diff --git a/pkg/agent/constants.go b/pkg/agent/constants.go
new file mode 100644
index 000000000..d84a77e7d
--- /dev/null
+++ b/pkg/agent/constants.go
@@ -0,0 +1,43 @@
+package agent
+
+import "time"
+
+// Agent loop constants — extracted from inline magic numbers for maintainability.
+const (
+	// DefaultMaxLLMRetries is the maximum number of retries for LLM calls
+	// when a context window error is detected.
+	DefaultMaxLLMRetries = 2
+
+	// SummarizeMessageThreshold is the minimum number of messages in session
+	// history before summarization is triggered.
+	SummarizeMessageThreshold = 20
+
+	// ContextWindowUsagePercent is the percentage of the context window that,
+	// when exceeded by the token estimate, triggers summarization.
+	ContextWindowUsagePercent = 75
+
+	// MessagesKeptAfterSummary is the number of most recent messages kept
+	// after summarization to maintain conversational continuity.
+	MessagesKeptAfterSummary = 4
+
+	// SummarizationTimeout is the maximum time allowed for the summarization
+	// LLM call(s) before they are cancelled.
+	SummarizationTimeout = 120 * time.Second
+
+	// SummarizeMaxTokens is the max tokens requested from the LLM for
+	// summarization responses.
+	SummarizeMaxTokens = 1024
+
+	// SummarizeTemperature is the temperature used for summarization calls
+	// (low for deterministic output).
+	SummarizeTemperature = 0.3
+
+	// MinHistoryForCompression is the minimum number of messages in history
+	// before force compression will attempt to reduce it.
+	MinHistoryForCompression = 4
+
+	// MultiPartSummarizationThreshold is the number of messages above which
+	// summarization splits messages into two batches for separate summarization
+	// before merging.
+	MultiPartSummarizationThreshold = 10
+)
diff --git a/pkg/agent/context_compressor.go b/pkg/agent/context_compressor.go
new file mode 100644
index 000000000..d9c3bd517
--- /dev/null
+++ b/pkg/agent/context_compressor.go
@@ -0,0 +1,237 @@
+package agent
+
+import (
+	"context"
+	"fmt"
+	"strings"
+	"sync"
+	"unicode/utf8"
+
+	"github.com/sipeed/picoclaw/pkg/bus"
+	"github.com/sipeed/picoclaw/pkg/constants"
+	"github.com/sipeed/picoclaw/pkg/logger"
+	"github.com/sipeed/picoclaw/pkg/providers"
+)
+
+// ContextCompressor handles context window management: force compression,
+// summarization triggers, and session history optimization.
+// Extracted from AgentLoop to improve separation of concerns.
+type ContextCompressor struct {
+	bus         *bus.MessageBus
+	summarizing *sync.Map
+}
+
+// NewContextCompressor creates a new ContextCompressor.
+func NewContextCompressor(msgBus *bus.MessageBus, summarizing *sync.Map) *ContextCompressor {
+	return &ContextCompressor{
+		bus:         msgBus,
+		summarizing: summarizing,
+	}
+}
+
+// MaybeSummarize triggers summarization if the session history exceeds thresholds.
+func (cc *ContextCompressor) MaybeSummarize(agent *AgentInstance, sessionKey, channel, chatID string) {
+	newHistory := agent.Sessions.GetHistory(sessionKey)
+	tokenEstimate := cc.EstimateTokens(newHistory)
+	threshold := agent.ContextWindow * ContextWindowUsagePercent / 100
+
+	if len(newHistory) > SummarizeMessageThreshold || tokenEstimate > threshold {
+		summarizeKey := agent.ID + ":" + sessionKey
+		if _, loading := cc.summarizing.LoadOrStore(summarizeKey, true); !loading {
+			go func() {
+				defer cc.summarizing.Delete(summarizeKey)
+				if !constants.IsInternalChannel(channel) {
+					cc.bus.PublishOutbound(bus.OutboundMessage{
+						Channel: channel,
+						ChatID:  chatID,
+						Content: "Memory threshold reached. Optimizing conversation history...",
+					})
+				}
+				cc.SummarizeSession(agent, sessionKey)
+			}()
+		}
+	}
+}
+
+// ForceCompression aggressively reduces context when the limit is hit.
+// It drops the oldest 50% of messages (keeping system prompt and last user message).
+func (cc *ContextCompressor) ForceCompression(agent *AgentInstance, sessionKey string) {
+	history := agent.Sessions.GetHistory(sessionKey)
+	if len(history) <= MinHistoryForCompression {
+		return
+	}
+
+	// Keep system prompt (usually [0]) and the very last message (user's trigger)
+	// We want to drop the oldest half of the *conversation*
+	// Assuming [0] is system, [1:] is conversation
+	conversation := history[1 : len(history)-1]
+	if len(conversation) == 0 {
+		return
+	}
+
+	// Helper to find the mid-point of the conversation
+	mid := len(conversation) / 2
+
+	// New history structure:
+	// 1. System Prompt (with compression note appended)
+	// 2. Second half of conversation
+	// 3. Last message
+
+	droppedCount := mid
+	keptConversation := conversation[mid:]
+
+	newHistory := make([]providers.Message, 0)
+
+	// Append compression note to the original system prompt instead of adding a new system message
+	// This avoids having two consecutive system messages which some APIs (like Zhipu) reject
+	compressionNote := fmt.Sprintf(
+		"\n\n[System Note: Emergency compression dropped %d oldest messages due to context limit]",
+		droppedCount,
+	)
+	enhancedSystemPrompt := history[0]
+	enhancedSystemPrompt.Content = enhancedSystemPrompt.Content + compressionNote
+	newHistory = append(newHistory, enhancedSystemPrompt)
+
+	newHistory = append(newHistory, keptConversation...)
+	newHistory = append(newHistory, history[len(history)-1]) // Last message
+
+	// Update session
+	agent.Sessions.SetHistory(sessionKey, newHistory)
+	agent.Sessions.Save(sessionKey)
+
+	logger.WarnCF("agent", "Forced compression executed", map[string]any{
+		"session_key":  sessionKey,
+		"dropped_msgs": droppedCount,
+		"new_count":    len(newHistory),
+	})
+}
+
+// SummarizeSession summarizes the conversation history for a session.
+func (cc *ContextCompressor) SummarizeSession(agent *AgentInstance, sessionKey string) {
+	ctx, cancel := context.WithTimeout(context.Background(), SummarizationTimeout)
+	defer cancel()
+
+	history := agent.Sessions.GetHistory(sessionKey)
+	summary := agent.Sessions.GetSummary(sessionKey)
+
+	// Keep last N messages for continuity
+	if len(history) <= MessagesKeptAfterSummary {
+		return
+	}
+
+	toSummarize := history[:len(history)-MessagesKeptAfterSummary]
+
+	// Oversized Message Guard
+	maxMessageTokens := agent.ContextWindow / 2
+	validMessages := make([]providers.Message, 0)
+	omitted := false
+
+	for _, m := range toSummarize {
+		if m.Role != "user" && m.Role != "assistant" {
+			continue
+		}
+		// Use character-based estimation (2.5 chars per token = totalChars * 2 / 5)
+		msgTokens := utf8.RuneCountInString(m.Content) * 2 / 5
+		if msgTokens > maxMessageTokens {
+			omitted = true
+			continue
+		}
+		validMessages = append(validMessages, m)
+	}
+
+	if len(validMessages) == 0 {
+		return
+	}
+
+	// Multi-Part Summarization
+	var finalSummary string
+	if len(validMessages) > MultiPartSummarizationThreshold {
+		mid := len(validMessages) / 2
+		part1 := validMessages[:mid]
+		part2 := validMessages[mid:]
+
+		s1, _ := cc.SummarizeBatch(ctx, agent, part1, "")
+		s2, _ := cc.SummarizeBatch(ctx, agent, part2, "")
+
+		mergePrompt := fmt.Sprintf(
+			"Merge these two conversation summaries into one cohesive summary:\n\n1: %s\n\n2: %s",
+			s1,
+			s2,
+		)
+		resp, err := agent.Provider.Chat(
+			ctx,
+			[]providers.Message{{Role: "user", Content: mergePrompt}},
+			nil,
+			agent.Model,
+			map[string]any{
+				"max_tokens":  SummarizeMaxTokens,
+				"temperature": SummarizeTemperature,
+			},
+		)
+		if err == nil {
+			finalSummary = resp.Content
+		} else {
+			finalSummary = s1 + " " + s2
+		}
+	} else {
+		finalSummary, _ = cc.SummarizeBatch(ctx, agent, validMessages, summary)
+	}
+
+	if omitted && finalSummary != "" {
+		finalSummary += "\n[Note: Some oversized messages were omitted from this summary for efficiency.]"
+	}
+
+	if finalSummary != "" {
+		agent.Sessions.SetSummary(sessionKey, finalSummary)
+		agent.Sessions.TruncateHistory(sessionKey, MessagesKeptAfterSummary)
+		agent.Sessions.Save(sessionKey)
+	}
+}
+
+// SummarizeBatch summarizes a batch of messages.
+func (cc *ContextCompressor) SummarizeBatch(
+	ctx context.Context,
+	agent *AgentInstance,
+	batch []providers.Message,
+	existingSummary string,
+) (string, error) {
+	var sb strings.Builder
+	sb.WriteString("Provide a concise summary of this conversation segment, preserving core context and key points.\n")
+	if existingSummary != "" {
+		sb.WriteString("Existing context: ")
+		sb.WriteString(existingSummary)
+		sb.WriteString("\n")
+	}
+	sb.WriteString("\nCONVERSATION:\n")
+	for _, m := range batch {
+		fmt.Fprintf(&sb, "%s: %s\n", m.Role, m.Content)
+	}
+	prompt := sb.String()
+
+	response, err := agent.Provider.Chat(
+		ctx,
+		[]providers.Message{{Role: "user", Content: prompt}},
+		nil,
+		agent.Model,
+		map[string]any{
+			"max_tokens":  SummarizeMaxTokens,
+			"temperature": SummarizeTemperature,
+		},
+	)
+	if err != nil {
+		return "", err
+	}
+	return response.Content, nil
+}
+
+// EstimateTokens estimates the number of tokens in a message list.
+// Uses a safe heuristic of 2.5 characters per token to account for CJK and other
+// overheads better than the previous 3 chars/token.
+func (cc *ContextCompressor) EstimateTokens(messages []providers.Message) int {
+	totalChars := 0
+	for _, m := range messages {
+		totalChars += utf8.RuneCountInString(m.Content)
+	}
+	// 2.5 chars per token = totalChars * 2 / 5
+	return totalChars * 2 / 5
+}
diff --git a/pkg/agent/loop.go b/pkg/agent/loop.go
index bf229ad74..2cfb77845 100644
--- a/pkg/agent/loop.go
+++ b/pkg/agent/loop.go
@@ -14,7 +14,6 @@ import (
 	"sync"
 	"sync/atomic"
 	"time"
-	"unicode/utf8"
 
