diff --git a/cmd/tsconnect/build.go b/cmd/tsconnect/build.go
index a42cef3ea..a47979acc 100644
--- a/cmd/tsconnect/build.go
+++ b/cmd/tsconnect/build.go
@@ -7,11 +7,14 @@ package main
 import (
 	"bytes"
 	"compress/gzip"
+	"encoding/json"
+	"fmt"
 	"io"
 	"io/fs"
 	"io/ioutil"
 	"log"
 	"os"
+	"path"
 	"path/filepath"
 
 	"github.com/andybalholm/brotli"
@@ -26,7 +29,7 @@ func runBuild() {
 	}
 
 	if err := cleanDist(); err != nil {
-		log.Fatalf("Cannot clean dist/: %v", err)
+		log.Fatalf("Cannot clean %s: %v", *distDir, err)
 	}
 
 	buildOptions.Write = true
@@ -55,7 +58,11 @@ func runBuild() {
 	}
 
 	// Preserve build metadata so we can extract hashed file names for serving.
-	if err := ioutil.WriteFile("./dist/esbuild-metadata.json", []byte(result.Metafile), 0666); err != nil {
+	metadataBytes, err := fixEsbuildMetadataPaths(result.Metafile)
+	if err != nil {
+		log.Fatalf("Cannot fix esbuild metadata paths: %v", err)
+	}
+	if err := ioutil.WriteFile(path.Join(*distDir, "/esbuild-metadata.json"), metadataBytes, 0666); err != nil {
 		log.Fatalf("Cannot write metadata: %v", err)
 	}
 
@@ -64,18 +71,48 @@ func runBuild() {
 	}
 }
 
+// fixEsbuildMetadataPaths re-keys the esbuild metadata file to use paths
+// relative to the dist directory (it normally uses paths relative to the cwd,
+// which are akward if we're running with a different cwd at serving time).
+func fixEsbuildMetadataPaths(metadataStr string) ([]byte, error) {
+	var metadata EsbuildMetadata
+	if err := json.Unmarshal([]byte(metadataStr), &metadata); err != nil {
+		return nil, fmt.Errorf("Cannot parse metadata: %w", err)
+	}
+	distAbsPath, err := filepath.Abs(*distDir)
+	if err != nil {
+		return nil, fmt.Errorf("Cannot get absolute path from %s: %w", *distDir, err)
+	}
+	for outputPath, output := range metadata.Outputs {
+		outputAbsPath, err := filepath.Abs(outputPath)
+		if err != nil {
+			return nil, fmt.Errorf("Cannot get absolute path from %s: %w", outputPath, err)
+		}
+		outputRelPath, err := filepath.Rel(distAbsPath, outputAbsPath)
+		if err != nil {
+			return nil, fmt.Errorf("Cannot get relative path from %s: %w", outputRelPath, err)
+		}
+		delete(metadata.Outputs, outputPath)
+		metadata.Outputs[outputRelPath] = output
+	}
+	return json.Marshal(metadata)
+}
+
 // cleanDist removes files from the dist build directory, except the placeholder
 // one that we keep to make sure Git still creates the directory.
 func cleanDist() error {
-	log.Printf("Cleaning dist/...\n")
-	files, err := os.ReadDir("dist")
+	log.Printf("Cleaning %s...\n", *distDir)
+	files, err := os.ReadDir(*distDir)
 	if err != nil {
+		if os.IsNotExist(err) {
+			return os.MkdirAll(*distDir, 0755)
+		}
 		return err
 	}
 
 	for _, file := range files {
 		if file.Name() != "placeholder" {
-			if err := os.Remove(filepath.Join("dist", file.Name())); err != nil {
+			if err := os.Remove(filepath.Join(*distDir, file.Name())); err != nil {
 				return err
 			}
 		}
@@ -84,22 +121,23 @@ func cleanDist() error {
 }
 
