diff --git a/src/common/security/v2token/context.go b/src/common/security/v2token/context.go
new file mode 100644
index 000000000..cc01e4113
--- /dev/null
+++ b/src/common/security/v2token/context.go
@@ -0,0 +1,115 @@
+package v2token
+
+import (
+	"context"
+	"strings"
+
+	registry_token "github.com/docker/distribution/registry/auth/token"
+	"github.com/goharbor/harbor/src/common/models"
+	"github.com/goharbor/harbor/src/common/rbac"
+	"github.com/goharbor/harbor/src/common/security"
+	"github.com/goharbor/harbor/src/lib/log"
+	"github.com/goharbor/harbor/src/pkg/permission/types"
+	"github.com/goharbor/harbor/src/pkg/project"
+)
+
+// tokenSecurityCtx is used for check permission of an internal signed token.
+// The intention for this guy is only for support CLI push/pull.  It should not be used in other scenario without careful review
+// Each request should have a different instance of tokenSecurityCtx
+type tokenSecurityCtx struct {
+	logger    *log.Logger
+	name      string
+	accessMap map[string]map[types.Action]struct{}
+	pm        project.Manager
+}
+
+func (t *tokenSecurityCtx) Name() string {
+	return "v2token"
+}
+
+func (t *tokenSecurityCtx) IsAuthenticated() bool {
+	return len(t.name) > 0
+}
+
+func (t *tokenSecurityCtx) GetUsername() string {
+	return t.name
+}
+
+func (t *tokenSecurityCtx) IsSysAdmin() bool {
+	return false
+}
+
+func (t *tokenSecurityCtx) IsSolutionUser() bool {
+	return false
+}
+
+func (t *tokenSecurityCtx) GetMyProjects() ([]*models.Project, error) {
+	return []*models.Project{}, nil
+}
+
+func (t *tokenSecurityCtx) GetProjectRoles(projectIDOrName interface{}) []int {
+	return []int{}
+}
+
+func (t *tokenSecurityCtx) Can(action types.Action, resource types.Resource) bool {
+	if !strings.HasSuffix(resource.String(), rbac.ResourceRepository.String()) {
+		return false
+	}
+	ns, ok := rbac.ProjectNamespaceParse(resource)
+	if !ok {
+		t.logger.Warningf("Failed to get namespace from resource: %s", resource)
+		return false
+	}
+	pid, ok := ns.Identity().(int64)
+	if !ok {
+		t.logger.Warningf("Failed to get project id from namespace: %s", ns)
+		return false
+	}
+	p, err := t.pm.Get(pid)
+	if err != nil {
+		t.logger.Warningf("Failed to get project, id: %d, error: %v", pid, err)
+		return false
+	}
+	actions, ok := t.accessMap[p.Name]
+	if !ok {
+		return false
+	}
+	_, hasAction := actions[action]
+	return hasAction
+}
+
+// New creates instance of token security context based on access list and name
+func New(ctx context.Context, name string, access []*registry_token.ResourceActions) security.Context {
+	logger := log.G(ctx)
+	m := make(map[string]map[types.Action]struct{})
+	for _, ac := range access {
+		if ac.Type != "repository" {
+			logger.Debugf("dropped unsupported type '%s' in token", ac.Type)
+			continue
+		}
+		l := strings.Split(ac.Name, "/")
+		if len(l) < 1 {
+			logger.Debugf("Unable to get project name from resource %s, drop the access", ac.Name)
+			continue
+		}
+		actionMap := make(map[types.Action]struct{})
+		for _, a := range ac.Actions {
+			if a == "pull" || a == "*" {
+				actionMap[rbac.ActionPull] = struct{}{}
+			}
+			if a == "push" || a == "*" {
+				actionMap[rbac.ActionPush] = struct{}{}
+			}
+			if a == "scanner-pull" {
+				actionMap[rbac.ActionScannerPull] = struct{}{}
+			}
+		}
+		m[l[0]] = actionMap
+	}
+	return &tokenSecurityCtx{
+		logger:    logger,
+		name:      name,
+		accessMap: m,
+		pm:        project.New(),
+	}
+}
diff --git a/src/common/security/v2token/context_test.go b/src/common/security/v2token/context_test.go
new file mode 100644
index 000000000..7b7b07e8f
--- /dev/null
+++ b/src/common/security/v2token/context_test.go