 	"github.com/sipeed/picoclaw/pkg/bus"
 	"github.com/sipeed/picoclaw/pkg/channels"
@@ -38,6 +37,15 @@ type AgentLoop struct {
 	summarizing    sync.Map
 	fallback       *providers.FallbackChain
 	channelManager *channels.Manager
+
+	// Extracted components for better separation of concerns
+	compressor *ContextCompressor
+	toolExec   *ToolExecutor
+
+	// Graceful shutdown support
+	cancelCtx  context.Context
+	cancelFunc context.CancelFunc
+	wg         sync.WaitGroup
 }
 
 // processOptions configures how a message is processed
@@ -69,13 +77,24 @@ func NewAgentLoop(cfg *config.Config, msgBus *bus.MessageBus, provider providers
 		stateManager = state.NewManager(defaultAgent.Workspace)
 	}
 
+	// Initialize extracted components
+	summarizing := &sync.Map{}
+	compressor := NewContextCompressor(msgBus, summarizing)
+	toolExec := NewToolExecutor(msgBus)
+
+	// Create cancellation context for graceful shutdown
+	cancelCtx, cancelFunc := context.WithCancel(context.Background())
+
 	return &AgentLoop{
-		bus:         msgBus,
-		cfg:         cfg,
-		registry:    registry,
-		state:       stateManager,
-		summarizing: sync.Map{},
-		fallback:    fallbackChain,
+		bus:        msgBus,
+		cfg:        cfg,
+		registry:   registry,
+		state:      stateManager,
+		fallback:   fallbackChain,
+		compressor: compressor,
+		toolExec:   toolExec,
+		cancelCtx:  cancelCtx,
+		cancelFunc: cancelFunc,
 	}
 }
 
@@ -202,6 +221,10 @@ func (al *AgentLoop) Run(ctx context.Context) error {
 
 func (al *AgentLoop) Stop() {
 	al.running.Store(false)
+	if al.cancelFunc != nil {
+		al.cancelFunc()
+	}
+	al.wg.Wait()
 }
 
 func (al *AgentLoop) RegisterTool(tool tools.Tool) {
@@ -404,7 +427,7 @@ func (al *AgentLoop) runAgentLoop(ctx context.Context, agent *AgentInstance, opt
 	}
 
 	// 1. Update tool contexts
-	al.updateToolContexts(agent, opts.Channel, opts.ChatID)
+	al.toolExec.UpdateToolContexts(agent, opts.Channel, opts.ChatID)
 
 	// 2. Build messages (skip history for heartbeat)
 	var history []providers.Message
@@ -445,7 +468,7 @@ func (al *AgentLoop) runAgentLoop(ctx context.Context, agent *AgentInstance, opt
 
 	// 7. Optional: summarization
 	if opts.EnableSummary {
-		al.maybeSummarize(agent, opts.SessionKey, opts.Channel, opts.ChatID)
+		al.compressor.MaybeSummarize(agent, opts.SessionKey, opts.Channel, opts.ChatID)
 	}
 
 	// 8. Optional: send response via bus
@@ -545,18 +568,14 @@ func (al *AgentLoop) runLLMIteration(
 		}
 
