diff --git a/cmd/tailscale/cli/cli.go b/cmd/tailscale/cli/cli.go
index 2fbee516a..b1a910295 100644
--- a/cmd/tailscale/cli/cli.go
+++ b/cmd/tailscale/cli/cli.go
@@ -207,6 +207,8 @@ func noDupFlagify(c *ffcli.Command) {
 	}
 }
 
+var fileCmd func() *ffcli.Command
+
 func newRootCmd() *ffcli.Command {
 	rootfs := newFlagSet("tailscale")
 	rootfs.Func("socket", "path to tailscaled socket", func(s string) error {
@@ -247,7 +249,7 @@ change in the future.
 			serveCmd(),
 			versionCmd,
 			webCmd,
-			fileCmd,
+			nilOrCall(fileCmd),
 			bugReportCmd,
 			certCmd,
 			netlockCmd,
@@ -286,6 +288,13 @@ func nonNilCmds(cmds ...*ffcli.Command) []*ffcli.Command {
 	return slicesx.AppendNonzero(cmds[:0], cmds)
 }
 
+func nilOrCall(f func() *ffcli.Command) *ffcli.Command {
+	if f == nil {
+		return nil
+	}
+	return f()
+}
+
 func fatalf(format string, a ...any) {
 	if Fatalf != nil {
 		Fatalf(format, a...)
diff --git a/cmd/tailscale/cli/file.go b/cmd/tailscale/cli/file.go
index 3de5f9766..6f3aa40b5 100644
--- a/cmd/tailscale/cli/file.go
+++ b/cmd/tailscale/cli/file.go
@@ -1,6 +1,8 @@
 // Copyright (c) Tailscale Inc & AUTHORS
 // SPDX-License-Identifier: BSD-3-Clause
 
+//go:build !ts_omit_taildrop
+
 package cli
 
 import (
@@ -38,14 +40,20 @@ import (
 	"tailscale.com/version"
 )
 
-var fileCmd = &ffcli.Command{
-	Name:       "file",
-	ShortUsage: "tailscale file <cp|get> ...",
-	ShortHelp:  "Send or receive files",
-	Subcommands: []*ffcli.Command{
-		fileCpCmd,
-		fileGetCmd,
-	},
+func init() {
+	fileCmd = getFileCmd
+}
+
+func getFileCmd() *ffcli.Command {
+	return &ffcli.Command{
+		Name:       "file",
+		ShortUsage: "tailscale file <cp|get> ...",
+		ShortHelp:  "Send or receive files",
+		Subcommands: []*ffcli.Command{
+			fileCpCmd,
+			fileGetCmd,
+		},
+	}
 }
 
 type countingReader struct {