diff --git a/cmd/tailscale/cli/up.go b/cmd/tailscale/cli/up.go
index 6bd5032c8..3a8a74e8b 100644
--- a/cmd/tailscale/cli/up.go
+++ b/cmd/tailscale/cli/up.go
@@ -143,17 +143,11 @@ var (
 	ipv6default = netaddr.MustParseIPPrefix("::/0")
 )
 
-// prefsFromUpArgs returns the ipn.Prefs for the provided args.
-//
-// Note that the parameters upArgs and warnf are named intentionally
-// to shadow the globals to prevent accidental misuse of them. This
-// function exists for testing and should have no side effects or
-// outside interactions (e.g. no making Tailscale local API calls).
-func prefsFromUpArgs(upArgs upArgsT, warnf logger.Logf, st *ipnstate.Status, goos string) (*ipn.Prefs, error) {
+func calcAdvertiseRoutes(advertiseRoutes string, advertiseDefaultRoute bool) ([]netaddr.IPPrefix, error) {
 	routeMap := map[netaddr.IPPrefix]bool{}
-	var default4, default6 bool
-	if upArgs.advertiseRoutes != "" {
-		advroutes := strings.Split(upArgs.advertiseRoutes, ",")
+	if advertiseRoutes != "" {
+		var default4, default6 bool
+		advroutes := strings.Split(advertiseRoutes, ",")
 		for _, s := range advroutes {
 			ipp, err := netaddr.ParseIPPrefix(s)
 			if err != nil {
@@ -175,7 +169,7 @@ func prefsFromUpArgs(upArgs upArgsT, warnf logger.Logf, st *ipnstate.Status, goo
 			return nil, fmt.Errorf("%s advertised without its IPv6 counterpart, please also advertise %s", ipv6default, ipv4default)
 		}
 	}
-	if upArgs.advertiseDefaultRoute {
+	if advertiseDefaultRoute {
 		routeMap[netaddr.MustParseIPPrefix("0.0.0.0/0")] = true
 		routeMap[netaddr.MustParseIPPrefix("::/0")] = true
 	}
@@ -189,6 +183,20 @@ func prefsFromUpArgs(upArgs upArgsT, warnf logger.Logf, st *ipnstate.Status, goo
 		}
 		return routes[i].IP().Less(routes[j].IP())
 	})
+	return routes, nil
+}
+
+// prefsFromUpArgs returns the ipn.Prefs for the provided args.
+//
+// Note that the parameters upArgs and warnf are named intentionally
+// to shadow the globals to prevent accidental misuse of them. This
+// function exists for testing and should have no side effects or
+// outside interactions (e.g. no making Tailscale local API calls).
+func prefsFromUpArgs(upArgs upArgsT, warnf logger.Logf, st *ipnstate.Status, goos string) (*ipn.Prefs, error) {
+	routes, err := calcAdvertiseRoutes(upArgs.advertiseRoutes, upArgs.advertiseDefaultRoute)
+	if err != nil {
+		return nil, err
+	}
 
 	var exitNodeIP netaddr.IP
 	if upArgs.exitNodeIP != "" {
diff --git a/cmd/tailscale/cli/web.css b/cmd/tailscale/cli/web.css
index 64672224d..0876c1b3c 100644
--- a/cmd/tailscale/cli/web.css
+++ b/cmd/tailscale/cli/web.css
@@ -1335,3 +1335,14 @@ html {
 	border-color: #6c94ec;
 	border-color: rgba(108, 148, 236, var(--border-opacity));
 }
+
+.button-red {
+	background-color: #d04841;
+	border-color: #d04841;
+	color: #fff;
+}
+
+.button-red:enabled:hover {
+	background-color: #b22d30;
+	border-color: #b22d30;
+}
diff --git a/cmd/tailscale/cli/web.go b/cmd/tailscale/cli/web.go
index cb2088618..07a6565b6 100644
--- a/cmd/tailscale/cli/web.go
+++ b/cmd/tailscale/cli/web.go
@@ -14,6 +14,7 @@ import (
 	"flag"
 	"fmt"
 	"html/template"
+	"io"
 	"io/ioutil"
 	"log"
 	"net"
@@ -26,6 +27,7 @@ import (
 	"strings"
 
