diff --git a/cli/server.go b/cli/server.go
index 3b2392f51dd9b..628671a8d7e3c 100644
--- a/cli/server.go
+++ b/cli/server.go
@@ -79,7 +79,7 @@ func server() *cobra.Command {
 		tlsKeyFile                       string
 		tlsMinVersion                    string
 		turnRelayAddress                 string
-		skipTunnel                       bool
+		tunnel                           bool
 		stunServers                      []string
 		traceDatadog                     bool
 		secureAuthCookie                 bool
@@ -138,7 +138,7 @@ func server() *cobra.Command {
 				accessURL = localURL.String()
 			} else {
 				// If an access URL is specified, always skip tunneling.
-				skipTunnel = true
+				tunnel = false
 			}
 
 			var (
@@ -149,7 +149,7 @@ func server() *cobra.Command {
 
 			// If we're attempting to tunnel in dev-mode, the access URL
 			// needs to be changed to use the tunnel.
-			if dev && !skipTunnel {
+			if dev && tunnel {
 				_, _ = fmt.Fprintln(cmd.ErrOrStderr(), cliui.Styles.Wrap.Render(
 					"Coder requires a URL accessible by workspaces you provision. "+
 						"A free tunnel can be created for simple setup. This will "+
@@ -157,12 +157,15 @@ func server() *cobra.Command {
 						cliui.Styles.Field.Render("--access-url")+" can be specified instead.\n",
 				))
 
-				_, err = cliui.Prompt(cmd, cliui.PromptOptions{
-					Text:      "Would you like to start a tunnel for simple setup?",
-					IsConfirm: true,
-				})
-				if errors.Is(err, cliui.Canceled) {
-					return err
+				// This skips the prompt if the flag is explicitly specified.
+				if !cmd.Flags().Changed("tunnel") {
+					_, err = cliui.Prompt(cmd, cliui.PromptOptions{
+						Text:      "Would you like to start a tunnel for simple setup?",
+						IsConfirm: true,
+					})
+					if errors.Is(err, cliui.Canceled) {
+						return err
+					}
 				}
 				if err == nil {
 					accessURL, tunnelErrChan, err = devtunnel.New(ctxTunnel, localURL)
@@ -418,7 +421,7 @@ func server() *cobra.Command {
 				spin.Stop()
 			}
 
-			if dev && !skipTunnel {
+			if dev && tunnel {
 				_, _ = fmt.Fprintf(cmd.OutOrStdout(), cliui.Styles.Prompt.String()+"Waiting for dev tunnel to close...\n")
 				closeTunnel()
 				<-tunnelErrChan
@@ -466,8 +469,8 @@ func server() *cobra.Command {
 		"Specifies the path to the private key for the certificate. It requires a PEM-encoded file")
 	cliflag.StringVarP(root.Flags(), &tlsMinVersion, "tls-min-version", "", "CODER_TLS_MIN_VERSION", "tls12",
 		`Specifies the minimum supported version of TLS. Accepted values are "tls10", "tls11", "tls12" or "tls13"`)
-	cliflag.BoolVarP(root.Flags(), &skipTunnel, "skip-tunnel", "", "CODER_DEV_SKIP_TUNNEL", false, "Skip serving dev mode through an exposed tunnel for simple setup.")
-	_ = root.Flags().MarkHidden("skip-tunnel")
+	cliflag.BoolVarP(root.Flags(), &tunnel, "tunnel", "", "CODER_DEV_TUNNEL", true,
+		"Specifies whether the dev tunnel will be enabled or not. If specified, the interactive prompt will not display.")
 	cliflag.StringArrayVarP(root.Flags(), &stunServers, "stun-server", "", "CODER_STUN_SERVERS", []string{
 		"stun:stun.l.google.com:19302",
 	}, "Specify URLs for STUN servers to enable P2P connections.")
diff --git a/cli/server_test.go b/cli/server_test.go
index 4066cb1e86ea2..f20944367853f 100644
--- a/cli/server_test.go
+++ b/cli/server_test.go
@@ -79,7 +79,7 @@ func TestServer(t *testing.T) {
 
 		wantEmail := "admin@coder.com"
 
-		root, cfg := clitest.New(t, "server", "--dev", "--skip-tunnel", "--address", ":0")
+		root, cfg := clitest.New(t, "server", "--dev", "--tunnel=false", "--address", ":0")
 		var buf strings.Builder
 		root.SetOutput(&buf)
 		var wg sync.WaitGroup
@@ -132,7 +132,7 @@ func TestServer(t *testing.T) {
 		t.Setenv("CODER_DEV_ADMIN_EMAIL", wantEmail)
 		t.Setenv("CODER_DEV_ADMIN_PASSWORD", wantPassword)
 
-		root, cfg := clitest.New(t, "server", "--dev", "--skip-tunnel", "--address", ":0")
+		root, cfg := clitest.New(t, "server", "--dev", "--tunnel=false", "--address", ":0")
 		var buf strings.Builder
 		root.SetOutput(&buf)
 		var wg sync.WaitGroup
@@ -170,7 +170,7 @@ func TestServer(t *testing.T) {
 		t.Parallel()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, _ := clitest.New(t, "server", "--dev", "--skip-tunnel", "--address", ":0",
+		root, _ := clitest.New(t, "server", "--dev", "--tunnel=false", "--address", ":0",
 			"--tls-enable", "--tls-min-version", "tls9")
 		err := root.ExecuteContext(ctx)
 		require.Error(t, err)
@@ -179,7 +179,7 @@ func TestServer(t *testing.T) {
 		t.Parallel()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, _ := clitest.New(t, "server", "--dev", "--skip-tunnel", "--address", ":0",
+		root, _ := clitest.New(t, "server", "--dev", "--tunnel=false", "--address", ":0",
 			"--tls-enable", "--tls-client-auth", "something")
 		err := root.ExecuteContext(ctx)
 		require.Error(t, err)
@@ -188,7 +188,7 @@ func TestServer(t *testing.T) {
 		t.Parallel()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, _ := clitest.New(t, "server", "--dev", "--skip-tunnel", "--address", ":0",
+		root, _ := clitest.New(t, "server", "--dev", "--tunnel=false", "--address", ":0",
 			"--tls-enable")
 		err := root.ExecuteContext(ctx)
 		require.Error(t, err)
@@ -199,7 +199,7 @@ func TestServer(t *testing.T) {
 		defer cancelFunc()
 
