diff --git a/internal/runtime/executor/codex_websockets_connect_retry_test.go b/internal/runtime/executor/codex_websockets_connect_retry_test.go
new file mode 100644
index 00000000000..469c2fc3ab6
--- /dev/null
+++ b/internal/runtime/executor/codex_websockets_connect_retry_test.go
@@ -0,0 +1,81 @@
+package executor
+
+import (
+	"context"
+	"net/http"
+	"net/http/httptest"
+	"strings"
+	"sync/atomic"
+	"testing"
+	"time"
+
+	"github.com/gorilla/websocket"
+	"github.com/router-for-me/CLIProxyAPI/v8/internal/config"
+	cliproxyauth "github.com/router-for-me/CLIProxyAPI/v8/sdk/cliproxy/auth"
+)
+
+func TestCodexWebsocketConnectRetriesHandshakeEOF(t *testing.T) {
+	for _, tc := range []struct {
+		name      string
+		failures  int32
+		status    int
+		wantDials int32
+		wantErr   bool
+	}{
+		{name: "third_retry_succeeds", failures: 3, wantDials: 4},
+		{name: "exhausted", failures: 10, wantDials: 4, wantErr: true},
+		{name: "status_not_retried", status: http.StatusBadGateway, wantDials: 1, wantErr: true},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			var dials atomic.Int32
+			upgrader := websocket.Upgrader{}
+			server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+				attempt := dials.Add(1)
+				if tc.status != 0 {
+					http.Error(w, "rejected", tc.status)
+					return
+				}
+				if attempt <= tc.failures {
+					raw, _, err := w.(http.Hijacker).Hijack()
+					if err != nil {
+						t.Error(err)
+						return
+					}
+					_ = raw.Close()
+					return
+				}
+				conn, err := upgrader.Upgrade(w, r, nil)
+				if err != nil {
+					t.Error(err)
+					return
+				}
+				_ = conn.Close()
+			}))
+			defer server.Close()
+			ctx, cancel := context.WithTimeout(t.Context(), 5*time.Second)
+			defer cancel()
+			exec := NewCodexWebsocketsExecutor(&config.Config{})
+			conn, closer, resp, err := exec.dialCodexWebsocket(ctx, &cliproxyauth.Auth{ProxyURL: "direct"}, "ws"+strings.TrimPrefix(server.URL, "http"), nil)
+			if resp != nil {
+				defer func() {
+					if errClose := resp.Body.Close(); errClose != nil {
+						t.Errorf("close response body: %v", errClose)
+					}
+				}()
+			}
+			if closer != nil {
+				defer func() {
+					if errClose := closer.Close(); errClose != nil {
+						t.Errorf("close websocket: %v", errClose)
+					}
+				}()
+			}
+			if (err != nil) != tc.wantErr || (err == nil && conn == nil) {
+				t.Errorf("dial error = %v, wantErr %v", err, tc.wantErr)
+			}
+			if got := dials.Load(); got != tc.wantDials {
+				t.Errorf("dial attempts = %d, want %d", got, tc.wantDials)
+			}
+		})
+	}
+}
diff --git a/internal/runtime/executor/codex_websockets_connection.go b/internal/runtime/executor/codex_websockets_connection.go
index 5af93548d34..64ce227d6b9 100644
--- a/internal/runtime/executor/codex_websockets_connection.go
+++ b/internal/runtime/executor/codex_websockets_connection.go
@@ -5,6 +5,7 @@ import (
 	"context"
 	"errors"
 	"fmt"
+	"io"
 	"net"
 	"net/http"
 	"net/url"
@@ -36,9 +37,29 @@ func (e *CodexWebsocketsExecutor) dialCodexWebsocket(ctx context.Context, auth *
 	if ctx == nil {
 		ctx = context.Background()
 	}
-	conn, resp, err := dialer.DialContext(ctx, wsURL, headers)
-	if err != nil {
+	// An EOF before any HTTP response is retried on a fresh connection; no response.create
+	// has been sent yet. All attempts share the one handshake time budget.
+	dialCtx, cancelDial := context.WithTimeout(ctx, codexResponsesWebsocketHandshakeTO)
+	defer cancelDial()
+	var conn *websocket.Conn
+	var resp *http.Response
+	var err error
+	for retry := 0; ; retry++ {
+		conn, resp, err = dialer.DialContext(dialCtx, wsURL, headers)
+		if err == nil {
+			break
+		}
 		cliproxyexecutor.MarkUpstreamAttempt(ctx)
+		if resp != nil || retry == 3 || !(errors.Is(err, io.EOF) || errors.Is(err, io.ErrUnexpectedEOF)) {
+			break
+		}
+		timer := time.NewTimer(time.Duration(100<<retry) * time.Millisecond)
+		select {
+		case <-dialCtx.Done():
+			timer.Stop()
+			return nil, nil, nil, dialCtx.Err()
+		case <-timer.C:
+		}
 	}
 	closer := newWebsocketConnectionCloser(conn)
 	if conn != nil {