytes.Buffer)