diff --git a/pkg/providers/claude_cli_provider.go b/pkg/providers/claude_cli_provider.go
index f514ba7f0..1183f5618 100644
--- a/pkg/providers/claude_cli_provider.go
+++ b/pkg/providers/claude_cli_provider.go
@@ -7,12 +7,14 @@ import (
 	"fmt"
 	"os/exec"
 	"strings"
+	"time"
 )
 
 // ClaudeCliProvider implements LLMProvider using the claude CLI as a subprocess.
 type ClaudeCliProvider struct {
 	command   string
 	workspace string
+	timeout   time.Duration
 }
 
 // NewClaudeCliProvider creates a new Claude CLI provider.
@@ -23,10 +25,25 @@ func NewClaudeCliProvider(workspace string) *ClaudeCliProvider {
 	}
 }
 
+// NewClaudeCliProviderWithTimeout creates a new Claude CLI provider with a request timeout.
+func NewClaudeCliProviderWithTimeout(workspace string, timeout time.Duration) *ClaudeCliProvider {
+	return &ClaudeCliProvider{
+		command:   "claude",
+		workspace: workspace,
+		timeout:   timeout,
+	}
+}
+
 // Chat implements LLMProvider.Chat by executing the claude CLI.
 func (p *ClaudeCliProvider) Chat(
 	ctx context.Context, messages []Message, tools []ToolDefinition, model string, options map[string]any,
 ) (*LLMResponse, error) {
+	if p.timeout > 0 {
+		var cancel context.CancelFunc
+		ctx, cancel = context.WithTimeout(ctx, p.timeout)
+		defer cancel()
+	}
+
 	prompt := p.buildStdinPrompt(messages, tools)
 
 	args := []string{"-p", "--output-format", "json", "--dangerously-skip-permissions", "--no-chrome"}
@@ -46,6 +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 13f53ad9e..7d347aa54 100644
--- a/pkg/providers/codex_cli_provider.go
+++ b/pkg/providers/codex_cli_provider.go
@@ -8,12 +8,14 @@ import (
 	"fmt"
 	"os/exec"
 	"strings"
+	"time"
 )
 
 // CodexCliProvider implements LLMProvider by wrapping the codex CLI as a subprocess.
 type CodexCliProvider struct {
 	command   string
 	workspace string
+	timeout   time.Duration
 }
 
 // NewCodexCliProvider creates a new Codex CLI provider.
@@ -24,6 +26,15 @@ func NewCodexCliProvider(workspace string) *CodexCliProvider {
 	}
 }
 
+// NewCodexCliProviderWithTimeout creates a new Codex CLI provider with a request timeout.
+func NewCodexCliProviderWithTimeout(workspace string, timeout time.Duration) *CodexCliProvider {
+	return &CodexCliProvider{
+		command:   "codex",
+		workspace: workspace,
+		timeout:   timeout,
+	}
+}
+
 // Chat implements LLMProvider.Chat by executing the codex CLI in non-interactive mode.
 func (p *CodexCliProvider) Chat(
 	ctx context.Context, messages []Message, tools []ToolDefinition, model string, options map[string]any,
@@ -32,6 +43,12 @@ func (p *CodexCliProvider) Chat(
 		return nil, fmt.Errorf("codex command not configured")
 	}
 
+	if p.timeout > 0 {
+		var cancel context.CancelFunc
+		ctx, cancel = context.WithTimeout(ctx, p.timeout)
+		defer cancel()
+	}
+
 	prompt := p.buildPrompt(messages, tools)
 
 	args := []string{
@@ -69,6 +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/factory_provider.go b/pkg/providers/factory_provider.go
index a460dec99..034f8b9c2 100644
--- a/pkg/providers/factory_provider.go
+++ b/pkg/providers/factory_provider.go
@@ -180,6 +180,9 @@ func CreateProviderFromConfig(cfg *config.ModelConfig) (LLMProvider, string, err
 		if workspace == "" {
 			workspace = "."
 		}
+		if cfg.RequestTimeout > 0 {
+			return NewClaudeCliProviderWithTimeout(workspace, time.Duration(cfg.RequestTimeout)*time.Second), modelID, nil
+		}
 		return NewClaudeCliProvider(workspace), modelID, nil
 
 	case "codex-cli", "codexcli":
@@ -187,6 +190,9 @@ func CreateProviderFromConfig(cfg *config.ModelConfig) (LLMProvider, string, err
 		if workspace == "" {
 			workspace = "."
 		}
+		if cfg.RequestTimeout > 0 {
+			return NewCodexCliProviderWithTimeout(workspace, time.Duration(cfg.RequestTimeout)*time.Second), modelID, nil
+		}
 		return NewCodexCliProvider(workspace), modelID, nil
 
 	case "gemini-cli", "geminicli":
@@ -194,6 +200,9 @@ func CreateProviderFromConfig(cfg *config.ModelConfig) (LLMProvider, string, err
 		if workspace == "" {
 			workspace = "."
 		}
+		if cfg.RequestTimeout > 0 {
+			return NewGeminiCliProviderWithTimeout(workspace, time.Duration(cfg.RequestTimeout)*time.Second), modelID, nil
+		}
 		return NewGeminiCliProvider(workspace), modelID, nil
 
 	case "github-copilot", "copilot":
diff --git a/pkg/providers/gemini_cli_provider.go b/pkg/providers/gemini_cli_provider.go
index 0042535f0..1a974754f 100644
--- a/pkg/providers/gemini_cli_provider.go
+++ b/pkg/providers/gemini_cli_provider.go
@@ -7,12 +7,14 @@ import (
 	"fmt"
 	"os/exec"
 	"strings"
+	"time"
 )
 
 // GeminiCliProvider implements LLMProvider using the gemini CLI as a subprocess.
 type GeminiCliProvider struct {
 	command   string
 	workspace string
+	timeout   time.Duration
 }
 
 // NewGeminiCliProvider creates a new Gemini CLI provider.
@@ -23,10 +25,25 @@ func NewGeminiCliProvider(workspace string) *GeminiCliProvider {
 	}
 }
 
+// NewGeminiCliProviderWithTimeout creates a new Gemini CLI provider with a request timeout.
+func NewGeminiCliProviderWithTimeout(workspace string, timeout time.Duration) *GeminiCliProvider {
+	return &GeminiCliProvider{
+		command:   "gemini",
+		workspace: workspace,
+		timeout:   timeout,
+	}
+}
+
 // Chat implements LLMProvider.Chat by executing the gemini CLI.
 func (p *GeminiCliProvider) Chat(
 	ctx context.Context, messages []Message, tools []ToolDefinition, model string, options map[string]any,
 ) (*LLMResponse, error) {
+	if p.timeout > 0 {
+		var cancel context.CancelFunc
+		ctx, cancel = context.WithTimeout(ctx, p.timeout)
+		defer cancel()
+	}
+
 	prompt := p.buildPrompt(messages, tools)
 
 	// --prompt "" triggers non-interactive stdin mode; the empty string is appended to stdin input.
@@ -46,6 +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 {