@@ -0,0 +1,97 @@
+package v2token
+
+import (
+	"testing"
+
+	"github.com/docker/distribution/registry/auth/token"
+	"github.com/goharbor/harbor/src/common/models"
+	"github.com/goharbor/harbor/src/common/rbac"
+	"github.com/goharbor/harbor/src/pkg/permission/types"
+	"github.com/goharbor/harbor/src/testing/pkg/project"
+	"github.com/stretchr/testify/assert"
+	"golang.org/x/net/context"
+)
+
+func TestAll(t *testing.T) {
+	mgr := &project.FakeManager{}
+	mgr.On("Get", int64(1)).Return(&models.Project{ProjectID: 1, Name: "library"}, nil)
+	mgr.On("Get", int64(2)).Return(&models.Project{ProjectID: 2, Name: "test"}, nil)
+	mgr.On("Get", int64(3)).Return(&models.Project{ProjectID: 3, Name: "development"}, nil)
+
+	access := []*token.ResourceActions{
+		{
+			Type: "repository",
+			Name: "library/ubuntu",
+			Actions: []string{
+				"pull",
+				"push",
+				"scanner-pull",
+			},
+		},
+		{
+			Type: "repository",
+			Name: "test/golang",
+			Actions: []string{
+				"pull",
+				"*",
+			},
+		},
+		{
+			Type: "cnab",
+			Name: "development/cnab",
+			Actions: []string{
+				"pull",
+				"push",
+			},
+		},
+	}
+	sc := New(context.Background(), "jack", access)
+	tsc := sc.(*tokenSecurityCtx)
+	tsc.pm = mgr
+
+	cases := []struct {
+		resource types.Resource
+		action   types.Action
+		expect   bool
+	}{
+		{
+			resource: rbac.NewProjectNamespace(1).Resource(rbac.ResourceRepository),
+			action:   rbac.ActionPush,
+			expect:   true,
+		},
+		{
+			resource: rbac.NewProjectNamespace(1).Resource(rbac.ResourceRepository),
+			action:   rbac.ActionScannerPull,
+			expect:   true,
+		},
+		{
+			resource: rbac.NewProjectNamespace(2).Resource(rbac.ResourceRepository),
+			action:   rbac.ActionPush,
+			expect:   true,
+		},
+		{
+			resource: rbac.NewProjectNamespace(2).Resource(rbac.ResourceRepository),
+			action:   rbac.ActionScannerPull,
+			expect:   false,
+		},
+		{
+			resource: rbac.NewProjectNamespace(3).Resource(rbac.ResourceRepository),
+			action:   rbac.ActionPush,
+			expect:   false,
+		},
+		{
+			resource: rbac.NewProjectNamespace(2).Resource(rbac.ResourceArtifact),
+			action:   rbac.ActionPush,
+			expect:   false,
+		},
+		{
+			resource: rbac.NewProjectNamespace(1).Resource(rbac.ResourceRepository),
+			action:   rbac.ActionCreate,
+			expect:   false,
+		},
+	}
+
+	for _, c := range cases {
+		assert.Equal(t, c.expect, sc.Can(c.action, c.resource))
+	}
+}
diff --git a/src/core/service/token/authutils.go b/src/core/service/token/authutils.go
index 3d9f204c1..0c15edbcb 100644
--- a/src/core/service/token/authutils.go
+++ b/src/core/service/token/authutils.go
@@ -33,7 +33,8 @@ import (
 )
 
 const (
-	issuer = "harbor-token-issuer"
+	// Issuer is the issuer of the internal token service in Harbor for registry
+	Issuer = "harbor-token-issuer"
 )
 
 var privateKey string
@@ -110,7 +111,7 @@ func MakeToken(username, service string, access []*token.ResourceActions) (*mode
 		return nil, err
 	}
 
-	tk, expiresIn, issuedAt, err := makeTokenCore(issuer, username, service, expiration, access, pk)
+	tk, expiresIn, issuedAt, err := makeTokenCore(Issuer, username, service, expiration, access, pk)
 	if err != nil {
 		return nil, err
 	}
diff --git a/src/server/middleware/contenttrust/contenttrust.go b/src/server/middleware/contenttrust/contenttrust.go
index b37ac216c..79b4b9a72 100644
--- a/src/server/middleware/contenttrust/contenttrust.go
+++ b/src/server/middleware/contenttrust/contenttrust.go
@@ -44,7 +44,7 @@ func Middleware() func(http.Handler) http.Handler {
 		securityCtx, ok := security.FromContext(ctx)
 		// only authenticated robot account with scanner pull access can bypass.
