diff --git a/pkg/v1/remote/transport/bearer.go b/pkg/v1/remote/transport/bearer.go
index bff2ece01..9c404df52 100644
--- a/pkg/v1/remote/transport/bearer.go
+++ b/pkg/v1/remote/transport/bearer.go
@@ -92,29 +92,25 @@ func (bt *bearerTransport) RoundTrip(in *http.Request) (*http.Response, error) {
 // The basic token exchange is attempted first, falling back to the oauth flow.
 // If the IdentityToken is set, this indicates that we should start with the oauth flow.
 func (bt *bearerTransport) refresh() error {
-	first, second := bt.refreshBasic, bt.refreshOauth
-
 	auth, err := bt.basic.Authorization()
 	if err != nil {
 		return err
 	}
+	var content []byte
 	if auth.IdentityToken != "" {
 		// If the secret being stored is an identity token,
 		// the Username should be set to <token>, which indicates
 		// we are using an oauth flow.
-		first, second = bt.refreshOauth, bt.refreshBasic
-	}
-
-	content, err := func() ([]byte, error) {
-		b, err := first()
-		if err != nil {
-			b, err = second()
-			if err != nil {
-				return nil, err
-			}
+		content, err = bt.refreshOauth()
+		if terr, ok := err.(*Error); ok && terr.StatusCode == http.StatusNotFound {
+			// Note: Not all token servers implement oauth2.
+			// If the request to the endpoint returns 404 using the HTTP POST method,
+			// refer to Token Documentation for using the HTTP GET method supported by all token servers.
+			content, err = bt.refreshBasic()
 		}
-		return b, err
-	}()
+	} else {
+		content, err = bt.refreshBasic()
+	}
 	if err != nil {
 		return err
 	}
@@ -209,6 +205,7 @@ func (bt *bearerTransport) refreshOauth() ([]byte, error) {
 		v.Set("grant_type", "refresh_token")
 		v.Set("refresh_token", auth.IdentityToken)
 	} else if auth.Username != "" && auth.Password != "" {
+		// TODO(#629): This is unreachable.
 		v.Set("grant_type", "password")
 		v.Set("username", auth.Username)
 		v.Set("password", auth.Password)
diff --git a/pkg/v1/remote/transport/bearer_test.go b/pkg/v1/remote/transport/bearer_test.go
index 01afa1e34..246e90d52 100644
--- a/pkg/v1/remote/transport/bearer_test.go
+++ b/pkg/v1/remote/transport/bearer_test.go
@@ -16,7 +16,6 @@ package transport
 
 import (
 	"fmt"
-	"io/ioutil"
 	"net/http"
 	"net/http/httptest"
 	"net/url"
@@ -198,25 +197,25 @@ func TestBearerTransportTokenRefresh(t *testing.T) {
 
 func TestBearerTransportOauthRefresh(t *testing.T) {
 	initialToken := "foo"
-	refreshedToken := "bar"
+	accessToken := "bar"
+	refreshToken := "baz"
 
 	server := httptest.NewServer(
 		http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 			if r.Method == http.MethodPost {
-				b, err := ioutil.ReadAll(r.Body)
-				if err != nil {
+				if err := r.ParseForm(); err != nil {
 					t.Fatal(err)
 				}
-				if len(b) == 0 {
-					t.Errorf("got empty request body for POST")
+				if it := r.FormValue("refresh_token"); it != initialToken {
+					t.Errorf("want %s got %s", initialToken, it)
 				}
 				w.WriteHeader(http.StatusOK)
-				w.Write([]byte(fmt.Sprintf(`{"access_token": %q}`, refreshedToken)))
+				w.Write([]byte(fmt.Sprintf(`{"access_token": %q, "refresh_token": %q}`, accessToken, refreshToken)))
 				return
 			}
 
 			hdr := r.Header.Get("Authorization")
-			if hdr == "Bearer "+refreshedToken {
+			if hdr == "Bearer "+accessToken {
 				w.WriteHeader(http.StatusOK)
 				return
 			}
@@ -234,11 +233,11 @@ func TestBearerTransportOauthRefresh(t *testing.T) {
 		t.Errorf("Unexpected error during NewRegistry: %v", err)
 	}
 
