diff --git a/internal/config/config.go b/internal/config/config.go
index 5a6595f778..d7b10afec2 100644
--- a/internal/config/config.go
+++ b/internal/config/config.go
@@ -339,6 +339,16 @@ type ClaudeKey struct {
 	// ExcludedModels lists model IDs that should be excluded for this provider.
 	ExcludedModels []string `yaml:"excluded-models,omitempty" json:"excluded-models,omitempty"`
 
+	// ResponseHeaderTimeout limits how long to wait for the upstream to start
+	// responding (in seconds). Once the first response byte arrives, this timeout
+	// no longer applies — streaming responses are not affected. 0 means no timeout.
+	ResponseHeaderTimeout int `yaml:"response-header-timeout,omitempty" json:"response-header-timeout,omitempty"`
+
+	// TransientErrorCooldown overrides the default 1-minute cooldown applied when
+	// a transient error (408/500/502/503/504/524) is received from this upstream
+	// (in seconds). 0 means use the default (60s).
+	TransientErrorCooldown int `yaml:"transient-error-cooldown,omitempty" json:"transient-error-cooldown,omitempty"`
+
 	// Cloak configures request cloaking for non-Claude-Code clients.
 	Cloak *CloakConfig `yaml:"cloak,omitempty" json:"cloak,omitempty"`
 }
diff --git a/internal/runtime/executor/claude_executor.go b/internal/runtime/executor/claude_executor.go
index 82b12a2f80..9baeec28cb 100644
--- a/internal/runtime/executor/claude_executor.go
+++ b/internal/runtime/executor/claude_executor.go
@@ -12,6 +12,7 @@ import (
 	"encoding/json"
 	"fmt"
 	"io"
+	"net"
 	"net/http"
 	"net/textproto"
 	"runtime"
@@ -183,6 +184,9 @@ func (e *ClaudeExecutor) Execute(ctx context.Context, auth *cliproxyauth.Auth, r
 	httpResp, err := httpClient.Do(httpReq)
 	if err != nil {
 		recordAPIResponseError(ctx, e.cfg, err)
+		if netErr, ok := err.(net.Error); ok && netErr.Timeout() {
+			return resp, statusErr{code: http.StatusGatewayTimeout, msg: fmt.Sprintf("upstream timeout: %v", err)}
+		}
 		return resp, err
 	}
 	recordAPIResponseMetadata(ctx, e.cfg, httpResp.StatusCode, httpResp.Header.Clone())
@@ -346,6 +350,9 @@ func (e *ClaudeExecutor) ExecuteStream(ctx context.Context, auth *cliproxyauth.A
 	httpResp, err := httpClient.Do(httpReq)
 	if err != nil {
 		recordAPIResponseError(ctx, e.cfg, err)
+		if netErr, ok := err.(net.Error); ok && netErr.Timeout() {
+			return nil, statusErr{code: http.StatusGatewayTimeout, msg: fmt.Sprintf("upstream timeout: %v", err)}
+		}
 		return nil, err
 	}
 	recordAPIResponseMetadata(ctx, e.cfg, httpResp.StatusCode, httpResp.Header.Clone())
diff --git a/internal/runtime/executor/proxy_helpers.go b/internal/runtime/executor/proxy_helpers.go
index ab0f626acc..7bc8b9575c 100644
--- a/internal/runtime/executor/proxy_helpers.go
+++ b/internal/runtime/executor/proxy_helpers.go
@@ -5,6 +5,7 @@ import (
 	"net"
 	"net/http"
 	"net/url"
+	"strconv"
 	"strings"
 	"time"
 
@@ -33,6 +34,16 @@ func newProxyAwareHTTPClient(ctx context.Context, cfg *config.Config, auth *clip
 		httpClient.Timeout = timeout
 	}
 
+	// Read per-auth response header timeout from attributes.
+	var respHeaderTimeout time.Duration
+	if auth != nil && auth.Attributes != nil {
+		if v, ok := auth.Attributes["response_header_timeout"]; ok {
+			if secs, err := strconv.Atoi(v); err == nil && secs > 0 {
+				respHeaderTimeout = time.Duration(secs) * time.Second
+			}
+		}
+	}
+
 	// Priority 1: Use auth.ProxyURL if configured
 	var proxyURL string
 	if auth != nil {
@@ -48,6 +59,9 @@ func newProxyAwareHTTPClient(ctx context.Context, cfg *config.Config, auth *clip
 	if proxyURL != "" {
 		transport := buildProxyTransport(proxyURL)
 		if transport != nil {
+			if respHeaderTimeout > 0 {
+				transport.ResponseHeaderTimeout = respHeaderTimeout
+			}
 			httpClient.Transport = transport
 			return httpClient
 		}
@@ -60,6 +74,20 @@ func newProxyAwareHTTPClient(ctx context.Context, cfg *config.Config, auth *clip
 		httpClient.Transport = rt
 	}
 