 		certPath, keyPath := generateTLSCertificate(t)
-		root, cfg := clitest.New(t, "server", "--dev", "--skip-tunnel", "--address", ":0",
+		root, cfg := clitest.New(t, "server", "--dev", "--tunnel=false", "--address", ":0",
 			"--tls-enable", "--tls-cert-file", certPath, "--tls-key-file", keyPath)
 		go func() {
 			err := root.ExecuteContext(ctx)
@@ -235,7 +235,7 @@ func TestServer(t *testing.T) {
 		}
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, cfg := clitest.New(t, "server", "--dev", "--skip-tunnel", "--address", ":0", "--provisioner-daemons", "0")
+		root, cfg := clitest.New(t, "server", "--dev", "--tunnel=false", "--address", ":0", "--provisioner-daemons", "0")
 		done := make(chan struct{})
 		go func() {
 			defer close(done)
@@ -283,7 +283,7 @@ func TestServer(t *testing.T) {
 		t.Parallel()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, _ := clitest.New(t, "server", "--dev", "--skip-tunnel", "--address", ":0", "--trace-datadog=true")
+		root, _ := clitest.New(t, "server", "--dev", "--tunnel=false", "--address", ":0", "--trace-datadog=true")
 		done := make(chan struct{})
 		go func() {
 			defer close(done)
diff --git a/develop.sh b/develop.sh
index d54af068f2165..da481317ad2dc 100755
--- a/develop.sh
+++ b/develop.sh
@@ -5,6 +5,9 @@ set -euo pipefail
 PROJECT_ROOT="$(git rev-parse --show-toplevel)"
 cd "${PROJECT_ROOT}"
 
+echo '== Run "make build" before running this command to build binaries.'
+echo '== Without these binaries, workspaces will fail to start!'
+
 # Run yarn install, to make sure node_modules are ready to go
 "$PROJECT_ROOT/scripts/yarn_install.sh"
 
@@ -18,6 +21,6 @@ export CODER_DEV_ADMIN_PASSWORD=password
 (
   trap 'kill 0' SIGINT
   CODERV2_HOST=http://127.0.0.1:3000 INSPECT_XSTATE=true yarn --cwd=./site dev &
-  go run cmd/coder/main.go server --dev --skip-tunnel &
+  go run -tags embed cmd/coder/main.go server --dev --tunnel=true &
   wait
 )
diff --git a/go.sum b/go.sum
index d058fc5f0b0e7..99ea1d9935b8f 100644
--- a/go.sum
+++ b/go.sum
@@ -960,7 +960,6 @@ github.com/hashicorp/go.net v0.0.1/go.mod h1:hjKkEWcCURg++eb33jQU7oqQcI9XDCnUzHA
 github.com/hashicorp/golang-lru v0.5.0/go.mod h1:/m3WP610KZHVQ1SGc6re/UDhFvYD7pJ4Ao+sR/qLZy8=
 github.com/hashicorp/golang-lru v0.5.1/go.mod h1:/m3WP610KZHVQ1SGc6re/UDhFvYD7pJ4Ao+sR/qLZy8=
 github.com/hashicorp/golang-lru v0.5.4/go.mod h1:iADmTwqILo4mZ8BN3D2Q6+9jd8WM5uGBxy+E8yxSoD4=
-github.com/hashicorp/hc-install v0.3.1 h1:VIjllE6KyAI1A244G8kTaHXy+TL5/XYzvrtFi8po/Yk=
 github.com/hashicorp/hc-install v0.3.1/go.mod h1:3LCdWcCDS1gaHC9mhHCGbkYfoY6vdsKohGjugbZdZak=
 github.com/hashicorp/hc-install v0.3.2 h1:oiQdJZvXmkNcRcEOOfM5n+VTsvNjWQeOjfAoO6dKSH8=
 github.com/hashicorp/hc-install v0.3.2/go.mod h1:xMG6Tr8Fw1WFjlxH0A9v61cW15pFwgEGqEz0V4jisHs=
diff --git a/site/e2e/playwright.config.ts b/site/e2e/playwright.config.ts
index 365e023d95f3e..a124b9b86d387 100644
--- a/site/e2e/playwright.config.ts
+++ b/site/e2e/playwright.config.ts
@@ -21,7 +21,7 @@ const config: PlaywrightTestConfig = {
     command: `go run -tags embed ${path.join(
       __dirname,
       "../../cmd/coder/main.go",
-    )} server --dev --skip-tunnel --dev-admin-email ${constants.email} --dev-admin-password ${constants.password}`,
+    )} server --dev --tunnel=false --dev-admin-email ${constants.email} --dev-admin-password ${constants.password}`,
     port: 3000,
     timeout: 120 * 10000,
     reuseExistingServer: false,