diff --git a/pkg/cmd/listen.go b/pkg/cmd/listen.go
index 87da4b7..29a6829 100644
--- a/pkg/cmd/listen.go
+++ b/pkg/cmd/listen.go
@@ -26,9 +26,9 @@ import (
 )
 
 type listenCmd struct {
-	cmd       *cobra.Command
-	wsBaseURL string
-	noWSS     bool
+	cmd   *cobra.Command
+	noWSS bool
+	path  string
 }
 
 func newListenCmd() *listenCmd {
@@ -75,6 +75,7 @@ func newListenCmd() *listenCmd {
 		RunE: lc.runListenCmd,
 	}
 	lc.cmd.Flags().BoolVar(&lc.noWSS, "no-wss", false, "Force unencrypted ws:// protocol instead of wss://")
+	lc.cmd.Flags().StringVar(&lc.path, "cli-path", "", "Sets the server path of that locally running web server the events will be forwarded to")
 
 	lc.cmd.SetUsageTemplate(
 		strings.Replace(
@@ -113,6 +114,7 @@ func (lc *listenCmd) runListenCmd(cmd *cobra.Command, args []string) error {
 	}
 
 	return listen.Listen(url, sourceQuery, connectionQuery, listen.Flags{
-		NoWSS: lc.noWSS,
+		NoWSS:   lc.noWSS,
+		CliPath: lc.path,
 	}, &Config)
 }
diff --git a/pkg/listen/connection.go b/pkg/listen/connection.go
index f5dc02d..901b6e2 100644
--- a/pkg/listen/connection.go
+++ b/pkg/listen/connection.go
@@ -12,7 +12,7 @@ import (
 	hookdeckclient "github.com/hookdeck/hookdeck-go-sdk/client"
 )
 
-func getConnections(client *hookdeckclient.Client, sources []*hookdecksdk.Source, connectionFilterString string, isMultiSource bool) ([]*hookdecksdk.Connection, error) {
+func getConnections(client *hookdeckclient.Client, sources []*hookdecksdk.Source, connectionFilterString string, isMultiSource bool, cliPath string) ([]*hookdecksdk.Connection, error) {
 	sourceIDs := []*string{}
 
 	for _, source := range sources {
@@ -31,7 +31,7 @@ func getConnections(client *hookdeckclient.Client, sources []*hookdecksdk.Source
 		return []*hookdecksdk.Connection{}, err
 	}
 
-	connections, err = ensureConnections(client, connections, sources, isMultiSource)
+	connections, err = ensureConnections(client, connections, sources, isMultiSource, cliPath)
 	if err != nil {
 		return []*hookdecksdk.Connection{}, err
 	}
@@ -71,47 +71,55 @@ func filterConnections(connections []*hookdecksdk.Connection, connectionFilterSt
 
 // When users want to listen to a single source but there is no connection for that source,
 // we can help user set up a new connection for it.
-func ensureConnections(client *hookdeckclient.Client, connections []*hookdecksdk.Connection, sources []*hookdecksdk.Source, isMultiSource bool) ([]*hookdecksdk.Connection, error) {
+func ensureConnections(client *hookdeckclient.Client, connections []*hookdecksdk.Connection, sources []*hookdecksdk.Source, isMultiSource bool, cliPath string) ([]*hookdecksdk.Connection, error) {
 	if len(connections) > 0 || isMultiSource {
 		return connections, nil
 	}
 
-	answers := struct {
+	connectionDetails := struct {
 		Label string `survey:"label"`
 		Path  string `survey:"path"`
 	}{}
-	var qs = []*survey.Question{
-		{
-			Name:   "path",
-			Prompt: &survey.Input{Message: "What path should the events be forwarded to (ie: /webhooks)?"},
-			Validate: func(val interface{}) error {
-				str, ok := val.(string)
-				isPath, err := isPath(str)
-				if !ok || !isPath || err != nil {
-					return errors.New("invalid path")
-				}
-				return nil
+
+	if len(cliPath) != 0 {
+		connectionDetails.Path = cliPath
+		connectionDetails.Label = "CLI"
+	} else {
+		var qs = []*survey.Question{
+			{
+				Name:   "path",
+				Prompt: &survey.Input{Message: "What path should the events be forwarded to (ie: /webhooks)?"},
+				Validate: func(val interface{}) error {
+					str, ok := val.(string)
+					isPath, err := isPath(str)
+					if !ok || !isPath || err != nil {
+						return errors.New("invalid path")
+					}
+					return nil
+				},
 			},
-		},
-		{
-			Name:     "label",
-			Prompt:   &survey.Input{Message: "What's your connection label (ie: My API)?"},
-			Validate: survey.Required,
-		},
-	}
+			{
+				Name:     "label",
+				Prompt:   &survey.Input{Message: "What's your connection label (ie: My API)?"},
+				Validate: survey.Required,
+			},
+		}
 
