diff --git a/cmd/mindthegap/create/imagebundle/image_bundle.go b/cmd/mindthegap/create/imagebundle/image_bundle.go
index 7d32deb5..09dd9389 100644
--- a/cmd/mindthegap/create/imagebundle/image_bundle.go
+++ b/cmd/mindthegap/create/imagebundle/image_bundle.go
@@ -14,7 +14,6 @@ import (
 	"github.com/google/go-containerregistry/pkg/name"
 	"github.com/google/go-containerregistry/pkg/v1/remote"
 	"github.com/spf13/cobra"
-	"k8s.io/client-go/transport"
 
 	"github.com/mesosphere/dkp-cli-runtime/core/output"
 
@@ -118,8 +117,9 @@ func NewCommand(out output.Output) *cobra.Command {
 				var remoteOpts []remote.Option
 				if registryConfig.TLSVerify != nil && !*registryConfig.TLSVerify {
 					transport := httputils.NewConfigurableTLSRoundTripper(
-						remote.DefaultTransport,
-						httputils.TLSHostsConfig{registryName: transport.TLSConfig{Insecure: true}},
+						httputils.TLSHostsConfig{
+							registryName: httputils.TLSHostConfig{Insecure: true},
+						},
 					)
 
 					remoteOpts = append(remoteOpts, remote.WithTransport(transport))
diff --git a/cmd/mindthegap/importcmd/imagebundle/image_bundle.go b/cmd/mindthegap/importcmd/imagebundle/image_bundle.go
index 4613da1b..3889a626 100644
--- a/cmd/mindthegap/importcmd/imagebundle/image_bundle.go
+++ b/cmd/mindthegap/importcmd/imagebundle/image_bundle.go
@@ -15,7 +15,6 @@ import (
 	"github.com/google/go-containerregistry/pkg/v1/remote"
 	"github.com/google/go-containerregistry/pkg/v1/tarball"
 	"github.com/spf13/cobra"
-	"k8s.io/client-go/transport"
 
 	"github.com/mesosphere/dkp-cli-runtime/core/output"
 
@@ -98,9 +97,8 @@ func NewCommand(out output.Output) *cobra.Command {
 							ref,
 							remote.WithTransport(
 								httputils.NewConfigurableTLSRoundTripper(
-									remote.DefaultTransport,
 									httputils.TLSHostsConfig{
-										reg.Address(): transport.TLSConfig{Insecure: true},
+										reg.Address(): httputils.TLSHostConfig{Insecure: true},
 									},
 								),
 							),
diff --git a/cmd/mindthegap/push/helmbundle/helm_bundle.go b/cmd/mindthegap/push/helmbundle/helm_bundle.go
index e1d6ec75..e0b907ba 100644
--- a/cmd/mindthegap/push/helmbundle/helm_bundle.go
+++ b/cmd/mindthegap/push/helmbundle/helm_bundle.go
@@ -13,7 +13,6 @@ import (
 	"github.com/google/go-containerregistry/pkg/name"
 	"github.com/google/go-containerregistry/pkg/v1/remote"
 	"github.com/spf13/cobra"
-	"k8s.io/client-go/transport"
 
 	"github.com/mesosphere/dkp-cli-runtime/core/output"
 
@@ -85,13 +84,12 @@ func NewCommand(out output.Output) *cobra.Command {
 			insecure := flags.SkipTLSVerify(destRegistrySkipTLSVerify, destRegistryURI)
 			if insecure || destRegistryCACertificateFile != "" {
 				transport := httputils.NewConfigurableTLSRoundTripper(
-					remote.DefaultTransport,
 					httputils.TLSHostsConfig{
-						destRegistryURI.Host(): transport.TLSConfig{
+						destRegistryURI.Host(): httputils.TLSHostConfig{
 							Insecure: insecure,
 							CAFile:   destRegistryCACertificateFile,
 						},
-						reg.Address(): transport.TLSConfig{Insecure: true},
+						reg.Address(): httputils.TLSHostConfig{Insecure: true},
 					},
 				)
 
diff --git a/cmd/mindthegap/push/imagebundle/image_bundle.go b/cmd/mindthegap/push/imagebundle/image_bundle.go
index 5a565973..6a70c033 100644
--- a/cmd/mindthegap/push/imagebundle/image_bundle.go
+++ b/cmd/mindthegap/push/imagebundle/image_bundle.go
@@ -13,7 +13,6 @@ import (
 	"github.com/google/go-containerregistry/pkg/name"
 	"github.com/google/go-containerregistry/pkg/v1/remote"
 	"github.com/spf13/cobra"
-	"k8s.io/client-go/transport"
 
