diff --git a/proxy/handlers.go b/proxy/handlers.go
index bf55a8f90..c05c94618 100644
--- a/proxy/handlers.go
+++ b/proxy/handlers.go
@@ -3,6 +3,7 @@ package proxy
 import (
 	"encoding/base64"
 	"fmt"
+	"io"
 	"net/http"
 	"net/url"
 
@@ -22,6 +23,7 @@ func (p *Proxy) registerDashboardHandlers(r *mux.Router) *mux.Router {
 	// dashboard endpoints can be used by user's to view, or modify their session
 	h.Path("/").HandlerFunc(p.UserDashboard).Methods(http.MethodGet)
 	h.Path("/sign_out").HandlerFunc(p.SignOut).Methods(http.MethodGet, http.MethodPost)
+	h.Path("/jwt").Handler(httputil.HandlerFunc(p.jwtAssertion)).Methods(http.MethodGet)
 
 	// Authenticate service callback handlers and middleware
 	// callback used to set route-scoped session and redirect back to destination
@@ -161,3 +163,25 @@ func (p *Proxy) ProgrammaticLogin(w http.ResponseWriter, r *http.Request) error
 	w.Write([]byte(response))
 	return nil
 }
+
+func (p *Proxy) jwtAssertion(w http.ResponseWriter, r *http.Request) error {
+	res, err := p.authorizeCheck(r)
+	if err != nil {
+		return httputil.NewError(http.StatusInternalServerError, err)
+	}
+
+	headers := append(res.GetOkResponse().GetHeaders(), res.GetDeniedResponse().GetHeaders()...)
+	for _, h := range headers {
+		if h.GetHeader().GetKey() == httputil.HeaderPomeriumJWTAssertion {
+			w.Header().Set("Content-Type", "application/jwt")
+			w.WriteHeader(http.StatusOK)
+			_, _ = io.WriteString(w, h.GetHeader().GetValue())
+			return nil
+		}
+	}
+
+	w.Header().Set("Content-Type", "text/plain")
+	w.WriteHeader(http.StatusNotFound)
+	_, _ = io.WriteString(w, "jwt not found")
+	return nil
+}
diff --git a/proxy/handlers_test.go b/proxy/handlers_test.go
index 5cf9ae264..5231d7156 100644
--- a/proxy/handlers_test.go
+++ b/proxy/handlers_test.go
@@ -11,6 +11,10 @@ import (
 	"testing"
 	"time"
 
+	envoy_api_v2_core "github.com/envoyproxy/go-control-plane/envoy/api/v2/core"
+	envoy_service_auth_v2 "github.com/envoyproxy/go-control-plane/envoy/service/auth/v2"
+	"github.com/stretchr/testify/assert"
+
 	mstore "github.com/pomerium/pomerium/internal/sessions/mock"
 	"github.com/pomerium/pomerium/pkg/cryptutil"
 
@@ -64,6 +68,39 @@ func TestProxy_Signout(t *testing.T) {
 	}
 }
 
+func TestProxy_jwt(t *testing.T) {
+	authzClient := &mockCheckClient{
+		response: &envoy_service_auth_v2.CheckResponse{
+			HttpResponse: &envoy_service_auth_v2.CheckResponse_OkResponse{
+				OkResponse: &envoy_service_auth_v2.OkHttpResponse{
+					Headers: []*envoy_api_v2_core.HeaderValueOption{
+						{Header: &envoy_api_v2_core.HeaderValue{
+							Key:   httputil.HeaderPomeriumJWTAssertion,
+							Value: "MOCK_JWT",
+						}},
+					},
+				},
+			},
+		},
+	}
+
+	req, _ := http.NewRequest("GET", "https://www.example.com/.pomerium/jwt", nil)
+	w := httptest.NewRecorder()
+
+	proxy := &Proxy{
+		state: newAtomicProxyState(&proxyState{
+			authzClient: authzClient,
+		}),
+	}
+	err := proxy.jwtAssertion(w, req)
+	if !assert.NoError(t, err) {
+		return
+	}
+
+	assert.Equal(t, "application/jwt", w.Header().Get("Content-Type"))
+	assert.Equal(t, w.Body.String(), "MOCK_JWT")
+}
+
 func TestProxy_UserDashboard(t *testing.T) {
 	opts := testOptions(t)
 	err := ValidateOptions(opts)
diff --git a/proxy/middleware.go b/proxy/middleware.go
index fed252a5e..28328422c 100644
--- a/proxy/middleware.go
+++ b/proxy/middleware.go
@@ -22,6 +22,28 @@ type authorizeResponse struct {
 }
 
 func (p *Proxy) isAuthorized(w http.ResponseWriter, r *http.Request) (*authorizeResponse, error) {
+	res, err := p.authorizeCheck(r)
+	if err != nil {
+		return nil, httputil.NewError(http.StatusInternalServerError, err)
+	}
+
+	ar := &authorizeResponse{}
+	switch res.HttpResponse.(type) {
+	case *envoy_service_auth_v2.CheckResponse_OkResponse:
+		for _, hdr := range res.GetOkResponse().GetHeaders() {
+			w.Header().Set(hdr.GetHeader().GetKey(), hdr.GetHeader().GetValue())
+		}
+		ar.authorized = true
+		ar.statusCode = res.GetStatus().Code
+	case *envoy_service_auth_v2.CheckResponse_DeniedResponse:
+		ar.statusCode = int32(res.GetDeniedResponse().GetStatus().Code)
+	default:
+		ar.statusCode = http.StatusInternalServerError
+	}
+	return ar, nil
+}
+
+func (p *Proxy) authorizeCheck(r *http.Request) (*envoy_service_auth_v2.CheckResponse, error) {
 	state := p.state.Load()
 
 	tm, err := ptypes.TimestampProto(time.Now())
@@ -45,7 +67,7 @@ func (p *Proxy) isAuthorized(w http.ResponseWriter, r *http.Request) (*authorize
 		httpAttrs.Path += "?" + r.URL.RawQuery
 	}
 
-	res, err := state.authzClient.Check(r.Context(), &envoy_service_auth_v2.CheckRequest{
+	return state.authzClient.Check(r.Context(), &envoy_service_auth_v2.CheckRequest{
 		Attributes: &envoy_service_auth_v2.AttributeContext{
 			Request: &envoy_service_auth_v2.AttributeContext_Request{
 				Time: tm,
@@ -53,24 +75,6 @@ func (p *Proxy) isAuthorized(w http.ResponseWriter, r *http.Request) (*authorize
 			},
 		},
 	})
-	if err != nil {
-		return nil, httputil.NewError(http.StatusInternalServerError, err)
-	}
-
-	ar := &authorizeResponse{}
-	switch res.HttpResponse.(type) {
-	case *envoy_service_auth_v2.CheckResponse_OkResponse:
-		for _, hdr := range res.GetOkResponse().GetHeaders() {
-			w.Header().Set(hdr.GetHeader().GetKey(), hdr.GetHeader().GetValue())
-		}
-		ar.authorized = true
-		ar.statusCode = res.GetStatus().Code
-	case *envoy_service_auth_v2.CheckResponse_DeniedResponse:
-		ar.statusCode = int32(res.GetDeniedResponse().GetStatus().Code)
-	default:
-		ar.statusCode = http.StatusInternalServerError
-	}
-	return ar, nil
 }
 
 // jwtClaimMiddleware logs and propagates JWT claim information via request headers