-	err := survey.Ask(qs, &answers)
-	if err != nil {
-		fmt.Println(err.Error())
-		return connections, err
+		err := survey.Ask(qs, &connectionDetails)
+		if err != nil {
+			fmt.Println(err.Error())
+			return connections, err
+		}
 	}
-	alias := slug.Make(answers.Label)
+
+	alias := slug.Make(connectionDetails.Label)
+
 	connection, err := client.Connection.Create(context.Background(), &hookdecksdk.ConnectionCreateRequest{
 		Name:     hookdecksdk.OptionalOrNull(&alias),
 		SourceId: hookdecksdk.OptionalOrNull(&sources[0].Id),
 		Destination: hookdecksdk.OptionalOrNull(&hookdecksdk.ConnectionCreateRequestDestination{
 			Name:    alias,
-			CliPath: &answers.Path,
+			CliPath: &connectionDetails.Path,
 		}),
 	})
 	if err != nil {
diff --git a/pkg/listen/listen.go b/pkg/listen/listen.go
index e98b03f..f3a019f 100644
--- a/pkg/listen/listen.go
+++ b/pkg/listen/listen.go
@@ -31,7 +31,8 @@ import (
 )
 
 type Flags struct {
-	NoWSS bool
+	NoWSS   bool
+	CliPath string
 }
 
 // listenCmd represents the listen command
@@ -46,6 +47,17 @@ func Listen(URL *url.URL, sourceQuery string, connectionFilterString string, fla
 
 	isMultiSource := len(sourceAliases) > 1 || (len(sourceAliases) == 1 && sourceAliases[0] == "*")
 
+	if flags.CliPath != "" {
+		if isMultiSource {
+			return errors.New("Can only set a CLI path when listening to a single source")
+		}
+
+		_, err = isPath(flags.CliPath)
+		if err != nil {
+			return errors.New("The CLI path must be in a valid format")
+		}
+	}
+
 	if config.Profile.APIKey == "" {
 		guestURL, err = login.GuestLogin(config)
 		if guestURL == "" {
@@ -62,11 +74,33 @@ func Listen(URL *url.URL, sourceQuery string, connectionFilterString string, fla
 		return err
 	}
 
-	connections, err := getConnections(sdkClient, sources, connectionFilterString, isMultiSource)
+	connections, err := getConnections(sdkClient, sources, connectionFilterString, isMultiSource, flags.CliPath)
 	if err != nil {
 		return err
 	}
 
+	// If the "clii-path" flag has been passed and the destination has a current cli path value but it's different, update destination path
+	if len(flags.CliPath) != 0 &&
+		len(connections) == 1 &&
+		*connections[0].Destination.CliPath != "" &&
+		*connections[0].Destination.CliPath != flags.CliPath {
+
+		l := log.StandardLogger()
+		updateMsg := fmt.Sprintf("Updating destination CLI path from \"%s\" to \"%s\"", *connections[0].Destination.CliPath, flags.CliPath)
+		l.Debug(updateMsg)
+
+		path := flags.CliPath
+		_, err := sdkClient.Destination.Update(context.Background(), connections[0].Destination.Id, &hookdecksdk.DestinationUpdateRequest{
+			CliPath: hookdecksdk.Optional[string](path),
+		})
+
+		if err != nil {
+			return err
+		}
+
+		connections[0].Destination.CliPath = &path
+	}
+
 	sources = getRelevantSources(sources, connections)
 
 	if err := validateData(sources, connections); err != nil {