diff --git a/pkg/providers/claude_cli_provider.go b/pkg/providers/claude_cli_provider.go
index f63b6f00d..1183f5618 100644
--- a/pkg/providers/claude_cli_provider.go
+++ b/pkg/providers/claude_cli_provider.go
@@ -63,6 +63,9 @@ func (p *ClaudeCliProvider) Chat(
 	cmd.Stderr = &stderr
 
 	if err := cmd.Run(); err != nil {
+		if ctx.Err() == context.DeadlineExceeded {
+			return nil, fmt.Errorf("claude cli timed out after %s: %w", p.timeout, context.DeadlineExceeded)
+		}
 		stderrStr := strings.TrimSpace(stderr.String())
 		stdoutStr := strings.TrimSpace(stdout.String())
 		switch {
diff --git a/pkg/providers/codex_cli_provider.go b/pkg/providers/codex_cli_provider.go
index 5cfca37f8..7d347aa54 100644
--- a/pkg/providers/codex_cli_provider.go
+++ b/pkg/providers/codex_cli_provider.go
@@ -86,6 +86,9 @@ func (p *CodexCliProvider) Chat(
 	}
 
 	if err != nil {
+		if ctx.Err() == context.DeadlineExceeded {
+			return nil, fmt.Errorf("codex cli timed out after %s: %w", p.timeout, context.DeadlineExceeded)
+		}
 		if ctx.Err() == context.Canceled {
 			return nil, ctx.Err()
 		}
diff --git a/pkg/providers/error_classifier.go b/pkg/providers/error_classifier.go
index fd9bf1e81..46d3b4c82 100644
--- a/pkg/providers/error_classifier.go
+++ b/pkg/providers/error_classifier.go
@@ -2,6 +2,7 @@ package providers
 
 import (
 	"context"
+	"errors"
 	"regexp"
 	"strings"
 )
@@ -114,7 +115,7 @@ func ClassifyError(err error, provider, model string) *FailoverError {
 	}
 
 	// Context deadline exceeded: treat as timeout, always fallback.
-	if err == context.DeadlineExceeded {
+	if errors.Is(err, context.DeadlineExceeded) {
 		return &FailoverError{
 			Reason:   FailoverTimeout,
 			Provider: provider,
diff --git a/pkg/providers/gemini_cli_provider.go b/pkg/providers/gemini_cli_provider.go
index 2c644f378..1a974754f 100644
--- a/pkg/providers/gemini_cli_provider.go
+++ b/pkg/providers/gemini_cli_provider.go
@@ -63,6 +63,9 @@ func (p *GeminiCliProvider) Chat(
 	cmd.Stderr = &stderr
 
 	if err := cmd.Run(); err != nil {
+		if ctx.Err() == context.DeadlineExceeded {
+			return nil, fmt.Errorf("gemini cli timed out after %s: %w", p.timeout, context.DeadlineExceeded)
+		}
 		stderrStr := strings.TrimSpace(stderr.String())
 		stdoutStr := strings.TrimSpace(stdout.String())
 		switch {