diff --git a/internal/agent/client.go b/internal/agent/client.go
index 7da6fcd..b437e9e 100644
--- a/internal/agent/client.go
+++ b/internal/agent/client.go
@@ -246,14 +246,14 @@ func (c *Client) handleResponse(resp *http.Response, dst any) error {
 		// Try to parse as JSON error
 		var errResp ErrorResponse
 		if json.Unmarshal(body, &errResp) == nil && errResp.Error != "" {
-			return fmt.Errorf("API error %d: %s", resp.StatusCode, errResp.Error)
+			return &HTTPError{StatusCode: resp.StatusCode, Message: errResp.Error}
 		}
 		// Non-JSON response (e.g. HTML error page) — truncate to something readable
 		msg := string(body)
 		if len(msg) > 120 || strings.Contains(msg, "<html") || strings.Contains(msg, "<!DOCTYPE") {
 			msg = fmt.Sprintf("server returned %s (non-JSON response, likely a server error)", resp.Status)
 		}
-		return fmt.Errorf("API error %d: %s", resp.StatusCode, msg)
+		return &HTTPError{StatusCode: resp.StatusCode, Message: msg}
 	}
 
 	if dst != nil {
diff --git a/internal/agent/daemon.go b/internal/agent/daemon.go
index 7b07cec..451e9d9 100644
--- a/internal/agent/daemon.go
+++ b/internal/agent/daemon.go
@@ -2,10 +2,12 @@ package agent
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"log"
 	"os"
 	"runtime"
+	"strings"
 	"sync/atomic"
 	"time"
 )
@@ -76,6 +78,7 @@ func NewDaemon(cfg DaemonConfig, transport Transport) *Daemon {
 func (d *Daemon) Transport() Transport { return d.transport }
 
 // Register registers the agent and fetches user info + features.
+// Retries with exponential backoff on transient errors (429, 5xx, network).
 func (d *Daemon) Register(ctx context.Context) error {
 	req := RegisterRequest{
 		AgentID:     d.cfg.AgentID,
@@ -90,9 +93,32 @@ func (d *Daemon) Register(ctx context.Context) error {
 		req.DiskTotalBytes = total
 	}
 
-	resp, err := d.transport.Register(ctx, req)
+	const maxRetries = 5
+	backoff := 5 * time.Second
+
+	var resp *RegisterResponse
+	var err error
+	for attempt := range maxRetries {
+		resp, err = d.transport.Register(ctx, req)
+		if err == nil {
+			break
+		}
+		// Only retry on transient errors (429, 5xx, network failures)
+		if !isTransientError(err) {
+			return fmt.Errorf("register: %w", err)
+		}
+		log.Printf("Register failed (attempt %d/%d): %v - retrying in %v", attempt+1, maxRetries, err, backoff)
+		timer := time.NewTimer(backoff)
+		select {
+		case <-ctx.Done():
+			timer.Stop()
+			return fmt.Errorf("register: %w", ctx.Err())
+		case <-timer.C:
+		}
+		backoff = min(backoff*2, 60*time.Second)
+	}
 	if err != nil {
-		return fmt.Errorf("register: %w", err)
+		return fmt.Errorf("register: %w (after %d retries)", err, maxRetries)
 	}
 
 	d.User = resp.User
@@ -118,8 +144,14 @@ func (d *Daemon) Register(ctx context.Context) error {
 	return nil
 }
 
-// Run starts the main daemon loop. Blocks until ctx is cancelled.
+// Run connects the transport, registers the agent, and starts the main loop.
+// Blocks until ctx is cancelled. Callers must NOT call transport.Connect before Run.
 func (d *Daemon) Run(ctx context.Context) error {
+	// Connect transport (establishes WebSocket if available, falls back to HTTP)
+	if err := d.transport.Connect(ctx); err != nil {
+		return fmt.Errorf("connect transport: %w", err)
+	}
+
 	// Register
 	if err := d.Register(ctx); err != nil {
 		return err
@@ -265,6 +297,26 @@ func (d *Daemon) deregister() {
 	RemoveState()
 }
 
+// isTransientError returns true for errors worth retrying (429, 5xx, network).
+func isTransientError(err error) bool {
+	if err == nil {
+		return false
+	}
+	// Structured check: HTTPError carries the status code directly
+	var httpErr *HTTPError
+	if errors.As(err, &httpErr) {
+		return httpErr.StatusCode == 429 || httpErr.StatusCode >= 500
+	}
+	// Fallback: network-level errors (no HTTP response received)
+	lower := strings.ToLower(err.Error())
+	for _, keyword := range []string{"connection refused", "no such host", "timeout", "request failed"} {
+		if strings.Contains(lower, keyword) {
+			return true
+		}
+	}
+	return false
+}
+
 func (d *Daemon) poll(ctx context.Context) {
 	resp, err := d.transport.ClaimTasks(ctx, d.cfg.AgentID)
 	if err != nil {
diff --git a/internal/agent/transport.go b/internal/agent/transport.go
index 4bae6d7..5e223fb 100644
--- a/internal/agent/transport.go
+++ b/internal/agent/transport.go
@@ -6,6 +6,7 @@ import "context"
 // Both WebSocket (via CF Durable Object) and HTTP (direct to origin) implement this.
 type Transport interface {
 	// Connect establishes the transport connection.
+	// Called internally by Daemon.Run — callers must NOT call Connect separately.
 	Connect(ctx context.Context) error
 
 	// Close tears down the connection gracefully.
diff --git a/internal/agent/types.go b/internal/agent/types.go
index 94e4751..dad1ddb 100644
--- a/internal/agent/types.go
+++ b/internal/agent/types.go
@@ -1,6 +1,9 @@
 package agent
 
-import "time"
+import (
+	"fmt"
+	"time"
+)
 
 // RegisterRequest is sent by the CLI on startup to register itself.
 type RegisterRequest struct {
@@ -147,6 +150,17 @@ type ErrorResponse struct {
 	Details any    `json:"details,omitempty"`
 }
 
+// HTTPError represents an HTTP API error with a status code.
+// Use errors.As to extract the status code for retry decisions.
+type HTTPError struct {
+	StatusCode int
+	Message    string
+}
+
+func (e *HTTPError) Error() string {
+	return fmt.Sprintf("API error %d: %s", e.StatusCode, e.Message)
+}
+
 // AgentInfo holds metadata about the running agent for display.
 type AgentInfo struct {
 	ID          string