 		// Retry loop for context/token errors
-		maxRetries := 2
+		maxRetries := DefaultMaxLLMRetries
 		for retry := 0; retry <= maxRetries; retry++ {
 			response, err = callLLM()
 			if err == nil {
 				break
 			}
 
-			errMsg := strings.ToLower(err.Error())
-			isContextError := strings.Contains(errMsg, "token") ||
-				strings.Contains(errMsg, "context") ||
-				strings.Contains(errMsg, "invalidparameter") ||
-				strings.Contains(errMsg, "length")
+			isContextError := providers.IsContextWindowError(err)
 
 			if isContextError && retry < maxRetries {
 				logger.WarnCF("agent", "Context window error detected, attempting compression", map[string]any{
@@ -572,7 +591,7 @@ func (al *AgentLoop) runLLMIteration(
 					})
 				}
 
-				al.forceCompression(agent, opts.SessionKey)
+				al.compressor.ForceCompression(agent, opts.SessionKey)
 				newHistory := agent.Sessions.GetHistory(opts.SessionKey)
 				newSummary := agent.Sessions.GetSummary(opts.SessionKey)
 				messages = agent.ContextBuilder.BuildMessages(
@@ -656,174 +675,17 @@ func (al *AgentLoop) runLLMIteration(
 		// Save assistant message with tool calls to session
 		agent.Sessions.AddFullMessage(opts.SessionKey, assistantMsg)
 
-		// Execute tool calls
-		for _, tc := range normalizedToolCalls {
-			argsJSON, _ := json.Marshal(tc.Arguments)
-			argsPreview := utils.Truncate(string(argsJSON), 200)
-			logger.InfoCF("agent", fmt.Sprintf("Tool call: %s(%s)", tc.Name, argsPreview),
-				map[string]any{
-					"agent_id":  agent.ID,
-					"tool":      tc.Name,
-					"iteration": iteration,
-				})
-
-			// Create async callback for tools that implement AsyncTool
-			// NOTE: Following openclaw's design, async tools do NOT send results directly to users.
-			// Instead, they notify the agent via PublishInbound, and the agent decides
-			// whether to forward the result to the user (in processSystemMessage).
-			asyncCallback := func(callbackCtx context.Context, result *tools.ToolResult) {
-				// Log the async completion but don't send directly to user
-				// The agent will handle user notification via processSystemMessage
-				if !result.Silent && result.ForUser != "" {
-					logger.InfoCF("agent", "Async tool completed, agent will handle notification",
-						map[string]any{
-							"tool":        tc.Name,
-							"content_len": len(result.ForUser),
-						})
-				}
-			}
-
-			toolResult := agent.Tools.ExecuteWithContext(
-				ctx,
-				tc.Name,
-				tc.Arguments,
-				opts.Channel,
-				opts.ChatID,
-				asyncCallback,
-			)
-
-			// Send ForUser content to user immediately if not Silent
-			if !toolResult.Silent && toolResult.ForUser != "" && opts.SendResponse {
-				al.bus.PublishOutbound(bus.OutboundMessage{
-					Channel: opts.Channel,
-					ChatID:  opts.ChatID,
-					Content: toolResult.ForUser,
-				})
-				logger.DebugCF("agent", "Sent tool result to user",
-					map[string]any{
-						"tool":        tc.Name,
-						"content_len": len(toolResult.ForUser),
-					})
-			}
-
-			// Determine content for LLM based on tool result
-			contentForLLM := toolResult.ForLLM
-			if contentForLLM == "" && toolResult.Err != nil {
-				contentForLLM = toolResult.Err.Error()
-			}
-
-			toolResultMsg := providers.Message{
-				Role:       "tool",
-				Content:    contentForLLM,
-				ToolCallID: tc.ID,
-			}
-			messages = append(messages, toolResultMsg)
-
-			// Save tool result message to session
-			agent.Sessions.AddFullMessage(opts.SessionKey, toolResultMsg)
+		// Execute tool calls via the ToolExecutor component
+		toolResultMsgs := al.toolExec.ExecuteToolCalls(ctx, agent, normalizedToolCalls, opts)
+		for _, resultMsg := range toolResultMsgs {
+			messages = append(messages, resultMsg)
+			agent.Sessions.AddFullMessage(opts.SessionKey, resultMsg)
 		}
 	}
 
 	return finalContent, iteration, nil
 }
 
-// updateToolContexts updates the context for tools that need channel/chatID info.
-func (al *AgentLoop) updateToolContexts(agent *AgentInstance, channel, chatID string) {
-	// Use ContextualTool interface instead of type assertions
-	if tool, ok := agent.Tools.Get("message"); ok {
-		if mt, ok := tool.(tools.ContextualTool); ok {
-			mt.SetContext(channel, chatID)
-		}
-	}
-	if tool, ok := agent.Tools.Get("spawn"); ok {
-		if st, ok := tool.(tools.ContextualTool); ok {
-			st.SetContext(channel, chatID)
-		}
-	}
-	if tool, ok := agent.Tools.Get("subagent"); ok {
-		if st, ok := tool.(tools.ContextualTool); ok {
-			st.SetContext(channel, chatID)
-		}
-	}
-}
-
-// maybeSummarize triggers summarization if the session history exceeds thresholds.
-func (al *AgentLoop) maybeSummarize(agent *AgentInstance, sessionKey, channel, chatID string) {
-	newHistory := agent.Sessions.GetHistory(sessionKey)
-	tokenEstimate := al.estimateTokens(newHistory)
-	threshold := agent.ContextWindow * 75 / 100
-
-	if len(newHistory) > 20 || tokenEstimate > threshold {
-		summarizeKey := agent.ID + ":" + sessionKey
-		if _, loading := al.summarizing.LoadOrStore(summarizeKey, true); !loading {
-			go func() {
-				defer al.summarizing.Delete(summarizeKey)
-				if !constants.IsInternalChannel(channel) {
-					al.bus.PublishOutbound(bus.OutboundMessage{
-						Channel: channel,
-						ChatID:  chatID,
-						Content: "Memory threshold reached. Optimizing conversation history...",
-					})
-				}
-				al.summarizeSession(agent, sessionKey)
-			}()
-		}
-	}
-}
-
-// forceCompression aggressively reduces context when the limit is hit.
-// It drops the oldest 50% of messages (keeping system prompt and last user message).
-func (al *AgentLoop) forceCompression(agent *AgentInstance, sessionKey string) {
-	history := agent.Sessions.GetHistory(sessionKey)
-	if len(history) <= 4 {
-		return
-	}
-
-	// Keep system prompt (usually [0]) and the very last message (user's trigger)
-	// We want to drop the oldest half of the *conversation*
-	// Assuming [0] is system, [1:] is conversation
-	conversation := history[1 : len(history)-1]
-	if len(conversation) == 0 {
-		return
-	}
-
-	// Helper to find the mid-point of the conversation
-	mid := len(conversation) / 2
-
-	// New history structure:
-	// 1. System Prompt (with compression note appended)
-	// 2. Second half of conversation
-	// 3. Last message
-
-	droppedCount := mid
-	keptConversation := conversation[mid:]
-
-	newHistory := make([]providers.Message, 0)
-
-	// Append compression note to the original system prompt instead of adding a new system message
-	// This avoids having two consecutive system messages which some APIs (like Zhipu) reject
-	compressionNote := fmt.Sprintf(
-		"\n\n[System Note: Emergency compression dropped %d oldest messages due to context limit]",
-		droppedCount,
-	)
-	enhancedSystemPrompt := history[0]
-	enhancedSystemPrompt.Content = enhancedSystemPrompt.Content + compressionNote
-	newHistory = append(newHistory, enhancedSystemPrompt)
-
-	newHistory = append(newHistory, keptConversation...)
-	newHistory = append(newHistory, history[len(history)-1]) // Last message
-
-	// Update session
-	agent.Sessions.SetHistory(sessionKey, newHistory)
-	agent.Sessions.Save(sessionKey)
-
-	logger.WarnCF("agent", "Forced compression executed", map[string]any{
-		"session_key":  sessionKey,
-		"dropped_msgs": droppedCount,
-		"new_count":    len(newHistory),
-	})
-}
-
 // GetStartupInfo returns information about loaded tools and skills for logging.
 func (al *AgentLoop) GetStartupInfo() map[string]any {
 	info := make(map[string]any)
@@ -903,135 +765,6 @@ func formatToolsForLog(toolDefs []providers.ToolDefinition) string {
 	return sb.String()
 }
 
