diff --git a/pkg/name/registry.go b/pkg/name/registry.go
index 5b0d01769..f73f1ef0e 100644
--- a/pkg/name/registry.go
+++ b/pkg/name/registry.go
@@ -77,6 +77,11 @@ func (r Registry) isRFC1918() bool {
 	return false
 }
 
+// IsInsecure checks whether the registry is insecure.
+func (r Registry) IsInsecure() bool {
+	return r.insecure
+}
+
 // Scheme returns https scheme for all the endpoints except localhost or when explicitly defined.
 func (r Registry) Scheme() string {
 	if r.insecure {
diff --git a/pkg/v1/remote/catalog.go b/pkg/v1/remote/catalog.go
index a0281b9fd..c51fe4a64 100644
--- a/pkg/v1/remote/catalog.go
+++ b/pkg/v1/remote/catalog.go
@@ -32,7 +32,7 @@ type Catalogs struct {
 
 // CatalogPage calls /_catalog, returning the list of repositories on the registry.
 func CatalogPage(target name.Registry, last string, n int, options ...Option) ([]string, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(target, options...)
 	if err != nil {
 		return nil, err
 	}
@@ -73,7 +73,7 @@ func CatalogPage(target name.Registry, last string, n int, options ...Option) ([
 
 // Catalog calls /_catalog, returning the list of repositories on the registry.
 func Catalog(ctx context.Context, target name.Registry, options ...Option) ([]string, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(target, options...)
 	if err != nil {
 		return nil, err
 	}
diff --git a/pkg/v1/remote/delete.go b/pkg/v1/remote/delete.go
index 36e1d0816..91da77737 100644
--- a/pkg/v1/remote/delete.go
+++ b/pkg/v1/remote/delete.go
@@ -20,7 +20,7 @@ import (
 
 // Delete removes the specified image reference from the remote registry.
 func Delete(ref name.Reference, options ...Option) error {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(ref.Context(), options...)
 	if err != nil {
 		return err
 	}
diff --git a/pkg/v1/remote/descriptor.go b/pkg/v1/remote/descriptor.go
index fafe910e9..26363e3bd 100644
--- a/pkg/v1/remote/descriptor.go
+++ b/pkg/v1/remote/descriptor.go
@@ -79,7 +79,7 @@ func Get(ref name.Reference, options ...Option) (*Descriptor, error) {
 // Note that the server response will not have a body, so any errors encountered
 // should be retried with Get to get more details.
 func Head(ref name.Reference, options ...Option) (*v1.Descriptor, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(ref.Context(), options...)
 	if err != nil {
 		return nil, err
 	}
@@ -90,7 +90,7 @@ func Head(ref name.Reference, options ...Option) (*v1.Descriptor, error) {
 // Handle options and fetch the manifest with the acceptable MediaTypes in the
 // Accept header.
 func get(ref name.Reference, acceptable []types.MediaType, options ...Option) (*Descriptor, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(ref.Context(), options...)
 	if err != nil {
 		return nil, err
 	}
diff --git a/pkg/v1/remote/layer.go b/pkg/v1/remote/layer.go
index 39c205950..e10081074 100644
--- a/pkg/v1/remote/layer.go
+++ b/pkg/v1/remote/layer.go
@@ -69,7 +69,7 @@ func (rl *remoteLayer) Exists() (bool, error) {
 // digest of the blob to be read and the repository portion is the repo where
 // that blob lives.
 func Layer(ref name.Digest, options ...Option) (v1.Layer, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(ref.Context(), options...)
 	if err != nil {
 		return nil, err
 	}
diff --git a/pkg/v1/remote/list.go b/pkg/v1/remote/list.go
index 910d2a94c..5b70de81f 100644
--- a/pkg/v1/remote/list.go
+++ b/pkg/v1/remote/list.go
@@ -36,7 +36,7 @@ func ListWithContext(ctx context.Context, repo name.Repository, options ...Optio
 // List calls /tags/list for the given repository, returning the list of tags
 // in the "tags" property.
 func List(repo name.Repository, options ...Option) ([]string, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(repo, options...)
 	if err != nil {
 		return nil, err
 	}
diff --git a/pkg/v1/remote/multi_write.go b/pkg/v1/remote/multi_write.go
index a6705de89..5077f57cb 100644
--- a/pkg/v1/remote/multi_write.go
+++ b/pkg/v1/remote/multi_write.go
@@ -23,7 +23,7 @@ import (
 // efficiently as possible, by deduping shared layer blobs while uploading them
 // in parallel.
 func MultiWrite(todo map[name.Reference]Taggable, options ...Option) (rerr error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(nil, options...)
 	if err != nil {
 		return err
 	}
diff --git a/pkg/v1/remote/options.go b/pkg/v1/remote/options.go
index 99a2bb2eb..554f969b3 100644
--- a/pkg/v1/remote/options.go
+++ b/pkg/v1/remote/options.go
@@ -16,6 +16,7 @@ package remote
 