+	// Apply ResponseHeaderTimeout if set.
+	if respHeaderTimeout > 0 {
+		if transport, ok := httpClient.Transport.(*http.Transport); ok {
+			// Clone the transport to avoid modifying a shared instance.
+			clonedTransport := transport.Clone()
+			clonedTransport.ResponseHeaderTimeout = respHeaderTimeout
+			httpClient.Transport = clonedTransport
+		} else if httpClient.Transport == nil {
+			transport := http.DefaultTransport.(*http.Transport).Clone()
+			transport.ResponseHeaderTimeout = respHeaderTimeout
+			httpClient.Transport = transport
+		}
+	}
+
 	return httpClient
 }
 
diff --git a/internal/watcher/synthesizer/config.go b/internal/watcher/synthesizer/config.go
index 52ae9a4808..ad36edf724 100644
--- a/internal/watcher/synthesizer/config.go
+++ b/internal/watcher/synthesizer/config.go
@@ -116,6 +116,12 @@ func (s *ConfigSynthesizer) synthesizeClaudeKeys(ctx *SynthesisContext) []*corea
 		if hash := diff.ComputeClaudeModelsHash(ck.Models); hash != "" {
 			attrs["models_hash"] = hash
 		}
+		if ck.ResponseHeaderTimeout > 0 {
+			attrs["response_header_timeout"] = strconv.Itoa(ck.ResponseHeaderTimeout)
+		}
+		if ck.TransientErrorCooldown > 0 {
+			attrs["transient_error_cooldown"] = strconv.Itoa(ck.TransientErrorCooldown)
+		}
 		addConfigHeadersToAttrs(ck.Headers, attrs)
 		proxyURL := strings.TrimSpace(ck.ProxyURL)
 		a := &coreauth.Auth{
diff --git a/sdk/cliproxy/auth/conductor.go b/sdk/cliproxy/auth/conductor.go
index b29e04db8c..c087a9937b 100644
--- a/sdk/cliproxy/auth/conductor.go
+++ b/sdk/cliproxy/auth/conductor.go
@@ -1665,11 +1665,19 @@ func (m *Manager) MarkResult(ctx context.Context, result Result) {
 					suspendReason = "quota"
 					shouldSuspendModel = true
 					setModelQuota = true
-				case 408, 500, 502, 503, 504:
+				case 408, 500, 502, 503, 504, 524:
 					if quotaCooldownDisabledForAuth(auth) {
 						state.NextRetryAfter = time.Time{}
 					} else {
-						next := now.Add(1 * time.Minute)
+						cooldown := 1 * time.Minute
+						if auth.Attributes != nil {
+							if v, ok := auth.Attributes["transient_error_cooldown"]; ok {
+								if secs, err := strconv.Atoi(v); err == nil && secs > 0 {
+									cooldown = time.Duration(secs) * time.Second
+								}
+							}
+						}
+						next := now.Add(cooldown)
 						state.NextRetryAfter = next
 					}
 				default:
@@ -1942,12 +1950,20 @@ func applyAuthFailureState(auth *Auth, resultErr *Error, retryAfter *time.Durati
 		}
 		auth.Quota.NextRecoverAt = next
 		auth.NextRetryAfter = next
-	case 408, 500, 502, 503, 504:
+	case 408, 500, 502, 503, 504, 524:
 		auth.StatusMessage = "transient upstream error"
 		if quotaCooldownDisabledForAuth(auth) {
 			auth.NextRetryAfter = time.Time{}
 		} else {
-			auth.NextRetryAfter = now.Add(1 * time.Minute)
+			cooldown := 1 * time.Minute
+			if auth.Attributes != nil {
+				if v, ok := auth.Attributes["transient_error_cooldown"]; ok {
+					if secs, err := strconv.Atoi(v); err == nil && secs > 0 {
+						cooldown = time.Duration(secs) * time.Second
+					}
+				}
+			}
+			auth.NextRetryAfter = now.Add(cooldown)
 		}
 	default:
 		if auth.StatusMessage == "" {