diff --git a/ext/updater.go b/ext/updater.go
index 45c1cdd5..b028245d 100644
--- a/ext/updater.go
+++ b/ext/updater.go
@@ -300,10 +300,6 @@ func (data botData) stop() {
 // This does NOT set the webhook on telegram - this should be done by the caller.
 // The opts parameter allows for specifying various webhook settings.
 func (u *Updater) StartWebhook(b *gotgbot.Bot, urlPath string, opts WebhookOpts) error {
-	if u.webhookServer != nil {
-		return ErrExpectedEmptyServer
-	}
-
 	err := u.AddWebhook(b, urlPath, opts)
 	if err != nil {
 		return fmt.Errorf("failed to add webhook: %w", err)
@@ -325,7 +321,7 @@ func (u *Updater) AddWebhook(b *gotgbot.Bot, urlPath string, opts WebhookOpts) e
 	err := u.botMapping.addBot(botData{
 		bot:           b,
 		updateChan:    updateChan,
-		urlPath:       urlPath,
+		urlPath:       strings.TrimPrefix(urlPath, "/"),
 		webhookSecret: opts.SecretToken,
 	})
 	if err != nil {
@@ -375,6 +371,10 @@ func (u *Updater) StartServer(opts WebhookOpts) error {
 		return fmt.Errorf("failed to listen on %s:%s: %w", opts.ListenNet, opts.ListenAddr, err)
 	}
 
+	if u.webhookServer != nil {
+		return ErrExpectedEmptyServer
+	}
+
 	u.webhookServer = &http.Server{
 		Handler:           u.GetHandlerFunc("/"),
 		ReadTimeout:       opts.ReadTimeout,
diff --git a/ext/updater_test.go b/ext/updater_test.go
index 72f68ceb..49e3957d 100644
--- a/ext/updater_test.go
+++ b/ext/updater_test.go
@@ -1,6 +1,7 @@
 package ext_test
 
 import (
+	"context"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -85,6 +86,134 @@ func TestUpdaterDisallowsEmptyWebhooks(t *testing.T) {
 	}
 }
 