 		if ok && securityCtx.IsAuthenticated() &&
-			securityCtx.Name() == "robot" &&
+			(securityCtx.Name() == "robot" || securityCtx.Name() == "v2token") &&
 			securityCtx.Can(rbac.ActionScannerPull, rbac.NewProjectNamespace(pro.ProjectID).Resource(rbac.ResourceRepository)) {
 			// the artifact is pulling by the scanner, skip the checking
 			logger.Debugf("artifact %s@%s is pulling by the scanner, skip the checking", af.Repository, af.Digest)
diff --git a/src/server/middleware/security/idtoken.go b/src/server/middleware/security/idtoken.go
index 192657756..323065198 100644
--- a/src/server/middleware/security/idtoken.go
+++ b/src/server/middleware/security/idtoken.go
@@ -40,12 +40,7 @@ func (i *idToken) Generate(req *http.Request) security.Context {
 	if !strings.HasPrefix(req.URL.Path, "/api") {
 		return nil
 	}
-	h := req.Header.Get("Authorization")
-	token := strings.Split(h, "Bearer")
-	if len(token) < 2 {
-		return nil
-	}
-	claims, err := oidc.VerifyToken(req.Context(), strings.TrimSpace(token[1]))
+	claims, err := oidc.VerifyToken(req.Context(), bearerToken(req))
 	if err != nil {
 		log.Warningf("failed to verify token: %v", err)
 		return nil
diff --git a/src/server/middleware/security/security.go b/src/server/middleware/security/security.go
index c5bc8fc31..b9764f72a 100644
--- a/src/server/middleware/security/security.go
+++ b/src/server/middleware/security/security.go
@@ -27,6 +27,7 @@ var (
 	generators = []generator{
 		&secret{},
 		&oidcCli{},
+		&v2Token{},
 		&idToken{},
 		&authProxy{},
 		&robot{},
diff --git a/src/server/middleware/security/utils.go b/src/server/middleware/security/utils.go
new file mode 100644
index 000000000..1e68c5472
--- /dev/null
+++ b/src/server/middleware/security/utils.go
@@ -0,0 +1,18 @@
+package security
+
+import (
+	"net/http"
+	"strings"
+)
+
+func bearerToken(req *http.Request) string {
+	if req == nil {
+		return ""
+	}
+	h := req.Header.Get("Authorization")
+	token := strings.Split(h, "Bearer")
+	if len(token) < 2 {
+		return ""
+	}
+	return strings.TrimSpace(token[1])
+}
diff --git a/src/server/middleware/security/utils_test.go b/src/server/middleware/security/utils_test.go
new file mode 100644
index 000000000..4c686b8a7
--- /dev/null
+++ b/src/server/middleware/security/utils_test.go
@@ -0,0 +1,40 @@
+package security
+
+import (
+	"net/http"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestBearerToken(t *testing.T) {
+	req1, _ := http.NewRequest(http.MethodHead, "/api", nil)
+	req1.Header.Set("Authorization", "Bearer token")
+	req2, _ := http.NewRequest(http.MethodPut, "/api", nil)
+	req2.SetBasicAuth("", "")
+	req3, _ := http.NewRequest(http.MethodPut, "/api", nil)
+	cases := []struct {
+		request *http.Request
+		token   string
+	}{
+		{
+			request: req1,
+			token:   "token",
+		},
+		{
+			request: req2,
+			token:   "",
+		},
+		{
+			request: req3,
+			token:   "",
+		},
+		{
+			request: nil,
+			token:   "",
+		},
+	}
+	for _, c := range cases {
+		assert.Equal(t, c.token, bearerToken(c.request))
+	}
+}
diff --git a/src/server/middleware/security/v2_token.go b/src/server/middleware/security/v2_token.go
new file mode 100644
index 000000000..c525847a1
--- /dev/null
+++ b/src/server/middleware/security/v2_token.go
@@ -0,0 +1,64 @@
+package security
+
+import (
+	"fmt"
+	"net/http"
+	"strings"
+
+	"github.com/dgrijalva/jwt-go"
+	registry_token "github.com/docker/distribution/registry/auth/token"
+	"github.com/goharbor/harbor/src/common/security"
+	"github.com/goharbor/harbor/src/common/security/v2token"
+	svc_token "github.com/goharbor/harbor/src/core/service/token"
+	"github.com/goharbor/harbor/src/lib/log"
+	"github.com/goharbor/harbor/src/pkg/token"
+)
+
+type v2TokenClaims struct {
+	jwt.StandardClaims
+	Access []*registry_token.ResourceActions `json:"access"`
+}
+
+func (vtc *v2TokenClaims) Valid() error {
+	if err := vtc.StandardClaims.Valid(); err != nil {
+		return err
+	}
+	if !vtc.VerifyAudience(svc_token.Registry, true) {
+		return fmt.Errorf("invalid token audience: %s", vtc.Audience)
+	}
+	if !vtc.VerifyIssuer(svc_token.Issuer, true) {
+		return fmt.Errorf("invalid token issuer: %s", vtc.Issuer)
+	}
+	return nil
+}
+
+type v2Token struct{}
+
+func (vt *v2Token) Generate(req *http.Request) security.Context {
+	logger := log.G(req.Context())
+	if !strings.HasPrefix(req.URL.Path, "/v2") {
+		return nil
+	}
+	tokenStr := bearerToken(req)
+	if len(tokenStr) == 0 {
+		return nil
+	}
+
+	opt := token.DefaultTokenOptions()
+	cl := &v2TokenClaims{}
+	t, err := token.Parse(opt, tokenStr, cl)
+	if err != nil {
+		logger.Warningf("failed to decode bearer token: %v", err)
+		return nil
+	}
+	if err := t.Claims.Valid(); err != nil {
+		logger.Warningf("failed to decode bearer token: %v", err)
+		return nil
+	}
+	claims, ok := t.Claims.(*v2TokenClaims)
+	if !ok {
+		logger.Warningf("invalid token claims.")