-// summarizeSession summarizes the conversation history for a session.
-func (al *AgentLoop) summarizeSession(agent *AgentInstance, sessionKey string) {
-	ctx, cancel := context.WithTimeout(context.Background(), 120*time.Second)
-	defer cancel()
-
-	history := agent.Sessions.GetHistory(sessionKey)
-	summary := agent.Sessions.GetSummary(sessionKey)
-
-	// Keep last 4 messages for continuity
-	if len(history) <= 4 {
-		return
-	}
-
-	toSummarize := history[:len(history)-4]
-
-	// Oversized Message Guard
-	maxMessageTokens := agent.ContextWindow / 2
-	validMessages := make([]providers.Message, 0)
-	omitted := false
-
-	for _, m := range toSummarize {
-		if m.Role != "user" && m.Role != "assistant" {
-			continue
-		}
-		msgTokens := len(m.Content) / 2
-		if msgTokens > maxMessageTokens {
-			omitted = true
-			continue
-		}
-		validMessages = append(validMessages, m)
-	}
-
-	if len(validMessages) == 0 {
-		return
-	}
-
-	// Multi-Part Summarization
-	var finalSummary string
-	if len(validMessages) > 10 {
-		mid := len(validMessages) / 2
-		part1 := validMessages[:mid]
-		part2 := validMessages[mid:]
-
-		s1, _ := al.summarizeBatch(ctx, agent, part1, "")
-		s2, _ := al.summarizeBatch(ctx, agent, part2, "")
-
-		mergePrompt := fmt.Sprintf(
-			"Merge these two conversation summaries into one cohesive summary:\n\n1: %s\n\n2: %s",
-			s1,
-			s2,
-		)
-		resp, err := agent.Provider.Chat(
-			ctx,
-			[]providers.Message{{Role: "user", Content: mergePrompt}},
-			nil,
-			agent.Model,
-			map[string]any{
-				"max_tokens":  1024,
-				"temperature": 0.3,
-			},
-		)
-		if err == nil {
-			finalSummary = resp.Content
-		} else {
-			finalSummary = s1 + " " + s2
-		}
-	} else {
-		finalSummary, _ = al.summarizeBatch(ctx, agent, validMessages, summary)
-	}
-
-	if omitted && finalSummary != "" {
-		finalSummary += "\n[Note: Some oversized messages were omitted from this summary for efficiency.]"
-	}
-
-	if finalSummary != "" {
-		agent.Sessions.SetSummary(sessionKey, finalSummary)
-		agent.Sessions.TruncateHistory(sessionKey, 4)
-		agent.Sessions.Save(sessionKey)
-	}
-}
-
-// summarizeBatch summarizes a batch of messages.
-func (al *AgentLoop) summarizeBatch(
-	ctx context.Context,
-	agent *AgentInstance,
-	batch []providers.Message,
-	existingSummary string,
-) (string, error) {
-	var sb strings.Builder
-	sb.WriteString("Provide a concise summary of this conversation segment, preserving core context and key points.\n")
-	if existingSummary != "" {
-		sb.WriteString("Existing context: ")
-		sb.WriteString(existingSummary)
-		sb.WriteString("\n")
-	}
-	sb.WriteString("\nCONVERSATION:\n")
-	for _, m := range batch {
-		fmt.Fprintf(&sb, "%s: %s\n", m.Role, m.Content)
-	}
-	prompt := sb.String()
-
-	response, err := agent.Provider.Chat(
-		ctx,
-		[]providers.Message{{Role: "user", Content: prompt}},
-		nil,
-		agent.Model,
-		map[string]any{
-			"max_tokens":  1024,
-			"temperature": 0.3,
-		},
-	)
-	if err != nil {
-		return "", err
-	}
-	return response.Content, nil
-}
-
-// estimateTokens estimates the number of tokens in a message list.
-// Uses a safe heuristic of 2.5 characters per token to account for CJK and other
-// overheads better than the previous 3 chars/token.
-func (al *AgentLoop) estimateTokens(messages []providers.Message) int {
-	totalChars := 0
-	for _, m := range messages {
-		totalChars += utf8.RuneCountInString(m.Content)
-	}
-	// 2.5 chars per token = totalChars * 2 / 5
-	return totalChars * 2 / 5
-}
-
 func (al *AgentLoop) handleCommand(ctx context.Context, msg bus.InboundMessage) (string, bool) {
 	content := strings.TrimSpace(msg.Content)
 	if !strings.HasPrefix(content, "/") {
diff --git a/pkg/agent/tool_executor.go b/pkg/agent/tool_executor.go
new file mode 100644
index 000000000..a13a0dccd
--- /dev/null
+++ b/pkg/agent/tool_executor.go
@@ -0,0 +1,111 @@
+package agent
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+
+	"github.com/sipeed/picoclaw/pkg/bus"
+	"github.com/sipeed/picoclaw/pkg/logger"
+	"github.com/sipeed/picoclaw/pkg/providers"
+	"github.com/sipeed/picoclaw/pkg/tools"
+	"github.com/sipeed/picoclaw/pkg/utils"
+)
+
+// ToolExecutor handles executing tool calls requested by the LLM,
+// including async callback setup, result routing, and context updates.
+// Extracted from AgentLoop to improve separation of concerns.
+type ToolExecutor struct {
+	bus *bus.MessageBus
+}
+
+// NewToolExecutor creates a new ToolExecutor.
+func NewToolExecutor(msgBus *bus.MessageBus) *ToolExecutor {
+	return &ToolExecutor{bus: msgBus}
+}
+
+// ExecuteToolCalls processes a list of normalized tool calls, executes each one,
+// sends user-facing results to the bus, and returns the tool result messages
+// to be appended to the conversation.
+func (te *ToolExecutor) ExecuteToolCalls(
+	ctx context.Context,
+	agent *AgentInstance,
+	toolCalls []providers.ToolCall,
+	opts processOptions,
+) []providers.Message {
+	var resultMessages []providers.Message
+
+	for _, tc := range toolCalls {
+		argsJSON, _ := json.Marshal(tc.Arguments)
+		argsPreview := utils.Truncate(string(argsJSON), 200)
+		logger.InfoCF("agent", fmt.Sprintf("Tool call: %s(%s)", tc.Name, argsPreview),
+			map[string]any{
+				"agent_id":  agent.ID,
+				"tool":      tc.Name,
+			})
+
+		// Create async callback for tools that implement AsyncTool
+		// NOTE: Following openclaw's design, async tools do NOT send results directly to users.
+		// Instead, they notify the agent via PublishInbound, and the agent decides
+		// whether to forward the result to the user (in processSystemMessage).
+		asyncCallback := func(callbackCtx context.Context, result *tools.ToolResult) {
+			if !result.Silent && result.ForUser != "" {
+				logger.InfoCF("agent", "Async tool completed, agent will handle notification",
+					map[string]any{
+						"tool":        tc.Name,
+						"content_len": len(result.ForUser),
+					})
+			}
+		}
+
+		toolResult := agent.Tools.ExecuteWithContext(
+			ctx,
+			tc.Name,
+			tc.Arguments,
+			opts.Channel,
+			opts.ChatID,
+			asyncCallback,
+		)
+
+		// Send ForUser content to user immediately if not Silent
+		if !toolResult.Silent && toolResult.ForUser != "" && opts.SendResponse {
+			te.bus.PublishOutbound(bus.OutboundMessage{
+				Channel: opts.Channel,
+				ChatID:  opts.ChatID,
+				Content: toolResult.ForUser,
+			})
+			logger.DebugCF("agent", "Sent tool result to user",
+				map[string]any{
+					"tool":        tc.Name,
+					"content_len": len(toolResult.ForUser),
+				})
+		}
+
+		// Determine content for LLM based on tool result
+		contentForLLM := toolResult.ForLLM
+		if contentForLLM == "" && toolResult.Err != nil {
+			contentForLLM = toolResult.Err.Error()
+		}
+
+		resultMessages = append(resultMessages, providers.Message{
+			Role:       "tool",
+			Content:    contentForLLM,
+			ToolCallID: tc.ID,
+		})
+	}
+
+	return resultMessages
+}
+
+// UpdateToolContexts updates the context for tools that need channel/chatID info.
+func (te *ToolExecutor) UpdateToolContexts(agent *AgentInstance, channel, chatID string) {
+	// Use ContextualTool interface instead of type assertions
+	contextualToolNames := []string{"message", "spawn", "subagent"}
+	for _, name := range contextualToolNames {
+		if tool, ok := agent.Tools.Get(name); ok {
+			if ct, ok := tool.(tools.ContextualTool); ok {
+				ct.SetContext(channel, chatID)
+			}
+		}
+	}
+}
diff --git a/pkg/providers/error_classifier.go b/pkg/providers/error_classifier.go
index a0f003006..9125f2f36 100644
--- a/pkg/providers/error_classifier.go
+++ b/pkg/providers/error_classifier.go
@@ -86,6 +86,18 @@ var (
 		rxp(`image exceeds.*mb`),
 	}
 
