diff --git a/staging/src/k8s.io/apimachinery/pkg/util/proxy/upgradeaware.go b/staging/src/k8s.io/apimachinery/pkg/util/proxy/upgradeaware.go
index 8ef16eeb63f..cda35380459 100644
--- a/staging/src/k8s.io/apimachinery/pkg/util/proxy/upgradeaware.go
+++ b/staging/src/k8s.io/apimachinery/pkg/util/proxy/upgradeaware.go
@@ -60,6 +60,8 @@ type UpgradeAwareHandler struct {
 	// Location is the location of the upstream proxy. It is used as the location to Dial on the upstream server
 	// for upgrade requests unless UseRequestLocationOnUpgrade is true.
 	Location *url.URL
+	// AppendLocationPath determines if the original path of the Location should be appended to the upstream proxy request path
+	AppendLocationPath bool
 	// Transport provides an optional round tripper to use to proxy. If nil, the default proxy transport is used
 	Transport http.RoundTripper
 	// UpgradeTransport, if specified, will be used as the backend transport when upgrade requests are provided.
@@ -239,7 +241,13 @@ func (h *UpgradeAwareHandler) ServeHTTP(w http.ResponseWriter, req *http.Request
 		newReq.Host = h.Location.Host
 	}
 
-	proxy := httputil.NewSingleHostReverseProxy(&url.URL{Scheme: h.Location.Scheme, Host: h.Location.Host})
+	// create the target location to use for the reverse proxy
+	reverseProxyLocation := &url.URL{Scheme: h.Location.Scheme, Host: h.Location.Host}
+	if h.AppendLocationPath {
+		reverseProxyLocation.Path = h.Location.Path
+	}
+
+	proxy := httputil.NewSingleHostReverseProxy(reverseProxyLocation)
 	proxy.Transport = h.Transport
 	proxy.FlushInterval = h.FlushInterval
 	proxy.ErrorLog = log.New(noSuppressPanicError{}, "", log.LstdFlags)
@@ -282,6 +290,9 @@ func (h *UpgradeAwareHandler) tryUpgrade(w http.ResponseWriter, req *http.Reques
 		location = *req.URL
 		location.Scheme = h.Location.Scheme
 		location.Host = h.Location.Host
+		if h.AppendLocationPath {
+			location.Path = singleJoiningSlash(h.Location.Path, location.Path)
+		}
 	}
 
 	clone := utilnet.CloneRequest(req)
@@ -414,6 +425,20 @@ func (h *UpgradeAwareHandler) tryUpgrade(w http.ResponseWriter, req *http.Reques
 	return true
 }
 
+// FIXME: Taken from net/http/httputil/reverseproxy.go as singleJoiningSlash is not exported to be re-used.
+// See-also: https://github.com/golang/go/issues/44290
+func singleJoiningSlash(a, b string) string {
+	aslash := strings.HasSuffix(a, "/")
+	bslash := strings.HasPrefix(b, "/")
+	switch {
+	case aslash && bslash:
+		return a + b[1:]
+	case !aslash && !bslash:
+		return a + "/" + b
+	}
+	return a + b
+}
+
 func (h *UpgradeAwareHandler) DialForUpgrade(req *http.Request) (net.Conn, error) {
 	if h.UpgradeTransport == nil {
 		return dial(req, h.Transport)
diff --git a/staging/src/k8s.io/apimachinery/pkg/util/proxy/upgradeaware_test.go b/staging/src/k8s.io/apimachinery/pkg/util/proxy/upgradeaware_test.go
index 02fc02ec73e..f7f34be5d53 100644
--- a/staging/src/k8s.io/apimachinery/pkg/util/proxy/upgradeaware_test.go
+++ b/staging/src/k8s.io/apimachinery/pkg/util/proxy/upgradeaware_test.go
@@ -163,6 +163,7 @@ func TestServeHTTP(t *testing.T) {
 		expectedRespHeader    map[string]string
 		notExpectedRespHeader []string
 		upgradeRequired       bool
+		appendLocationPath    bool
 		expectError           func(err error) bool
 		useLocationHost       bool
 	}{
@@ -246,6 +247,27 @@ func TestServeHTTP(t *testing.T) {
 			expectedPath:    "/some/path",
 			useLocationHost: true,
 		},
+		{
+			name:               "append server path to request path",
+			method:             "GET",
+			requestPath:        "/base",
+			expectedPath:       "/base/base",
+			appendLocationPath: true,
+		},
+		{
+			name:               "append server path to request path with ending slash",
+			method:             "GET",
+			requestPath:        "/base/",
+			expectedPath:       "/base/base/",
+			appendLocationPath: true,
+		},
+		{
+			name:               "don't append server path to request path",
+			method:             "GET",
+			requestPath:        "/base",
+			expectedPath:       "/base",
+			appendLocationPath: false,
+		},
 	}
 