+		return nil
+	}
+	return v2token.New(req.Context(), claims.Subject, claims.Access)
+}
diff --git a/src/server/middleware/security/v2_token_test.go b/src/server/middleware/security/v2_token_test.go
new file mode 100644
index 000000000..79d0183d4
--- /dev/null
+++ b/src/server/middleware/security/v2_token_test.go
@@ -0,0 +1,34 @@
+package security
+
+import (
+	"fmt"
+	"net/http"
+	"testing"
+
+	"github.com/goharbor/harbor/src/core/config"
+	"github.com/goharbor/harbor/src/core/service/token"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	registry_token "github.com/docker/distribution/registry/auth/token"
+)
+
+func TestGenerate(t *testing.T) {
+	config.Init()
+	vt := &v2Token{}
+	req1, _ := http.NewRequest(http.MethodHead, "/api/2.0/", nil)
+	assert.Nil(t, vt.Generate(req1))
+	req2, _ := http.NewRequest(http.MethodGet, "/v2/library/ubuntu/manifests/v1.0", nil)
+	req2.Header.Set("Authorization", "Bearer 123")
+	assert.Nil(t, vt.Generate(req2))
+	mt, err := token.MakeToken("admin", "none", []*registry_token.ResourceActions{})
+	require.Nil(t, err)
+	req3 := req2.Clone(req2.Context())
+	req3.Header.Set("Authorization", fmt.Sprintf("Bearer %s", mt.Token))
+	assert.Nil(t, vt.Generate(req3))
+	req4 := req3.Clone(req3.Context())
+	mt2, err2 := token.MakeToken("admin", token.Registry, []*registry_token.ResourceActions{})
+	require.Nil(t, err2)
+	req4.Header.Set("Authorization", fmt.Sprintf("Bearer %s", mt2.Token))
+	assert.NotNil(t, vt.Generate(req4))
+}
diff --git a/src/server/middleware/v2auth/access.go b/src/server/middleware/v2auth/access.go
new file mode 100644
index 000000000..8dff98a0d
--- /dev/null
+++ b/src/server/middleware/v2auth/access.go
@@ -0,0 +1,101 @@
+package v2auth
+
+import (
+	"context"
+	"fmt"
+	"net/http"
+
+	"github.com/goharbor/harbor/src/common/rbac"
+	"github.com/goharbor/harbor/src/lib"
+	"github.com/goharbor/harbor/src/lib/log"
+	"github.com/goharbor/harbor/src/server/middleware"
+)
+
+type target int
+
+const (
+	login target = iota
+	catalog
+	repository
+)
+
+func (t target) String() string {
+	return []string{"login", "catalog", "repository"}[t]
+}
+
+type access struct {
+	target target
+	name   string
+	action rbac.Action
+}
+
+func (a access) scopeStr(ctx context.Context) string {
+	logger := log.G(ctx)
+	if a.target != repository {
+		// Currently we do not support providing a token to list catalog
+		return ""
+	}
+	act := ""
+	if a.action == rbac.ActionPull {
+		act = "pull"
+	} else if a.action == rbac.ActionPush {
+		act = "pull,push"
+	} else if a.action == rbac.ActionDelete {
+		act = "delete"
+	} else {
+		logger.Warningf("Invalid action in access: %s, returning empty scope", a.action)
+		return ""
+	}
+	return fmt.Sprintf("repository:%s:%s", a.name, act)
+}
+
+func getAction(req *http.Request) rbac.Action {
+	actions := map[string]rbac.Action{
+		http.MethodPost:   rbac.ActionPush,
+		http.MethodPatch:  rbac.ActionPush,
+		http.MethodPut:    rbac.ActionPush,
+		http.MethodGet:    rbac.ActionPull,
+		http.MethodHead:   rbac.ActionPull,
+		http.MethodDelete: rbac.ActionDelete,
+	}
+	if action, ok := actions[req.Method]; ok {
+		return action
+	}
+	return ""
+}
+
+func accessList(req *http.Request) []access {
+	l := make([]access, 0, 4)
+	if req.URL.Path == "/v2/" {
+		l = append(l, access{
+			target: login,
+		})
+		return l
+	}
+	if len(middleware.V2CatalogURLRe.FindStringSubmatch(req.URL.Path)) == 1 {
+		l = append(l, access{
+			target: catalog,
+		})
+		return l
+	}
+	none := lib.ArtifactInfo{}
+	if a := lib.GetArtifactInfo(req.Context()); a != none {
+		action := getAction(req)
+		if action == "" {
+			return l
+		}
+		l = append(l, access{
+			target: repository,
+			name:   a.Repository,
+			action: action,
+		})
+		if req.Method == http.MethodPost && a.BlobMountRepository != "" { // need pull access for blob mount
+			l = append(l, access{
+				target: repository,
+				name:   a.BlobMountRepository,
+				action: rbac.ActionPull,
+			})
+		}
+	}
+	return l
+}
