diff --git a/pkg/agent/loop_execute_llm.go b/pkg/agent/loop_execute_llm.go
index 50e10d082..fd4ec75f4 100644
--- a/pkg/agent/loop_execute_llm.go
+++ b/pkg/agent/loop_execute_llm.go
@@ -4,7 +4,6 @@ import (
 	"context"
 	"errors"
 	"fmt"
-	"strings"
 	"time"
 
 	"jane/pkg/bus"
@@ -77,25 +76,27 @@ func (al *AgentLoop) executeLLMWithRetry(
 			break
 		}
 
-		errMsg := strings.ToLower(err.Error())
+		isTimeoutError := false
+		isContextError := false
 
-		// Check if this is a network/HTTP timeout — not a context window error.
-		isTimeoutError := errors.Is(err, context.DeadlineExceeded) ||
-			strings.Contains(errMsg, "deadline exceeded") ||
-			strings.Contains(errMsg, "client.timeout") ||
-			strings.Contains(errMsg, "timed out") ||
-			strings.Contains(errMsg, "timeout exceeded")
-
-		// Detect real context window / token limit errors, excluding network timeouts.
-		isContextError := !isTimeoutError && (strings.Contains(errMsg, "context_length_exceeded") ||
-			strings.Contains(errMsg, "context window") ||
-			strings.Contains(errMsg, "maximum context length") ||
-			strings.Contains(errMsg, "token limit") ||
-			strings.Contains(errMsg, "too many tokens") ||
-			strings.Contains(errMsg, "max_tokens") ||
-			strings.Contains(errMsg, "invalidparameter") ||
-			strings.Contains(errMsg, "prompt is too long") ||
-			strings.Contains(errMsg, "request too large"))
+		var failErr *providers.FailoverError
+		if errors.As(err, &failErr) {
+			if failErr.Reason == providers.FailoverTimeout {
+				isTimeoutError = true
+			} else if failErr.Reason == providers.FailoverContextLength {
+				isContextError = true
+			}
+		} else {
+			// If not a fallback error, check directly using ClassifyError
+			// The provider might not be wrapped if no fallback chain is active
+			if directFailErr := providers.ClassifyError(err, "", ""); directFailErr != nil {
+				if directFailErr.Reason == providers.FailoverTimeout {
+					isTimeoutError = true
+				} else if directFailErr.Reason == providers.FailoverContextLength {
+					isContextError = true
+				}
+			}
+		}
 
 		if isTimeoutError && retry < maxRetries {
 			// Exponential backoff: 2s, 4s, 8s
diff --git a/pkg/providers/error_classifier.go b/pkg/providers/error_classifier.go
index fd9bf1e81..c3901d52c 100644
--- a/pkg/providers/error_classifier.go
+++ b/pkg/providers/error_classifier.go
@@ -85,6 +85,18 @@ var (
 		substr("invalid request format"),
 	}
 
+	contextLengthPatterns = []errorPattern{
+		substr("context_length_exceeded"),
+		substr("context window"),
+		substr("maximum context length"),
+		substr("token limit"),
+		substr("too many tokens"),
+		substr("max_tokens"),
+		substr("invalidparameter"),
+		substr("prompt is too long"),
+		substr("request too large"),
+	}
+
 	imageDimensionPatterns = []errorPattern{
 		rxp(`image dimensions exceed max`),
 	}
@@ -201,6 +213,9 @@ func classifyByMessage(msg string) FailoverReason {
 	if matchesAny(msg, formatPatterns) {
 		return FailoverFormat
 	}
+	if matchesAny(msg, contextLengthPatterns) {
+		return FailoverContextLength
+	}
 	return ""
 }
 
diff --git a/pkg/providers/error_classifier_test.go b/pkg/providers/error_classifier_test.go
index 67d9af62b..5826dfef0 100644
--- a/pkg/providers/error_classifier_test.go
+++ b/pkg/providers/error_classifier_test.go
@@ -207,6 +207,32 @@ func TestClassifyError_FormatPatterns(t *testing.T) {
 	}
 }
 
+func TestClassifyError_ContextLengthPatterns(t *testing.T) {
+	patterns := []string{
+		"context_length_exceeded",
+		"context window reached",
+		"maximum context length exceeded",
+		"token limit reached",
+		"too many tokens for this model",
+		"max_tokens limit hit",
+		"invalidparameter",
+		"prompt is too long",
+		"request too large",
+	}
+
+	for _, msg := range patterns {
+		err := errors.New(msg)
+		result := ClassifyError(err, "anthropic", "claude")
+		if result == nil {
+			t.Errorf("pattern %q: expected non-nil", msg)
+			continue
+		}
+		if result.Reason != FailoverContextLength {
+			t.Errorf("pattern %q: reason = %q, want context_length", msg, result.Reason)
+		}
+	}
+}
+
 func TestClassifyError_ImageDimensionError(t *testing.T) {
 	err := errors.New("image dimensions exceed max allowed 2048x2048")
 	result := ClassifyError(err, "openai", "gpt-4o")
@@ -265,6 +291,7 @@ func TestFailoverError_IsRetriable(t *testing.T) {
 		{FailoverTimeout, true},
 		{FailoverOverloaded, true},
 		{FailoverFormat, false},
+		{FailoverContextLength, false},
 		{FailoverUnknown, true},
 	}
 
diff --git a/pkg/providers/types.go b/pkg/providers/types.go
index 11114f3df..da0a6317f 100644
--- a/pkg/providers/types.go
+++ b/pkg/providers/types.go
@@ -48,13 +48,14 @@ type ThinkingCapable interface {
 type FailoverReason string
 
 const (
-	FailoverAuth       FailoverReason = "auth"
-	FailoverRateLimit  FailoverReason = "rate_limit"
-	FailoverBilling    FailoverReason = "billing"
-	FailoverTimeout    FailoverReason = "timeout"
-	FailoverFormat     FailoverReason = "format"
-	FailoverOverloaded FailoverReason = "overloaded"
-	FailoverUnknown    FailoverReason = "unknown"
+	FailoverAuth          FailoverReason = "auth"
+	FailoverRateLimit     FailoverReason = "rate_limit"
+	FailoverBilling       FailoverReason = "billing"
+	FailoverTimeout       FailoverReason = "timeout"
+	FailoverFormat        FailoverReason = "format"
+	FailoverContextLength FailoverReason = "context_length"
+	FailoverOverloaded    FailoverReason = "overloaded"
+	FailoverUnknown       FailoverReason = "unknown"
 )
 
 // FailoverError wraps an LLM provider error with classification metadata.
@@ -76,9 +77,9 @@ func (e *FailoverError) Unwrap() error {
 }
 
 // IsRetriable returns true if this error should trigger fallback to next candidate.
-// Non-retriable: Format errors (bad request structure, image dimension/size).
+// Non-retriable: Format errors (bad request structure, image dimension/size), Context length exceeded.
 func (e *FailoverError) IsRetriable() bool {
-	return e.Reason != FailoverFormat
+	return e.Reason != FailoverFormat && e.Reason != FailoverContextLength
 }
 
 // ModelConfig holds primary model and fallback list.