diff --git a/modules/caddyhttp/reverseproxy/httptransport.go b/modules/caddyhttp/reverseproxy/httptransport.go
index fa73f9d7e22..8b1832ff481 100644
--- a/modules/caddyhttp/reverseproxy/httptransport.go
+++ b/modules/caddyhttp/reverseproxy/httptransport.go
@@ -27,6 +27,7 @@ import (
 	"time"
 
 	"github.com/caddyserver/caddy/v2"
+	"github.com/caddyserver/caddy/v2/modules/caddytls"
 	"golang.org/x/net/http2"
 )
 
@@ -68,12 +69,12 @@ func (HTTPTransport) CaddyModule() caddy.ModuleInfo {
 
 // Provision sets up h.Transport with a *http.Transport
 // that is ready to use.
-func (h *HTTPTransport) Provision(_ caddy.Context) error {
+func (h *HTTPTransport) Provision(ctx caddy.Context) error {
 	if len(h.Versions) == 0 {
 		h.Versions = []string{"1.1", "2"}
 	}
 
-	rt, err := h.newTransport()
+	rt, err := h.newTransport(ctx)
 	if err != nil {
 		return err
 	}
@@ -82,7 +83,7 @@ func (h *HTTPTransport) Provision(_ caddy.Context) error {
 	return nil
 }
 
-func (h *HTTPTransport) newTransport() (*http.Transport, error) {
+func (h *HTTPTransport) newTransport(ctx caddy.Context) (*http.Transport, error) {
 	dialer := &net.Dialer{
 		Timeout:       time.Duration(h.DialTimeout),
 		FallbackDelay: time.Duration(h.FallbackDelay),
@@ -115,9 +116,8 @@ func (h *HTTPTransport) newTransport() (*http.Transport, error) {
 
 	if h.TLS != nil {
 		rt.TLSHandshakeTimeout = time.Duration(h.TLS.HandshakeTimeout)
-
 		var err error
-		rt.TLSClientConfig, err = h.TLS.MakeTLSClientConfig()
+		rt.TLSClientConfig, err = h.TLS.MakeTLSClientConfig(ctx)
 		if err != nil {
 			return nil, fmt.Errorf("making TLS client config: %v", err)
 		}
@@ -178,7 +178,8 @@ func (h HTTPTransport) Cleanup() error {
 type TLSConfig struct {
 	RootCAPool []string `json:"root_ca_pool,omitempty"`
 	// Added to the same pool as above, but brought in from files
-	RootCAPEMFiles []string `json:"root_ca_pem_files,omitempty"`
+	RootCAPEMFiles            []string `json:"root_ca_pem_files,omitempty"`
+	ClientCertificateAutomate string   `json:"client_certificate_automate,omitempty"`
 	// TODO: Should the client cert+key config use caddytls.CertificateLoader modules?
 	ClientCertificateFile    string         `json:"client_certificate_file,omitempty"`
 	ClientCertificateKeyFile string         `json:"client_certificate_key_file,omitempty"`
@@ -189,7 +190,7 @@ type TLSConfig struct {
 
 // MakeTLSClientConfig returns a tls.Config usable by a client to a backend.
 // If there is no custom TLS configuration, a nil config may be returned.
-func (t TLSConfig) MakeTLSClientConfig() (*tls.Config, error) {
+func (t TLSConfig) MakeTLSClientConfig(ctx caddy.Context) (*tls.Config, error) {
 	cfg := new(tls.Config)
 
 	// client auth
@@ -206,6 +207,28 @@ func (t TLSConfig) MakeTLSClientConfig() (*tls.Config, error) {
 		}
 		cfg.Certificates = []tls.Certificate{cert}
 	}
+	if t.ClientCertificateAutomate != "" {
+		tlsAppIface, err := ctx.App("tls")
+		if err != nil {
+			return nil, fmt.Errorf("getting tls app: %v", err)
+		}
+		tlsApp := tlsAppIface.(*caddytls.TLS)
+		err = tlsApp.Manage([]string{t.ClientCertificateAutomate})
+		if err != nil {
+			return nil, fmt.Errorf("managing client certificate: %v", err)
+		}
+		cfg.GetClientCertificate = func(cri *tls.CertificateRequestInfo) (*tls.Certificate, error) {
+			certs := tlsApp.AllMatchingCertificates(t.ClientCertificateAutomate)
+			var err error
+			for _, cert := range certs {
+				err = cri.SupportsCertificate(&cert.Certificate)
+				if err == nil {
+					return &cert.Certificate, nil
+				}
+			}
+			return nil, err
+		}
+	}
 
 	// trusted root CAs
 	if len(t.RootCAPool) > 0 || len(t.RootCAPEMFiles) > 0 {
diff --git a/modules/caddyhttp/reverseproxy/ntlm.go b/modules/caddyhttp/reverseproxy/ntlm.go
index 270135a9678..ef6712a747c 100644
--- a/modules/caddyhttp/reverseproxy/ntlm.go
+++ b/modules/caddyhttp/reverseproxy/ntlm.go
@@ -55,6 +55,7 @@ type NTLMTransport struct {
 
 	transports   map[string]*http.Transport
 	transportsMu *sync.RWMutex
+	ctx          caddy.Context
 }
 
 // CaddyModule returns the Caddy module information.
@@ -73,6 +74,7 @@ func (NTLMTransport) CaddyModule() caddy.ModuleInfo {
 func (n *NTLMTransport) Provision(ctx caddy.Context) error {
 	n.transports = make(map[string]*http.Transport)
 	n.transportsMu = new(sync.RWMutex)
+	n.ctx = ctx
 
 	if n.HTTPTransport == nil {
 		n.HTTPTransport = new(HTTPTransport)
@@ -141,7 +143,7 @@ func (n *NTLMTransport) RoundTrip(req *http.Request) (*http.Response, error) {
 	// process, we need to pin it to a specific transport
 	if requestHasAuth(req) {
 		var err error
-		transport, err = n.newTransport()
+		transport, err = n.newTransport(n.ctx)
 		if err != nil {
 			return nil, fmt.Errorf("making new transport for %s: %v", req.RemoteAddr, err)
 		}
@@ -155,9 +157,9 @@ func (n *NTLMTransport) RoundTrip(req *http.Request) (*http.Response, error) {
 }
 
 // newTransport makes an NTLM-compatible transport.
-func (n *NTLMTransport) newTransport() (*http.Transport, error) {
+func (n *NTLMTransport) newTransport(ctx caddy.Context) (*http.Transport, error) {
 	// start with a regular HTTP transport
-	transport, err := n.HTTPTransport.newTransport()
+	transport, err := n.HTTPTransport.newTransport(ctx)
 	if err != nil {
 		return nil, err
 	}