diff --git a/cli/command/cli.go b/cli/command/cli.go
index 91c4ebd0ef12..5d7572a6cb14 100644
--- a/cli/command/cli.go
+++ b/cli/command/cli.go
@@ -105,7 +105,7 @@ func (cli *DockerCli) CurrentVersion() string {
 // Client returns the APIClient
 func (cli *DockerCli) Client() client.APIClient {
 	if err := cli.initialize(); err != nil {
-		_, _ = fmt.Fprintf(cli.Err(), "Failed to initialize: %s\n", err)
+		_, _ = fmt.Fprintf(cli.Err(), "failed to initialize: %s\n", err)
 		os.Exit(1)
 	}
 	return cli.client
@@ -152,7 +152,7 @@ func (cli *DockerCli) ConfigFile() *configfile.ConfigFile {
 // ServerInfo returns the server version details for the host this client is
 // connected to
 func (cli *DockerCli) ServerInfo() ServerInfo {
-	// TODO(thaJeztah) make ServerInfo() lazily load the info (ping only when needed)
+	_ = cli.initialize()
 	return cli.serverInfo
 }
 
@@ -429,16 +429,24 @@ func (cli *DockerCli) DockerEndpoint() docker.Endpoint {
 	if err := cli.initialize(); err != nil {
 		// Note that we're not terminating here, as this function may be used
 		// in cases where we're able to continue.
-		_, _ = fmt.Fprintf(cli.Err(), "Failed to initialize: %s\n", cli.initErr)
+		_, _ = fmt.Fprintf(cli.Err(), "%s\n", cli.initErr)
 	}
 	return cli.dockerEndpoint
 }
 
+func (cli *DockerCli) getDockerEndPoint() (ep docker.Endpoint, err error) {
+	cn := cli.CurrentContext()
+	if cn == DefaultContextName {
+		return resolveDefaultDockerEndpoint(cli.options)
+	}
+	return resolveDockerEndpoint(cli.contextStore, cn)
+}
+
 func (cli *DockerCli) initialize() error {
 	cli.init.Do(func() {
-		cli.dockerEndpoint, cli.initErr = resolveDockerEndpoint(cli.contextStore, resolveContextName(cli.options, cli.configFile))
+		cli.dockerEndpoint, cli.initErr = cli.getDockerEndPoint()
 		if cli.initErr != nil {
-			cli.initErr = errors.Wrap(cli.initErr, "unable to resolve docker endpoint")
+			cli.initErr = errors.Wrap(cli.initErr, "failed to initialize")
 			return
 		}
 		if cli.client == nil {
diff --git a/cli/command/cli_test.go b/cli/command/cli_test.go
index ea82d3a41205..4b29605ae0a9 100644
--- a/cli/command/cli_test.go
+++ b/cli/command/cli_test.go
@@ -118,7 +118,7 @@ func (c *fakeClient) NegotiateAPIVersionPing(types.Ping) {
 }
 
 func TestInitializeFromClient(t *testing.T) {
-	defaultVersion := "v1.55"
+	const defaultVersion = "v1.55"
 
 	testcases := []struct {
 		doc            string
@@ -160,10 +160,13 @@ func TestInitializeFromClient(t *testing.T) {
 			}
 
 			cli := &DockerCli{
-				client: apiclient,
-				err:    io.Discard,
+				client:         apiclient,
+				currentContext: DefaultContextName,
+				err:            io.Discard,
+				options:        flags.NewClientOptions(),
 			}
-			cli.initializeFromClient()
+			err := cli.initialize()
+			assert.NilError(t, err)
 			assert.DeepEqual(t, cli.ServerInfo(), testcase.expectedServer)
 			assert.Equal(t, apiclient.negotiated, testcase.negotiated)
 		})
diff --git a/e2e/global/cli_test.go b/e2e/global/cli_test.go
index 863079b1c32c..96880b38a57d 100644
--- a/e2e/global/cli_test.go
+++ b/e2e/global/cli_test.go
@@ -21,7 +21,7 @@ func TestTLSVerify(t *testing.T) {
 	// Regardless of whether we specify true or false we need to
 	// test to make sure tls is turned on if --tlsverify is specified at all
 	result := icmd.RunCmd(icmd.Command("docker", "--tlsverify=false", "ps"))
-	result.Assert(t, icmd.Expected{ExitCode: 1, Err: "unable to resolve docker endpoint:"})
+	result.Assert(t, icmd.Expected{ExitCode: 1, Err: "failed to initialize:"})
 
 	result = icmd.RunCmd(icmd.Command("docker", "--tlsverify=true", "ps"))
 	result.Assert(t, icmd.Expected{ExitCode: 1, Err: "ca.pem"})