 	"github.com/peterbourgon/ff/v3/ffcli"
+	"inet.af/netaddr"
 	"tailscale.com/client/tailscale"
 	"tailscale.com/ipn"
 	"tailscale.com/tailcfg"
@@ -51,11 +53,13 @@ func init() {
 }
 
 type tmplData struct {
-	Profile      tailcfg.UserProfile
-	SynologyUser string
-	Status       string
-	DeviceName   string
-	IP           string
+	Profile           tailcfg.UserProfile
+	SynologyUser      string
+	Status            string
+	DeviceName        string
+	IP                string
+	AdvertiseExitNode bool
+	AdvertiseRoutes   string
 }
 
 var webCmd = &ffcli.Command{
@@ -303,15 +307,45 @@ func webHandler(w http.ResponseWriter, r *http.Request) {
 	}
 
 	if r.Method == "POST" {
+		defer r.Body.Close()
+		var postData struct {
+			AdvertiseRoutes   string
+			AdvertiseExitNode bool
+			Reauthenticate    bool
+		}
 		type mi map[string]interface{}
+		if err := json.NewDecoder(r.Body).Decode(&postData); err != nil {
+			w.WriteHeader(400)
+			json.NewEncoder(w).Encode(mi{"error": err.Error()})
+			return
+		}
+		prefs, err := tailscale.GetPrefs(r.Context())
+		if err != nil && !postData.Reauthenticate {
+			w.WriteHeader(http.StatusInternalServerError)
+			json.NewEncoder(w).Encode(mi{"error": err.Error()})
+			return
+		} else {
+			routes, err := calcAdvertiseRoutes(postData.AdvertiseRoutes, postData.AdvertiseExitNode)
+			if err != nil {
+				w.WriteHeader(http.StatusInternalServerError)
+				json.NewEncoder(w).Encode(mi{"error": err.Error()})
+				return
+			}
+			prefs.AdvertiseRoutes = routes
+		}
+
 		w.Header().Set("Content-Type", "application/json")
-		url, err := tailscaleUpForceReauth(r.Context())
+		url, err := tailscaleUp(r.Context(), prefs, postData.Reauthenticate)
 		if err != nil {
 			w.WriteHeader(http.StatusInternalServerError)
 			json.NewEncoder(w).Encode(mi{"error": err.Error()})
 			return
 		}
-		json.NewEncoder(w).Encode(mi{"url": url})
+		if url != "" {
+			json.NewEncoder(w).Encode(mi{"url": url})
+		} else {
+			io.WriteString(w, "{}")
+		}
 		return
 	}
 
@@ -320,6 +354,11 @@ func webHandler(w http.ResponseWriter, r *http.Request) {
 		http.Error(w, err.Error(), http.StatusInternalServerError)
 		return
 	}
+	prefs, err := tailscale.GetPrefs(r.Context())
+	if err != nil {
+		http.Error(w, err.Error(), http.StatusInternalServerError)
+		return
+	}
 
 	profile := st.User[st.Self.UserID]
 	deviceName := strings.Split(st.Self.DNSName, ".")[0]
@@ -329,6 +368,18 @@ func webHandler(w http.ResponseWriter, r *http.Request) {
 		Status:       st.BackendState,
 		DeviceName:   deviceName,
 	}
+	exitNodeRouteV4 := netaddr.MustParseIPPrefix("0.0.0.0/0")
+	exitNodeRouteV6 := netaddr.MustParseIPPrefix("::/0")
+	for _, r := range prefs.AdvertiseRoutes {
+		if r == exitNodeRouteV4 || r == exitNodeRouteV6 {
+			data.AdvertiseExitNode = true
+		} else {
+			if data.AdvertiseRoutes != "" {
+				data.AdvertiseRoutes = ","
+			}
+			data.AdvertiseRoutes += r.String()
+		}
+	}
 	if len(st.TailscaleIPs) != 0 {
 		data.IP = st.TailscaleIPs[0].String()
 	}
@@ -342,13 +393,15 @@ func webHandler(w http.ResponseWriter, r *http.Request) {
 }
 