 import (
 	"context"
+	"crypto/tls"
 	"errors"
 	"io"
 	"net"
@@ -26,6 +27,7 @@ import (
 	"github.com/google/go-containerregistry/internal/retry"
 	"github.com/google/go-containerregistry/pkg/authn"
 	"github.com/google/go-containerregistry/pkg/logs"
+	"github.com/google/go-containerregistry/pkg/name"
 	v1 "github.com/google/go-containerregistry/pkg/v1"
 	"github.com/google/go-containerregistry/pkg/v1/remote/transport"
 )
@@ -125,9 +127,37 @@ var DefaultTransport http.RoundTripper = &http.Transport{
 	MaxIdleConnsPerHost: 50,
 }
 
-func makeOptions(opts ...Option) (*options, error) {
+// create transport once to allow connection sharing.
+var defaultTransportInsecure = func() http.RoundTripper {
+	tr := DefaultTransport.(*http.Transport).Clone()
+	tr.TLSClientConfig = &tls.Config{InsecureSkipVerify: true}
+	return tr
+}()
+
+func targetIsInsecure(target resource) bool {
+	switch target := target.(type) {
+	case name.Registry:
+		return target.IsInsecure()
+
+	case name.Repository:
+		return target.Registry.IsInsecure()
+
+	case name.Digest:
+		return target.Registry.IsInsecure()
+	}
+	return false
+}
+
+func makeOptions(target resource, opts ...Option) (*options, error) {
+	var tr http.RoundTripper
+	if target != nil && targetIsInsecure(target) {
+		tr = defaultTransportInsecure
+	} else {
+		tr = DefaultTransport
+	}
+
 	o := &options{
-		transport:        DefaultTransport,
+		transport:        tr,
 		platform:         defaultPlatform,
 		context:          context.Background(),
 		jobs:             defaultJobs,
diff --git a/pkg/v1/remote/options_test.go b/pkg/v1/remote/options_test.go
new file mode 100644
index 000000000..8563805d1
--- /dev/null
+++ b/pkg/v1/remote/options_test.go
@@ -0,0 +1,95 @@
+package remote
+
+import (
+	"crypto/tls"
+	"fmt"
+	"net/http"
+	"net/http/httptest"
+	"net/url"
+	"testing"
+
+	"github.com/google/go-containerregistry/pkg/name"
+)
+
+func TestOptionsInsecure(t *testing.T) {
+	for _, targetType := range []string{
+		"registry",
+		"repository",
+		"digest",
+	} {
+		for _, mode := range []string{
+			"secure",
+			"insecure",
+		} {
+			t.Run(targetType+"_"+mode, func(t *testing.T) {
+				server := httptest.NewTLSServer(
+					http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+						w.WriteHeader(http.StatusOK)
+					}))
+				defer server.Close()
+
+				u, err := url.Parse(server.URL)
+				if err != nil {
+					t.Fatal(err)
+				}
+
+				options := []name.Option{}
+
+				if mode == "insecure" {
+					options = append(options, name.Insecure)
+				}
+
+				var target resource
+
+				switch targetType {
+				case "registry":
+					reg, err := name.NewRegistry("myregistry", options...)
+					if err != nil {
+						t.Fatal(err)
+					}
+					target = reg
+
+				case "repository":
+					ref, err := name.ParseReference("myregistry/name:tag", options...)
+					if err != nil {
+						t.Fatal(err)
+					}
+					target = ref.Context()
+
+				case "digest":
+					d, err := name.NewDigest("myregistry/name@sha256:e3b0c44298fc1c149afbf4c8996fb92427ae41e4649b934ca495991b7852b855", options...)
+					if err != nil {
+						t.Fatal(err)
+					}
+					target = d
+				}
+
+				opts, err := makeOptions(target, []Option{}...)
+				if err != nil {
+					t.Fatal(err)
+				}
+
+				c := &http.Client{Transport: opts.transport}
+
+				res, err := c.Get(u.String())
+
+				if mode == "secure" {
+					if ue, ok := err.(*url.Error); !ok {
+						t.Fatal(err)
+					} else if _, ok := ue.Err.(*tls.CertificateVerificationError); !ok {
+						t.Fatal(err)
+					}
+				} else {
+					if err != nil {
+						t.Fatal(err)
+					}
+					defer res.Body.Close()
+
+					if res.StatusCode != http.StatusOK {
+						t.Fatal(fmt.Printf("unexpected status code: %d", res.StatusCode))
+					}
+				}
+			})
+		}
+	}
+}
diff --git a/pkg/v1/remote/puller.go b/pkg/v1/remote/puller.go
index 7da8017ee..5f0a1185a 100644
--- a/pkg/v1/remote/puller.go
+++ b/pkg/v1/remote/puller.go
@@ -32,7 +32,7 @@ type Puller struct {
 }
 