+	// contextWindowPatterns detects context window / token limit exhaustion errors.
+	contextWindowPatterns = []errorPattern{
+		rxp(`context.*(window|length).*exceed`),
+		rxp(`max.*token.*(limit|exceed)`),
+		rxp(`total tokens.*exceed`),
+		substr("context_length_exceeded"),
+		substr("maximum context length"),
+		substr("invalidparameter"),
+		rxp(`tokens?.*exceed`),
+		rxp(`exceeds? the (model|max).*token`),
+	}
+
 	// Transient HTTP status codes that map to timeout (server-side failures).
 	transientStatusCodes = map[int]bool{
 		500: true, 502: true, 503: true,
@@ -225,6 +237,17 @@ func IsImageSizeError(msg string) bool {
 	return matchesAny(msg, imageSizePatterns)
 }
 
+// IsContextWindowError returns true if the error indicates a context window / token limit
+// exhaustion. This is more precise than naive string matching and avoids false positives
+// on errors like "invalid authentication token".
+func IsContextWindowError(err error) bool {
+	if err == nil {
+		return false
+	}
+	msg := strings.ToLower(err.Error())
+	return matchesAny(msg, contextWindowPatterns)
+}
+
 // matchesAny checks if msg matches any of the patterns.
 func matchesAny(msg string, patterns []errorPattern) bool {
 	for _, p := range patterns {
diff --git a/pkg/providers/factory.go b/pkg/providers/factory.go
index cda4753ea..9a2c7a771 100644
--- a/pkg/providers/factory.go
+++ b/pkg/providers/factory.go
@@ -35,6 +35,268 @@ type providerSelection struct {
 	enableWebSearch bool
 }
 