 // TODO(crawshaw): some of this is very similar to the code in 'tailscale up', can we share anything?
-func tailscaleUpForceReauth(ctx context.Context) (authURL string, retErr error) {
-	prefs := ipn.NewPrefs()
-	prefs.ControlURL = ipn.DefaultControlURL
-	prefs.WantRunning = true
-	prefs.CorpDNS = true
-	prefs.AllowSingleHosts = true
-	prefs.ForceDaemon = (runtime.GOOS == "windows")
+func tailscaleUp(ctx context.Context, prefs *ipn.Prefs, forceReauth bool) (authURL string, retErr error) {
+	if prefs == nil {
+		prefs = ipn.NewPrefs()
+		prefs.ControlURL = ipn.DefaultControlURL
+		prefs.WantRunning = true
+		prefs.CorpDNS = true
+		prefs.AllowSingleHosts = true
+		prefs.ForceDaemon = (runtime.GOOS == "windows")
+	}
 
 	if distro.Get() == distro.Synology {
 		prefs.NetfilterMode = preftype.NetfilterOff
@@ -395,6 +448,14 @@ func tailscaleUpForceReauth(ctx context.Context) (authURL string, retErr error)
 			authURL = *url
 			cancel()
 		}
+		if !forceReauth && n.Prefs != nil {
+			p1, p2 := *n.Prefs, *prefs
+			p1.Persist = nil
+			p2.Persist = nil
+			if p1.Equals(&p2) {
+				cancel()
+			}
+		}
 	})
 	// Wait for backend client to be connected so we know
 	// we're subscribed to updates. Otherwise we can miss
@@ -412,10 +473,15 @@ func tailscaleUpForceReauth(ctx context.Context) (authURL string, retErr error)
 	bc.Start(ipn.Options{
 		StateKey: ipn.GlobalDaemonStateKey,
 	})
-	bc.StartLoginInteractive()
+	if forceReauth {
+		bc.StartLoginInteractive()
+	}
 
 	<-pumpCtx.Done() // wait for authURL or complete failure
 	if authURL == "" && retErr == nil {
+		if !forceReauth {
+			return "", nil // no auth URL is fine
+		}
 		retErr = pumpCtx.Err()
 	}
 	if authURL == "" && retErr == nil {
diff --git a/cmd/tailscale/cli/web.html b/cmd/tailscale/cli/web.html
index 93fc9f2e0..429708cf8 100644
--- a/cmd/tailscale/cli/web.html
+++ b/cmd/tailscale/cli/web.html
@@ -86,14 +86,30 @@
 	<div class="mb-4">
 		<p>You are connected! Access this device over Tailscale using the device name or IP address above.</p>
 	</div>
-	<a href="#" class="mb-4 link font-medium js-loginButton" target="_blank">Reauthenticate</a>
+	<div class="mb-4">
+	<a href="#" class="mb-4 js-advertiseExitNode">
+		{{if .AdvertiseExitNode}}
+		<button class="button button-red button-medium" id="enabled">Stop advertising Exit Node</button>
+		{{else}}
+		<button class="button button-blue button-medium" id="enabled">Advertise as Exit Node</button>
+		{{end}}
+	</a>
+	</div>
+	<div class="mb-4">
+		<a href="#" class="mb-4 link font-medium js-loginButton" target="_blank">Reauthenticate</a>
+	</div>
 	{{ end }}
 </main>
 <script>(function () {
-let loginButtons = document.querySelectorAll(".js-loginButton");
+const advertiseExitNode = {{.AdvertiseExitNode}};
 let fetchingUrl = false;
+var data = {
+	AdvertiseRoutes: "{{.AdvertiseRoutes}}",
+	AdvertiseExitNode: advertiseExitNode,
+	Reauthenticate: false
+};
 
-function handleClick(e) {
+function postData(e) {
 	e.preventDefault();
 
 	if (fetchingUrl) {
@@ -116,7 +132,8 @@ function handleClick(e) {
 		headers: {
 			"Accept": "application/json",
 			"Content-Type": "application/json",
-		}
+		},
+		body: JSON.stringify(data)
 	}).then(res => res.json()).then(res => {
 		fetchingUrl = false;
 		const err = res["error"];
@@ -134,9 +151,19 @@ function handleClick(e) {
 	});
 }
 
-Array.from(loginButtons).forEach(el => {
-	el.addEventListener("click", handleClick);
+Array.from(document.querySelectorAll(".js-loginButton")).forEach(el => {
+	el.addEventListener("click", function(e) {
+		data.Reauthenticate = true;
+		postData(e);
+	});
 })
+Array.from(document.querySelectorAll(".js-advertiseExitNode")).forEach(el => {
+	el.addEventListener("click", function(e) {
+		data.AdvertiseExitNode = !advertiseExitNode;
+		postData(e);
+	});
+})
+
 })();</script>
 </body>