diff --git a/src/server/middleware/v2auth/access_test.go b/src/server/middleware/v2auth/access_test.go
new file mode 100644
index 000000000..c43f2e693
--- /dev/null
+++ b/src/server/middleware/v2auth/access_test.go
@@ -0,0 +1,147 @@
+package v2auth
+
+import (
+	"net/http"
+	"testing"
+
+	"github.com/goharbor/harbor/src/common/rbac"
+	"github.com/goharbor/harbor/src/lib"
+	"github.com/stretchr/testify/assert"
+	"golang.org/x/net/context"
+)
+
+func TestAccessList(t *testing.T) {
+	req1, _ := http.NewRequest(http.MethodGet, "https://registry.test/v2/", nil)
+	req2, _ := http.NewRequest(http.MethodGet, "https://registry.test/v2/_catalog", nil)
+	req3, _ := http.NewRequest(http.MethodPost, "https://registry.test/v2/library/ubuntu/blobs/uploads/?mount=sha256:08e4a417ff4e3913d8723a05cc34055db01c2fd165b588e049c5bad16ce6094f&from=base/ubuntu", nil)
+	ctx3 := lib.WithArtifactInfo(context.Background(), lib.ArtifactInfo{
+		Repository:          "library/ubuntu",
+		BlobMountRepository: "base/ubuntu",
+		BlobMountDigest:     "sha256:08e4a417ff4e3913d8723a05cc34055db01c2fd165b588e049c5bad16ce6094f",
+	})
+	req3 = req3.WithContext(ctx3)
+	req4, _ := http.NewRequest(http.MethodGet, "https://registry.test/v2/goharbor/registry/manifests/v1.0", nil)
+	req4d, _ := http.NewRequest(http.MethodDelete, "https://registry.test/v2/goharbor/registry/manifests/v1.0", nil)
+	ctx4 := lib.WithArtifactInfo(context.Background(), lib.ArtifactInfo{
+		Repository: "goharbor/registry",
+		Tag:        "v1.0",
+		Reference:  "v1.0",
+	})
+	req4 = req4.WithContext(ctx4)
+	req4d = req4d.WithContext(ctx4)
+	req5, _ := http.NewRequest(http.MethodGet, "https://registry.test/api/v2.0/users", nil)
+	cases := []struct {
+		input  *http.Request
+		expect []access
+	}{
+		{
+			input: req1,
+			expect: []access{{
+				target: login,
+			}},
+		},
+		{
+			input: req2,
+			expect: []access{{
+				target: catalog,
+			}},
+		},
+		{
+			input: req3,
+			expect: []access{{
+				target: repository,
+				name:   "library/ubuntu",
+				action: rbac.ActionPush,
+			},
+				{
+					target: repository,
+					name:   "base/ubuntu",
+					action: rbac.ActionPull,
+				}},
+		},
+		{
+			input: req4,
+			expect: []access{{
+				target: repository,
+				name:   "goharbor/registry",
+				action: rbac.ActionPull,
+			}},
+		},
+		{
+			input: req4d,
+			expect: []access{{
+				target: repository,
+				name:   "goharbor/registry",
+				action: rbac.ActionDelete,
+			}},
+		},
+		{
+			input:  req5,
+			expect: []access{},
+		},
+	}
+	for _, c := range cases {
+		assert.Equal(t, c.expect, accessList(c.input))
+	}
+}
+
+func TestScopeStr(t *testing.T) {
+	cases := []struct {
+		acs   access
+		scope string
+	}{
+		{
+			acs: access{
+				target: login,
+			},
+			scope: "",
+		},
+		{
+			acs: access{
+				target: catalog,
+			},
+			scope: "",
+		},
+		{
+			acs: access{
+				target: repository,
+				name:   "goharbor/registry",
+				action: rbac.ActionPull,
+			},
+			scope: "repository:goharbor/registry:pull",
+		},
+		{
+			acs: access{
+				target: repository,
+				name:   "library/golang",
+				action: rbac.ActionPush,
+			},
+			scope: "repository:library/golang:pull,push",
+		},
+		{
+			acs: access{
+				target: repository,
+				name:   "library/golang",
+				action: rbac.ActionDelete,
+			},
+			scope: "repository:library/golang:delete",
+		},
+		{
+			acs: access{
+				target: repository,
+				name:   "library/golang",
+				action: rbac.ActionList,
+			},
+			scope: "",
+		},
+		{
+			acs:   access{},
+			scope: "",
+		},
+	}
+
+	for _, c := range cases {
+		a := c.acs
+		assert.Equal(t, c.scope, a.scopeStr(context.Background()))
+	}
+}
diff --git a/src/server/middleware/v2auth/auth.go b/src/server/middleware/v2auth/auth.go
index b48f88797..826c29af0 100644
--- a/src/server/middleware/v2auth/auth.go
+++ b/src/server/middleware/v2auth/auth.go
@@ -17,59 +17,54 @@ package v2auth
 import (
 	"fmt"
 	"net/http"
+	"strings"
 	"sync"
 
 	"github.com/goharbor/harbor/src/common/rbac"
 	"github.com/goharbor/harbor/src/common/security"