-	bearer := &authn.Bearer{Token: initialToken}
+	bearer := &authn.Bearer{}
 	transport := &bearerTransport{
 		inner:    http.DefaultTransport,
 		bearer:   bearer,
-		basic:    authn.FromConfig(authn.AuthConfig{IdentityToken: "baz"}),
+		basic:    authn.FromConfig(authn.AuthConfig{IdentityToken: initialToken}),
 		registry: registry,
 		realm:    server.URL,
 		scheme:   "http",
@@ -254,32 +253,34 @@ func TestBearerTransportOauthRefresh(t *testing.T) {
 	if res.StatusCode != http.StatusOK {
 		t.Errorf("client.Get final StatusCode got %v, want: %v", res.StatusCode, http.StatusOK)
 	}
-	if transport.bearer.Token != refreshedToken {
-		t.Errorf("Expected Bearer token to be refreshed, got %v, want %v", bearer.Token, refreshedToken)
+	if transport.bearer.Token != accessToken {
+		t.Errorf("Expected Bearer token to be refreshed, got %v, want %v", bearer.Token, accessToken)
+	}
+	basicAuthConfig, err := transport.basic.Authorization()
+	if err != nil {
+		t.Fatal(err)
+	}
+	if got, want := basicAuthConfig.IdentityToken, refreshToken; got != want {
+		t.Errorf("Expected Basic IdentityToken to be refreshed, got %v, want %v", got, want)
 	}
 }
 
-func TestBearerTransportOauthRefreshToken(t *testing.T) {
-	initialToken := "initial_token"
+func TestBearerTransportOauth404Fallback(t *testing.T) {
+	basicAuth := "basic_auth"
+	identityToken := "identity_token"
 	accessToken := "access_token"
-	refreshToken := "refresh_token"
 
 	server := httptest.NewServer(
 		http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 			if r.Method == http.MethodPost {
-				b, err := ioutil.ReadAll(r.Body)
-				if err != nil {
-					t.Fatal(err)
-				}
-				if len(b) == 0 {
-					t.Errorf("got empty request body for POST")
-				}
-				w.WriteHeader(http.StatusOK)
-				w.Write([]byte(fmt.Sprintf(`{"access_token": %q, "refresh_token": %q}`, accessToken, refreshToken)))
-				return
+				w.WriteHeader(http.StatusNotFound)
 			}
 
 			hdr := r.Header.Get("Authorization")
+			if hdr == "Basic "+basicAuth {
+				w.WriteHeader(http.StatusOK)
+				w.Write([]byte(fmt.Sprintf(`{"access_token": %q}`, accessToken)))
+			}
 			if hdr == "Bearer "+accessToken {
 				w.WriteHeader(http.StatusOK)
 				return
@@ -298,11 +299,14 @@ func TestBearerTransportOauthRefreshToken(t *testing.T) {
 		t.Errorf("Unexpected error during NewRegistry: %v", err)
 	}
 
-	bearer := &authn.Bearer{Token: initialToken}
+	bearer := &authn.Bearer{}
 	transport := &bearerTransport{
-		inner:    http.DefaultTransport,
-		basic:    authn.FromConfig(authn.AuthConfig{Username: "user", Password: "pass"}),
-		bearer:   bearer,
+		inner:  http.DefaultTransport,
+		bearer: bearer,
+		basic: authn.FromConfig(authn.AuthConfig{
+			IdentityToken: identityToken,
+			Auth:          basicAuth,
+		}),
 		registry: registry,
 		realm:    server.URL,
 		scheme:   "http",