 	"github.com/mesosphere/dkp-cli-runtime/core/output"
 
@@ -86,13 +85,12 @@ func NewCommand(out output.Output) *cobra.Command {
 			insecure := flags.SkipTLSVerify(destRegistrySkipTLSVerify, destRegistryURI)
 			if insecure || destRegistryCACertificateFile != "" {
 				transport := httputils.NewConfigurableTLSRoundTripper(
-					remote.DefaultTransport,
 					httputils.TLSHostsConfig{
-						destRegistryURI.Host(): transport.TLSConfig{
+						destRegistryURI.Host(): httputils.TLSHostConfig{
 							Insecure: insecure,
 							CAFile:   destRegistryCACertificateFile,
 						},
-						reg.Address(): transport.TLSConfig{Insecure: true},
+						reg.Address(): httputils.TLSHostConfig{Insecure: true},
 					},
 				)
 
diff --git a/go.mod b/go.mod
index e2dcb393..658f3713 100644
--- a/go.mod
+++ b/go.mod
@@ -10,8 +10,10 @@ require (
 	github.com/aws/aws-sdk-go-v2/service/ecr v1.18.0
 	github.com/containers/image/v5 v5.23.1
 	github.com/distribution/distribution/v3 v3.0.0-20220907155224-78b9c98c5c31
+	github.com/docker/cli v20.10.22+incompatible
 	github.com/docker/docker v20.10.22+incompatible
 	github.com/docker/docker-credential-helpers v0.7.0
+	github.com/docker/go-connections v0.4.0
 	github.com/google/go-containerregistry v0.12.1
 	github.com/hashicorp/go-getter v1.6.2
 	github.com/mesosphere/dkp-cli-runtime/core v0.7.1
@@ -27,7 +29,6 @@ require (
 	gopkg.in/yaml.v3 v3.0.1
 	helm.sh/helm/v3 v3.10.3
 	k8s.io/apimachinery v0.26.0
-	k8s.io/client-go v0.26.0
 	k8s.io/klog/v2 v2.80.1
 	k8s.io/utils v0.0.0-20221107191617-1a15be271d1d
 )
@@ -66,9 +67,7 @@ require (
 	github.com/cpuguy83/go-md2man/v2 v2.0.2 // indirect
 	github.com/cyphar/filepath-securejoin v0.2.3 // indirect
 	github.com/davecgh/go-spew v1.1.1 // indirect
-	github.com/docker/cli v20.10.22+incompatible // indirect
 	github.com/docker/distribution v2.8.1+incompatible // indirect
-	github.com/docker/go-connections v0.4.0 // indirect
 	github.com/docker/go-events v0.0.0-20190806004212-e31b211e4f1c // indirect
 	github.com/docker/go-metrics v0.0.1 // indirect
 	github.com/docker/go-units v0.5.0 // indirect
@@ -185,6 +184,7 @@ require (
 	k8s.io/apiextensions-apiserver v0.25.2 // indirect
 	k8s.io/apiserver v0.25.2 // indirect
 	k8s.io/cli-runtime v0.25.2 // indirect
+	k8s.io/client-go v0.26.0 // indirect
 	k8s.io/component-base v0.25.2 // indirect
 	k8s.io/kube-openapi v0.0.0-20221012153701-172d655c2280 // indirect
 	k8s.io/kubectl v0.25.2 // indirect
diff --git a/images/httputils/configurable_tls_transport.go b/images/httputils/configurable_tls_transport.go
index 00b8afcc..93813926 100644
--- a/images/httputils/configurable_tls_transport.go
+++ b/images/httputils/configurable_tls_transport.go
@@ -4,45 +4,118 @@
 package httputils
 
 import (
+	"fmt"
 	"net/http"
+	"os"
+	"path/filepath"
+	"strings"
 
