diff --git a/AGENTS.md b/AGENTS.md
new file mode 100644
index 0000000..8d2bfa6
--- /dev/null
+++ b/AGENTS.md
@@ -0,0 +1,71 @@
+# Conduit — Agent Guidelines
+
+## Project Overview
+
+Conduit is a self-hosted tunneling service (Go, single binary). A **server** (`conduit serve`) runs on a public host and routes incoming HTTP requests by subdomain to registered **tunnels**. A **client** (`conduit tunnel`) connects via WebSocket, receives forwarded traffic, and relays it to a local target using either an HTTP reverse-proxy or raw TCP dial.
+
+## Build & Test
+
+```bash
+# Build all platforms
+make build_local
+
+# Run tests
+make tests              # includes coverage
+
+# Lint
+golangci-lint run
+```
+
+Go 1.25+ is required (`go.mod`). Nix devshell provides Go, gopls, golangci-lint.
+
+## Architecture at a Glance
+
+```
+server/server.go   — Raw TCP listener, reads Host header, routes to tunnel or control API
+tunnel/tunnel.go   — Core Tunnel struct, WebSocket message loop, stream management
+tunnel/forwarder.go — Forwarder interface; factory selects HTTP or TCP forwarder
+tunnel/http_forwarder.go — httputil.ReverseProxy served over net.Pipe via multiConnListener
+tunnel/tcp_forwarder.go  — Direct net.Dial TCP forwarding
+tunnel/stream.go   — Stream interface (io.ReadWriteCloser + Source/Target)
+store/store.go     — In-memory request/response recorder with pub/sub (SSE)
+web/web.go         — Local tunnel monitor (port 8181), SSE endpoint
+config/config.go   — Reflection-based config from struct tags → flags + env vars
+pkg/maps/map.go    — Generic sync.RWMutex-guarded map
+types/message.go   — WebSocket message envelope (data | close)
+```
+
+## Code Conventions
+
+- **Go style**: standard `gofmt`, golangci-lint with `.golangci.toml`
+- **Comment style**: Title Case heading above logical blocks (see root `AGENTS.md`)
+- **Config**: add struct tags (`json`, `default`, `description`) to `ServerConfig` or `ClientConfig` — flags and env vars are auto-derived
+- **Logging**: use `logrus` (`log` alias); structured fields preferred
+- **Concurrency**: use `pkg/maps.Map` for shared maps; protect other shared state with `sync.Mutex`
+- **Error handling**: return errors up; log at command/entry-point level. Use `fmt.Errorf` with `%w` for wrapping
+
+## Key Patterns
+
+1. **Raw TCP → HTTP upgrade**: The server reads from a raw TCP connection to inspect the Host header before deciding whether to handle as a control API request or tunnel the connection via WebSocket.
+2. **Reconstructed connection**: After reading the HTTP request from the raw conn, `reconstructedConn` replays the consumed bytes so the full TCP stream can be forwarded.
+3. **Forwarder abstraction**: `Forwarder` interface decouples tunnel transport from protocol handling. HTTP forwarder uses `net.Pipe` + `multiConnListener` to feed connections into a standard `http.Server`.
+4. **Context-threaded records**: Request records are attached to context in `RecordRequest` and retrieved in `RecordResponse` via the `ModifyResponse` hook.
+
+## Adding a New Forwarder
+
+1. Implement `tunnel.Forwarder` interface (`Type()`, `Initialize()`, `Start()`)
+2. Add a case in `tunnel.NewForwarder()` factory
+3. Add corresponding `ForwarderType` const
+
+## File Locations
+
+| Concern | Files |
+|---------|-------|
+| CLI entry | `main.go`, `cmd/` |
+| Server | `server/` |
+| Tunneling | `tunnel/` |
+| Config | `config/` |
+| Storage | `store/` |
+| Web UI | `web/`, `web/pages/` |
+| Shared types | `types/` |
+| Utilities | `pkg/maps/` |
diff --git a/README.md b/README.md
index d2be5bb..0d17fe9 100644
--- a/README.md
+++ b/README.md
@@ -1,18 +1,143 @@
 # Conduit
 
-A lightweight tunneling service that enables secure connection forwarding through a remote server.
+A lightweight tunneling service that exposes local services to the internet through a public server — similar to ngrok, but self-hosted.