+func TestUpdater_GetHandlerFunc(t *testing.T) {
+	b := &gotgbot.Bot{
+		Token:     "SOME_TOKEN",
+		BotClient: &gotgbot.BaseBotClient{},
+	}
+
+	type args struct {
+		urlPath       string
+		opts          ext.WebhookOpts
+		httpResponse  int
+		handlerPrefix string
+		requestPath   string // Should start with '/'
+		headers       map[string]string
+	}
+	tests := []struct {
+		name string
+		args args
+	}{
+		{
+			name: "simple path",
+			args: args{
+				urlPath:       "123:hello",
+				httpResponse:  http.StatusOK,
+				handlerPrefix: "/",
+				requestPath:   "/123:hello",
+			},
+		}, {
+			name: "slash prefixed path",
+			args: args{
+				urlPath:       "/123:hello",
+				httpResponse:  http.StatusOK,
+				handlerPrefix: "/",
+				requestPath:   "/123:hello",
+			},
+		}, {
+			name: "using subpath",
+			args: args{
+				urlPath:       "123:hello",
+				httpResponse:  http.StatusOK,
+				handlerPrefix: "/test/",
+				requestPath:   "/test/123:hello",
+			},
+		}, {
+			name: "unknown path",
+			args: args{
+				urlPath:       "123:hello",
+				httpResponse:  http.StatusNotFound,
+				handlerPrefix: "/",
+				requestPath:   "/this-path-doesnt-exist",
+			},
+		}, {
+			name: "missing secret token",
+			args: args{
+				urlPath: "123:hello",
+				opts: ext.WebhookOpts{
+					SecretToken: "secret",
+				},
+				httpResponse:  http.StatusUnauthorized,
+				handlerPrefix: "/",
+				requestPath:   "/123:hello",
+			},
+		}, {
+			name: "matching secret token",
+			args: args{
+				urlPath: "123:hello",
+				opts: ext.WebhookOpts{
+					SecretToken: "secret",
+				},
+				httpResponse:  http.StatusOK,
+				handlerPrefix: "/",
+				requestPath:   "/123:hello",
+				headers: map[string]string{
+					"X-Telegram-Bot-Api-Secret-Token": "secret",
+				},
+			},
+		}, {
+			name: "invalid secret token",
+			args: args{
+				urlPath: "123:hello",
+				opts: ext.WebhookOpts{
+					SecretToken: "secret",
+				},
+				httpResponse:  http.StatusUnauthorized,
+				handlerPrefix: "/",
+				requestPath:   "/123:hello",
+				headers: map[string]string{
+					"X-Telegram-Bot-Api-Secret-Token": "wrong",
+				},
+			},
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			d := ext.NewDispatcher(nil)
+			u := ext.NewUpdater(d, nil)
+
+			if err := u.AddWebhook(b, tt.args.urlPath, tt.args.opts); err != nil {
+				t.Errorf("failed to add webhook: %v", err)
+				return
+			}
+
+			s := httptest.NewServer(u.GetHandlerFunc(tt.args.handlerPrefix))
+			url := s.URL + tt.args.requestPath
+			// We pass {} to satisfy JSON handling
+			req, err := http.NewRequestWithContext(context.Background(), http.MethodPost, url, strings.NewReader("{}"))
+			if err != nil {
+				t.Errorf("Failed to build request, should have worked: %v", err.Error())
+				return
+			}
+
+			for k, v := range tt.args.headers {
+				req.Header.Set(k, v)
+			}
+
+			r, err := s.Client().Do(req)
+			if err != nil {
+				t.Fatal()
+			}
+
+			defer r.Body.Close()
+			if r.StatusCode != tt.args.httpResponse {
+				t.Errorf("Expected code %d, got %d", tt.args.httpResponse, r.StatusCode)
+				return
+			}
+		})
+	}
+}
+
 func TestUpdaterAllowsWebhookDeletion(t *testing.T) {
 	server := basicTestServer(t, map[string]string{
 		"getUpdates":    `{}`,
@@ -116,6 +245,12 @@ func TestUpdaterAllowsWebhookDeletion(t *testing.T) {
 		t.Errorf("failed to start long poll on first bot: %v", err)
 		return
 	}
+
+	err = u.Stop()
+	if err != nil {
+		t.Errorf("failed to stop updater: %v", err)
+		return
+	}
 }
 
 func TestUpdaterSupportsTwoPollingBots(t *testing.T) {
@@ -165,6 +300,12 @@ func TestUpdaterSupportsTwoPollingBots(t *testing.T) {
 		t.Errorf("should be able to add two different polling bots")
 		return
 	}
+
+	err = u.Stop()
+	if err != nil {
+		t.Errorf("failed to stop updater: %v", err)
+		return
+	}
 }
 
 func TestUpdaterThrowsErrorWhenSameLongPollAddedTwice(t *testing.T) {
@@ -207,6 +348,12 @@ func TestUpdaterThrowsErrorWhenSameLongPollAddedTwice(t *testing.T) {
 		t.Errorf("should have failed to start the same long poll twice, but didnt")
 		return
 	}
+
+	err = u.Stop()
+	if err != nil {
+		t.Errorf("failed to stop updater: %v", err)
+		return
+	}
 }
 
 func TestUpdaterSupportsLongPollReAdding(t *testing.T) {
@@ -252,6 +399,12 @@ func TestUpdaterSupportsLongPollReAdding(t *testing.T) {
 		t.Errorf("Failed to re-start a previously removed bot: %v", err)
 		return
 	}
+
+	err = u.Stop()
+	if err != nil {
+		t.Errorf("failed to stop updater: %v", err)
+		return
+	}
 }
 
 func basicTestServer(t *testing.T, methods map[string]string) *httptest.Server {