+// providerDefaults holds the default API base URL and a config accessor for a standard HTTP-compatible provider.
+type providerDefaults struct {
+	defaultBase string
+	getConfig   func(cfg *config.Config) (apiKey, apiBase, proxy string)
+	// hasKey returns true if the provider has credentials configured.
+	// If nil, checks that getConfig returns a non-empty apiKey.
+	hasKey func(cfg *config.Config) bool
+}
+
+// standardProviderRegistry maps provider names to their defaults.
+// Only covers providers that follow the standard pattern: apiKey + apiBase + proxy.
+// Special-case providers (CLI, OAuth, Copilot) are handled separately.
+var standardProviderRegistry = map[string]providerDefaults{
+	"groq": {
+		defaultBase: "https://api.groq.com/openai/v1",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.Groq.APIKey, cfg.Providers.Groq.APIBase, cfg.Providers.Groq.Proxy
+		},
+	},
+	"openrouter": {
+		defaultBase: "https://openrouter.ai/api/v1",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.OpenRouter.APIKey, cfg.Providers.OpenRouter.APIBase, cfg.Providers.OpenRouter.Proxy
+		},
+	},
+	"zhipu": {
+		defaultBase: "https://open.bigmodel.cn/api/paas/v4",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.Zhipu.APIKey, cfg.Providers.Zhipu.APIBase, cfg.Providers.Zhipu.Proxy
+		},
+	},
+	"gemini": {
+		defaultBase: "https://generativelanguage.googleapis.com/v1beta",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.Gemini.APIKey, cfg.Providers.Gemini.APIBase, cfg.Providers.Gemini.Proxy
+		},
+	},
+	"vllm": {
+		defaultBase: "", // no default base; requires explicit config
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.VLLM.APIKey, cfg.Providers.VLLM.APIBase, cfg.Providers.VLLM.Proxy
+		},
+		hasKey: func(cfg *config.Config) bool {
+			return cfg.Providers.VLLM.APIBase != ""
+		},
+	},
+	"shengsuanyun": {
+		defaultBase: "https://router.shengsuanyun.com/api/v1",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.ShengSuanYun.APIKey, cfg.Providers.ShengSuanYun.APIBase, cfg.Providers.ShengSuanYun.Proxy
+		},
+	},
+	"nvidia": {
+		defaultBase: "https://integrate.api.nvidia.com/v1",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.Nvidia.APIKey, cfg.Providers.Nvidia.APIBase, cfg.Providers.Nvidia.Proxy
+		},
+	},
+	"deepseek": {
+		defaultBase: "https://api.deepseek.com/v1",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.DeepSeek.APIKey, cfg.Providers.DeepSeek.APIBase, cfg.Providers.DeepSeek.Proxy
+		},
+	},
+	"mistral": {
+		defaultBase: "https://api.mistral.ai/v1",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.Mistral.APIKey, cfg.Providers.Mistral.APIBase, cfg.Providers.Mistral.Proxy
+		},
+	},
+	"ollama": {
+		defaultBase: "http://localhost:11434/v1",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.Ollama.APIKey, cfg.Providers.Ollama.APIBase, cfg.Providers.Ollama.Proxy
+		},
+	},
+	"moonshot": {
+		defaultBase: "https://api.moonshot.cn/v1",
+		getConfig: func(cfg *config.Config) (string, string, string) {
+			return cfg.Providers.Moonshot.APIKey, cfg.Providers.Moonshot.APIBase, cfg.Providers.Moonshot.Proxy
+		},
+	},
+}
+
+// providerNameAliases maps alternative provider names to their canonical names in the registry.
+var providerNameAliases = map[string]string{
+	"glm":    "zhipu",
+	"google": "gemini",
+}
+
+// applyStandardProvider applies config from a standardProviderRegistry entry to sel.
+// Returns true if the provider had credentials configured.
+func applyStandardProvider(cfg *config.Config, sel *providerSelection, entry providerDefaults) bool {
+	apiKey, apiBase, proxy := entry.getConfig(cfg)
+
+	hasCredentials := apiKey != ""
+	if entry.hasKey != nil {
+		hasCredentials = entry.hasKey(cfg)
+	}
+
+	if !hasCredentials {
+		return false
+	}
+
+	sel.apiKey = apiKey
+	sel.apiBase = apiBase
+	sel.proxy = proxy
+	if sel.apiBase == "" && entry.defaultBase != "" {
+		sel.apiBase = entry.defaultBase
+	}
+	return true
+}
+
+// modelInferenceEntry maps a model name pattern to a provider and optional match function.
+type modelInferenceEntry struct {
+	// matches returns true if this entry should handle the given model name (lowercase) and original model.
+	matches func(lowerModel, model string, cfg *config.Config) bool
+	// apply sets up the provider selection. Returns true on success.
+	apply func(cfg *config.Config, sel *providerSelection) bool
+}
+
+// modelInferenceRegistry defines fallback model → provider inference rules.
+// Order matters: first match wins.
+var modelInferenceRegistry = []modelInferenceEntry{
+	// Moonshot/Kimi
+	{
+		matches: func(lm, m string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "kimi") || strings.Contains(lm, "moonshot") || strings.HasPrefix(m, "moonshot/")) &&
+				cfg.Providers.Moonshot.APIKey != ""
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["moonshot"])
+		},
+	},
+	// OpenRouter-prefixed models (openrouter/, anthropic/, openai/, meta-llama/, deepseek/, google/)
+	{
+		matches: func(_, m string, _ *config.Config) bool {
+			for _, prefix := range []string{"openrouter/", "anthropic/", "openai/", "meta-llama/", "deepseek/", "google/"} {
+				if strings.HasPrefix(m, prefix) {
+					return true
+				}
+			}
+			return false
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["openrouter"])
+		},
+	},
+	// Claude models → Anthropic (with OAuth support)
+	{
+		matches: func(lm, m string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "claude") || strings.HasPrefix(m, "anthropic/")) &&
+				(cfg.Providers.Anthropic.APIKey != "" || cfg.Providers.Anthropic.AuthMethod != "")
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			if cfg.Providers.Anthropic.AuthMethod == "oauth" || cfg.Providers.Anthropic.AuthMethod == "token" {
+				sel.apiBase = cfg.Providers.Anthropic.APIBase
+				if sel.apiBase == "" {
+					sel.apiBase = defaultAnthropicAPIBase
+				}
+				sel.providerType = providerTypeClaudeAuth
+				return true
+			}
+			sel.apiKey = cfg.Providers.Anthropic.APIKey
+			sel.apiBase = cfg.Providers.Anthropic.APIBase
+			sel.proxy = cfg.Providers.Anthropic.Proxy
+			if sel.apiBase == "" {
+				sel.apiBase = defaultAnthropicAPIBase
+			}
+			return true
+		},
+	},
+	// GPT models → OpenAI (with OAuth/codex-cli support)
+	{
+		matches: func(lm, m string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "gpt") || strings.HasPrefix(m, "openai/")) &&
+				(cfg.Providers.OpenAI.APIKey != "" || cfg.Providers.OpenAI.AuthMethod != "")
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			sel.enableWebSearch = cfg.Providers.OpenAI.WebSearch
+			if cfg.Providers.OpenAI.AuthMethod == "codex-cli" {
+				sel.providerType = providerTypeCodexCLIToken
+				return true
+			}
+			if cfg.Providers.OpenAI.AuthMethod == "oauth" || cfg.Providers.OpenAI.AuthMethod == "token" {
+				sel.providerType = providerTypeCodexAuth
+				return true
+			}
+			sel.apiKey = cfg.Providers.OpenAI.APIKey
+			sel.apiBase = cfg.Providers.OpenAI.APIBase
+			sel.proxy = cfg.Providers.OpenAI.Proxy
+			if sel.apiBase == "" {
+				sel.apiBase = "https://api.openai.com/v1"
+			}
+			return true
+		},
+	},
+	// Gemini
+	{
+		matches: func(lm, m string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "gemini") || strings.HasPrefix(m, "google/")) && cfg.Providers.Gemini.APIKey != ""
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["gemini"])
+		},
+	},
+	// Zhipu/GLM
+	{
+		matches: func(lm, _ string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "glm") || strings.Contains(lm, "zhipu") || strings.Contains(lm, "zai")) && cfg.Providers.Zhipu.APIKey != ""
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["zhipu"])
+		},
+	},
+	// Groq
+	{
+		matches: func(lm, m string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "groq") || strings.HasPrefix(m, "groq/")) && cfg.Providers.Groq.APIKey != ""
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["groq"])
+		},
+	},
+	// Nvidia
+	{
+		matches: func(lm, m string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "nvidia") || strings.HasPrefix(m, "nvidia/")) && cfg.Providers.Nvidia.APIKey != ""
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["nvidia"])
+		},
+	},
+	// Ollama
+	{
+		matches: func(lm, m string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "ollama") || strings.HasPrefix(m, "ollama/")) && cfg.Providers.Ollama.APIKey != ""
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["ollama"])
+		},
+	},
+	// Mistral
+	{
+		matches: func(lm, m string, cfg *config.Config) bool {
+			return (strings.Contains(lm, "mistral") || strings.HasPrefix(m, "mistral/")) && cfg.Providers.Mistral.APIKey != ""
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["mistral"])
+		},
+	},
+	// VLLM (fallback if API base is configured)
+	{
+		matches: func(_, _ string, cfg *config.Config) bool {
+			return cfg.Providers.VLLM.APIBase != ""
+		},
+		apply: func(cfg *config.Config, sel *providerSelection) bool {
+			return applyStandardProvider(cfg, sel, standardProviderRegistry["vllm"])
+		},
+	},
+}
+
 func resolveProviderSelection(cfg *config.Config) (providerSelection, error) {
 	model := cfg.Agents.Defaults.Model
 	providerName := strings.ToLower(cfg.Agents.Defaults.Provider)
@@ -47,16 +309,8 @@ func resolveProviderSelection(cfg *config.Config) (providerSelection, error) {
 