 
-**How:** Deploy Conduit on a public server (e.g., `https://conduit.example.com`) to create tunnels from local services to the internet. Simply point a tunnel to your local endpoint (such as `localhost:8000`) and assign it a custom subdomain identifier like `black-fox-123`. Your local service becomes instantly accessible at `https://black-fox-123.conduit.example.com`.
-
-**Key Benefits:**
-
-- Expose local development servers to the internet
-- Share work-in-progress applications with clients or teammates
-- Test webhooks and external integrations
-- Bypass firewall restrictions for remote access
-
-Perfect for developers who need quick, temporary public access to local services without complex networking setup.
-
-### Example
+Deploy Conduit on a public server (e.g., `https://conduit.example.com`), then create tunnels from your local machine. Point a tunnel at a local endpoint (e.g., `localhost:8000`) and it becomes accessible at a subdomain like `https://black-fox-123.conduit.example.com`.
 
 ![Example](https://gitea.va.reichard.io/evan/conduit/raw/branch/main/assets/example.gif)
+
+## Features
+
+- **HTTP & TCP tunneling** — automatically detected based on the target scheme
+- **Subdomain routing** — each tunnel gets a unique subdomain on the server
+- **Auto-generated tunnel names** — random `color-animal-number` names when none is provided
+- **Local tunnel monitor** — web UI on `:8181` with SSE-based live request/response inspection
+- **API key authentication** — simple shared-key auth between client and server
+- **Minimal footprint** — single binary, no external dependencies
+
+## Architecture
+
+```
+┌──────────────┐         WebSocket          ┌──────────────────┐
+│ conduit      │◄──────────────────────────► │ conduit          │
+│ tunnel       │    (control + streams)      │ serve            │
+│ (client)     │                             │ (public server)  │
+├──────────────┤                             ├──────────────────┤
+│ HTTP Fwd  or │                             │ Raw TCP listener │
+│ TCP Fwd      │                             │ Subdomain router │
+├──────────────┤                             │ WS upgrade       │
+│ Tunnel       │                             └──────────────────┘
+│ Monitor :8181│
+└──────────────┘
+```
+
+The server accepts raw TCP connections, reads the HTTP `Host` header to determine routing. Requests to the base domain hit the control API; requests to subdomains are forwarded over WebSocket to the matching tunnel client. The client then forwards traffic to the local target via either a reverse-proxy (HTTP) or direct TCP dial.
+
+## Quick Start
+
+### Prerequisites
+
+- Go 1.25+ (or Docker)
+
+### Build
+
+```bash
+# Local build (all platforms)
+make build_local
+
+# Docker
+make docker_build_local
+```
+
+### Server
+
+Run the server on a publicly accessible host:
+
+```bash
+conduit serve \
+  --server https://conduit.example.com \
+  --bind 0.0.0.0:8080 \
+  --api_key your-secret-key
+```
+
+Or with Docker:
+
+```bash
+docker run -p 8080:8080 \
+  -e CONDUIT_SERVER=https://conduit.example.com \
+  -e CONDUIT_API_KEY=your-secret-key \
+  conduit:latest
+```
+
+### Client
+
+Create a tunnel to expose a local service:
+
+```bash
+# HTTP tunnel (auto-generates name)
+conduit tunnel \
+  --server https://conduit.example.com \
+  --api_key your-secret-key \
+  --target http://localhost:8000
+
+# Named TCP tunnel
+conduit tunnel \
+  --server https://conduit.example.com \
+  --api_key your-secret-key \
+  --name my-service \
+  --target localhost:5432
+```
+
+The local tunnel monitor is available at `http://localhost:8181` for HTTP tunnels.