 	for i, test := range tests {
@@ -269,6 +291,7 @@ func TestServeHTTP(t *testing.T) {
 			backendURL.Path = test.requestPath
 			proxyHandler := NewUpgradeAwareHandler(backendURL, nil, false, test.upgradeRequired, responder)
 			proxyHandler.UseLocationHost = test.useLocationHost
+			proxyHandler.AppendLocationPath = test.appendLocationPath
 			proxyServer := httptest.NewServer(proxyHandler)
 			defer proxyServer.Close()
 			proxyURL, _ := url.Parse(proxyServer.URL)
diff --git a/staging/src/k8s.io/kubectl/pkg/cmd/proxy/proxy.go b/staging/src/k8s.io/kubectl/pkg/cmd/proxy/proxy.go
index 76c60dc9ebd..8d9b64ec409 100644
--- a/staging/src/k8s.io/kubectl/pkg/cmd/proxy/proxy.go
+++ b/staging/src/k8s.io/kubectl/pkg/cmd/proxy/proxy.go
@@ -20,6 +20,7 @@ import (
 	"errors"
 	"fmt"
 	"net"
+	"net/url"
 	"os"
 	"strings"
 	"time"
@@ -50,6 +51,8 @@ type ProxyOptions struct {
 	unixSocket    string
 	keepalive     time.Duration
 
+	appendServerPath bool
+
 	clientConfig *rest.Config
 	filter       *proxy.FilterServer
 
@@ -138,6 +141,7 @@ func NewCmdProxy(f cmdutil.Factory, ioStreams genericclioptions.IOStreams) *cobr
 	cmd.Flags().BoolVar(&o.disableFilter, "disable-filter", o.disableFilter, "If true, disable request filtering in the proxy. This is dangerous, and can leave you vulnerable to XSRF attacks, when used with an accessible port.")
 	cmd.Flags().StringVarP(&o.unixSocket, "unix-socket", "u", o.unixSocket, "Unix socket on which to run the proxy.")
 	cmd.Flags().DurationVar(&o.keepalive, "keepalive", o.keepalive, "keepalive specifies the keep-alive period for an active network connection. Set to 0 to disable keepalive.")
+	cmd.Flags().BoolVar(&o.appendServerPath, "append-server-path", o.appendServerPath, "If true, enables automatic path appending of the kube context server path to each request.")
 	return cmd
 }
 
@@ -157,6 +161,15 @@ func (o *ProxyOptions) Complete(f cmdutil.Factory) error {
 		o.apiPrefix += "/"
 	}
 
+	if o.appendServerPath == false {
+		target, err := url.Parse(clientConfig.Host)
+		if err != nil {
+			return err
+		}
+		if target.Path != "" && target.Path != "/" {
+			klog.Warning("Your kube context contains a server path " + target.Path + ", use --append-server-path to automatically append the path to each request")
+		}
+	}
 	if o.disableFilter {
 		if o.unixSocket == "" {
 			klog.Warning("Request filter disabled, your proxy is vulnerable to XSRF attacks, please be cautious")
@@ -193,7 +206,7 @@ func (o ProxyOptions) Validate() error {
 
 // RunProxy checks given arguments and executes command
 func (o ProxyOptions) RunProxy() error {
-	server, err := proxy.NewServer(o.staticDir, o.apiPrefix, o.staticPrefix, o.filter, o.clientConfig, o.keepalive)
+	server, err := proxy.NewServer(o.staticDir, o.apiPrefix, o.staticPrefix, o.filter, o.clientConfig, o.keepalive, o.appendServerPath)
 
 	if err != nil {
 		return err
diff --git a/staging/src/k8s.io/kubectl/pkg/proxy/proxy_server.go b/staging/src/k8s.io/kubectl/pkg/proxy/proxy_server.go
index 2362e22b2a0..bf0c3050f47 100644
--- a/staging/src/k8s.io/kubectl/pkg/proxy/proxy_server.go
+++ b/staging/src/k8s.io/kubectl/pkg/proxy/proxy_server.go
@@ -176,8 +176,8 @@ func makeUpgradeTransport(config *rest.Config, keepalive time.Duration) (proxy.U
 
 // NewServer creates and installs a new Server.
 // 'filter', if non-nil, protects requests to the api only.
-func NewServer(filebase string, apiProxyPrefix string, staticPrefix string, filter *FilterServer, cfg *rest.Config, keepalive time.Duration) (*Server, error) {
-	proxyHandler, err := NewProxyHandler(apiProxyPrefix, filter, cfg, keepalive)
+func NewServer(filebase string, apiProxyPrefix string, staticPrefix string, filter *FilterServer, cfg *rest.Config, keepalive time.Duration, appendLocationPath bool) (*Server, error) {
+	proxyHandler, err := NewProxyHandler(apiProxyPrefix, filter, cfg, keepalive, appendLocationPath)
 	if err != nil {
 		return nil, err
 	}
@@ -192,7 +192,7 @@ func NewServer(filebase string, apiProxyPrefix string, staticPrefix string, filt
 }
 