 	"github.com/goharbor/harbor/src/core/config"
 	"github.com/goharbor/harbor/src/core/promgr"
-	"github.com/goharbor/harbor/src/lib"
+	"github.com/goharbor/harbor/src/core/service/token"
 	"github.com/goharbor/harbor/src/lib/errors"
 	"github.com/goharbor/harbor/src/lib/log"
 	serror "github.com/goharbor/harbor/src/server/error"
-	"github.com/goharbor/harbor/src/server/middleware"
 )
 
+const authHeader = "Authorization"
+
 type reqChecker struct {
 	pm promgr.ProjectManager
 }
 
-func (rc *reqChecker) check(req *http.Request) error {
+func (rc *reqChecker) check(req *http.Request) (string, error) {
 	securityCtx, ok := security.FromContext(req.Context())
 	if !ok {
-		return fmt.Errorf("the security context got from request is nil")
+		return "", fmt.Errorf("the security context got from request is nil")
 	}
-	none := lib.ArtifactInfo{}
-	if a := lib.GetArtifactInfo(req.Context()); a != none {
-		action := getAction(req)
-		if action == "" {
-			return nil
+	al := accessList(req)
+
+	for _, a := range al {
+		if a.target == login && !securityCtx.IsAuthenticated() {
+			return getChallenge(req, al), errors.New("unauthorized")
 		}
-		log.Debugf("action: %s, repository: %s", action, a.Repository)
-		pid, err := rc.projectID(a.ProjectName)
-		if err != nil {
-			return err
+		if a.target == catalog && !securityCtx.IsSysAdmin() {
+			return getChallenge(req, al), fmt.Errorf("unauthorized to list catalog")
 		}
-		resource := rbac.NewProjectNamespace(pid).Resource(rbac.ResourceRepository)
-		if !securityCtx.Can(action, resource) {
-			return fmt.Errorf("unauthorized to access repository: %s, action: %s", a.Repository, action)
-		}
-		if req.Method == http.MethodPost && a.BlobMountProjectName != "" { // check permission for the source of blob mount
-			pid, err := rc.projectID(a.BlobMountProjectName)
+		if a.target == repository && req.Header.Get(authHeader) == "" && req.Method == http.MethodHead { // make sure 401 is returned for CLI HEAD, see #11271
+			return getChallenge(req, al), fmt.Errorf("authorize header needed to send HEAD to repository")
+		} else if a.target == repository {
+			pn := strings.Split(a.name, "/")[0]
+			pid, err := rc.projectID(pn)
 			if err != nil {
-				return err
+				return "", err
 			}
 			resource := rbac.NewProjectNamespace(pid).Resource(rbac.ResourceRepository)
-			if !securityCtx.Can(rbac.ActionPull, resource) {
-				return fmt.Errorf("unauthorized to access repository from which to mount blob: %s, action: %s", a.BlobMountRepository, rbac.ActionPull)
+			if !securityCtx.Can(a.action, resource) {
+				return getChallenge(req, al), fmt.Errorf("unauthorized to access repository: %s, action: %s", a.name, a.action)
 			}
 		}
-	} else if len(middleware.V2CatalogURLRe.FindStringSubmatch(req.URL.Path)) == 1 && !securityCtx.IsSysAdmin() {
-		return fmt.Errorf("unauthorized to list catalog")
-	} else if req.URL.Path == "/v2/" && !securityCtx.IsAuthenticated() {
-		return errors.New("unauthorized")
 	}
-	return nil
+	return "", nil
 }
 
 func (rc *reqChecker) projectID(name string) (int64, error) {
@@ -83,25 +78,31 @@ func (rc *reqChecker) projectID(name string) (int64, error) {
 	return p.ProjectID, nil
 }
 
-func getAction(req *http.Request) rbac.Action {
-	pushActions := map[string]struct{}{
-		http.MethodPost:   {},
-		http.MethodDelete: {},
-		http.MethodPatch:  {},
-		http.MethodPut:    {},
+func getChallenge(req *http.Request, accessList []access) string {
+	logger := log.G(req.Context())
+	auth := req.Header.Get(authHeader)
+	if len(auth) > 0 {
+		// Return basic auth challenge by default
+		return `Basic realm="harbor"`
 	}
-	pullActions := map[string]struct{}{
-		http.MethodGet:  {},
-		http.MethodHead: {},
+	// No auth header, treat it as CLI and redirect to token service
+	ep, err := config.ExtEndpoint()
+	if err != nil {
+		logger.Errorf("failed to get the external endpoint, error: %v", err)
 	}
-	if _, ok := pushActions[req.Method]; ok {
-		return rbac.ActionPush
+	tokenSvc := fmt.Sprintf("%s/service/token", strings.TrimSuffix(ep, "/"))
