diff --git a/authorize/evaluator/evaluator.go b/authorize/evaluator/evaluator.go
index 3bee9423e..07726ce20 100644
--- a/authorize/evaluator/evaluator.go
+++ b/authorize/evaluator/evaluator.go
@@ -44,6 +44,7 @@ type Evaluator struct {
 	clientCA         string
 	authenticateHost string
 	jwk              interface{}
+	kid              string
 }
 
 // New creates a new Evaluator.
@@ -77,11 +78,16 @@ func New(options *config.Options) (*Evaluator, error) {
 		if err != nil {
 			return nil, fmt.Errorf("authorize: failed to decode certificate cert %v: %w", decodedCert, err)
 		}
-		keyBytes, err := cryptutil.DecodePrivateKey((decodedCert))
+		key, err := cryptutil.DecodePrivateKey(decodedCert)
 		if err != nil {
 			return nil, fmt.Errorf("authorize: couldn't generate signing key: %w", err)
 		}
-		e.jwk = keyBytes
+		e.jwk = key
+		jwk, err := cryptutil.PublicJWKFromBytes(decodedCert, jose.ES256)
+		if err != nil {
+			return nil, fmt.Errorf("authorize: failed to convert jwk: %w", err)
+		}
+		e.kid = jwk.KeyID
 	}
 
 	authzPolicy, err := readPolicy("/authz.rego")
@@ -163,10 +169,11 @@ func (e *Evaluator) ParseSignedJWT(signature string) ([]byte, error) {
 
 // SignedJWT returns the signature of given request.
 func (e *Evaluator) SignedJWT(req *Request) (string, error) {
+	signerOpt := &jose.SignerOptions{}
 	signer, err := jose.NewSigner(jose.SigningKey{
 		Algorithm: jose.ES256,
 		Key:       e.jwk,
-	}, nil)
+	}, signerOpt.WithHeader("kid", e.kid))
 	if err != nil {
 		return "", err
 	}
diff --git a/authorize/evaluator/evaluator_test.go b/authorize/evaluator/evaluator_test.go
index 69cf26a1e..6fc7c9887 100644
--- a/authorize/evaluator/evaluator_test.go
+++ b/authorize/evaluator/evaluator_test.go
@@ -12,6 +12,7 @@ import (
 	"github.com/google/uuid"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
+	"gopkg.in/square/go-jose.v2/jwt"
 
 	"github.com/pomerium/pomerium/config"
 	"github.com/pomerium/pomerium/pkg/grpc/databroker"
@@ -88,6 +89,28 @@ func TestEvaluator_SignedJWT(t *testing.T) {
 	assert.NotEmpty(t, payload)
 }
 
+func TestEvaluator_JWTWithKID(t *testing.T) {
+	opt := config.NewDefaultOptions()
+	opt.AuthenticateURL = mustParseURL("https://authenticate.example.com")
+	opt.SigningKey = "LS0tLS1CRUdJTiBFQyBQUklWQVRFIEtFWS0tLS0tCk1IY0NBUUVFSUpCMFZkbko1VjEvbVlpYUlIWHhnd2Q0Yzd5YWRTeXMxb3Y0bzA1b0F3ekdvQW9HQ0NxR1NNNDkKQXdFSG9VUURRZ0FFVUc1eENQMEpUVDFINklvbDhqS3VUSVBWTE0wNENnVzlQbEV5cE5SbVdsb29LRVhSOUhUMwpPYnp6aktZaWN6YjArMUt3VjJmTVRFMTh1dy82MXJVQ0JBPT0KLS0tLS1FTkQgRUMgUFJJVkFURSBLRVktLS0tLQo="
+	e, err := New(opt)
+	require.NoError(t, err)
+	req := &Request{
+		HTTP: RequestHTTP{
+			Method: http.MethodGet,
+			URL:    "https://example.com",
+		},
+	}
+	signedJWT, err := e.SignedJWT(req)
+	require.NoError(t, err)
+	assert.NotEmpty(t, signedJWT)
+
+	tok, err := jwt.ParseSigned(signedJWT)
+	require.NoError(t, err)
+	require.Len(t, tok.Headers, 1)
+	assert.Equal(t, "5b419ade1895fec2d2def6cd33b1b9a018df60db231dc5ecb85cbed6d942813c", tok.Headers[0].KeyID)
+}
+
 func mustParseURL(str string) *url.URL {
 	u, err := url.Parse(str)
 	if err != nil {
diff --git a/docs/docs/CHANGELOG.md b/docs/docs/CHANGELOG.md
index 1befa59ec..0193f2fa9 100644
--- a/docs/docs/CHANGELOG.md
+++ b/docs/docs/CHANGELOG.md
@@ -8,6 +8,7 @@
 - config: change default log level to INFO  @cuonglm [GH-902]
 - config: add pass_identity_headers @cuonglm [GH-903]
 - authenticate: allow hot reloaded admin users config @cuonglm [GH-984]
+- authorize: include "kid" in JWT headers @cuonglm [GH-1046]
 
 ### Changes