 	// First, prefer explicit provider configuration.
 	if providerName != "" {
+		// Handle special-case providers that have unique instantiation logic.
 		switch providerName {
-		case "groq":
-			if cfg.Providers.Groq.APIKey != "" {
-				sel.apiKey = cfg.Providers.Groq.APIKey
-				sel.apiBase = cfg.Providers.Groq.APIBase
-				sel.proxy = cfg.Providers.Groq.Proxy
-				if sel.apiBase == "" {
-					sel.apiBase = "https://api.groq.com/openai/v1"
-				}
-			}
 		case "openai", "gpt":
 			if cfg.Providers.OpenAI.APIKey != "" || cfg.Providers.OpenAI.AuthMethod != "" {
 				sel.enableWebSearch = cfg.Providers.OpenAI.WebSearch
@@ -92,58 +346,6 @@ func resolveProviderSelection(cfg *config.Config) (providerSelection, error) {
 					sel.apiBase = defaultAnthropicAPIBase
 				}
 			}
-		case "openrouter":
-			if cfg.Providers.OpenRouter.APIKey != "" {
-				sel.apiKey = cfg.Providers.OpenRouter.APIKey
-				sel.proxy = cfg.Providers.OpenRouter.Proxy
-				if cfg.Providers.OpenRouter.APIBase != "" {
-					sel.apiBase = cfg.Providers.OpenRouter.APIBase
-				} else {
-					sel.apiBase = "https://openrouter.ai/api/v1"
-				}
-			}
-		case "zhipu", "glm":
-			if cfg.Providers.Zhipu.APIKey != "" {
-				sel.apiKey = cfg.Providers.Zhipu.APIKey
-				sel.apiBase = cfg.Providers.Zhipu.APIBase
-				sel.proxy = cfg.Providers.Zhipu.Proxy
-				if sel.apiBase == "" {
-					sel.apiBase = "https://open.bigmodel.cn/api/paas/v4"
-				}
-			}
-		case "gemini", "google":
-			if cfg.Providers.Gemini.APIKey != "" {
-				sel.apiKey = cfg.Providers.Gemini.APIKey
-				sel.apiBase = cfg.Providers.Gemini.APIBase
-				sel.proxy = cfg.Providers.Gemini.Proxy
-				if sel.apiBase == "" {
-					sel.apiBase = "https://generativelanguage.googleapis.com/v1beta"
-				}
-			}
-		case "vllm":
-			if cfg.Providers.VLLM.APIBase != "" {
-				sel.apiKey = cfg.Providers.VLLM.APIKey
-				sel.apiBase = cfg.Providers.VLLM.APIBase
-				sel.proxy = cfg.Providers.VLLM.Proxy
-			}
-		case "shengsuanyun":
-			if cfg.Providers.ShengSuanYun.APIKey != "" {
-				sel.apiKey = cfg.Providers.ShengSuanYun.APIKey
-				sel.apiBase = cfg.Providers.ShengSuanYun.APIBase
-				sel.proxy = cfg.Providers.ShengSuanYun.Proxy
-				if sel.apiBase == "" {
-					sel.apiBase = "https://router.shengsuanyun.com/api/v1"
-				}
-			}
-		case "nvidia":
-			if cfg.Providers.Nvidia.APIKey != "" {
-				sel.apiKey = cfg.Providers.Nvidia.APIKey
-				sel.apiBase = cfg.Providers.Nvidia.APIBase
-				sel.proxy = cfg.Providers.Nvidia.Proxy
-				if sel.apiBase == "" {
-					sel.apiBase = "https://integrate.api.nvidia.com/v1"
-				}
-			}
 		case "claude-cli", "claude-code", "claudecode":
 			workspace := cfg.WorkspacePath()
 			if workspace == "" {
@@ -160,27 +362,6 @@ func resolveProviderSelection(cfg *config.Config) (providerSelection, error) {
 			sel.providerType = providerTypeCodexCLI
 			sel.workspace = workspace
 			return sel, nil
-		case "deepseek":
-			if cfg.Providers.DeepSeek.APIKey != "" {
-				sel.apiKey = cfg.Providers.DeepSeek.APIKey
-				sel.apiBase = cfg.Providers.DeepSeek.APIBase
-				sel.proxy = cfg.Providers.DeepSeek.Proxy
-				if sel.apiBase == "" {
-					sel.apiBase = "https://api.deepseek.com/v1"
-				}
-				if model != "deepseek-chat" && model != "deepseek-reasoner" {
-					sel.model = "deepseek-chat"
-				}
-			}
-		case "mistral":
-			if cfg.Providers.Mistral.APIKey != "" {
-				sel.apiKey = cfg.Providers.Mistral.APIKey
-				sel.apiBase = cfg.Providers.Mistral.APIBase
-				sel.proxy = cfg.Providers.Mistral.Proxy
-				if sel.apiBase == "" {
-					sel.apiBase = "https://api.mistral.ai/v1"
-				}
-			}
 		case "github_copilot", "copilot":
 			sel.providerType = providerTypeGitHubCopilot
 			if cfg.Providers.GitHubCopilot.APIBase != "" {
@@ -190,120 +371,38 @@ func resolveProviderSelection(cfg *config.Config) (providerSelection, error) {
 			}
 			sel.connectMode = cfg.Providers.GitHubCopilot.ConnectMode
 			return sel, nil
+		default:
+			// Try standard provider registry lookup.
+			canonicalName := providerName
+			if alias, ok := providerNameAliases[providerName]; ok {
+				canonicalName = alias
+			}
+			if entry, ok := standardProviderRegistry[canonicalName]; ok {
+				if applyStandardProvider(cfg, &sel, entry) {
+					// Handle deepseek model override.
+					if canonicalName == "deepseek" && model != "deepseek-chat" && model != "deepseek-reasoner" {
+						sel.model = "deepseek-chat"
+					}
+				}
+			}
 		}
 	}
 