+	scope := ""
+	for _, a := range accessList {
+		if len(scope) > 0 {
+			scope += " "
+		}
+		scope += a.scopeStr(req.Context())
 	}
-	if _, ok := pullActions[req.Method]; ok {
-		return rbac.ActionPull
+	challenge := fmt.Sprintf(`Bearer realm="%s",service="%s"`, tokenSvc, token.Registry)
+	if len(scope) > 0 {
+		challenge = fmt.Sprintf(`%s,scope="%s"`, challenge, scope)
 	}
-	return ""
-
+	return challenge
 }
 
 var (
@@ -120,10 +121,10 @@ func Middleware() func(http.Handler) http.Handler {
 	})
 	return func(next http.Handler) http.Handler {
 		return http.HandlerFunc(func(rw http.ResponseWriter, req *http.Request) {
-			if err := checker.check(req); err != nil {
+			if challenge, err := checker.check(req); err != nil {
 				// the header is needed for "docker manifest" commands: https://github.com/docker/cli/issues/989
 				rw.Header().Set("Docker-Distribution-Api-Version", "registry/2.0")
-				rw.Header().Set("Www-Authenticate", `Basic realm="harbor"`)
+				rw.Header().Set("Www-Authenticate", challenge)
 				serror.SendError(rw, errors.UnauthorizedError(err).WithMessage(err.Error()))
 				return
 			}
diff --git a/src/server/middleware/v2auth/auth_test.go b/src/server/middleware/v2auth/auth_test.go
index cf5c12cd1..77b577d8f 100644
--- a/src/server/middleware/v2auth/auth_test.go
+++ b/src/server/middleware/v2auth/auth_test.go
@@ -23,9 +23,11 @@ import (
 	"strings"
 	"testing"
 
+	"github.com/goharbor/harbor/src/common"
 	"github.com/goharbor/harbor/src/common/models"
 	"github.com/goharbor/harbor/src/common/rbac"
 	"github.com/goharbor/harbor/src/common/security"
+	"github.com/goharbor/harbor/src/core/config"
 	"github.com/goharbor/harbor/src/core/promgr/metamgr"
 	"github.com/goharbor/harbor/src/lib"
 	"github.com/goharbor/harbor/src/pkg/permission/types"
@@ -84,6 +86,10 @@ func TestMain(m *testing.M) {
 	checker = reqChecker{
 		pm: mockPM{},
 	}
+	conf := map[string]interface{}{
+		common.ExtEndpoint: "https://harbor.test",
+	}
+	config.InitWithSettings(conf)
 	if rc := m.Run(); rc != 0 {
 		os.Exit(rc)
 	}
@@ -158,6 +164,7 @@ func TestMiddleware(t *testing.T) {
 	ctx5 := lib.WithArtifactInfo(baseCtx, ar5)
 	req1a, _ := http.NewRequest(http.MethodGet, "/v2/project_1/hello-world/manifest/v1", nil)
 	req1b, _ := http.NewRequest(http.MethodDelete, "/v2/project_1/hello-world/manifest/v1", nil)
+	req1c, _ := http.NewRequest(http.MethodHead, "/v2/project_1/hello-world/manifest/v1", nil)
 	req2, _ := http.NewRequest(http.MethodGet, "/v2/library/ubuntu/manifest/14.04", nil)
 	req3, _ := http.NewRequest(http.MethodGet, "/v2/_catalog", nil)
 	req4, _ := http.NewRequest(http.MethodPost, "/v2/project_1/ubuntu/blobs/uploads/mount=?mount=sha256:08e4a417ff4e3913d8723a05cc34055db01c2fd165b588e049c5bad16ce6094f&from=project_2/ubuntu", nil)
@@ -174,7 +181,11 @@ func TestMiddleware(t *testing.T) {
 		},
 		{
 			input:  req1b.WithContext(ctx1),
-			status: http.StatusOK,
+			status: http.StatusUnauthorized,
+		},
+		{
+			input:  req1c.WithContext(ctx1),
+			status: http.StatusUnauthorized,
 		},
 		{
 			input:  req2.WithContext(ctx2),
@@ -204,3 +215,68 @@ func TestMiddleware(t *testing.T) {
 		assert.Equal(t, c.status, rec.Result().StatusCode)
 	}
 }
+
+func TestGetChallenge(t *testing.T) {
+	req1, _ := http.NewRequest(http.MethodGet, "https://registry.test/v2/", nil)
+	req1x := req1.Clone(req1.Context())
+	req1x.SetBasicAuth("u", "p")
+	req2, _ := http.NewRequest(http.MethodGet, "https://registry.test/v2/_catalog", nil)
+	req2x := req2.Clone(req2.Context())
+	req2x.Header.Set("Authorization", "Bearer xx")
+	req3, _ := http.NewRequest(http.MethodPost, "https://registry.test/v2/project_1/ubuntu/blobs/uploads/mount=?mount=sha256:08e4a417ff4e3913d8723a05cc34055db01c2fd165b588e049c5bad16ce6094f&from=project_2/ubuntu", nil)
+	req3 = req3.WithContext(lib.WithArtifactInfo(context.Background(), lib.ArtifactInfo{
+		Repository:           "project_1/ubuntu",
+		Reference:            "14.04",
+		ProjectName:          "project_1",