 func NewPuller(options ...Option) (*Puller, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(nil, options...)
 	if err != nil {
 		return nil, err
 	}
diff --git a/pkg/v1/remote/pusher.go b/pkg/v1/remote/pusher.go
index 332d8ca0a..8b4619823 100644
--- a/pkg/v1/remote/pusher.go
+++ b/pkg/v1/remote/pusher.go
@@ -99,7 +99,7 @@ type Pusher struct {
 }
 
 func NewPusher(options ...Option) (*Pusher, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(nil, options...)
 	if err != nil {
 		return nil, err
 	}
diff --git a/pkg/v1/remote/referrers.go b/pkg/v1/remote/referrers.go
index 48e3835f9..828786c11 100644
--- a/pkg/v1/remote/referrers.go
+++ b/pkg/v1/remote/referrers.go
@@ -34,7 +34,7 @@ import (
 //
 // The subject manifest doesn't have to exist in the registry for there to be descriptors that refer to it.
 func Referrers(d name.Digest, options ...Option) (v1.ImageIndex, error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(d, options...)
 	if err != nil {
 		return nil, err
 	}
diff --git a/pkg/v1/remote/write.go b/pkg/v1/remote/write.go
index 1167cb793..502e66ce6 100644
--- a/pkg/v1/remote/write.go
+++ b/pkg/v1/remote/write.go
@@ -654,7 +654,7 @@ func WriteIndex(ref name.Reference, ii v1.ImageIndex, options ...Option) (rerr e
 
 // WriteLayer uploads the provided Layer to the specified repo.
 func WriteLayer(repo name.Repository, layer v1.Layer, options ...Option) (rerr error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(repo, options...)
 	if err != nil {
 		return err
 	}
@@ -691,7 +691,7 @@ func Tag(tag name.Tag, t Taggable, options ...Option) error {
 // should ensure that all blobs or manifests that are referenced by t exist
 // in the target registry.
 func Put(ref name.Reference, t Taggable, options ...Option) error {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(ref.Context(), options...)
 	if err != nil {
 		return err
 	}
@@ -700,7 +700,7 @@ func Put(ref name.Reference, t Taggable, options ...Option) error {
 
 // Push uploads the given Taggable to the specified reference.
 func Push(ref name.Reference, t Taggable, options ...Option) (rerr error) {
-	o, err := makeOptions(options...)
+	o, err := makeOptions(ref.Context(), options...)
 	if err != nil {
 		return err
 	}