diff --git a/cli/command/cli.go b/cli/command/cli.go
index e405c2cc4f..0d2f4b506f 100644
--- a/cli/command/cli.go
+++ b/cli/command/cli.go
@@ -68,6 +68,7 @@ type DockerCli struct {
 	serverInfo         ServerInfo
 	contextStore       store.Store
 	currentContext     string
+	contextResolver    func(*DockerCli) (string, error)
 	init               sync.Once
 	initErr            error
 	dockerEndpoint     docker.Endpoint
@@ -208,6 +209,8 @@ func (cli *DockerCli) HooksEnabled() bool {
 
 // Initialize the dockerCli runs initialization that must happen after command
 // line flags are parsed.
+//
+//nolint:gocyclo
 func (cli *DockerCli) Initialize(opts *cliflags.ClientOptions, ops ...CLIOption) error {
 	for _, o := range ops {
 		if err := o(cli); err != nil {
@@ -257,6 +260,16 @@ func (cli *DockerCli) Initialize(opts *cliflags.ClientOptions, ops ...CLIOption)
 		},
 	}
 
+	if cli.contextResolver != nil {
+		contextName, err := cli.contextResolver(cli)
+		if err != nil {
+			return err
+		}
+		if contextName != "" {
+			cli.currentContext = contextName
+		}
+	}
+
 	// TODO(krissetto): pass ctx to the funcs instead of using this
 	if cli.enableGlobalMeter {
 		cli.createGlobalMeterProvider(cli.baseCtx)
diff --git a/cli/command/cli_options.go b/cli/command/cli_options.go
index 469932f9c3..733cfbdf64 100644
--- a/cli/command/cli_options.go
+++ b/cli/command/cli_options.go
@@ -84,6 +84,19 @@ func WithDefaultContextStoreConfig() CLIOption {
 	}
 }
 
+// WithContextResolver overrides context selection during [DockerCli.Initialize].
+// The resolver runs after configuration and the context store are loaded, but
+// before telemetry and endpoint initialization.
+// An empty result preserves normal context selection; an error aborts
+// initialization.
+// The resolver must not initialize the API client.
+func WithContextResolver(resolve func(*DockerCli) (string, error)) CLIOption {
+	return func(cli *DockerCli) error {
+		cli.contextResolver = resolve
+		return nil
+	}
+}
+
 // WithAPIClient configures the cli to use the given API client.
 func WithAPIClient(c client.APIClient) CLIOption {
 	return func(cli *DockerCli) error {
diff --git a/cli/command/cli_test.go b/cli/command/cli_test.go
index 27be8d348c..09c093d5dd 100644
--- a/cli/command/cli_test.go
+++ b/cli/command/cli_test.go
@@ -325,6 +325,64 @@ func TestInitializeShouldAlwaysCreateTheContextStore(t *testing.T) {
 	assert.Check(t, cli.ContextStore() != nil)
 }
 
+func TestInitializeContextResolver(t *testing.T) {
+	resolverErr := errors.New("resolver failed")
+
+	for _, tc := range []struct {
+		name    string
+		context string
+		err     error
+	}{
+		{name: "resolved context", context: "resolved"},
+		{name: "normal selection"},
+		{name: "resolver failure", err: resolverErr},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			originalConfigDir := config.Dir()
+			t.Cleanup(func() { config.SetDir(originalConfigDir) })
+			config.SetDir(t.TempDir())
+
+			configDir := t.TempDir()
+			cfg := configfile.New(filepath.Join(configDir, config.ConfigFileName))
+			cfg.Features = map[string]string{"cloud": "foobar"}
+			assert.NilError(t, cfg.Save())
+
+			cli, err := NewDockerCli()
+			assert.NilError(t, err)
+
+			var loadedConfig *configfile.ConfigFile
+			calls := 0
+
+			err = cli.Initialize(&flags.ClientOptions{ConfigDir: configDir, Context: "original"},
+				WithContextResolver(func(cli *DockerCli) (string, error) {
+					calls++
+					assert.Equal(t, config.Dir(), configDir)
+					loadedConfig = cli.ConfigFile()
+					assert.Equal(t, loadedConfig.Features["cloud"], "foobar")
+					assert.Assert(t, cli.ContextStore() != nil)
+					assert.Assert(t, cli.client == nil)
+					return tc.context, tc.err
+				}),
+			)
+			assert.Equal(t, calls, 1)
+			assert.Assert(t, cli.ConfigFile() == loadedConfig)
+			assert.Assert(t, cli.client == nil)
+
+			if tc.err != nil {
+				assert.ErrorIs(t, err, tc.err)
+				return
+			}
+			assert.NilError(t, err)
+
+			wantContext := tc.context
+			if wantContext == "" {
+				wantContext = "original"
+			}
+			assert.Equal(t, cli.CurrentContext(), wantContext)
+		})
+	}
+}
+
 func TestHooksEnabled(t *testing.T) {
 	t.Run("disabled by default", func(t *testing.T) {
 		// Make sure we don't depend on any existing ~/.docker/config.json