 func precompressDist() error {
-	log.Printf("Pre-compressing files in dist/...\n")
+	log.Printf("Pre-compressing files in %s/...\n", *distDir)
 	var eg errgroup.Group
-	err := fs.WalkDir(os.DirFS("./"), "dist", func(path string, d fs.DirEntry, err error) error {
+	err := fs.WalkDir(os.DirFS(*distDir), ".", func(p string, d fs.DirEntry, err error) error {
 		if err != nil {
 			return err
 		}
 		if d.IsDir() {
 			return nil
 		}
-		if !compressibleExtensions[filepath.Ext(path)] {
+		if !compressibleExtensions[filepath.Ext(p)] {
 			return nil
 		}
-		log.Printf("Pre-compressing %v\n", path)
+		p = path.Join(*distDir, p)
+		log.Printf("Pre-compressing %v\n", p)
 
 		eg.Go(func() error {
-			return precompress(path)
+			return precompress(p)
 		})
 		return nil
 	})
diff --git a/cmd/tsconnect/common.go b/cmd/tsconnect/common.go
index c9a22f4eb..b77402a44 100644
--- a/cmd/tsconnect/common.go
+++ b/cmd/tsconnect/common.go
@@ -38,7 +38,7 @@ func commonSetup(dev bool) (*esbuild.BuildOptions, error) {
 	return &esbuild.BuildOptions{
 		EntryPoints: []string{"src/index.js", "src/index.css"},
 		Loader:      map[string]esbuild.Loader{".wasm": esbuild.LoaderFile},
-		Outdir:      "./dist",
+		Outdir:      *distDir,
 		Bundle:      true,
 		Sourcemap:   esbuild.SourceMapLinked,
 		LogLevel:    esbuild.LogLevelInfo,
@@ -103,3 +103,12 @@ func installJSDeps() error {
 	}
 	return err
 }
+
+// EsbuildMetadata is the subset of metadata struct (described by
+// https://esbuild.github.io/api/#metafile) that we care about for mapping
+// from entry points to hashed file names.
+type EsbuildMetadata struct {
+	Outputs map[string]struct {
+		EntryPoint string `json:"entryPoint,omitempty"`
+	} `json:"outputs,omitempty"`
+}
diff --git a/cmd/tsconnect/serve.go b/cmd/tsconnect/serve.go
index 5f5faf8c0..65f14c267 100644
--- a/cmd/tsconnect/serve.go
+++ b/cmd/tsconnect/serve.go
@@ -11,30 +11,48 @@ import (
 	"fmt"
 	"io"
 	"io/fs"
+	"io/ioutil"
 	"log"
 	"net/http"
+	"os"
 	"path"
 	"time"
 
 	"tailscale.com/tsweb"
 )
 
-//go:embed dist/* index.html
+//go:embed index.html
 var embeddedFS embed.FS
 
+//go:embed dist/*
+var embeddedDistFS embed.FS
+
 var serveStartTime = time.Now()
 
 func runServe() {
 	mux := http.NewServeMux()
 
-	indexBytes, err := generateServeIndex()
+	var distFS fs.FS
+	if *distDir == "./dist" {
+		var err error
+		distFS, err = fs.Sub(embeddedDistFS, "dist")
+		if err != nil {
+			log.Fatalf("Could not drop dist/ prefix from embedded FS: %v", err)
+		}
+	} else {
+		distFS = os.DirFS(*distDir)
+	}
+
+	indexBytes, err := generateServeIndex(distFS)
 	if err != nil {
 		log.Fatalf("Could not generate index.html: %v", err)
 	}
 	mux.Handle("/", http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		http.ServeContent(w, r, "index.html", serveStartTime, bytes.NewReader(indexBytes))
 	}))
-	mux.Handle("/dist/", http.HandlerFunc(handleServeDist))
+	mux.Handle("/dist/", http.StripPrefix("/dist/", http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		handleServeDist(w, r, distFS)
+	})))
 	tsweb.Debugger(mux)
 
 	log.Printf("Listening on %s", *addr)
@@ -44,14 +62,19 @@ func runServe() {
 	}
 }
 
-func generateServeIndex() ([]byte, error) {
+func generateServeIndex(distFS fs.FS) ([]byte, error) {
 	log.Printf("Generating index.html...\n")
 	rawIndexBytes, err := embeddedFS.ReadFile("index.html")
 	if err != nil {
 		return nil, fmt.Errorf("Could not read index.html: %w", err)
 	}
 