 // NewProxyHandler creates an api proxy handler for the cluster
-func NewProxyHandler(apiProxyPrefix string, filter *FilterServer, cfg *rest.Config, keepalive time.Duration) (http.Handler, error) {
+func NewProxyHandler(apiProxyPrefix string, filter *FilterServer, cfg *rest.Config, keepalive time.Duration, appendLocationPath bool) (http.Handler, error) {
 	host := cfg.Host
 	if !strings.HasSuffix(host, "/") {
 		host = host + "/"
@@ -215,6 +215,7 @@ func NewProxyHandler(apiProxyPrefix string, filter *FilterServer, cfg *rest.Conf
 	proxy.UpgradeTransport = upgradeTransport
 	proxy.UseRequestLocation = true
 	proxy.UseLocationHost = true
+	proxy.AppendLocationPath = appendLocationPath
 
 	proxyServer := http.Handler(proxy)
 	if filter != nil {
diff --git a/staging/src/k8s.io/kubectl/pkg/proxy/proxy_server_test.go b/staging/src/k8s.io/kubectl/pkg/proxy/proxy_server_test.go
index f9a80d13d39..7055b751d54 100644
--- a/staging/src/k8s.io/kubectl/pkg/proxy/proxy_server_test.go
+++ b/staging/src/k8s.io/kubectl/pkg/proxy/proxy_server_test.go
@@ -455,17 +455,19 @@ func TestPathHandling(t *testing.T) {
 		prefix     string
 		reqPath    string
 		expectPath string
+		appendPath bool
 	}{
-		{"test1", "/api/", "/metrics", "404 page not found\n"},
-		{"test2", "/api/", "/api/metrics", "/api/metrics"},
-		{"test3", "/api/", "/api/v1/pods/", "/api/v1/pods/"},
-		{"test4", "/", "/metrics", "/metrics"},
-		{"test5", "/", "/api/v1/pods/", "/api/v1/pods/"},
-		{"test6", "/custom/", "/metrics", "404 page not found\n"},
-		{"test7", "/custom/", "/api/metrics", "404 page not found\n"},
-		{"test8", "/custom/", "/api/v1/pods/", "404 page not found\n"},
-		{"test9", "/custom/", "/custom/api/metrics", "/api/metrics"},
-		{"test10", "/custom/", "/custom/api/v1/pods/", "/api/v1/pods/"},
+		{"test1", "/api/", "/metrics", "404 page not found\n", false},
+		{"test2", "/api/", "/api/metrics", "/api/metrics", false},
+		{"test3", "/api/", "/api/v1/pods/", "/api/v1/pods/", false},
+		{"test4", "/", "/metrics", "/metrics", false},
+		{"test5", "/", "/api/v1/pods/", "/api/v1/pods/", false},
+		{"test6", "/custom/", "/metrics", "404 page not found\n", false},
+		{"test7", "/custom/", "/api/metrics", "404 page not found\n", false},
+		{"test8", "/custom/", "/api/v1/pods/", "404 page not found\n", false},
+		{"test9", "/custom/", "/custom/api/metrics", "/api/metrics", false},
+		{"test10", "/custom/", "/custom/api/v1/pods/", "/api/v1/pods/", false},
+		{"test11", "/custom/", "/custom/api/v1/services/", "/api/v1/services/", true},
 	}
 
 	cc := &rest.Config{
@@ -474,7 +476,7 @@ func TestPathHandling(t *testing.T) {
 
 	for _, tt := range table {
 		t.Run(tt.name, func(t *testing.T) {
-			p, err := NewServer("", tt.prefix, "/not/used/for/this/test", nil, cc, 0)
+			p, err := NewServer("", tt.prefix, "/not/used/for/this/test", nil, cc, 0, tt.appendPath)
 			if err != nil {
 				t.Fatalf("%#v: %v", tt, err)
 			}
diff --git a/test/integration/apimachinery/watch_timeout_test.go b/test/integration/apimachinery/watch_timeout_test.go
index 46c65410bbc..b7ba18cf9fc 100644
--- a/test/integration/apimachinery/watch_timeout_test.go
+++ b/test/integration/apimachinery/watch_timeout_test.go
@@ -164,7 +164,7 @@ func TestWatchClientTimeout(t *testing.T) {
 	})
 
 	t.Run("kubectl proxy", func(t *testing.T) {
-		kubectlProxyServer, err := kubectlproxy.NewServer("", "/", "/static/", nil, &restclient.Config{Host: s.URL, Timeout: 2 * time.Second}, 0)
+		kubectlProxyServer, err := kubectlproxy.NewServer("", "/", "/static/", nil, &restclient.Config{Host: s.URL, Timeout: 2 * time.Second}, 0, false)
 		if err != nil {
 			t.Fatal(err)
 		}