-	"k8s.io/client-go/transport"
+	"github.com/docker/cli/cli/config"
+	"github.com/docker/docker/registry"
+	"github.com/docker/go-connections/tlsconfig"
+	"github.com/google/go-containerregistry/pkg/logs"
+	"github.com/google/go-containerregistry/pkg/v1/remote"
 )
 
 type configurableTLSTransport struct {
 	cfg               TLSHostsConfig
-	delegateTransport http.RoundTripper
+	delegateTransport *http.Transport
 }
 
 func (rt *configurableTLSTransport) RoundTrip(req *http.Request) (*http.Response, error) {
+	tr := rt.delegateTransport.Clone()
+
+	if tr.TLSClientConfig.RootCAs == nil {
+		systemPool, err := tlsconfig.SystemCertPool()
+		if err != nil {
+			return nil, fmt.Errorf("unable to get system cert pool: %v", err)
+		}
+		tr.TLSClientConfig.RootCAs = systemPool
+	} else {
+		tr.TLSClientConfig.RootCAs = tr.TLSClientConfig.RootCAs.Clone()
+	}
+
 	host := req.Host
 	if host == "" {
 		host = req.URL.Host
 	}
 
-	if tlsConfig, ok := rt.cfg[host]; ok {
-		t, err := transport.New(
-			&transport.Config{
-				TLS: tlsConfig,
-			},
-		)
+	tlsHostConfig, tlsHostConfigFound := rt.cfg[host]
+
+	// Always returns nil error...
+	hostDockerCertsDir, _ := registry.HostCertsDir(host)
+	fs, err := os.ReadDir(hostDockerCertsDir)
+	if err != nil && !os.IsNotExist(err) {
+		return nil, fmt.Errorf("failed to read from Docker registry certs: %w", err)
+	}
+
+	for _, f := range fs {
+		if strings.HasSuffix(f.Name(), ".crt") {
+			data, err := os.ReadFile(filepath.Join(hostDockerCertsDir, f.Name()))
+			if err != nil {
+				return nil, fmt.Errorf("failed tp read CA certificate from Docker certs.d: %w", err)
+			}
+			_ = tr.TLSClientConfig.RootCAs.AppendCertsFromPEM(data)
+		}
+	}
+
+	tr.TLSClientConfig.InsecureSkipVerify = tlsHostConfigFound && tlsHostConfig.Insecure
+
+	if tlsHostConfigFound && tlsHostConfig.CAFile != "" {
+		b, err := os.ReadFile(tlsHostConfig.CAFile)
 		if err != nil {
-			return nil, err
+			return nil, fmt.Errorf("failed to read specified CA file: %w", err)
 		}
-		return t.RoundTrip(req)
+		_ = tr.TLSClientConfig.RootCAs.AppendCertsFromPEM(b)
 	}
 
-	return rt.delegateTransport.RoundTrip(req)
+	return tr.RoundTrip(req)
 }
 
-type TLSHostsConfig map[string]transport.TLSConfig
+type TLSHostConfig struct {
+	CAFile   string // Path of the PEM-encoded server trusted root certificates.
+	Insecure bool   // Server should be accessed without verifying the certificate. For testing only.
+}
+
+type TLSHostsConfig map[string]TLSHostConfig
 