-	esbuildMetadataBytes, err := embeddedFS.ReadFile("dist/esbuild-metadata.json")
+	esbuildMetadataFile, err := distFS.Open("esbuild-metadata.json")
+	if err != nil {
+		return nil, fmt.Errorf("Could not open esbuild-metadata.json: %w", err)
+	}
+	defer esbuildMetadataFile.Close()
+	esbuildMetadataBytes, err := ioutil.ReadAll(esbuildMetadataFile)
 	if err != nil {
 		return nil, fmt.Errorf("Could not read esbuild-metadata.json: %w", err)
 	}
@@ -62,7 +85,7 @@ func generateServeIndex() ([]byte, error) {
 	entryPointsToHashedDistPaths := make(map[string]string)
 	for outputPath, output := range esbuildMetadata.Outputs {
 		if output.EntryPoint != "" {
-			entryPointsToHashedDistPaths[output.EntryPoint] = outputPath
+			entryPointsToHashedDistPaths[output.EntryPoint] = path.Join("dist", outputPath)
 		}
 	}
 
@@ -77,39 +100,30 @@ func generateServeIndex() ([]byte, error) {
 	return indexBytes, nil
 }
 
-// EsbuildMetadata is the subset of metadata struct (described by
-// https://esbuild.github.io/api/#metafile) that we care about for mapping
-// from entry points to hashed file names.
-type EsbuildMetadata = struct {
-	Outputs map[string]struct {
-		EntryPoint string `json:"entryPoint,omitempty"`
-	} `json:"outputs,omitempty"`
-}
-
 var entryPointsToDefaultDistPaths = map[string]string{
 	"src/index.css": "dist/index.css",
 	"src/index.js":  "dist/index.js",
 }
 
-func handleServeDist(w http.ResponseWriter, r *http.Request) {
-	p := r.URL.Path[1:]
+func handleServeDist(w http.ResponseWriter, r *http.Request, distFS fs.FS) {
+	path := r.URL.Path
 	var f fs.File
 	// Prefer pre-compressed versions generated during the build step.
 	if tsweb.AcceptsEncoding(r, "br") {
-		if brotliFile, err := embeddedFS.Open(p + ".br"); err == nil {
+		if brotliFile, err := distFS.Open(path + ".br"); err == nil {
 			f = brotliFile
 			w.Header().Set("Content-Encoding", "br")
 		}
 	}
 	if f == nil && tsweb.AcceptsEncoding(r, "gzip") {
-		if gzipFile, err := embeddedFS.Open(p + ".gz"); err == nil {
+		if gzipFile, err := distFS.Open(path + ".gz"); err == nil {
 			f = gzipFile
 			w.Header().Set("Content-Encoding", "gzip")
 		}
 	}
 
 	if f == nil {
-		if rawFile, err := embeddedFS.Open(r.URL.Path[1:]); err == nil {
+		if rawFile, err := distFS.Open(path); err == nil {
 			f = rawFile
 		} else {
 			http.Error(w, err.Error(), http.StatusNotFound)
@@ -130,5 +144,5 @@ func handleServeDist(w http.ResponseWriter, r *http.Request) {
 	w.Header().Set("Cache-Control", "public, max-age=31535996")
 	w.Header().Set("Vary", "Accept-Encoding")
 
-	http.ServeContent(w, r, path.Base(r.URL.Path), serveStartTime, fSeeker)
+	http.ServeContent(w, r, path, serveStartTime, fSeeker)
 }
diff --git a/cmd/tsconnect/tsconnect.go b/cmd/tsconnect/tsconnect.go
index 6beb981ed..d5d152d2f 100644
--- a/cmd/tsconnect/tsconnect.go
+++ b/cmd/tsconnect/tsconnect.go
@@ -18,7 +18,8 @@ import (
 )
 
 var (
-	addr = flag.String("addr", ":9090", "address to listen on")
+	addr    = flag.String("addr", ":9090", "address to listen on")
+	distDir = flag.String("distdir", "./dist", "path of directory to place build output in")
 )
 
 func main() {