+
+## Configuration
+
+All options can be set via CLI flags or environment variables (`CONDUIT_` prefix):
+
+### Server (`conduit serve`)
+
+| Flag | Env Var | Default | Description |
+|------|---------|---------|-------------|
+| `--server` | `CONDUIT_SERVER` | `http://localhost:8080` | Public server address |
+| `--api_key` | `CONDUIT_API_KEY` | — | API key (required) |
+| `--bind` | `CONDUIT_BIND` | `0.0.0.0:8080` | Listen address |
+| `--log_level` | `CONDUIT_LOG_LEVEL` | `info` | Log level |
+| `--log_format` | `CONDUIT_LOG_FORMAT` | `text` | Log format (`text` or `json`) |
+
+### Client (`conduit tunnel`)
+
+| Flag | Env Var | Default | Description |
+|------|---------|---------|-------------|
+| `--server` | `CONDUIT_SERVER` | `http://localhost:8080` | Conduit server address |
+| `--api_key` | `CONDUIT_API_KEY` | — | API key (required) |
+| `--name` | `CONDUIT_NAME` | (auto-generated) | Tunnel subdomain name |
+| `--target` | `CONDUIT_TARGET` | — | Local target address (required) |
+| `--log_level` | `CONDUIT_LOG_LEVEL` | `info` | Log level |
+| `--log_format` | `CONDUIT_LOG_FORMAT` | `text` | Log format (`text` or `json`) |
+
+## Server API
+
+| Endpoint | Description |
+|----------|-------------|
+| `/_conduit/tunnel?tunnelName=<name>&apiKey=<key>` | WebSocket tunnel registration |
+| `/_conduit/info?apiKey=<key>` | JSON list of active tunnels |
+
+## Project Structure
+
+```
+├── cmd/             # Cobra CLI commands (root, serve, tunnel)
+├── config/          # Configuration parsing & logging setup
+├── server/          # TCP listener, subdomain routing, WebSocket upgrade
+├── tunnel/          # Tunnel, Stream, and Forwarder abstractions
+├── store/           # In-memory request/response recording for the monitor
+├── web/             # Local tunnel monitor HTTP server & SSE streaming
+├── types/           # Shared message types
+├── pkg/maps/        # Generic concurrent map
+├── build/           # Compiled binaries (gitignored in practice)
+├── Dockerfile       # Single-stage Docker build
+└── Makefile         # Build & release targets
+```
+
+## License
+
+See repository for license details.
diff --git a/e2e_test.go b/e2e_test.go
new file mode 100644
index 0000000..8a948e6
--- /dev/null
+++ b/e2e_test.go
@@ -0,0 +1,507 @@
+package main
+
+import (
+	"context"
+	"fmt"
+	"io"
+	"net"
+	"net/http"
+	"strings"
+	"sync"
+	"testing"
+	"time"
+
+	"reichard.io/conduit/config"
+	"reichard.io/conduit/server"
+	"reichard.io/conduit/store"
+	"reichard.io/conduit/tunnel"
+	"reichard.io/conduit/web"
+)
+
+// ---------- Helpers ----------
+
+// startConduitServer creates and starts a conduit server on a random port.
+// Returns the server address (host:port) and a cancel func for teardown.
+func startConduitServer(t *testing.T, apiKey string) (string, context.CancelFunc) {
+	t.Helper()
+
+	// Find Free Port
+	port := getFreePort(t)
+	bindAddr := fmt.Sprintf("127.0.0.1:%d", port)
+	serverAddr := fmt.Sprintf("http://%s", bindAddr)
+
+	cfg := &config.ServerConfig{
+		BaseConfig: config.BaseConfig{
+			ServerAddress: serverAddr,
+			APIKey:        apiKey,
+			LogLevel:      "error",
+			LogFormat:     "text",
+		},
+		BindAddress: bindAddr,
+	}
+
+	ctx, cancel := context.WithCancel(context.Background())
+	srv, err := server.NewServer(ctx, cfg)
+	if err != nil {
+		cancel()
+		t.Fatalf("failed to create server: %v", err)
+	}
+
+	// Start Server in Background
+	errCh := make(chan error, 1)
+	go func() { errCh <- srv.Start() }()
+
+	// Wait for Server to Accept
+	waitForPort(t, bindAddr, 3*time.Second)
+
+	// Check Early Errors
+	select {
+	case err := <-errCh:
+		cancel()
+		t.Fatalf("server exited early: %v", err)
+	default:
+	}
+
+	return bindAddr, cancel
+}
+
+// startHTTPTarget creates a simple HTTP server that echoes request info.
+func startHTTPTarget(t *testing.T) (string, context.CancelFunc) {
+	t.Helper()
+
+	port := getFreePort(t)
+	addr := fmt.Sprintf("127.0.0.1:%d", port)
+
+	mux := http.NewServeMux()
+	mux.HandleFunc("/", func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("X-Test-Header", "present")
+		w.WriteHeader(http.StatusOK)
+		fmt.Fprintf(w, "echo: %s %s", r.Method, r.URL.Path)
+	})
+	mux.HandleFunc("/health", func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusOK)
+		w.Write([]byte("ok"))
+	})
+	mux.HandleFunc("/post", func(w http.ResponseWriter, r *http.Request) {
+		body, _ := io.ReadAll(r.Body)
+		w.WriteHeader(http.StatusOK)
+		fmt.Fprintf(w, "received: %s", string(body))
+	})
+
+	srv := &http.Server{Addr: addr, Handler: mux}
+	ctx, cancel := context.WithCancel(context.Background())
+
+	go func() { srv.ListenAndServe() }()
+	go func() { <-ctx.Done(); srv.Close() }()
+
+	waitForPort(t, addr, 3*time.Second)
+
+	return addr, cancel
+}
+
+// startTCPEchoTarget creates a TCP server that echoes back whatever it receives.
