diff --git a/lib/httplib/reverseproxy/rewriter.go b/lib/httplib/reverseproxy/rewriter.go
index 507d2eecc0543..2a23dc272308d 100644
--- a/lib/httplib/reverseproxy/rewriter.go
+++ b/lib/httplib/reverseproxy/rewriter.go
@@ -126,9 +126,11 @@ func maybeSetXRealIP(req *http.Request) {
 // maybeSetForwarded sets X-Forwarded-* headers if it is not set to the
 // scheme of the request.
 func maybeSetForwarded(req *http.Request) {
-	// We need to delete the value because httputil.ReverseProxy
-	// appends to the existing value.
-	req.Header.Del(XForwardedFor)
+	// Set X-Forwarded-For since net/http/httputil.ReverseProxy won't
+	// do this when Rewrite is set.
+	if clientIP, _, err := net.SplitHostPort(req.RemoteAddr); err == nil {
+		req.Header.Set(XForwardedFor, clientIP)
+	}
 
 	if req.Header.Get(XForwardedProto) != "" {
 		return
diff --git a/lib/httplib/reverseproxy/rewriter_test.go b/lib/httplib/reverseproxy/rewriter_test.go
index b1da6c7241213..0656708523c4e 100644
--- a/lib/httplib/reverseproxy/rewriter_test.go
+++ b/lib/httplib/reverseproxy/rewriter_test.go
@@ -100,6 +100,7 @@ func TestRewriter(t *testing.T) {
 			hostReq:    "teleport.dev:3543",
 			remoteAddr: "1.2.3.4:1234",
 			expected: http.Header{
+				XForwardedFor:    []string{"1.2.3.4"},
 				XForwardedHost:   []string{"teleport.dev:3543"},
 				XForwardedPort:   []string{"3543"},
 				XForwardedProto:  []string{"https"},
@@ -117,6 +118,7 @@ func TestRewriter(t *testing.T) {
 			hostReq:    "teleport.dev:3543",
 			remoteAddr: "1.2.3.4:1234",
 			expected: http.Header{
+				XForwardedFor:    []string{"1.2.3.4"},
 				XForwardedHost:   []string{"teleport.dev:3543"},
 				XForwardedPort:   []string{"3543"},
 				XForwardedProto:  []string{"http"},
@@ -133,6 +135,7 @@ func TestRewriter(t *testing.T) {
 			hostReq:    "teleport.dev",
 			remoteAddr: "1.2.3.4:1234",
 			expected: http.Header{
+				XForwardedFor:    []string{"1.2.3.4"},
 				XForwardedHost:   []string{"teleport.dev"},
 				XForwardedPort:   []string{"80"},
 				XForwardedProto:  []string{"http"},
@@ -141,9 +144,11 @@ func TestRewriter(t *testing.T) {
 			},
 		},
 	}
+
 	rewriter := NewHeaderRewriter()
 	// set hostname to make sure it's the same in all tests.
 	rewriter.Hostname = hostname
+
 	for _, test := range testCases {
 		test := test
 		t.Run(test.desc, func(t *testing.T) {