diff --git a/mcp/payment/blockrun_base.go b/mcp/payment/blockrun_base.go
index 5953417e..edc27ad5 100644
--- a/mcp/payment/blockrun_base.go
+++ b/mcp/payment/blockrun_base.go
@@ -72,6 +72,7 @@ func NewBlockRunBaseClientWithOptions(opts ...mcp.ClientOption) mcp.AIClient {
 		mcp.WithProvider(mcp.ProviderBlockRunBase),
 		mcp.WithModel(DefaultBlockRunModel),
 		mcp.WithBaseURL(DefaultBlockRunBaseURL),
+		mcp.WithTimeout(X402Timeout),
 	}
 	allOpts := append(baseOpts, opts...)
 	baseClient := mcp.NewClient(allOpts...).(*mcp.Client)
diff --git a/mcp/payment/blockrun_sol.go b/mcp/payment/blockrun_sol.go
index dc78c29e..3cad783e 100644
--- a/mcp/payment/blockrun_sol.go
+++ b/mcp/payment/blockrun_sol.go
@@ -52,6 +52,7 @@ func NewBlockRunSolClientWithOptions(opts ...mcp.ClientOption) mcp.AIClient {
 		mcp.WithProvider(mcp.ProviderBlockRunSol),
 		mcp.WithModel(DefaultBlockRunModel),
 		mcp.WithBaseURL(DefaultBlockRunSolURL),
+		mcp.WithTimeout(X402Timeout),
 	}
 	allOpts := append(baseOpts, opts...)
 	baseClient := mcp.NewClient(allOpts...).(*mcp.Client)
diff --git a/mcp/payment/claw402.go b/mcp/payment/claw402.go
index 177f0626..90713f59 100644
--- a/mcp/payment/claw402.go
+++ b/mcp/payment/claw402.go
@@ -69,6 +69,7 @@ func NewClaw402ClientWithOptions(opts ...mcp.ClientOption) mcp.AIClient {
 		mcp.WithProvider(mcp.ProviderClaw402),
 		mcp.WithModel(DefaultClaw402Model),
 		mcp.WithBaseURL(DefaultClaw402URL),
+		mcp.WithTimeout(X402Timeout),
 	}
 	allOpts := append(baseOpts, opts...)
 	baseClient := mcp.NewClient(allOpts...).(*mcp.Client)
diff --git a/mcp/payment/x402.go b/mcp/payment/x402.go
index 852d2fc1..7116f503 100644
--- a/mcp/payment/x402.go
+++ b/mcp/payment/x402.go
@@ -16,12 +16,17 @@ import (
 )
 
 const (
-	// X402MaxPaymentRetries is the number of retries for 5xx errors on the
-	// payment-signed request. The same payment signature is reused (no double-charge).
-	X402MaxPaymentRetries = 3
+	// X402MaxPaymentRetries is the number of retries for 5xx/expired-402 errors
+	// on the payment-signed request. Payment is re-signed on 402 (no double-charge).
+	X402MaxPaymentRetries = 5
 
 	// X402RetryBaseWait is the base wait between payment retry attempts.
 	X402RetryBaseWait = 3 * time.Second
+
+	// X402Timeout is the HTTP timeout for x402 payment providers.
+	// AI inference (especially DeepSeek) can take several minutes; the default
+	// 120s causes premature timeouts that trigger duplicate payments.
+	X402Timeout = 5 * time.Minute
 )
 
 // ── Shared x402 types ────────────────────────────────────────────────────────
@@ -131,7 +136,7 @@ func DoX402Request(
 			return nil, fmt.Errorf("failed to sign x402 payment: %w", err)
 		}
 
-		// Retry loop for 5xx errors on the payment-signed request.
+		// Retry loop for 5xx / expired-402 errors on the payment-signed request.
 		var lastBody []byte
 		var lastStatus int
 		for attempt := 1; attempt <= X402MaxPaymentRetries; attempt++ {
@@ -173,16 +178,41 @@ func DoX402Request(
 			lastBody = body2
 			lastStatus = resp2.StatusCode
 
-			// Retry on 5xx server errors
-			if resp2.StatusCode >= 500 && attempt < X402MaxPaymentRetries {
+			retryable := resp2.StatusCode >= 500 || resp2.StatusCode == http.StatusPaymentRequired
+
+			if retryable && attempt < X402MaxPaymentRetries {
 				wait := X402RetryBaseWait * time.Duration(attempt)
-				logger.Warnf("⚠️  [%s] Server error (status %d), retrying in %v (%d/%d)...",
-					providerTag, resp2.StatusCode, wait, attempt+1, X402MaxPaymentRetries)
+
+				// If we got 402 again, the payment signature expired — re-sign.
+				if resp2.StatusCode == http.StatusPaymentRequired {
+					newHeader := resp2.Header.Get("Payment-Required")
+					if newHeader == "" {
+						newHeader = resp2.Header.Get("X-Payment-Required")
+					}
+					if newHeader != "" {
+						newSig, signErr := signFn(newHeader)
+						if signErr == nil {
+							paymentSig = newSig
+							logger.Warnf("⚠️  [%s] Payment expired (402), re-signed and retrying in %v (%d/%d)...",
+								providerTag, wait, attempt+1, X402MaxPaymentRetries)
+						} else {
+							logger.Warnf("⚠️  [%s] Payment expired (402), re-sign failed: %v, retrying in %v (%d/%d)...",
+								providerTag, signErr, wait, attempt+1, X402MaxPaymentRetries)
+						}
+					} else {
+						logger.Warnf("⚠️  [%s] Got 402 but no new Payment-Required header, retrying in %v (%d/%d)...",
+							providerTag, wait, attempt+1, X402MaxPaymentRetries)
+					}
+				} else {
+					logger.Warnf("⚠️  [%s] Server error (status %d), retrying in %v (%d/%d)...",
+						providerTag, resp2.StatusCode, wait, attempt+1, X402MaxPaymentRetries)
+				}
+
 				time.Sleep(wait)
 				continue
 			}
 
-			// Non-5xx error or final attempt — fail
+			// Non-retryable error or final attempt — fail
 			break
 		}