+func startTCPEchoTarget(t *testing.T) (string, context.CancelFunc) {
+	t.Helper()
+
+	listener, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("failed to start tcp echo: %v", err)
+	}
+	addr := listener.Addr().String()
+
+	ctx, cancel := context.WithCancel(context.Background())
+
+	go func() {
+		<-ctx.Done()
+		listener.Close()
+	}()
+
+	go func() {
+		for {
+			conn, err := listener.Accept()
+			if err != nil {
+				return
+			}
+			go func(c net.Conn) {
+				defer c.Close()
+				io.Copy(c, c)
+			}(conn)
+		}
+	}()
+
+	return addr, cancel
+}
+
+// connectTunnel creates a conduit tunnel client and starts it.
+func connectTunnel(t *testing.T, serverAddr, targetAddr, tunnelName, apiKey string) context.CancelFunc {
+	t.Helper()
+
+	cfg := &config.ClientConfig{
+		BaseConfig: config.BaseConfig{
+			ServerAddress: fmt.Sprintf("http://%s", serverAddr),
+			APIKey:        apiKey,
+			LogLevel:      "error",
+			LogFormat:     "text",
+		},
+		TunnelName:   tunnelName,
+		TunnelTarget: targetAddr,
+	}
+
+	// Create Tunnel Store
+	tunnelStore := store.NewTunnelStore(100)
+
+	// Create Forwarder
+	forwarder, err := tunnel.NewForwarder(cfg.TunnelTarget, tunnelStore)
+	if err != nil {
+		t.Fatalf("failed to create forwarder: %v", err)
+	}
+
+	var wg sync.WaitGroup
+	ctx, cancel := context.WithCancel(context.Background())
+
+	// Start Forwarder
+	wg.Add(1)
+	go func() {
+		defer wg.Done()
+		forwarder.Start(ctx)
+	}()
+
+	// Create & Start Tunnel
+	tun, err := tunnel.NewClientTunnel(cfg, forwarder)
+	if err != nil {
+		cancel()
+		t.Fatalf("failed to create tunnel: %v", err)
+	}
+
+	wg.Add(1)
+	go func() {
+		defer wg.Done()
+		tun.Start(ctx)
+	}()
+
+	// Start Web Server
+	webServer := web.NewWebServer(tunnelStore)
+	wg.Add(1)
+	go func() {
+		defer wg.Done()
+		webServer.Start(ctx)
+	}()
+
+	// Brief Settle Time
+	time.Sleep(100 * time.Millisecond)
+
+	cleanup := func() {
+		cancel()
+		wg.Wait()
+	}
+	return cleanup
+}
+
+// sendHTTPViaTunnel sends an HTTP request through the conduit server to a tunnel.