+		BlobMountRepository:  "project_2/ubuntu",
+		BlobMountProjectName: "project_2",
+		BlobMountDigest:      "sha256:08e4a417ff4e3913d8723a05cc34055db01c2fd165b588e049c5bad16ce6094f",
+	}))
+	req3x := req3.Clone(req3.Context())
+	req3x.SetBasicAuth("", "")
+	req4, _ := http.NewRequest(http.MethodGet, "https://registry.test/v2/project_1/hello-world/manifests/v1", nil)
+	req4 = req4.WithContext(lib.WithArtifactInfo(context.Background(), lib.ArtifactInfo{
+		Repository:  "project_1/hello-world",
+		Reference:   "v1",
+		ProjectName: "project_1",
+	}))
+
+	cases := []struct {
+		request   *http.Request
+		challenge string
+	}{
+		{
+			request:   req1,
+			challenge: `Bearer realm="https://harbor.test/service/token",service="harbor-registry"`,
+		},
+		{
+			request:   req1x,
+			challenge: `Basic realm="harbor"`,
+		},
+		{
+			request:   req2,
+			challenge: `Bearer realm="https://harbor.test/service/token",service="harbor-registry"`,
+		},
+		{
+			request:   req2x,
+			challenge: `Basic realm="harbor"`,
+		},
+		{
+			request:   req3,
+			challenge: `Bearer realm="https://harbor.test/service/token",service="harbor-registry",scope="repository:project_1/ubuntu:pull,push repository:project_2/ubuntu:pull"`,
+		},
+		{
+			request:   req3x,
+			challenge: `Basic realm="harbor"`,
+		},
+		{
+			request:   req4,
+			challenge: `Bearer realm="https://harbor.test/service/token",service="harbor-registry",scope="repository:project_1/hello-world:pull"`,
+		},
+	}
+	for _, c := range cases {
+		acs := accessList(c.request)
+		assert.Equal(t, c.challenge, getChallenge(c.request, acs))
+	}
+
+}
diff --git a/src/server/middleware/vulnerable/vulnerable.go b/src/server/middleware/vulnerable/vulnerable.go
index dce45bfe2..5efbb080e 100644
--- a/src/server/middleware/vulnerable/vulnerable.go
+++ b/src/server/middleware/vulnerable/vulnerable.go
@@ -73,7 +73,7 @@ func Middleware() func(http.Handler) http.Handler {
 
 		securityCtx, ok := security.FromContext(ctx)
 		if ok &&
-			securityCtx.Name() == "robot" &&
+			(securityCtx.Name() == "robot" || securityCtx.Name() == "v2token") &&
 			securityCtx.Can(rbac.ActionScannerPull, rbac.NewProjectNamespace(proj.ProjectID).Resource(rbac.ResourceRepository)) {
 			// the artifact is pulling by the scanner, skip the checking
 			logger.Debugf("artifact %s@%s is pulling by the scanner, skip the checking", art.RepositoryName, art.Digest)
diff --git a/tests/apitests/python/test_robot_account.py b/tests/apitests/python/test_robot_account.py
index 83040d4d9..5a6a7c7b6 100644
--- a/tests/apitests/python/test_robot_account.py
+++ b/tests/apitests/python/test_robot_account.py
@@ -120,10 +120,10 @@ class TestProjects(unittest.TestCase):
         self.project.disable_project_robot_account(TestProjects.project_ra_id_a, robot_id, True, **TestProjects.USER_RA_CLIENT)
 
         print "#13. Pull image(ImagePA) from project(PA) by robot account(RA), it must be not successful;"
-        pull_harbor_image(harbor_server, robot_account.name, robot_account.token, TestProjects.repo_name_in_project_a, tag_a, expected_login_error_message = "401 Unauthorized")
+        pull_harbor_image(harbor_server, robot_account.name, robot_account.token, TestProjects.repo_name_in_project_a, tag_a, expected_login_error_message = "unauthorized: authentication required")
 
         print "#14. Push image(ImageRA) to project(PA) by robot account(RA), it must be not successful;"
-        push_image_to_project(TestProjects.project_ra_name_a, harbor_server, robot_account.name, robot_account.token, image_robot_account, tag, expected_login_error_message = "401 Unauthorized")
+        push_image_to_project(TestProjects.project_ra_name_a, harbor_server, robot_account.name, robot_account.token, image_robot_account, tag, expected_login_error_message = "unauthorized: authentication required")
 
         print "#15. Delete robot account(RA), it must be not successful."
         self.project.delete_project_robot_account(TestProjects.project_ra_id_a, robot_id, **TestProjects.USER_RA_CLIENT)