diff --git a/cfapi/client.go b/cfapi/client.go
index 0431ad53..4b7e3508 100644
--- a/cfapi/client.go
+++ b/cfapi/client.go
@@ -9,7 +9,7 @@ type TunnelClient interface {
 	GetTunnel(tunnelID uuid.UUID) (*Tunnel, error)
 	GetTunnelToken(tunnelID uuid.UUID) (string, error)
 	GetManagementToken(tunnelID uuid.UUID) (string, error)
-	DeleteTunnel(tunnelID uuid.UUID) error
+	DeleteTunnel(tunnelID uuid.UUID, cascade bool) error
 	ListTunnels(filter *TunnelFilter) ([]*Tunnel, error)
 	ListActiveClients(tunnelID uuid.UUID) ([]*ActiveClient, error)
 	CleanupConnections(tunnelID uuid.UUID, params *CleanupParams) error
diff --git a/cfapi/tunnel.go b/cfapi/tunnel.go
index fa6f8f33..d1b5f3a2 100644
--- a/cfapi/tunnel.go
+++ b/cfapi/tunnel.go
@@ -159,9 +159,14 @@ func (r *RESTClient) GetManagementToken(tunnelID uuid.UUID) (token string, err e
 	return "", r.statusCodeToError("get tunnel token", resp)
 }
 
-func (r *RESTClient) DeleteTunnel(tunnelID uuid.UUID) error {
+func (r *RESTClient) DeleteTunnel(tunnelID uuid.UUID, cascade bool) error {
 	endpoint := r.baseEndpoints.accountLevel
 	endpoint.Path = path.Join(endpoint.Path, fmt.Sprintf("%v", tunnelID))
+	// Cascade will delete all tunnel dependencies (connections, routes, etc.) that
+	// are linked to the deleted tunnel.
+	if cascade {
+		endpoint.RawQuery = "cascade=true"
+	}
 	resp, err := r.sendRequest("DELETE", endpoint, nil)
 	if err != nil {
 		return errors.Wrap(err, "REST request failed")
diff --git a/cmd/cloudflared/tunnel/subcommand_context.go b/cmd/cloudflared/tunnel/subcommand_context.go
index f49c15eb..c0bddd9d 100644
--- a/cmd/cloudflared/tunnel/subcommand_context.go
+++ b/cmd/cloudflared/tunnel/subcommand_context.go
@@ -156,7 +156,7 @@ func (sc *subcommandContext) create(name string, credentialsFilePath string, sec
 		var errorLines []string
 		errorLines = append(errorLines, fmt.Sprintf("Your tunnel '%v' was created with ID %v. However, cloudflared couldn't write tunnel credentials to %s.", tunnel.Name, tunnel.ID, credentialsFilePath))
 		errorLines = append(errorLines, fmt.Sprintf("The file-writing error is: %v", writeFileErr))
-		if deleteErr := client.DeleteTunnel(tunnel.ID); deleteErr != nil {
+		if deleteErr := client.DeleteTunnel(tunnel.ID, true); deleteErr != nil {
 			errorLines = append(errorLines, fmt.Sprintf("Cloudflared tried to delete the tunnel for you, but encountered an error. You should use `cloudflared tunnel delete %v` to delete the tunnel yourself, because the tunnel can't be run without the tunnelfile.", tunnel.ID))
 			errorLines = append(errorLines, fmt.Sprintf("The delete tunnel error is: %v", deleteErr))
 		} else {
@@ -206,13 +206,8 @@ func (sc *subcommandContext) delete(tunnelIDs []uuid.UUID) error {
 		if !tunnel.DeletedAt.IsZero() {
 			return fmt.Errorf("Tunnel %s has already been deleted", tunnel.ID)
 		}
-		if forceFlagSet {
-			if err := client.CleanupConnections(tunnel.ID, cfapi.NewCleanupParams()); err != nil {
-				return errors.Wrapf(err, "Error cleaning up connections for tunnel %s", tunnel.ID)
-			}
-		}
 
-		if err := client.DeleteTunnel(tunnel.ID); err != nil {
+		if err := client.DeleteTunnel(tunnel.ID, forceFlagSet); err != nil {
 			return errors.Wrapf(err, "Error deleting tunnel %s", tunnel.ID)
 		}
 
diff --git a/cmd/cloudflared/tunnel/subcommand_context_test.go b/cmd/cloudflared/tunnel/subcommand_context_test.go
index c2293463..ca2a42b2 100644
--- a/cmd/cloudflared/tunnel/subcommand_context_test.go
+++ b/cmd/cloudflared/tunnel/subcommand_context_test.go
@@ -219,7 +219,7 @@ func (d *deleteMockTunnelStore) GetTunnelToken(tunnelID uuid.UUID) (string, erro
 	return "token", nil
 }
 
-func (d *deleteMockTunnelStore) DeleteTunnel(tunnelID uuid.UUID) error {
+func (d *deleteMockTunnelStore) DeleteTunnel(tunnelID uuid.UUID, cascade bool) error {
 	tunnel, ok := d.mockTunnels[tunnelID]
 	if !ok {
 		return fmt.Errorf("Couldn't find tunnel: %v", tunnelID)
diff --git a/cmd/cloudflared/tunnel/subcommands.go b/cmd/cloudflared/tunnel/subcommands.go
index 8da12c19..bef86887 100644
--- a/cmd/cloudflared/tunnel/subcommands.go
+++ b/cmd/cloudflared/tunnel/subcommands.go
@@ -119,8 +119,8 @@ var (
 	forceDeleteFlag = &cli.BoolFlag{
 		Name:    "force",
 		Aliases: []string{"f"},
-		Usage: "Cleans up any stale connections before the tunnel is deleted. cloudflared will not " +
-			"delete a tunnel with connections without this flag.",
+		Usage: "Deletes a tunnel even if tunnel is connected and it has dependencies associated to it. (eg. IP routes)." +
+			" It is not possible to delete tunnels that have connections or non-deleted dependencies, without this flag.",
 		EnvVars: []string{"TUNNEL_RUN_FORCE_OVERWRITE"},
 	}
 	selectProtocolFlag = altsrc.NewStringFlag(&cli.StringFlag{