+func sendHTTPViaTunnel(t *testing.T, serverAddr, tunnelName, method, path, body string) *http.Response {
+	t.Helper()
+
+	url := fmt.Sprintf("http://%s%s", serverAddr, path)
+	var bodyReader io.Reader
+	if body != "" {
+		bodyReader = strings.NewReader(body)
+	}
+
+	req, err := http.NewRequest(method, url, bodyReader)
+	if err != nil {
+		t.Fatalf("failed to create request: %v", err)
+	}
+
+	// Route via Subdomain
+	req.Host = fmt.Sprintf("%s.%s", tunnelName, serverAddr)
+
+	client := &http.Client{
+		Timeout: 10 * time.Second,
+		Transport: &http.Transport{DisableKeepAlives: true},
+	}
+	resp, err := client.Do(req)
+	if err != nil {
+		t.Fatalf("request failed: %v", err)
+	}
+	return resp
+}
+
+func readBody(t *testing.T, resp *http.Response) string {
+	t.Helper()
+	defer resp.Body.Close()
+	b, err := io.ReadAll(resp.Body)
+	if err != nil {
+		t.Fatalf("failed to read body: %v", err)
+	}
+	return string(b)
+}
+
+func getFreePort(t *testing.T) int {
+	t.Helper()
+	l, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("failed to get free port: %v", err)
+	}
+	port := l.Addr().(*net.TCPAddr).Port
+	l.Close()
+	return port
+}
+
+func waitForPort(t *testing.T, addr string, timeout time.Duration) {
+	t.Helper()
+	deadline := time.Now().Add(timeout)
+	for time.Now().Before(deadline) {
+		conn, err := net.DialTimeout("tcp", addr, 100*time.Millisecond)
+		if err == nil {
+			conn.Close()
+			return
+		}
+		time.Sleep(25 * time.Millisecond)
+	}
+	t.Fatalf("port %s not ready after %s", addr, timeout)
+}
+
+// ---------- Tests ----------
+
+func TestHTTPTunnelRoundTrip(t *testing.T) {
+	apiKey := "test-key-http"
+
+	// Start Target HTTP Server
+	targetAddr, stopTarget := startHTTPTarget(t)
+	defer stopTarget()
+
+	// Start Conduit Server
+	serverAddr, stopServer := startConduitServer(t, apiKey)
+	defer stopServer()
+
+	// Connect Tunnel
+	stopTunnel := connectTunnel(t, serverAddr, fmt.Sprintf("http://%s", targetAddr), "http-test", apiKey)
+	defer stopTunnel()
+
+	// GET /
+	resp := sendHTTPViaTunnel(t, serverAddr, "http-test", "GET", "/", "")
+	body := readBody(t, resp)
+
+	if resp.StatusCode != http.StatusOK {
+		t.Errorf("expected 200, got %d", resp.StatusCode)
+	}
+	if !strings.Contains(body, "echo: GET /") {
+		t.Errorf("unexpected body: %s", body)
+	}
+
+	// GET /health
+	resp = sendHTTPViaTunnel(t, serverAddr, "http-test", "GET", "/health", "")
+	body = readBody(t, resp)
+
+	if resp.StatusCode != http.StatusOK {
+		t.Errorf("expected 200, got %d", resp.StatusCode)
+	}
+	if body != "ok" {
+		t.Errorf("expected 'ok', got %q", body)
+	}
+}
+
+func TestHTTPTunnelPOST(t *testing.T) {
+	apiKey := "test-key-post"
+
+	// Start Target HTTP Server
+	targetAddr, stopTarget := startHTTPTarget(t)
+	defer stopTarget()
+
+	// Start Conduit Server
+	serverAddr, stopServer := startConduitServer(t, apiKey)
+	defer stopServer()
+
+	// Connect Tunnel
+	stopTunnel := connectTunnel(t, serverAddr, fmt.Sprintf("http://%s", targetAddr), "post-test", apiKey)
+	defer stopTunnel()
+
+	// POST /post
+	resp := sendHTTPViaTunnel(t, serverAddr, "post-test", "POST", "/post", "hello world")
+	body := readBody(t, resp)
+
+	if resp.StatusCode != http.StatusOK {
+		t.Errorf("expected 200, got %d", resp.StatusCode)
+	}
+	if !strings.Contains(body, "received: hello world") {
+		t.Errorf("unexpected body: %s", body)
+	}
+}
+
+func TestUnknownTunnelReturns404(t *testing.T) {
+	apiKey := "test-key-404"
+
+	// Start Conduit Server
+	serverAddr, stopServer := startConduitServer(t, apiKey)
+	defer stopServer()
+
+	// Request to Non-Existent Tunnel
+	resp := sendHTTPViaTunnel(t, serverAddr, "no-such-tunnel", "GET", "/", "")