-	// Fallback: infer provider from model and configured keys.
+	// Fallback: infer provider from model name and configured keys.
 	if sel.apiKey == "" && sel.apiBase == "" {
-		switch {
-		case (strings.Contains(lowerModel, "kimi") || strings.Contains(lowerModel, "moonshot") || strings.HasPrefix(model, "moonshot/")) && cfg.Providers.Moonshot.APIKey != "":
-			sel.apiKey = cfg.Providers.Moonshot.APIKey
-			sel.apiBase = cfg.Providers.Moonshot.APIBase
-			sel.proxy = cfg.Providers.Moonshot.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = "https://api.moonshot.cn/v1"
+		matched := false
+		for _, entry := range modelInferenceRegistry {
+			if entry.matches(lowerModel, model, cfg) {
+				entry.apply(cfg, &sel)
+				matched = true
+				break
 			}
-		case strings.HasPrefix(model, "openrouter/") ||
-			strings.HasPrefix(model, "anthropic/") ||
-			strings.HasPrefix(model, "openai/") ||
-			strings.HasPrefix(model, "meta-llama/") ||
-			strings.HasPrefix(model, "deepseek/") ||
-			strings.HasPrefix(model, "google/"):
-			sel.apiKey = cfg.Providers.OpenRouter.APIKey
-			sel.proxy = cfg.Providers.OpenRouter.Proxy
-			if cfg.Providers.OpenRouter.APIBase != "" {
-				sel.apiBase = cfg.Providers.OpenRouter.APIBase
-			} else {
-				sel.apiBase = "https://openrouter.ai/api/v1"
-			}
-		case (strings.Contains(lowerModel, "claude") || strings.HasPrefix(model, "anthropic/")) &&
-			(cfg.Providers.Anthropic.APIKey != "" || cfg.Providers.Anthropic.AuthMethod != ""):
-			if cfg.Providers.Anthropic.AuthMethod == "oauth" || cfg.Providers.Anthropic.AuthMethod == "token" {
-				sel.apiBase = cfg.Providers.Anthropic.APIBase
-				if sel.apiBase == "" {
-					sel.apiBase = defaultAnthropicAPIBase
-				}
-				sel.providerType = providerTypeClaudeAuth
-				return sel, nil
-			}
-			sel.apiKey = cfg.Providers.Anthropic.APIKey
-			sel.apiBase = cfg.Providers.Anthropic.APIBase
-			sel.proxy = cfg.Providers.Anthropic.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = defaultAnthropicAPIBase
-			}
-		case (strings.Contains(lowerModel, "gpt") || strings.HasPrefix(model, "openai/")) &&
-			(cfg.Providers.OpenAI.APIKey != "" || cfg.Providers.OpenAI.AuthMethod != ""):
-			sel.enableWebSearch = cfg.Providers.OpenAI.WebSearch
-			if cfg.Providers.OpenAI.AuthMethod == "codex-cli" {
-				sel.providerType = providerTypeCodexCLIToken
-				return sel, nil
-			}
-			if cfg.Providers.OpenAI.AuthMethod == "oauth" || cfg.Providers.OpenAI.AuthMethod == "token" {
-				sel.providerType = providerTypeCodexAuth
-				return sel, nil
-			}
-			sel.apiKey = cfg.Providers.OpenAI.APIKey
-			sel.apiBase = cfg.Providers.OpenAI.APIBase
-			sel.proxy = cfg.Providers.OpenAI.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = "https://api.openai.com/v1"
-			}
-		case (strings.Contains(lowerModel, "gemini") || strings.HasPrefix(model, "google/")) && cfg.Providers.Gemini.APIKey != "":
-			sel.apiKey = cfg.Providers.Gemini.APIKey
-			sel.apiBase = cfg.Providers.Gemini.APIBase
-			sel.proxy = cfg.Providers.Gemini.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = "https://generativelanguage.googleapis.com/v1beta"
-			}
-		case (strings.Contains(lowerModel, "glm") || strings.Contains(lowerModel, "zhipu") || strings.Contains(lowerModel, "zai")) && cfg.Providers.Zhipu.APIKey != "":
-			sel.apiKey = cfg.Providers.Zhipu.APIKey
-			sel.apiBase = cfg.Providers.Zhipu.APIBase
-			sel.proxy = cfg.Providers.Zhipu.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = "https://open.bigmodel.cn/api/paas/v4"
-			}
-		case (strings.Contains(lowerModel, "groq") || strings.HasPrefix(model, "groq/")) && cfg.Providers.Groq.APIKey != "":
-			sel.apiKey = cfg.Providers.Groq.APIKey
-			sel.apiBase = cfg.Providers.Groq.APIBase
-			sel.proxy = cfg.Providers.Groq.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = "https://api.groq.com/openai/v1"
-			}
-		case (strings.Contains(lowerModel, "nvidia") || strings.HasPrefix(model, "nvidia/")) && cfg.Providers.Nvidia.APIKey != "":
-			sel.apiKey = cfg.Providers.Nvidia.APIKey
-			sel.apiBase = cfg.Providers.Nvidia.APIBase
-			sel.proxy = cfg.Providers.Nvidia.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = "https://integrate.api.nvidia.com/v1"
-			}
-		case (strings.Contains(lowerModel, "ollama") || strings.HasPrefix(model, "ollama/")) && cfg.Providers.Ollama.APIKey != "":
-			sel.apiKey = cfg.Providers.Ollama.APIKey
-			sel.apiBase = cfg.Providers.Ollama.APIBase
-			sel.proxy = cfg.Providers.Ollama.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = "http://localhost:11434/v1"
-			}
-		case (strings.Contains(lowerModel, "mistral") || strings.HasPrefix(model, "mistral/")) && cfg.Providers.Mistral.APIKey != "":
-			sel.apiKey = cfg.Providers.Mistral.APIKey
-			sel.apiBase = cfg.Providers.Mistral.APIBase
-			sel.proxy = cfg.Providers.Mistral.Proxy
-			if sel.apiBase == "" {
-				sel.apiBase = "https://api.mistral.ai/v1"
-			}
-		case cfg.Providers.VLLM.APIBase != "":
-			sel.apiKey = cfg.Providers.VLLM.APIKey
-			sel.apiBase = cfg.Providers.VLLM.APIBase
-			sel.proxy = cfg.Providers.VLLM.Proxy
-		default:
+		}
+
+		// Ultimate fallback: try OpenRouter if configured.
+		if !matched {
 			if cfg.Providers.OpenRouter.APIKey != "" {
-				sel.apiKey = cfg.Providers.OpenRouter.APIKey
-				sel.proxy = cfg.Providers.OpenRouter.Proxy
-				if cfg.Providers.OpenRouter.APIBase != "" {
-					sel.apiBase = cfg.Providers.OpenRouter.APIBase
-				} else {
-					sel.apiBase = "https://openrouter.ai/api/v1"
-				}
+				applyStandardProvider(cfg, &sel, standardProviderRegistry["openrouter"])
 			} else {
 				return providerSelection{}, fmt.Errorf("no API key configured for model: %s", model)
 			}
@@ -321,3 +420,4 @@ func resolveProviderSelection(cfg *config.Config) (providerSelection, error) {
 
 	return sel, nil
 }
+
diff --git a/pkg/providers/types.go b/pkg/providers/types.go
index f711e7803..9a4ee3533 100644
--- a/pkg/providers/types.go
+++ b/pkg/providers/types.go
@@ -34,13 +34,14 @@ type LLMProvider 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"
+	FailoverOverloaded    FailoverReason = "overloaded"
+	FailoverContextWindow FailoverReason = "context_window"
+	FailoverUnknown       FailoverReason = "unknown"
 )
 
 // FailoverError wraps an LLM provider error with classification metadata.