 func NewConfigurableTLSRoundTripper(
-	delegate http.RoundTripper,
 	cfg TLSHostsConfig,
 ) http.RoundTripper {
+	var tr http.RoundTripper = remote.DefaultTransport.(*http.Transport).Clone()
+
+	// Add any http headers if they are set in the config file.
+	cf, err := config.Load(os.Getenv("DOCKER_CONFIG"))
+	if err != nil {
+		logs.Debug.Printf("failed to read config file: %v", err)
+	} else if len(cf.HTTPHeaders) != 0 {
+		tr = &headerTransport{
+			inner:       tr,
+			httpHeaders: cf.HTTPHeaders,
+		}
+	}
+
 	return &configurableTLSTransport{
 		cfg:               cfg,
-		delegateTransport: delegate,
+		delegateTransport: tr.(*http.Transport),
+	}
+}
+
+// headerTransport sets headers on outgoing requests.
+type headerTransport struct {
+	httpHeaders map[string]string
+	inner       http.RoundTripper
+}
+
+// RoundTrip implements http.RoundTripper.
+func (ht *headerTransport) RoundTrip(in *http.Request) (*http.Response, error) {
+	for k, v := range ht.httpHeaders {
+		if http.CanonicalHeaderKey(k) == "User-Agent" {
+			// Docker sets this, which is annoying, since we're not docker.
+			// We might want to revisit completely ignoring this.
+			continue
+		}
+		in.Header.Set(k, v)
 	}
+	return ht.inner.RoundTrip(in)
 }
diff --git a/images/manifest.go b/images/manifest.go
index 469a6169..1dd13352 100644
--- a/images/manifest.go
+++ b/images/manifest.go
@@ -29,7 +29,11 @@ func ManifestListForImage(
 	if err != nil {
 		localImage, localErr := daemon.Image(ref)
 		if localErr != nil {
-			return nil, fmt.Errorf("failed to read image descriptor for %q from registry: %w", img, err)
+			return nil, fmt.Errorf(
+				"failed to read image descriptor for %q from registry: %w",
+				img,
+				err,
+			)
 		}
 
 		return indexForSinglePlatformImage(ref, localImage, platforms...)
diff --git a/test/e2e/imagebundle/push_bundle_test.go b/test/e2e/imagebundle/push_bundle_test.go
index 43bb4839..a761c8ca 100644
--- a/test/e2e/imagebundle/push_bundle_test.go
+++ b/test/e2e/imagebundle/push_bundle_test.go
@@ -19,7 +19,6 @@ import (
 	. "github.com/onsi/gomega"
 	"github.com/phayes/freeport"
 	"github.com/spf13/cobra"
-	"k8s.io/client-go/transport"
 
 	pushimagebundle "github.com/mesosphere/mindthegap/cmd/mindthegap/push/imagebundle"
 	"github.com/mesosphere/mindthegap/docker/registry"
@@ -153,8 +152,8 @@ var _ = Describe("Push Bundle", func() {
 			}},
 			remote.WithTransport(
 				httputils.NewConfigurableTLSRoundTripper(
-					remote.DefaultTransport, httputils.TLSHostsConfig{
-						net.JoinHostPort(ipAddr.String(), strconv.Itoa(port)): transport.TLSConfig{
+					httputils.TLSHostsConfig{
+						net.JoinHostPort(ipAddr.String(), strconv.Itoa(port)): httputils.TLSHostConfig{
 							CAFile: caCertFile,
 						},
 					},
@@ -227,8 +226,8 @@ var _ = Describe("Push Bundle", func() {
 			}},
 			remote.WithTransport(
 				httputils.NewConfigurableTLSRoundTripper(
-					remote.DefaultTransport, httputils.TLSHostsConfig{
-						net.JoinHostPort(ipAddr.String(), strconv.Itoa(port)): transport.TLSConfig{
+					httputils.TLSHostsConfig{
+						net.JoinHostPort(ipAddr.String(), strconv.Itoa(port)): httputils.TLSHostConfig{
 							CAFile: caCertFile,
 						},
 					},
diff --git a/test/e2e/imagebundle/serve_bundle_test.go b/test/e2e/imagebundle/serve_bundle_test.go
index 62702524..79236144 100644
--- a/test/e2e/imagebundle/serve_bundle_test.go
+++ b/test/e2e/imagebundle/serve_bundle_test.go
@@ -18,7 +18,6 @@ import (
 	. "github.com/onsi/gomega"
 	"github.com/phayes/freeport"
 	"github.com/spf13/cobra"
-	"k8s.io/client-go/transport"
 
 	"github.com/mesosphere/dkp-cli-runtime/core/output"
 
@@ -137,8 +136,8 @@ var _ = Describe("Serve Bundle", func() {
 			}},
 			remote.WithTransport(
 				httputils.NewConfigurableTLSRoundTripper(
-					remote.DefaultTransport, httputils.TLSHostsConfig{
-						net.JoinHostPort(ipAddr.String(), strconv.Itoa(port)): transport.TLSConfig{
+					httputils.TLSHostsConfig{
+						net.JoinHostPort(ipAddr.String(), strconv.Itoa(port)): httputils.TLSHostConfig{
 							CAFile: caCertFile,
 						},
 					},