+	body := readBody(t, resp)
+
+	if resp.StatusCode != http.StatusNotFound {
+		t.Errorf("expected 404, got %d", resp.StatusCode)
+	}
+	if !strings.Contains(body, "unknown tunnel") {
+		t.Errorf("expected 'unknown tunnel' error, got: %s", body)
+	}
+}
+
+func TestDuplicateTunnelNameRejected(t *testing.T) {
+	apiKey := "test-key-dup"
+
+	// Start Target HTTP Server
+	targetAddr, stopTarget := startHTTPTarget(t)
+	defer stopTarget()
+
+	// Start Conduit Server
+	serverAddr, stopServer := startConduitServer(t, apiKey)
+	defer stopServer()
+
+	// Connect First Tunnel
+	stopTunnel1 := connectTunnel(t, serverAddr, fmt.Sprintf("http://%s", targetAddr), "dup-test", apiKey)
+	defer stopTunnel1()
+
+	// Attempt Duplicate — this should fail at WebSocket dial
+	cfg := &config.ClientConfig{
+		BaseConfig: config.BaseConfig{
+			ServerAddress: fmt.Sprintf("http://%s", serverAddr),
+			APIKey:        apiKey,
+			LogLevel:      "error",
+			LogFormat:     "text",
+		},
+		TunnelName:   "dup-test",
+		TunnelTarget: fmt.Sprintf("http://%s", targetAddr),
+	}
+
+	tunnelStore := store.NewTunnelStore(100)
+	forwarder, err := tunnel.NewForwarder(cfg.TunnelTarget, tunnelStore)
+	if err != nil {
+		t.Fatalf("failed to create forwarder: %v", err)
+	}
+
+	_, err = tunnel.NewClientTunnel(cfg, forwarder)
+	if err == nil {
+		t.Error("expected error for duplicate tunnel name, got nil")
+	}
+}
+
+func TestUnauthorizedControlAccess(t *testing.T) {
+	apiKey := "test-key-auth"
+
+	// Start Conduit Server
+	serverAddr, stopServer := startConduitServer(t, apiKey)
+	defer stopServer()
+
+	// Request Info with Wrong API Key
+	url := fmt.Sprintf("http://%s/_conduit/info?apiKey=wrong-key", serverAddr)
+	req, _ := http.NewRequest("GET", url, nil)
+	req.Host = serverAddr
+
+	resp, err := http.DefaultClient.Do(req)
+	if err != nil {
+		t.Fatalf("request failed: %v", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode != http.StatusUnauthorized {
+		t.Errorf("expected 401, got %d", resp.StatusCode)
+	}
+}
+
+func TestInfoEndpointListsTunnels(t *testing.T) {
+	apiKey := "test-key-info"
+
+	// Start Target HTTP Server
+	targetAddr, stopTarget := startHTTPTarget(t)
+	defer stopTarget()
+
+	// Start Conduit Server
+	serverAddr, stopServer := startConduitServer(t, apiKey)
+	defer stopServer()
+
+	// Connect Tunnel
+	stopTunnel := connectTunnel(t, serverAddr, fmt.Sprintf("http://%s", targetAddr), "info-test", apiKey)
+	defer stopTunnel()
+
+	// Query Info Endpoint
+	url := fmt.Sprintf("http://%s/_conduit/info?apiKey=%s", serverAddr, apiKey)
+	req, _ := http.NewRequest("GET", url, nil)
+	req.Host = serverAddr
+
+	resp, err := http.DefaultClient.Do(req)
+	if err != nil {
+		t.Fatalf("request failed: %v", err)
+	}
+	body := readBody(t, resp)
+
+	if resp.StatusCode != http.StatusOK {
+		t.Errorf("expected 200, got %d", resp.StatusCode)
+	}
+	if !strings.Contains(body, "info-test") {
+		t.Errorf("expected tunnel 'info-test' in response: %s", body)
+	}
+}
+
+func TestMultipleTunnelsRouteCorrectly(t *testing.T) {
+	apiKey := "test-key-multi"
+
+	// Start Two Separate Target Servers
+	target1Addr, stopTarget1 := startHTTPTarget(t)
+	defer stopTarget1()
+
+	port2 := getFreePort(t)
+	addr2 := fmt.Sprintf("127.0.0.1:%d", port2)
+	mux2 := http.NewServeMux()
+	mux2.HandleFunc("/", func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusOK)
+		fmt.Fprint(w, "target-two")
+	})
+	srv2 := &http.Server{Addr: addr2, Handler: mux2}
+	go srv2.ListenAndServe()
+	defer srv2.Close()
+	waitForPort(t, addr2, 3*time.Second)
+
+	// Start Conduit Server
+	serverAddr, stopServer := startConduitServer(t, apiKey)
+	defer stopServer()
+
+	// Connect Two Tunnels
+	stopTunnel1 := connectTunnel(t, serverAddr, fmt.Sprintf("http://%s", target1Addr), "multi-one", apiKey)
+	defer stopTunnel1()
+
+	stopTunnel2 := connectTunnel(t, serverAddr, fmt.Sprintf("http://%s", addr2), "multi-two", apiKey)
+	defer stopTunnel2()
+
+	// Request to First Tunnel
+	resp1 := sendHTTPViaTunnel(t, serverAddr, "multi-one", "GET", "/", "")
+	body1 := readBody(t, resp1)
+	if !strings.Contains(body1, "echo: GET /") {
+		t.Errorf("tunnel one unexpected body: %s", body1)
+	}
+
+	// Request to Second Tunnel
+	resp2 := sendHTTPViaTunnel(t, serverAddr, "multi-two", "GET", "/", "")
+	body2 := readBody(t, resp2)
+	if body2 != "target-two" {
+		t.Errorf("tunnel two expected 'target-two', got: %s", body2)
+	}
+}
+
+func TestServerGracefulShutdown(t *testing.T) {
+	apiKey := "test-key-shutdown"
+
+	// Start Conduit Server
+	serverAddr, stopServer := startConduitServer(t, apiKey)
+
+	// Cancel Server
+	stopServer()
+
+	// Verify Port Is Closed
+	time.Sleep(200 * time.Millisecond)
+	conn, err := net.DialTimeout("tcp", serverAddr, 500*time.Millisecond)
+	if err == nil {
+		conn.Close()
+		t.Error("expected server port to be closed after shutdown")
+	}
+}
diff --git a/flake.lock b/flake.lock
index 9aa7f11..dedd329 100644
--- a/flake.lock
+++ b/flake.lock
@@ -20,11 +20,11 @@
     },
     "nixpkgs": {
       "locked": {
-        "lastModified": 1760038930,
-        "narHash": "sha256-Oncbh0UmHjSlxO7ErQDM3KM0A5/Znfofj2BSzlHLeVw=",
+        "lastModified": 1777578337,
+        "narHash": "sha256-Ad49moKWeXtKBJNy2ebiTQUEgdLyvGmTeykAQ9xM+Z4=",
         "owner": "NixOS",
         "repo": "nixpkgs",
-        "rev": "0b4defa2584313f3b781240b29d61f6f9f7e0df3",
+        "rev": "15f4ee454b1dce334612fa6843b3e05cf546efab",
         "type": "github"
       },
       "original": {
diff --git a/flake.nix b/flake.nix
index 7ce2df7..caeec10 100644
--- a/flake.nix
+++ b/flake.nix
@@ -6,8 +6,14 @@
     flake-utils.url = "github:numtide/flake-utils";
   };
 
-  outputs = { self, nixpkgs, flake-utils }:
-    flake-utils.lib.eachDefaultSystem (system:
+  outputs =
+    { self
+    , nixpkgs
+    , flake-utils
+    ,
+    }:
+    flake-utils.lib.eachDefaultSystem (
+      system:
       let
         pkgs = nixpkgs.legacyPackages.${system};
       in
@@ -15,6 +21,7 @@
         devShells.default = pkgs.mkShell {
           packages = with pkgs; [
             go
+            gopls
             golangci-lint
           ];
           shellHook = ''
diff --git a/pkg/maps/map.go b/pkg/maps/map.go
index 3cbedb7..c18be59 100644
--- a/pkg/maps/map.go
+++ b/pkg/maps/map.go
@@ -42,6 +42,8 @@ func (m *Map[K, V]) HasKey(key K) bool {
 
 func (m *Map[K, V]) Entries() iter.Seq2[K, V] {
 	return func(yield func(K, V) bool) {
+		m.mu.RLock()
+		defer m.mu.RUnlock()
 		for k, v := range m.items {
 			if !yield(k, v) {
 				return
diff --git a/server/server.go b/server/server.go
index b1ef1ce..38a057c 100644
--- a/server/server.go
+++ b/server/server.go
@@ -70,11 +70,23 @@ func (s *Server) Start() error {
 	}
 	defer listener.Close()
 
+	// Context Cancellation - Close the listener when the context is cancelled
+	// so that Accept() unblocks and the loop exits cleanly.
+	go func() {
+		<-s.ctx.Done()
+		listener.Close()
+	}()
+
 	// Start Listening
 	log.Infof("conduit server listening on %s", s.cfg.BindAddress)
 	for {
 		conn, err := listener.Accept()
 		if err != nil {
+			// Expected Error on Shutdown
+			if s.ctx.Err() != nil {
+				log.Info("conduit server shutting down")
+				return nil
+			}
 			log.WithError(err).Error("error accepting connection")
 			continue
 		}